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Identification
NameBiotin
Accession NumberDB00121  (NUTR00019)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

A water-soluble, enzyme co-factor present in minute amounts in every living cell. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acidNot AvailableNot Available
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acidNot AvailableNot Available
5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoic acidNot AvailableNot Available
BiotinNot AvailableNot Available
BiotinaNot AvailableNot Available
BiotineNot AvailableNot Available
BiotinumNot AvailableNot Available
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acidNot AvailableNot Available
cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acidNot AvailableNot Available
cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valeric acidNot AvailableNot Available
Coenzyme RNot AvailableNot Available
D-(+)-BiotinNot AvailableNot Available
D-BiotinNot AvailableNot Available
D(+)-BiotinNot AvailableNot Available
Vitamin B7Not AvailableNot Available
Vitamin HNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AppearexNot Available
BiodermatinNot Available
Biotin ForteNot Available
MeribinNot Available
Nail-exNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number58-85-5
WeightAverage: 244.311
Monoisotopic: 244.088163078
Chemical FormulaC10H16N2O3S
InChI KeyYBJHBAHKTGYVGT-ZKWXMUAHSA-N
InChI
InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
IUPAC Name
5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
SMILES
[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBiotin and derivatives
Sub ClassNot Available
Direct ParentBiotin and derivatives
Alternative Parents
Substituents
  • Biotin
  • Medium-chain fatty acid
  • Imidazolyl carboxylic acid derivative
  • Thia fatty acid
  • Heterocyclic fatty acid
  • Fatty acyl
  • Fatty acid
  • 2-imidazoline
  • Isourea
  • Azacycle
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor nutritional supplementation, also for treating dietary shortage or imbalance.
PharmacodynamicsBiotin is a water-soluble B-complex vitamin which is composed of an ureido ring fused with a tetrahydrothiophene ring. A valeric acid substituent is attached to one of the carbon atoms of the tetrahydrothiophene ring. Biotin is used in cell growth, the production of fatty acids, metabolism of fats, and amino acids. It plays a role in the Kreb cycle, which is the process in which energy is released from food. Biotin not only assists in various metabolic chemical conversions, but also helps with the transfer of carbon dioxide. Biotin is also helpful in maintaining a steady blood sugar level. Biotin is often recommended for strengthening hair and nails. Consequenty, it is found in many cosmetic and health products for the hair and skin. Biotin deficiency is a rare nutritional disorder caused by a deficiency of biotin. Initial symptoms of biotin deficiency include: Dry skin, Seborrheic dermatitis, Fungal infections, rashes including erythematous periorofacial macular rash, fine and brittle hair, and hair loss or total alopecia. If left untreated, neurological symptoms can develop, including mild depression, which may progress to profound lassitude and, eventually, to somnolence; changes in mental status, generalized muscular pains (myalgias), hyperesthesias and paresthesias. The treatment for biotin deficiency is to simply start taking some biotin supplements. A lack of biotin in infants will lead to a condition called seborrheic dermatitis or "cradle cap". Biotin deficiencies are extremely rare in adults but if it does occur, it will lead to anemia, depression, hair loss, high blood sugar levels, muscle pain, nausea, loss of appetite and inflamed mucous membranes.
Mechanism of actionBiotin is necessary for the proper functioning of enzymes that transport carboxyl units and fix carbon dioxide, and is required for various metabolic functions, including gluconeogenesis, lipogenesis, fatty acid biosynthesis, propionate metabolism, and catabolism of branched-chain amino acids.
AbsorptionSystemic - approximately 50%
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityProlonged skin contact may cause irritation.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Biotinidase DeficiencyDiseaseSMP00174
Multiple carboxylase deficiency, neonatal or early onset formDiseaseSMP00564
Biotin MetabolismMetabolicSMP00066
Transfer of Acetyl Groups into MitochondriaMetabolicSMP00466
Threonine and 2-Oxobutanoate DegradationMetabolicSMP00452
Fumarase deficiencyDiseaseSMP00547
Citric Acid CycleMetabolicSMP00057
Mitochondrial complex II deficiencyDiseaseSMP00548
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)DiseaseSMP00560
Glycogenosis, Type ICDiseaseSMP00574
Pyruvate dehydrogenase deficiency (E3)DiseaseSMP00550
Fructose-1,6-diphosphatase deficiencyDiseaseSMP00562
Glycogenosis, Type IA. Von gierke diseaseDiseaseSMP00581
GluconeogenesisMetabolicSMP00128
2-ketoglutarate dehydrogenase complex deficiencyDiseaseSMP00549
Glycogenosis, Type IBDiseaseSMP00573
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseDiseaseSMP00374
Congenital lactic acidosisDiseaseSMP00546
Pyruvate dehydrogenase deficiency (E2)DiseaseSMP00551
Triosephosphate isomeraseDiseaseSMP00563
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyDiseaseSMP00137
3-Methylglutaconic Aciduria Type IDiseaseSMP00139
Fatty Acid BiosynthesisMetabolicSMP00456
Propionic AcidemiaDiseaseSMP00236
3-Methylglutaconic Aciduria Type IIIDiseaseSMP00140
Propanoate MetabolismMetabolicSMP00016
Malonic AciduriaDiseaseSMP00198
3-Methylglutaconic Aciduria Type IVDiseaseSMP00141
Malonyl-coa decarboxylase deficiencyDiseaseSMP00502
3-hydroxyisobutyric acid dehydrogenase deficiencyDiseaseSMP00521
Isovaleric acidemiaDiseaseSMP00524
Primary Hyperoxaluria Type IDiseaseSMP00352
Maple Syrup Urine DiseaseDiseaseSMP00199
Methylmalonic AciduriaDiseaseSMP00200
Isobutyryl-coa dehydrogenase deficiencyDiseaseSMP00523
Alanine MetabolismMetabolicSMP00055
Valine, Leucine and Isoleucine DegradationMetabolicSMP00032
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDiseaseSMP00138
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00384
Lactic AcidemiaDiseaseSMP00313
Methylmalonic Aciduria Due to Cobalamin-Related DisordersDiseaseSMP00201
3-hydroxyisobutyric aciduriaDiseaseSMP00522
Pyruvate Carboxylase DeficiencyDiseaseSMP00350
Beta-Ketothiolase DeficiencyDiseaseSMP00173
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDiseaseSMP00237
Isovaleric AciduriaDiseaseSMP00238
Pyruvate kinase deficiencyDiseaseSMP00559
Ammonia RecyclingMetabolicSMP00009
Pyruvate MetabolismMetabolicSMP00060
Pyruvate Dehydrogenase Complex DeficiencyDiseaseSMP00212
Leigh SyndromeDiseaseSMP00196
Primary hyperoxaluria II, PH2DiseaseSMP00558
Warburg EffectMetabolicSMP00654
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)DiseaseSMP00334
Succinic semialdehyde dehydrogenase deficiencyDiseaseSMP00567
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00243
HomocarnosinosisDiseaseSMP00385
Glutamate MetabolismMetabolicSMP00072
Hyperinsulinism-Hyperammonemia SyndromeDiseaseSMP00339
2-Hydroxyglutric Aciduria (D And L Form)DiseaseSMP00136
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7395
Blood Brain Barrier+0.9383
Caco-2 permeable-0.7206
P-glycoprotein substrateSubstrate0.6413
P-glycoprotein inhibitor INon-inhibitor0.9561
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.8803
CYP450 2C9 substrateNon-substrate0.7602
CYP450 2D6 substrateNon-substrate0.7872
CYP450 3A4 substrateNon-substrate0.6911
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.9252
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.8959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9762
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9598
BiodegradationNot ready biodegradable0.8923
Rat acute toxicity2.0581 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9596
hERG inhibition (predictor II)Non-inhibitor0.9145
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Biotin powder14.69USD g
D-biotin powder12.0USD g
Diachrome capsule0.29USD capsule
Appearex 2.5 mg tablet0.26USD tablet
Stress b tablet0.1USD tablet
Stress 600 tablet0.08USD tablet
Biotin 800 mcg tablet0.06USD tablet
Biotin 300 mcg tablet0.03USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point232 dec °CPhysProp
water solubility220 mg/L (at 25 °C)MERCK INDEX (1996)
logP0.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 mg/mLALOGPS
logP0.17ALOGPS
logP0.32ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.05 m3·mol-1ChemAxon
Polarizability24.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.84 KB)
SpectraGC-MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Takayoshi Mitsunaga, Kiyoto Chinushi, Tadashi Umezu, “Water-soluble biotin-containing preparation.” U.S. Patent US4277488, issued May, 1940.

US4277488
General Reference
  1. Holmberg A, Blomstergren A, Nord O, Lukacs M, Lundeberg J, Uhlen M: The biotin-streptavidin interaction can be reversibly broken using water at elevated temperatures. Electrophoresis. 2005 Feb;26(3):501-10. Pubmed
External Links
ATC CodesA11HA05
AHFS Codes
  • 88:08.00
PDB Entries
FDA labelNot Available
MSDSDownload (71.9 KB)
Interactions
Drug Interactions
Drug
Aluminum hydroxideMay decrease the absorption of Tetracycline Derivatives.
AmdinocillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
AmoxicillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
AmpicillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
AripiprazoleCYP3A4 Inhibitors (Moderate) may increase the serum concentration of ARIPiprazole.
AtovaquoneTetracycline may decrease the serum concentration of Atovaquone.
AvanafilCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Avanafil.
AzidocillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
AzlocillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
BacampicillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
BenzylpenicillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
Bismuth SubsalicylateMay decrease the serum concentration of Tetracycline Derivatives.
BosentanMay decrease the serum concentration of CYP3A4 Substrates.
BosutinibCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Bosutinib.
Calcium carbonateMay decrease the absorption of Tetracycline Derivatives.
CarbenicillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
CilostazolCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Cilostazol.
CloxacillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
ColchicineCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Colchicine.
ColesevelamMay decrease the absorption of Tetracycline Derivatives.
CyclacillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
DabrafenibMay decrease the serum concentration of CYP3A4 Substrates.
DapoxetineCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Dapoxetine.
DeferasiroxMay decrease the serum concentration of CYP3A4 Substrates.
DicloxacillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
DofetilideCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Dofetilide.
DomperidoneCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Domperidone.
DronabinolCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Dronabinol.
EliglustatCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Eliglustat.
EplerenoneCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Eplerenone.
EverolimusCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Everolimus.
FentanylCYP3A4 Inhibitors (Moderate) may increase the serum concentration of FentaNYL.
FlucloxacillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
HalofantrineCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Halofantrine.
HetacillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
HydrocodoneCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Hydrocodone.
IfosfamideCYP3A4 Inhibitors (Moderate) may decrease serum concentrations of the active metabolite(s) of Ifosfamide.
ImatinibCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Imatinib.
IvacaftorCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Ivacaftor.
LomitapideCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Lomitapide.
LurasidoneCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Lurasidone.
Magnesium oxideMay decrease the absorption of Tetracycline Derivatives.
MeticillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
MezlocillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
MipomersenTetracycline Derivatives may enhance the hepatotoxic effect of Mipomersen.
MitotaneMay decrease the serum concentration of CYP3A4 Substrates.
NafcillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
OxacillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
OxycodoneCYP3A4 Inhibitors (Moderate) may enhance the adverse/toxic effect of OxyCODONE. CYP3A4 Inhibitors (Moderate) may increase the serum concentration of OxyCODONE. Serum concentrations of the active metabolite Oxymorphone may also be increased.
Penicillin VTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
PimecrolimusCYP3A4 Inhibitors (Moderate) may decrease the metabolism of Pimecrolimus.
PimozideCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Pimozide.
PiperacillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
PivampicillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
PivmecillinamTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
PorfimerPhotosensitizing Agents may enhance the photosensitizing effect of Porfimer.
PropafenoneCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Propafenone.
QuinaprilMay decrease the serum concentration of Tetracycline Derivatives.
QuinineTetracycline may increase the serum concentration of QuiNINE.
RanolazineCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Ranolazine.
RivaroxabanCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Rivaroxaban. This warning is more specifically for drugs that are inhibitors of both CYP3A4 and P-glycoprotein. For erythromycin, refer to more specific erythromycin-rivaroxaban monograph recommendations.
SalmeterolCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Salmeterol.
SaxagliptinCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Saxagliptin.
SiltuximabMay decrease the serum concentration of CYP3A4 Substrates.
SimeprevirCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Simeprevir.
SucralfateMay decrease the absorption of Tetracycline Derivatives.
SuvorexantCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Suvorexant.
TicarcillinTetracycline Derivatives may diminish the therapeutic effect of Penicillins.
TocilizumabMay decrease the serum concentration of CYP3A4 Substrates.
TolvaptanCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Tolvaptan.
TrabectedinCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Trabectedin.
UlipristalCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Ulipristal.
VerteporfinPhotosensitizing Agents may enhance the photosensitizing effect of Verteporfin.
VilazodoneCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Vilazodone.
ZopicloneCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zopiclone.
ZuclopenthixolCYP3A4 Inhibitors (Moderate) may increase the serum concentration of Zuclopenthixol.
Food InteractionsNot Available

Targets

1. Propionyl-CoA carboxylase beta chain, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Propionyl-CoA carboxylase beta chain, mitochondrial P05166 Details

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
  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
  3. Vlasova TI, Stratton SL, Wells AM, Mock NI, Mock DM: Biotin deficiency reduces expression of SLC19A3, a potential biotin transporter, in leukocytes from human blood. J Nutr. 2005 Jan;135(1):42-7. Pubmed
  4. Cherbonnel-Lasserre CL, Linares-Cruz G, Rigaut JP, Sabatier L, Dutrillaux B: Strong decrease in biotin content may correlate with metabolic alterations in colorectal adenocarcinoma. Int J Cancer. 1997 Sep 4;72(5):768-75. Pubmed
  5. Ishii M, Chuakrut S, Arai H, Igarashi Y: Occurrence, biochemistry and possible biotechnological application of the 3-hydroxypropionate cycle. Appl Microbiol Biotechnol. 2004 Jun;64(5):605-10. Epub 2004 Feb 28. Pubmed

2. Biotin--protein ligase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Biotin--protein ligase P50747 Details

References:

  1. Velazquez-Arellano A: From an inborn error patient to a search for regulatory meaning: a biotin conducted voyage. Mol Genet Metab. 2006 Mar;87(3):194-7. Epub 2005 Dec 15. Pubmed
  2. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. Pubmed
  3. Camporeale G, Giordano E, Rendina R, Zempleni J, Eissenberg JC: Drosophila melanogaster holocarboxylase synthetase is a chromosomal protein required for normal histone biotinylation, gene transcription patterns, lifespan, and heat tolerance. J Nutr. 2006 Nov;136(11):2735-42. Pubmed

3. Sodium-dependent multivitamin transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sodium-dependent multivitamin transporter Q9Y289 Details

References:

  1. Luo S, Kansara VS, Zhu X, Mandava NK, Pal D, Mitra AK: Functional characterization of sodium-dependent multivitamin transporter in MDCK-MDR1 cells and its utilization as a target for drug delivery. Mol Pharm. 2006 May-Jun;3(3):329-39. Pubmed
  2. Janoria KG, Hariharan S, Paturi D, Pal D, Mitra AK: Biotin uptake by rabbit corneal epithelial cells: role of sodium-dependent multivitamin transporter (SMVT). Curr Eye Res. 2006 Oct;31(10):797-809. Pubmed
  3. Reidling JC, Said HM: Regulation of the human biotin transporter hSMVT promoter by KLF-4 and AP-2: confirmation of promoter activity in vivo. Am J Physiol Cell Physiol. 2007 Apr;292(4):C1305-12. Epub 2006 Nov 29. Pubmed
  4. Camporeale G, Zempleni J, Eissenberg JC: Susceptibility to heat stress and aberrant gene expression patterns in holocarboxylase synthetase-deficient Drosophila melanogaster are caused by decreased biotinylation of histones, not of carboxylases. J Nutr. 2007 Apr;137(4):885-9. Pubmed

4. Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial Q9HCC0 Details

References:

  1. Santoro N, Brtva T, Roest SV, Siegel K, Waldrop GL: A high-throughput screening assay for the carboxyltransferase subunit of acetyl-CoA carboxylase. Anal Biochem. 2006 Jul 1;354(1):70-7. Epub 2006 May 3. Pubmed
  2. de Queiroz MS, Waldrop GL: Modeling and numerical simulation of biotin carboxylase kinetics: implications for half-sites reactivity. J Theor Biol. 2007 May 7;246(1):167-75. Epub 2006 Dec 28. Pubmed
  3. Ludke A, Kramer R, Burkovski A, Schluesener D, Poetsch A: A proteomic study of Corynebacterium glutamicum AAA+ protease FtsH. BMC Microbiol. 2007 Jan 25;7:6. Pubmed
  4. Jitrapakdee S, Surinya KH, Adina-Zada A, Polyak SW, Stojkoski C, Smyth R, Booker GW, Cleland WW, Attwood PV, Wallace JC: Conserved Glu40 and Glu433 of the biotin carboxylase domain of yeast pyruvate carboxylase I isoenzyme are essential for the association of tetramers. Int J Biochem Cell Biol. 2007;39(11):2120-34. Epub 2007 Jun 27. Pubmed

5. Acetyl-CoA carboxylase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Acetyl-CoA carboxylase 2 O00763 Details

References:

  1. Liu Y, Zalameda L, Kim KW, Wang M, McCarter JD: Discovery of acetyl-coenzyme A carboxylase 2 inhibitors: comparison of a fluorescence intensity-based phosphate assay and a fluorescence polarization-based ADP Assay for high-throughput screening. Assay Drug Dev Technol. 2007 Apr;5(2):225-35. Pubmed

6. Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial Q96RQ3 Details

References:

  1. Friebel D, von der Hagen M, Baumgartner ER, Fowler B, Hahn G, Feyh P, Heubner G, Baumgartner MR, Hoffmann GF: The first case of 3-methylcrotonyl-CoA carboxylase (MCC) deficiency responsive to biotin. Neuropediatrics. 2006 Apr;37(2):72-8. Pubmed

7. Pyruvate carboxylase, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Pyruvate carboxylase, mitochondrial P11498 Details

References:

  1. Liu L, Li Y, Zhu Y, Du G, Chen J: Redistribution of carbon flux in Torulopsis glabrata by altering vitamin and calcium level. Metab Eng. 2007 Jan;9(1):21-9. Epub 2006 Aug 12. Pubmed
  2. Ferreira G, Weiss WP: Effect of biotin on activity and gene expression of biotin-dependent carboxylases in the liver of dairy cows. J Dairy Sci. 2007 Mar;90(3):1460-6. Pubmed
  3. Jitrapakdee S, Surinya KH, Adina-Zada A, Polyak SW, Stojkoski C, Smyth R, Booker GW, Cleland WW, Attwood PV, Wallace JC: Conserved Glu40 and Glu433 of the biotin carboxylase domain of yeast pyruvate carboxylase I isoenzyme are essential for the association of tetramers. Int J Biochem Cell Biol. 2007;39(11):2120-34. Epub 2007 Jun 27. Pubmed
  4. Jitrapakdee S, Adina-Zada A, Besant PG, Surinya KH, Cleland WW, Wallace JC, Attwood PV: Differential regulation of the yeast isozymes of pyruvate carboxylase and the locus of action of acetyl CoA. Int J Biochem Cell Biol. 2007;39(6):1211-23. Epub 2007 Mar 30. Pubmed
  5. Ozimek PZ, Klompmaker SH, Visser N, Veenhuis M, van der Klei IJ: The transcarboxylase domain of pyruvate carboxylase is essential for assembly of the peroxisomal flavoenzyme alcohol oxidase. FEMS Yeast Res. 2007 Oct;7(7):1082-92. Epub 2007 Feb 20. Pubmed

8. Propionyl-CoA carboxylase alpha chain, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Propionyl-CoA carboxylase alpha chain, mitochondrial P05165 Details

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
  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
  3. Clavero S, Martinez MA, Perez B, Perez-Cerda C, Ugarte M, Desviat LR: Functional characterization of PCCA mutations causing propionic acidemia. Biochim Biophys Acta. 2002 Nov 20;1588(2):119-25. Pubmed
  4. Cherbonnel-Lasserre CL, Linares-Cruz G, Rigaut JP, Sabatier L, Dutrillaux B: Strong decrease in biotin content may correlate with metabolic alterations in colorectal adenocarcinoma. Int J Cancer. 1997 Sep 4;72(5):768-75. Pubmed
  5. Vlasova TI, Stratton SL, Wells AM, Mock NI, Mock DM: Biotin deficiency reduces expression of SLC19A3, a potential biotin transporter, in leukocytes from human blood. J Nutr. 2005 Jan;135(1):42-7. Pubmed

9. Acetyl-CoA carboxylase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Acetyl-CoA carboxylase 1 Q13085 Details

References:

  1. Bilder P, Lightle S, Bainbridge G, Ohren J, Finzel B, Sun F, Holley S, Al-Kassim L, Spessard C, Melnick M, Newcomer M, Waldrop GL: The structure of the carboxyltransferase component of acetyl-coA carboxylase reveals a zinc-binding motif unique to the bacterial enzyme. Biochemistry. 2006 Feb 14;45(6):1712-22. Pubmed
  2. Brownsey RW, Boone AN, Elliott JE, Kulpa JE, Lee WM: Regulation of acetyl-CoA carboxylase. Biochem Soc Trans. 2006 Apr;34(Pt 2):223-7. Pubmed
  3. Aoki H, Kimura K, Igarashi K, Takenaka A: Soy protein suppresses gene expression of acetyl-coA carboxylase alpha from promoter PI in rat liver. Biosci Biotechnol Biochem. 2006 Apr;70(4):843-9. Pubmed
  4. Santoro N, Brtva T, Roest SV, Siegel K, Waldrop GL: A high-throughput screening assay for the carboxyltransferase subunit of acetyl-CoA carboxylase. Anal Biochem. 2006 Jul 1;354(1):70-7. Epub 2006 May 3. Pubmed
  5. Leonard E, Lim KH, Saw PN, Koffas MA: Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Appl Environ Microbiol. 2007 Jun;73(12):3877-86. Epub 2007 Apr 27. Pubmed

Enzymes

1. Cytochrome P450 1B1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1B1 Q16678 Details

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. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08