Identification

Name
Vitamin A
Accession Number
DB00162  (NUTR00007, APRD00486)
Type
Small Molecule
Groups
Approved, Nutraceutical, Vet Approved
Description

Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products. [PubChem]

Structure
Thumb
Synonyms
  • (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
  • all-trans-retinol
  • all-trans-retinyl alcohol
  • all-trans-vitamin A alcohol
  • Retinol
  • Vitamin A1
External IDs
11103-57-4
Product Ingredients
IngredientUNIICASInChI Key
Vitamin A acetate3LE3D9D6OY127-47-9QGNJRVVDBSJHIZ-QHLGVNSISA-N
Vitamin A palmitate1D1K0N0VVC79-81-2VYGQUTWHTHXGQB-FFHKNEKCSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aquasol AInjection, solution15 mg/mLIntramuscularHospira Worldwide, Inc.1949-05-18Not applicableUs
Aquasol A Cap 25000unitCapsule25000 unitOralRhone Poulenc Rorer1992-12-311996-09-09Canada
Aquasol A Cap 50000unitCapsule50000 unitOralRhone Poulenc Rorer1992-12-311996-09-09Canada
Cataplex A Tab 1500unitTablet1500 unitOralStandard Process Inc.Not applicableNot applicableCanada
Formula 7115 Tab 700unitTablet700 unitOralStandard Process Inc.Not applicableNot applicableCanada
Vitamin A Cap 25000iuCapsule25000 unitOralNovopharm Limited1967-12-312015-10-26Canada
Vitamin A Cap 25000iuCapsule25000 unitOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada
Vitamin A Cap 50000iuCapsule50000 unitOralNovopharm Limited1967-12-312015-10-26Canada
Vitamin A Cap 50000iuCapsule50000 unitOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
400 Vitamin A 10000iuCapsule10000 unitOralHerbes Universelles Inc.1972-12-312009-07-15Canada
A Caps 10000 I.U.Capsule10000 unitOralTwin Laboratories Inc.1995-12-311999-11-10Canada
A Mulsion 10Emulsion10000 unitOralSeroyal International Inc.1982-12-312008-10-09Canada
Arovit Vitamine A Tab 10000unitTablet10000 unitOralLes Laboratoires Bio SantÉ Inc.1986-12-311996-09-10Canada
Beta CaroteneLiquid10000 unitOralSeroyal International Inc.1982-12-312001-08-09Canada
Pro-sol A Liq 5000unit/minSolution / drops5000 unitOralProfessional Health Products1990-12-311998-08-13Canada
Super A 40Capsule10000 unitOralFrega Inc.1979-12-312008-07-09Canada
Vitamin ACapsule10000 unitOralSeroyal International Inc.1996-12-312009-07-06Canada
Vitamin A 10000I.U. CapCapsule10000 unitOralNutricorp International1993-12-312009-08-05Canada
Vitamin A 5000 I.U. Dietary SupplementTablet5000 unitOralGarden State Nutritionals1998-09-252000-06-07Canada
International/Other Brands
Alphalin / Chocola A
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
A & C PowderVitamin A (930 unit) + Vitamin C (7 mg)Powder, for solutionOralStandard Process Inc.Not applicableNot applicableCanada
A + D OintmentVitamin A palmitate (2000 unit) + Cholecalciferol (500 unit)OintmentTopicalNational Care Products Ltd.1993-12-312002-10-10Canada
A + ZincVitamin A (10000 unit) + Zinc (15 mg)TabletOralNutrilite, A Division Of Access Business Group, Llc2000-09-012007-07-06Canada
A and D OintmentVitamin A (1500 unit) + Vitamin D (213 unit)OintmentTopicalSchering Plough1951-12-312002-07-12Canada
A D Calcium TabVitamin A (5000 unit) + Calcium (126 mg) + Vitamin D (400 unit)TabletOralStar Pharmaceuticals, Llc1979-12-311999-07-21Canada
A-D Calcium CapVitamin A (2500 unit) + Calcium (170 mg) + Vitamin D (133 unit)CapsuleOralVitalab1990-12-312005-07-12Canada
Acti-retinol & Zn CapletVitamin A (3333 unit) + Beta carotene (20000 unit) + Zinc (7 mg) + Zinc (1 mg) + Zinc (.5 mg) + Zinc (1 mg) + Zinc (.5 mg)TabletOralActi Form Ltd.1991-12-312005-03-03Canada
Ad & Calcium CapVitamin A (2500 unit) + Calcium (170 mg) + Vitamin D (133 unit)CapsuleOralLaboratoire Lalco Inc.1977-12-312001-10-15Canada
Ad Calcium CapVitamin A (2500 unit) + Calcium (170 mg) + Vitamin D (133 unit)CapsuleOralLes Produits Gerbex Inc.1979-12-311997-08-11Canada
Adc ComprimesVitamin A acetate (5000 unit) + Vitamin C (250 mg) + Vitamin D (200 unit)TabletOralBio Vita1990-12-311996-09-09Canada
Categories
UNII
G2SH0XKK91
CAS number
68-26-8
Weight
Average: 286.4516
Monoisotopic: 286.229665582
Chemical Formula
C20H30O
InChI Key
FPIPGXGPPPQFEQ-OVSJKPMPSA-N
InChI
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
IUPAC Name
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
SMILES
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

Pharmacology

Indication

For the treatment of vitamin A deficiency.

Structured Indications
Not Available
Pharmacodynamics

Vitamin A is effective for the treatment of Vitamin A deficiency. Vitamin A refers to a group of fat-soluble substances that are structurally related to and possess the biological activity of the parent substance of the group called all-trans retinol or retinol. Vitamin A plays vital roles in vision, epithelial differentiation, growth, reproduction, pattern formation during embryogenesis, bone development, hematopoiesis and brain development. It is also important for the maintenance of the proper functioning of the immune system.

Mechanism of action

Vision:Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 11-cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to re-synthesize 11-cis retinal rapidly.
Epithelial differentiation: The role of Vitamin A in epithelial differentiation, as well as in other physiological processes, involves the binding of Vitamin A to two families of nuclear retinoid receptors (retinoic acid receptors, RARs; and retinoid-X receptors, RXRs). These receptors function as ligand-activated transcription factors that modulate gene transcription. When there is not enough Vitamin A to bind these receptors, natural cell differentiation and growth are interrupted.

TargetActionsOrganism
URetinol dehydrogenase 12Not AvailableHuman
URetinol-binding protein 1Not AvailableHuman
U11-cis retinol dehydrogenaseNot AvailableHuman
URetinol dehydrogenase 13Not AvailableHuman
URetinol-binding protein 3Not AvailableHuman
URetinal dehydrogenase 2Not AvailableHuman
URetinal dehydrogenase 1Not AvailableHuman
URetinaldehyde-binding protein 1Not AvailableHuman
ULecithin retinol acyltransferaseNot AvailableHuman
UShort-chain dehydrogenase/reductase 3Not AvailableHuman
UAldehyde dehydrogenase family 1 member A3Not AvailableHuman
UAll-trans-retinol 13,14-reductaseNot AvailableHuman
URetinol dehydrogenase 11Not AvailableHuman
UDehydrogenase/reductase SDR family member 4Not AvailableHuman
URetinol dehydrogenase 14Not AvailableHuman
URetinol dehydrogenase 8Not AvailableHuman
UApolipoprotein DNot AvailableHuman
UHematopoietic prostaglandin D synthaseNot AvailableHuman
Absorption

Readily absorbed from the normal gastrointestinal tract

Volume of distribution
Not Available
Protein binding

<5% of circulating vitamin A is bound to lipoproteins in blood in normal condition, but may be up to 65% when hepatic stores are saturated because of excessive intake. When released from liver, vitamin A is bound to retinol-binding protein (RBP). Most vitamin A circulates in the form of retinol bound to RBP.

Metabolism

Hepatic. Retinol is conjugated with glucuronic acid; the B-glucuronide undergoes enterohepatic circulation and oxidation to retinol and retinoic acid. Retinoic acid undergoes decarboxylation and conjugation with glucuronic acid.

Route of elimination
Not Available
Half life

1.9 hours

Clearance
Not Available
Toxicity

Acute toxicity (single ingestion of 7 500 RE or 25 000 IU per kg or more): Signs and symptoms may be delayed for 8 to 24 hours and include: increased intracranial pressure, headache, irritability, drowsiness, dizziness, lethargy, vomiting, diarrhea, bulging of fontanels in infants, diplopia, papilledema. Peeling of skin around mouth may be observed from 1 to several days after ingestion and may spread to the rest of the body. Chronic, excessive ingestion (1 200 RE or 4 000 IU/kg daily for 6 to 15 months) may produce symptoms of pseudotumor cerebri, anorexia, weakness, arthralgias, bone pain, bone demineralization, dry skin, cracked lips, brittle nails, hair loss, splenomegaly, hepatomegaly, hypoplastic anemia, leukopenia, optic neuropathy, and blindness. Increased plasma concentrations of vitamin A occur but do not necessarily correlate with toxicity.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Retinol MetabolismMetabolic
Vitamin A DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Vitamin A.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Vitamin A.Experimental
AcitretinThe risk or severity of adverse effects can be increased when Vitamin A is combined with Acitretin.Approved
AdapaleneThe risk or severity of adverse effects can be increased when Vitamin A is combined with Adapalene.Approved
AlitretinoinThe risk or severity of adverse effects can be increased when Vitamin A is combined with Alitretinoin.Approved, Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Vitamin A.Approved, Investigational
BexaroteneThe risk or severity of adverse effects can be increased when Vitamin A is combined with Bexarotene.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Vitamin A.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Vitamin A.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Vitamin A.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Vitamin A.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Vitamin A.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Vitamin A.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Vitamin A.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Vitamin A.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Vitamin A.Experimental
IsotretinoinThe risk or severity of adverse effects can be increased when Vitamin A is combined with Isotretinoin.Approved
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Vitamin A.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Vitamin A.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Vitamin A.Experimental, Investigational
OrlistatThe serum concentration of Vitamin A can be decreased when it is combined with Orlistat.Approved, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Vitamin A.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Vitamin A.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Vitamin A.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Vitamin A.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Vitamin A.Approved, Investigational
TretinoinThe risk or severity of adverse effects can be increased when Vitamin A is combined with Tretinoin.Approved, Investigational, Nutraceutical
Food Interactions
Not Available

References

Synthesis Reference

William Oroshnik, "Synthesis of Vitamin A, intermediates and conversion thereof to Vitamin A." U.S. Patent US4092366, issued May, 1948.

US4092366
General References
  1. Roncone DP: Xerophthalmia secondary to alcohol-induced malnutrition. Optometry. 2006 Mar;77(3):124-33. [PubMed:16513513]
External Links
Human Metabolome Database
HMDB00305
KEGG Drug
D00069
KEGG Compound
C17276
PubChem Compound
445354
PubChem Substance
46508191
ChemSpider
393012
BindingDB
50092056
ChEBI
17336
ChEMBL
CHEMBL986
Therapeutic Targets Database
DNC001498
PharmGKB
PA451884
HET
RTL
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Vitamin_A
ATC Codes
R01AX02 — RetinolA11CA01 — Retinol (vit a)D10AD02 — RetinolV04CB01 — Vitamin a concentratesS01XA02 — Retinol
AHFS Codes
  • 88:04.00 — Vitamin A
PDB Entries
1aqb / 1brp / 1crb / 1eii / 1fbm / 1fmj / 1fml / 1gx8 / 1hbp / 1iiu
show 21 more
MSDS
Download (74.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentAcne Vulgaris1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I / Mycobacterium avium complex infection1
1CompletedDiagnosticHealthy Volunteers1
1CompletedPreventionHIV-infection/Aids1
1CompletedTreatmentCancers / Metastases1
1CompletedTreatmentRetinitis Pigmentosa (RP)1
1Not Yet RecruitingBasic ScienceAging / Mineral deficiency / Vitamin Deficiency1
1RecruitingBasic ScienceCYP2D6 Polymorphism1
1, 2CompletedPreventionChronic Lung Disease of Prematurity / Infant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Respiration, Artificial / Respiratory Distress Syndrome, Newborn / Sepsis1
1, 2SuspendedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
2Active Not RecruitingTreatmentDeficiency, Vitamin A / Human Immunodeficiency Virus (HIV)1
2CompletedPreventionDeficiency, Vitamin A / HIV Seronegativity / Human Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionPurpura / Skin Aging1
2CompletedTreatmentCancer, Breast1
2CompletedTreatmentEnteric Infections1
2CompletedTreatmentFacial fine wrinkling / Photodamaged Skin1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kidney Diseases1
2, 3CompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Mortality1
3CompletedPreventionComplications, Pregnancy / Human Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionNewborn Infants1
3CompletedTreatmentAnemias1
3CompletedTreatmentDiarrheal Illnesses / Growth Faltering / Respiratory Illness1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis, Pulmonary1
3CompletedTreatmentMycobacterium Tuberculosis1
3CompletedTreatmentRetinitis Pigmentosa (RP)2
3Unknown StatusNot AvailableAnemias / Low Birth Weight / Neonatal Mortality1
3Unknown StatusTreatmentAlzheimer's Disease (AD) / Down Syndrome (DS)1
3Unknown StatusTreatmentDiarrheal Disorder1
4CompletedPreventionLung Cancers1
4CompletedPreventionMorbidity / Mortality3
4CompletedPreventionPremature Births / Retinopathy of Prematurity1
4CompletedPreventionVillage Children1
4CompletedScreeningType 2 Diabetes Mellitus1
4CompletedTreatmentAnemias / Worm Infections1
4CompletedTreatmentHyperemesis Gravidarum / Morning Sickness / Nausea / Pregnancy / Vomiting1
4CompletedTreatmentSepsis1
4RecruitingOtherIntrinsic Aging of Skin1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedPreventionMorbidity / Mortality1
4Unknown StatusPreventionAtherosclerosis2
4Unknown StatusPreventionMorbidity / Mortality1
4Unknown StatusPreventionMorbidity / Mortality, Infant1
4Unknown StatusTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
4WithdrawnTreatmentNephritis / Proteinuria / Systemic Lupus Erythematosus (SLE)1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedPreventionIron Metabolic Homeostasis1
Not AvailableCompletedPreventionNeonatal Vitamin A Supplementation1
Not AvailableCompletedPreventionNeural Tube Defects (NTDs)1
Not AvailableCompletedPreventionVisceral Leishmaniasis1
Not AvailableCompletedTreatmentDiarrhea / Malnutrition / Respiratory Tract Infections (RTI)1
Not AvailableCompletedTreatmentGlaucoma, Primary Open Angle (POAG)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableRecruitingPreventionRetinopathy of Prematurity1
Not AvailableUnknown StatusNot AvailableEndotoxin Levels / TNF-alfa1
Not AvailableWithdrawnNot AvailableLatent Tuberculosis Infection (LTI)1

Pharmacoeconomics

Manufacturers
  • Astrazeneca lp
  • Banner pharmacaps inc
  • Chase chemical co lp
  • Everylife
  • Impax laboratories inc
  • West ward pharmaceutical corp
  • Sterling winthrop inc
  • Eli lilly and co
  • Del ray laboratories inc
  • Bayer pharmaceuticals corp
  • Bristol myers squibb co
  • Elkins sinn div ah robins co inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mk laboratories inc
  • Wharton laboratories inc div us ethicals
  • Arcum pharmaceutical corp
  • Teva pharmaceuticals usa inc
  • Hospira inc
  • Bel mar laboratories inc
Packagers
Dosage forms
FormRouteStrength
Powder, for solutionOral
OintmentTopical
EmulsionOral10000 unit
Injection, solutionIntramuscular15 mg/mL
CapsuleOral25000 unit
CapsuleOral50000 unit
LiquidOral10000 unit
CreamTopical
TabletOral1500 unit
Tablet, extended releaseOral
TabletOral700 unit
CapsuleOral
Tablet, coatedOral
Tablet, chewableOral
LiquidIntravenous
Injection, powder, lyophilized, for solutionIntravenous
Liquid; tabletOral
Solution / dropsOral
Injection, solution, concentrateIntravenous
SolutionIntravenous
LiquidOral
SolutionOral
SyrupOral
Injection, solutionIntravenous
TabletOral
Tablet, film coatedOral
Solution / dropsOral5000 unit
PowderOral
LozengeOral
Capsule; liquidOral
Capsule, gelatin coatedOral
Capsule, liquid filledOral
TabletOral5000 unit
CapsuleOral10000 unit
TabletOral10000 unit
TabletOral2000 unit
Prices
Unit descriptionCostUnit
Avita 0.025% Cream 45 gm Tube149.39USD tube
Avita 0.025% Gel 45 gm Tube149.39USD tube
Avita 0.025% Cream 20 gm Tube69.21USD tube
Vitamin a palmitate liquid22.33USD ml
Aquasol a 50000 unit/ml vial17.69USD ml
Vitamin a acetate crystals1.99USD g
Gordon's vite a creme0.13USD g
Vitamin a palm 10000 unit tablet0.06USD tablet
Vitamin a cream0.03USD g
Vitamin a 10000 unit tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)63.5 °CPhysProp
water solubility0.671 mg/LNot Available
logP5.68BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00758 mg/mLALOGPS
logP6.38ALOGPS
logP4.69ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.44ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.92 m3·mol-1ChemAxon
Polarizability36.43 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9938
Blood Brain Barrier+0.9665
Caco-2 permeable+0.7272
P-glycoprotein substrateNon-substrate0.5939
P-glycoprotein inhibitor INon-inhibitor0.8205
P-glycoprotein inhibitor IINon-inhibitor0.5631
Renal organic cation transporterNon-inhibitor0.7646
CYP450 2C9 substrateNon-substrate0.8193
CYP450 2D6 substrateNon-substrate0.8324
CYP450 3A4 substrateSubstrate0.5522
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.842
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7388
Ames testAMES toxic0.6952
CarcinogenicityNon-carcinogens0.7004
BiodegradationReady biodegradable0.5504
Rat acute toxicity2.1249 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8563
hERG inhibition (predictor II)Non-inhibitor0.8853
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.5 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-052r-2950000000-c24ec8ff8d0ba6c1f23f
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0290000000-25c523b646154b291da8
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-05gj-3900000000-a63c286f931608f650a3
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-05mo-9700000000-e627db30469c74bb037f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Retinoids
Direct Parent
Retinoids
Alternative Parents
Diterpenoids / Fatty alcohols / Primary alcohols / Hydrocarbon derivatives
Substituents
Retinoid skeleton / Diterpenoid / Fatty alcohol / Fatty acyl / Organic oxygen compound / Hydrocarbon derivative / Primary alcohol / Organooxygen compound / Alcohol / Aliphatic homomonocyclic compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
retinol (CHEBI:17336) / Retinoids, Fat-soluble vitamins (C00473) / Retinoids (LMPR01090000)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Retinol dehydrogenase activity
Specific Function
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity toward 9-cis and all-trans-retinol. Also involved in ...
Gene Name
RDH12
Uniprot ID
Q96NR8
Uniprot Name
Retinol dehydrogenase 12
Molecular Weight
35093.455 Da
References
  1. Maeda A, Maeda T, Imanishi Y, Sun W, Jastrzebska B, Hatala DA, Winkens HJ, Hofmann KP, Janssen JJ, Baehr W, Driessen CA, Palczewski K: Retinol dehydrogenase (RDH12) protects photoreceptors from light-induced degeneration in mice. J Biol Chem. 2006 Dec 8;281(49):37697-704. Epub 2006 Oct 10. [PubMed:17032653]
  2. Thompson DA, Janecke AR, Lange J, Feathers KL, Hubner CA, McHenry CL, Stockton DW, Rammesmayer G, Lupski JR, Antinolo G, Ayuso C, Baiget M, Gouras P, Heckenlively JR, den Hollander A, Jacobson SG, Lewis RA, Sieving PA, Wissinger B, Yzer S, Zrenner E, Utermann G, Gal A: Retinal degeneration associated with RDH12 mutations results from decreased 11-cis retinal synthesis due to disruption of the visual cycle. Hum Mol Genet. 2005 Dec 15;14(24):3865-75. Epub 2005 Nov 3. [PubMed:16269441]
  3. Keller B, Adamski J: RDH12, a retinol dehydrogenase causing Leber's congenital amaurosis, is also involved in steroid metabolism. J Steroid Biochem Mol Biol. 2007 May;104(3-5):190-4. Epub 2007 Mar 23. [PubMed:17512723]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Intracellular transport of retinol.
Gene Name
RBP1
Uniprot ID
P09455
Uniprot Name
Retinol-binding protein 1
Molecular Weight
15850.13 Da
References
  1. Yapi HF, Ahiboh H, Ago K, Ake M, Monnet D: [Protein profile and vitamin A in children of school age in Ivory Coast]. Ann Biol Clin (Paris). 2005 May-Jun;63(3):291-5. [PubMed:15951260]
  2. Quadro L, Hamberger L, Gottesman ME, Wang F, Colantuoni V, Blaner WS, Mendelsohn CL: Pathways of vitamin A delivery to the embryo: insights from a new tunable model of embryonic vitamin A deficiency. Endocrinology. 2005 Oct;146(10):4479-90. Epub 2005 Jun 30. [PubMed:15994349]
  3. Harrison EH: Mechanisms of digestion and absorption of dietary vitamin A. Annu Rev Nutr. 2005;25:87-103. [PubMed:16011460]
  4. Paci E, Greene LH, Jones RM, Smith LJ: Characterization of the molten globule state of retinol-binding protein using a molecular dynamics simulation approach. FEBS J. 2005 Sep;272(18):4826-38. [PubMed:16156801]
  5. Folli C, Viglione S, Busconi M, Berni R: Biochemical basis for retinol deficiency induced by the I41N and G75D mutations in human plasma retinol-binding protein. Biochem Biophys Res Commun. 2005 Nov 4;336(4):1017-22. [PubMed:16157297]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Retinol dehydrogenase activity
Specific Function
Stereospecific 11-cis retinol dehydrogenase, which catalyzes the final step in the biosynthesis of 11-cis retinaldehyde, the universal chromophore of visual pigments. Also able to oxidize 9-cis-ret...
Gene Name
RDH5
Uniprot ID
Q92781
Uniprot Name
11-cis retinol dehydrogenase
Molecular Weight
34978.425 Da
References
  1. Zhang M, Hu P, Krois CR, Kane MA, Napoli JL: Altered vitamin A homeostasis and increased size and adiposity in the rdh1-null mouse. FASEB J. 2007 Sep;21(11):2886-96. Epub 2007 Apr 13. [PubMed:17435174]
  2. Maeda A, Maeda T, Imanishi Y, Golczak M, Moise AR, Palczewski K: Aberrant metabolites in mouse models of congenital blinding diseases: formation and storage of retinyl esters. Biochemistry. 2006 Apr 4;45(13):4210-9. [PubMed:16566595]
  3. Dalfo D, Marques N, Albalat R: Analysis of the NADH-dependent retinaldehyde reductase activity of amphioxus retinol dehydrogenase enzymes enhances our understanding of the evolution of the retinol dehydrogenase family. FEBS J. 2007 Jul;274(14):3739-52. Epub 2007 Jul 2. [PubMed:17608724]
  4. Gidlof AC, Ocaya P, Olofsson PS, Torma H, Sirsjo A: Differences in retinol metabolism and proliferative response between neointimal and medial smooth muscle cells. J Vasc Res. 2006;43(4):392-8. Epub 2006 Jul 6. [PubMed:16837774]
  5. Belyaeva OV, Kedishvili NY: Comparative genomic and phylogenetic analysis of short-chain dehydrogenases/reductases with dual retinol/sterol substrate specificity. Genomics. 2006 Dec;88(6):820-30. Epub 2006 Jul 24. [PubMed:16860536]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Does not exhibit retinol dehydrogenase (RDH) activity in vitro.
Gene Name
RDH13
Uniprot ID
Q8NBN7
Uniprot Name
Retinol dehydrogenase 13
Molecular Weight
35931.85 Da
References
  1. Keller B, Adamski J: RDH12, a retinol dehydrogenase causing Leber's congenital amaurosis, is also involved in steroid metabolism. J Steroid Biochem Mol Biol. 2007 May;104(3-5):190-4. Epub 2007 Mar 23. [PubMed:17512723]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine-type peptidase activity
Specific Function
IRBP shuttles 11-cis and all trans retinoids between the retinol isomerase in the pigment epithelium and the visual pigments in the photoreceptor cells of the retina.
Gene Name
RBP3
Uniprot ID
P10745
Uniprot Name
Retinol-binding protein 3
Molecular Weight
135361.46 Da
References
  1. Qtaishat NM, Wiggert B, Pepperberg DR: Interphotoreceptor retinoid-binding protein (IRBP) promotes the release of all-trans retinol from the isolated retina following rhodopsin bleaching illumination. Exp Eye Res. 2005 Oct;81(4):455-63. Epub 2005 Jun 2. [PubMed:15935345]
  2. Wu Q, Blakeley LR, Cornwall MC, Crouch RK, Wiggert BN, Koutalos Y: Interphotoreceptor retinoid-binding protein is the physiologically relevant carrier that removes retinol from rod photoreceptor outer segments. Biochemistry. 2007 Jul 24;46(29):8669-79. Epub 2007 Jun 30. [PubMed:17602665]
  3. Kolesnikov AV, Ala-Laurila P, Shukolyukov SA, Crouch RK, Wiggert B, Estevez ME, Govardovskii VI, Cornwall MC: Visual cycle and its metabolic support in gecko photoreceptors. Vision Res. 2007 Feb;47(3):363-74. Epub 2006 Oct 16. [PubMed:17049961]
  4. Duncan T, Fariss RN, Wiggert B: Confocal immunolocalization of bovine serum albumin, serum retinol-binding protein, and interphotoreceptor retinoid-binding protein in bovine retina. Mol Vis. 2006 Dec 22;12:1632-9. [PubMed:17200663]
  5. Salvador-Silva M, Ghosh S, Bertazolli-Filho R, Boatright JH, Nickerson JM, Garwin GG, Saari JC, Coca-Prados M: Retinoid processing proteins in the ocular ciliary epithelium. Mol Vis. 2005 May 18;11:356-65. [PubMed:15928609]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Retinal dehydrogenase activity
Specific Function
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal...
Gene Name
ALDH1A2
Uniprot ID
O94788
Uniprot Name
Retinal dehydrogenase 2
Molecular Weight
56723.495 Da
References
  1. Isken A, Holzschuh J, Lampert JM, Fischer L, Oberhauser V, Palczewski K, von Lintig J: Sequestration of retinyl esters is essential for retinoid signaling in the zebrafish embryo. J Biol Chem. 2007 Jan 12;282(2):1144-51. Epub 2006 Nov 10. [PubMed:17098734]
  2. Halilagic A, Ribes V, Ghyselinck NB, Zile MH, Dolle P, Studer M: Retinoids control anterior and dorsal properties in the developing forebrain. Dev Biol. 2007 Mar 1;303(1):362-75. Epub 2006 Nov 17. [PubMed:17184764]
  3. Asson-Batres MA, Smith WB: Localization of retinaldehyde dehydrogenases and retinoid binding proteins to sustentacular cells, glia, Bowman's gland cells, and stroma: potential sites of retinoic acid synthesis in the postnatal rat olfactory organ. J Comp Neurol. 2006 May 10;496(2):149-71. [PubMed:16538685]
  4. Szatmari I, Pap A, Ruhl R, Ma JX, Illarionov PA, Besra GS, Rajnavolgyi E, Dezso B, Nagy L: PPARgamma controls CD1d expression by turning on retinoic acid synthesis in developing human dendritic cells. J Exp Med. 2006 Oct 2;203(10):2351-62. Epub 2006 Sep 18. [PubMed:16982809]
  5. Nakazawa N, Montedonico S, Takayasu H, Paradisi F, Puri P: Disturbance of retinol transportation causes nitrofen-induced hypoplastic lung. J Pediatr Surg. 2007 Feb;42(2):345-9. [PubMed:17270546]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Retinal dehydrogenase activity
Specific Function
Binds free retinal and cellular retinol-binding protein-bound retinal. Can convert/oxidize retinaldehyde to retinoic acid (By similarity).
Gene Name
ALDH1A1
Uniprot ID
P00352
Uniprot Name
Retinal dehydrogenase 1
Molecular Weight
54861.44 Da
References
  1. Asson-Batres MA, Smith WB: Localization of retinaldehyde dehydrogenases and retinoid binding proteins to sustentacular cells, glia, Bowman's gland cells, and stroma: potential sites of retinoic acid synthesis in the postnatal rat olfactory organ. J Comp Neurol. 2006 May 10;496(2):149-71. [PubMed:16538685]
  2. Chambers D, Wilson L, Maden M, Lumsden A: RALDH-independent generation of retinoic acid during vertebrate embryogenesis by CYP1B1. Development. 2007 Apr;134(7):1369-83. Epub 2007 Feb 28. [PubMed:17329364]
  3. Gyamfi MA, Kocsis MG, He L, Dai G, Mendy AJ, Wan YJ: The role of retinoid X receptor alpha in regulating alcohol metabolism. J Pharmacol Exp Ther. 2006 Oct;319(1):360-8. Epub 2006 Jul 7. [PubMed:16829625]
  4. Maden M, Blentic A, Reijntjes S, Seguin S, Gale E, Graham A: Retinoic acid is required for specification of the ventral eye field and for Rathke's pouch in the avian embryo. Int J Dev Biol. 2007;51(3):191-200. [PubMed:17486539]
  5. Huq MD, Tsai NP, Gupta P, Wei LN: Regulation of retinal dehydrogenases and retinoic acid synthesis by cholesterol metabolites. EMBO J. 2006 Jul 12;25(13):3203-13. Epub 2006 Jun 8. [PubMed:16763553]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Soluble retinoid carrier essential the proper function of both rod and cone photoreceptors. Participates in the regeneration of active 11-cis-retinol and 11-cis-retinaldehyde, from the inactive 11-...
Gene Name
RLBP1
Uniprot ID
P12271
Uniprot Name
Retinaldehyde-binding protein 1
Molecular Weight
36474.02 Da
References
  1. Muniz A, Villazana-Espinoza ET, Thackeray B, Tsin AT: 11-cis-Acyl-CoA:retinol O-acyltransferase activity in the primary culture of chicken Muller cells. Biochemistry. 2006 Oct 10;45(40):12265-73. [PubMed:17014079]
  2. Wenzel A, von Lintig J, Oberhauser V, Tanimoto N, Grimm C, Seeliger MW: RPE65 is essential for the function of cone photoreceptors in NRL-deficient mice. Invest Ophthalmol Vis Sci. 2007 Feb;48(2):534-42. [PubMed:17251447]
  3. Vogel JS, Bullen EC, Teygong CL, Howard EW: Identification of the RLBP1 gene promoter. Invest Ophthalmol Vis Sci. 2007 Aug;48(8):3872-7. [PubMed:17652763]
  4. Salvador-Silva M, Ghosh S, Bertazolli-Filho R, Boatright JH, Nickerson JM, Garwin GG, Saari JC, Coca-Prados M: Retinoid processing proteins in the ocular ciliary epithelium. Mol Vis. 2005 May 18;11:356-65. [PubMed:15928609]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transferase activity, transferring acyl groups
Specific Function
Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical...
Gene Name
LRAT
Uniprot ID
O95237
Uniprot Name
Lecithin retinol acyltransferase
Molecular Weight
25702.635 Da
References
  1. Kaschula CH, Jin MH, Desmond-Smith NS, Travis GH: Acyl CoA:retinol acyltransferase (ARAT) activity is present in bovine retinal pigment epithelium. Exp Eye Res. 2006 Jan;82(1):111-21. Epub 2005 Jul 27. [PubMed:16054134]
  2. Liu L, Gudas LJ: Disruption of the lecithin:retinol acyltransferase gene makes mice more susceptible to vitamin A deficiency. J Biol Chem. 2005 Dec 2;280(48):40226-34. Epub 2005 Sep 20. [PubMed:16174770]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Retinol dehydrogenase activity
Specific Function
Catalyzes the reduction of all-trans-retinal to all-trans-retinol in the presence of NADPH.
Gene Name
DHRS3
Uniprot ID
O75911
Uniprot Name
Short-chain dehydrogenase/reductase 3
Molecular Weight
33548.115 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Haeseleer F, Huang J, Lebioda L, Saari JC, Palczewski K: Molecular characterization of a novel short-chain dehydrogenase/reductase that reduces all-trans-retinal. J Biol Chem. 1998 Aug 21;273(34):21790-9. [PubMed:9705317]
  4. Cerignoli F, Guo X, Cardinali B, Rinaldi C, Casaletto J, Frati L, Screpanti I, Gudas LJ, Gulino A, Thiele CJ, Giannini G: retSDR1, a short-chain retinol dehydrogenase/reductase, is retinoic acid-inducible and frequently deleted in human neuroblastoma cell lines. Cancer Res. 2002 Feb 15;62(4):1196-204. [PubMed:11861404]
  5. Chai Z, Brereton P, Suzuki T, Sasano H, Obeyesekere V, Escher G, Saffery R, Fuller P, Enriquez C, Krozowski Z: 17 beta-hydroxysteroid dehydrogenase type XI localizes to human steroidogenic cells. Endocrinology. 2003 May;144(5):2084-91. [PubMed:12697717]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Thyroid hormone binding
Specific Function
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early...
Gene Name
ALDH1A3
Uniprot ID
P47895
Uniprot Name
Aldehyde dehydrogenase family 1 member A3
Molecular Weight
56107.995 Da
References
  1. Nakazawa N, Montedonico S, Takayasu H, Paradisi F, Puri P: Disturbance of retinol transportation causes nitrofen-induced hypoplastic lung. J Pediatr Surg. 2007 Feb;42(2):345-9. [PubMed:17270546]
  2. Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [PubMed:15950969]
  3. Halilagic A, Ribes V, Ghyselinck NB, Zile MH, Dolle P, Studer M: Retinoids control anterior and dorsal properties in the developing forebrain. Dev Biol. 2007 Mar 1;303(1):362-75. Epub 2006 Nov 17. [PubMed:17184764]
  4. Maden M, Blentic A, Reijntjes S, Seguin S, Gale E, Graham A: Retinoic acid is required for specification of the ventral eye field and for Rathke's pouch in the avian embryo. Int J Dev Biol. 2007;51(3):191-200. [PubMed:17486539]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Retinol saturase carrying out the saturation of the 13-14 double bond of all-trans-retinol to produce all-trans-13,14-dihydroretinol. Has activity toward all-trans-retinol as substrate. Does not us...
Gene Name
RETSAT
Uniprot ID
Q6NUM9
Uniprot Name
All-trans-retinol 13,14-reductase
Molecular Weight
66818.935 Da
References
  1. Moise AR, Isken A, Dominguez M, de Lera AR, von Lintig J, Palczewski K: Specificity of zebrafish retinol saturase: formation of all-trans-13,14-dihydroretinol and all-trans-7,8- dihydroretinol. Biochemistry. 2007 Feb 20;46(7):1811-20. Epub 2007 Jan 25. [PubMed:17253779]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Retinol dehydrogenase activity
Specific Function
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity towards 9-cis and all-trans-retinol. Also involved in...
Gene Name
RDH11
Uniprot ID
Q8TC12
Uniprot Name
Retinol dehydrogenase 11
Molecular Weight
35385.955 Da
References
  1. Gallego O, Belyaeva OV, Porte S, Ruiz FX, Stetsenko AV, Shabrova EV, Kostereva NV, Farres J, Pares X, Kedishvili NY: Comparative functional analysis of human medium-chain dehydrogenases, short-chain dehydrogenases/reductases and aldo-keto reductases with retinoids. Biochem J. 2006 Oct 1;399(1):101-9. [PubMed:16787387]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
Reduces all-trans-retinal and 9-cis retinal. Can also catalyze the oxidation of all-trans-retinol with NADP as co-factor, but with much lower efficiency. Reduces alkyl phenyl ketones and alpha-dica...
Gene Name
DHRS4
Uniprot ID
Q9BTZ2
Uniprot Name
Dehydrogenase/reductase SDR family member 4
Molecular Weight
29536.885 Da
References
  1. Du K, Liu GF, Xie JP, Song XH, Li R, Liang B, Huang DY: A 27.368 kDa retinal reductase in New Zealand white rabbit liver cytosol encoded by the peroxisomal retinol dehydrogenase-reductase cDNA: purification and characterization of the enzyme. Biochem Cell Biol. 2007 Apr;85(2):209-17. [PubMed:17534402]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Alcohol dehydrogenase (nadp+) activity
Specific Function
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity toward 9-cis and all-trans-retinol. No steroid dehydr...
Gene Name
RDH14
Uniprot ID
Q9HBH5
Uniprot Name
Retinol dehydrogenase 14
Molecular Weight
36864.355 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Retinol dehydrogenase activity
Specific Function
Retinol dehydrogenase with a clear preference for NADP. Converts all-trans-retinal to all-trans-retinol. May play a role in the regeneration of visual pigment at high light intensity (By similarity).
Gene Name
RDH8
Uniprot ID
Q9NYR8
Uniprot Name
Retinol dehydrogenase 8
Molecular Weight
33755.02 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Han W, Shen Y, Wang J, Yip S, Yap MK: [Establishing the linkage disequilibrium pattern for the all-trans-retinol dehydrogenase (RDH8) gene]. Zhonghua Yan Ke Za Zhi. 2006 Jul;42(7):642-8. [PubMed:17081426]
  4. Han W, Yip SP, Wang J, Yap MK: Using denaturing HPLC for SNP discovery and genotyping, and establishing the linkage disequilibrium pattern for the all-trans-retinol dehydrogenase (RDH8) gene. J Hum Genet. 2004;49(1):16-23. Epub 2003 Dec 6. [PubMed:14661078]
  5. Fishman GA, Roberts MF, Derlacki DJ, Grimsby JL, Yamamoto H, Sharon D, Nishiguchi KM, Dryja TP: Novel mutations in the cellular retinaldehyde-binding protein gene (RLBP1) associated with retinitis punctata albescens: evidence of interfamilial genetic heterogeneity and fundus changes in heterozygotes. Arch Ophthalmol. 2004 Jan;122(1):70-5. [PubMed:14718298]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Lipid transporter activity
Specific Function
APOD occurs in the macromolecular complex with lecithin-cholesterol acyltransferase. It is probably involved in the transport and binding of bilin. Appears to be able to transport a variety of liga...
Gene Name
APOD
Uniprot ID
P05090
Uniprot Name
Apolipoprotein D
Molecular Weight
21275.37 Da
References
  1. Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [PubMed:16461020]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Bifunctional enzyme which catalyzes both the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation, and the con...
Gene Name
HPGDS
Uniprot ID
O60760
Uniprot Name
Hematopoietic prostaglandin D synthase
Molecular Weight
23343.65 Da
References
  1. Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [PubMed:16461020]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Retinoic acid binding
Specific Function
Plays a key role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA. Capable of both 4-hydroxylation and 18-hydroxylation. Responsi...
Gene Name
CYP26A1
Uniprot ID
O43174
Uniprot Name
Cytochrome P450 26A1
Molecular Weight
56198.11 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Intracellular transport of retinol.
Gene Name
RBP5
Uniprot ID
P82980
Uniprot Name
Retinol-binding protein 5
Molecular Weight
15931.17 Da
References
  1. O'Byrne SM, Wongsiriroj N, Libien J, Vogel S, Goldberg IJ, Baehr W, Palczewski K, Blaner WS: Retinoid absorption and storage is impaired in mice lacking lecithin:retinol acyltransferase (LRAT). J Biol Chem. 2005 Oct 21;280(42):35647-57. Epub 2005 Aug 22. [PubMed:16115871]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Intracellular transport of retinol.
Gene Name
RBP7
Uniprot ID
Q96R05
Uniprot Name
Retinoid-binding protein 7
Molecular Weight
15535.585 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Caprioli A, Zhu H, Sato TN: CRBP-III:lacZ expression pattern reveals a novel heterogeneity of vascular endothelial cells. Genesis. 2004 Nov;40(3):139-45. [PubMed:15493015]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Retinol transporter activity
Specific Function
Delivers retinol from the liver stores to the peripheral tissues. In plasma, the RBP-retinol complex interacts with transthyretin, this prevents its loss by filtration through the kidney glomeruli.
Gene Name
RBP4
Uniprot ID
P02753
Uniprot Name
Retinol-binding protein 4
Molecular Weight
23009.8 Da
References
  1. Goodman AB: Retinoid receptors, transporters, and metabolizers as therapeutic targets in late onset Alzheimer disease. J Cell Physiol. 2006 Dec;209(3):598-603. [PubMed:17001693]
  2. Ziouzenkova O, Orasanu G, Sharlach M, Akiyama TE, Berger JP, Viereck J, Hamilton JA, Tang G, Dolnikowski GG, Vogel S, Duester G, Plutzky J: Retinaldehyde represses adipogenesis and diet-induced obesity. Nat Med. 2007 Jun;13(6):695-702. Epub 2007 May 27. [PubMed:17529981]
  3. Wolf G: Serum retinol-binding protein: a link between obesity, insulin resistance, and type 2 diabetes. Nutr Rev. 2007 May;65(5):251-6. [PubMed:17566551]
  4. Liden M, Eriksson U: Development of a versatile reporter assay for studies of retinol uptake and metabolism in vivo. Exp Cell Res. 2005 Nov 1;310(2):401-8. Epub 2005 Sep 8. [PubMed:16150442]
  5. Hinterhuber G, Cauza K, Dingelmaier-Hovorka R, Diem E, Horvat R, Wolff K, Foedinger D: Expression of RPE65, a putative receptor for plasma retinol-binding protein, in nonmelanocytic skin tumours. Br J Dermatol. 2005 Oct;153(4):785-9. [PubMed:16181461]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Intracellular transport of retinol.
Gene Name
RBP2
Uniprot ID
P50120
Uniprot Name
Retinol-binding protein 2
Molecular Weight
15706.595 Da
References
  1. Suruga K, Kitagawa M, Yasutake H, Takase S, Goda T: Diet-related variation in cellular retinol-binding protein type II gene expression in rat jejunum. Br J Nutr. 2005 Dec;94(6):890-5. [PubMed:16351764]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Karnaukhova E: Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. Biochem Pharmacol. 2007 Mar 15;73(6):901-10. Epub 2006 Dec 2. [PubMed:17217919]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18