Identification

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Name
Cholesterol
Accession Number
DB04540  (EXPT00945)
Type
Small Molecule
Groups
Approved, Investigational
Description

The principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.

Structure
Thumb
Synonyms
  • (3β,14β,17α)-cholest-5-en-3-ol
  • Cholest-5-en-3beta-ol
  • Cholesterin
External IDs
NSC-8798
Categories
UNII
97C5T2UQ7J
CAS number
57-88-5
Weight
Average: 386.6535
Monoisotopic: 386.354866094
Chemical Formula
C27H46O
InChI Key
HVYWMOMLDIMFJA-DPAQBDIFSA-N
InChI
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
IUPAC Name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNuclear receptor ROR-alphaNot AvailableHumans
UNuclear receptor subfamily 1 group I member 3Not AvailableHumans
UVitamin D3 receptorNot AvailableHumans
UC-type lectin domain family 4 member E
ligand
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Lovastatin Action PathwayDrug action
Cerivastatin Action PathwayDrug action
HypercholesterolemiaDisease
Zellweger SyndromeDisease
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase DeficiencyDisease
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)Disease
Smith-Lemli-Opitz Syndrome (SLOS)Disease
Mevalonic AciduriaDisease
Corticosterone Methyl Oxidase I Deficiency (CMO I)Disease
3-beta-Hydroxysteroid Dehydrogenase DeficiencyDisease
Simvastatin Action PathwayDrug action
Pravastatin Action PathwayDrug action
Rosuvastatin Action PathwayDrug action
Zoledronate Action PathwayDrug action
Pamidronate Action PathwayDrug action
Fluvastatin Action PathwayDrug action
Congenital Bile Acid Synthesis Defect Type IIDisease
Lysosomal Acid Lipase Deficiency (Wolman Disease)Disease
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHDisease
Cholesteryl Ester Storage DiseaseDisease
11-beta-Hydroxylase Deficiency (CYP11B1)Disease
Apparent Mineralocorticoid Excess SyndromeDisease
27-Hydroxylase DeficiencyDisease
Steroid BiosynthesisMetabolic
Bile Acid BiosynthesisMetabolic
Ibandronate Action PathwayDrug action
Alendronate Action PathwayDrug action
Risedronate Action PathwayDrug action
SteroidogenesisMetabolic
Atorvastatin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Cholesterol.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Cholesterol.
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Cholesterol.
AcetyldigoxinCholesterol may decrease the excretion rate of Acetyldigoxin which could result in a higher serum level.
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Cholesterol.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Cholesterol.
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Cholesterol.
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Cholesterol.
AllopurinolCholesterol may increase the excretion rate of Allopurinol which could result in a lower serum level and potentially a reduction in efficacy.
AlvocidibCholesterol may increase the excretion rate of Alvocidib which could result in a lower serum level and potentially a reduction in efficacy.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Evidence Level

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

Synthesis Reference

Tatu Miettenen, Ingmar Wester, Hannu Vanhanen, "Substance for lowering high cholesterol level in serum and methods for preparing and using the same." U.S. Patent US6174560, issued February, 1944.

US6174560
General References
Not Available
External Links
Human Metabolome Database
HMDB0000067
KEGG Drug
D00040
KEGG Compound
C00187
PubChem Compound
5997
PubChem Substance
46508234
ChemSpider
5775
BindingDB
20192
ChEBI
16113
ChEMBL
CHEMBL112570
HET
CLR
Wikipedia
Cholesterol
PDB Entries
1lri / 1n83 / 1zhy / 2rh1 / 2zxe / 3a3y / 3am6 / 3d4s / 3gki / 3jd8
show 138 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2RecruitingTreatmentCone-Rod Dystrophy / Hearing loss or impairment / Smith-Lemli-Opitz Syndrome1
4CompletedPreventionCardiovascular Disease (CVD) / Carotid Atherosclerosis / Diabetes Mellitus (DM) / High Blood Pressure (Hypertension) / Hyperlipidemias1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)148.5 °CPhysProp
boiling point (°C)360 °CPhysProp
water solubility0.095 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility2.79e-05 mg/mLALOGPS
logP7.02ALOGPS
logP7.11ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.62 m3·mol-1ChemAxon
Polarizability50.64 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9749
Caco-2 permeable+0.8184
P-glycoprotein substrateSubstrate0.6477
P-glycoprotein inhibitor IInhibitor0.6404
P-glycoprotein inhibitor IINon-inhibitor0.529
Renal organic cation transporterNon-inhibitor0.7691
CYP450 2C9 substrateNon-substrate0.8257
CYP450 2D6 substrateNon-substrate0.8794
CYP450 3A4 substrateSubstrate0.7439
CYP450 1A2 substrateNon-inhibitor0.9355
CYP450 2C9 inhibitorNon-inhibitor0.9194
CYP450 2D6 inhibitorNon-inhibitor0.9519
CYP450 2C19 inhibitorNon-inhibitor0.9177
CYP450 3A4 inhibitorNon-inhibitor0.8638
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6721
Ames testNon AMES toxic0.8888
CarcinogenicityNon-carcinogens0.932
BiodegradationNot ready biodegradable0.9825
Rat acute toxicity2.8078 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.773
hERG inhibition (predictor II)Non-inhibitor0.7552
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-004i-3911000000-52f5261007adc218f8f8
GC-MS Spectrum - EI-BGC-MSsplash10-052b-2932000000-1667c83d002043a59fff
GC-MS Spectrum - EI-BGC-MSsplash10-000l-9527000000-5529a262047f5369c9c1
GC-MS Spectrum - EI-BGC-MSsplash10-0mkr-2954000000-60e7d1f5973e4de33dec
GC-MS Spectrum - CI-BGC-MSsplash10-014i-1009000000-e82b8e23dedb45ce70e6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-056v-2900000000-04687c9f19ff52ba4654
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0a4l-7922000000-36e8a5e1a77d2e71d1d1
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 NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Cholestane steroids
Direct Parent
Cholesterols and derivatives
Alternative Parents
3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-5-steroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Cholesterol-skeleton / Cholesterol / 3-beta-hydroxysteroid / 3-beta-hydroxy-delta-5-steroid / Hydroxysteroid / 3-hydroxysteroid / 3-hydroxy-delta-5-steroid / Delta-5-steroid / Cyclic alcohol / Secondary alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
cholestanoid, 3beta-sterol (CHEBI:16113) / cholestane, Cholesterol and derivatives, Cholestane and derivatives (C00187) / Cholesterol and derivatives (LMST01010001)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Key regulator of embryonic ...
Gene Name
RORA
Uniprot ID
P35398
Uniprot Name
Nuclear receptor ROR-alpha
Molecular Weight
58974.35 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. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
Gene Name
NR1I3
Uniprot ID
Q14994
Uniprot Name
Nuclear receptor subfamily 1 group I member 3
Molecular Weight
39942.145 Da
References
  1. Mooijaart SP, Brandt BW, Baldal EA, Pijpe J, Kuningas M, Beekman M, Zwaan BJ, Slagboom PE, Westendorp RG, van Heemst D: C. elegans DAF-12, Nuclear Hormone Receptors and human longevity and disease at old age. Ageing Res Rev. 2005 Aug;4(3):351-71. [PubMed:16051528]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
Gene Name
VDR
Uniprot ID
P11473
Uniprot Name
Vitamin D3 receptor
Molecular Weight
48288.64 Da
References
  1. Mooijaart SP, Brandt BW, Baldal EA, Pijpe J, Kuningas M, Beekman M, Zwaan BJ, Slagboom PE, Westendorp RG, van Heemst D: C. elegans DAF-12, Nuclear Hormone Receptors and human longevity and disease at old age. Ageing Res Rev. 2005 Aug;4(3):351-71. [PubMed:16051528]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
C-type lectin that functions as cell-surface receptor for a wide variety of ligands such as damaged cells, fungi and mycobacteria. Plays a role in the recognition of pathogenic fungi, such as Candida albicans. The detection of mycobacteria is via trehalose 6,6'-dimycolate (TDM), a cell wall glycolipid. Specifically recognizes alpha-mannose residues on pathogenic fungi of the genus Malassezia. Recognizes also SAP130, a nuclear protein, that is released by dead or dying cells. Transduces signals through an ITAM-containing adapter protein, Fc receptor gamma chain /FCER1G. Induces secretion of inflammatory cytokines through a pathway that depends on SYK, CARD9 and NF-kappa-B.
Specific Function
Carbohydrate binding
Gene Name
CLEC4E
Uniprot ID
Q9ULY5
Uniprot Name
C-type lectin domain family 4 member E
Molecular Weight
25072.31 Da
References
  1. Kiyotake R, Oh-Hora M, Ishikawa E, Miyamoto T, Ishibashi T, Yamasaki S: Human Mincle Binds to Cholesterol Crystals and Triggers Innate Immune Responses. J Biol Chem. 2015 Oct 16;290(42):25322-32. doi: 10.1074/jbc.M115.645234. Epub 2015 Aug 20. [PubMed:26296894]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Wang E, Casciano CN, Clement RP, Johnson WW: Cholesterol interaction with the daunorubicin binding site of P-glycoprotein. Biochem Biophys Res Commun. 2000 Oct 5;276(3):909-16. [PubMed:11027568]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Janvilisri T, Venter H, Shahi S, Reuter G, Balakrishnan L, van Veen HW: Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51. Epub 2003 Mar 28. [PubMed:12668685]

Drug created on June 13, 2005 07:24 / Updated on May 01, 2019 09:44