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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:16:34 UTC
Update Date2021-09-16 15:27:37 UTC
HMDB IDHMDB0006283
Secondary Accession Numbers
  • HMDB06283
Metabolite Identification
Common Name20alpha-Hydroxycholesterol
Description20alpha-Hydroxycholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 20alpha-hydroxycholesterol is considered to be a sterol. Based on a literature review very few articles have been published on 20alpha-Hydroxycholesterol.
Structure
Data?1582752379
Synonyms
ValueSource
20a-HydroxycholesterolGenerator
20Α-hydroxycholesterolGenerator
(20S)-20-HydroxycholesterolMeSH
(20S)-Cholest-5-ene-3 beta,20-diolMeSH
20 alpha-HydroxycholesterolMeSH
20-HydroxycholesterolMeSH
20-Hydroxycholesterol, (3beta,20 xi)-isomerMeSH
20-Hydroxycholesterol, 3H-labeled, (3beta,20 xi)-isomerMeSH
20R-HydroxycholesterolMeSH
(3beta,20R)-Cholest-5-ene-3,20-diolHMDB
20alpha-Hydroxy cholesterolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,5S,10S,11S,14S,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name20a-hydroxy cholesterol
CAS Registry Number516-72-3
SMILES
CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI Identifier
InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1
InChI KeyMCKLJFJEQRYRQT-MGNSQDQZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • 20-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Delta-5-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00057 g/LALOGPS
logP10(6.06) g/LALOGPS
logP10(5.8) g/LChemAxon
logS10(-5.8) g/LALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.3 m³·mol⁻¹ChemAxon
Polarizability51.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.91331661259
DarkChem[M-H]-196.86731661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
20alpha-Hydroxycholesterol,1TMS,#1CC(C)CCC[C@@](C)(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3323.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
20alpha-Hydroxycholesterol,1TMS,#2CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3336.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
20alpha-Hydroxycholesterol,2TMS,#1CC(C)CCC[C@@](C)(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3346.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
20alpha-Hydroxycholesterol,1TBDMS,#1CC(C)CCC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3568.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
20alpha-Hydroxycholesterol,1TBDMS,#2CC(C)CCC[C@@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3574.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
20alpha-Hydroxycholesterol,2TBDMS,#1CC(C)CCC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3822.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04704
Phenol Explorer Compound IDNot Available
FooDB IDFDB023876
KNApSAcK IDNot Available
Chemspider ID389586
KEGG Compound IDC05500
BioCyc ID20A-HYDROXY-CHOLESTEROL
BiGG ID1443018
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440711
PDB IDHC2
ChEBI ID1296
Food Biomarker OntologyNot Available
VMH ID20AHCHSTEROL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMijares, A.; Cargill, David I.; Glasel, Jay A.; Lieberman, Seymour. C-20 epimers of 20-hydroxycholesterol. Journal of Organic Chemistry (1967), 32(3), 810-12.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sharma RK, Ahmed NK, Shanker G: Metabolic regulation of steroidogenesis in isolated adrenal cells of rat. Relationship of adrenocorticotropin-, adenosine 3':5'-monophosphate-and guanosine 3':5'-monophosphate-stimulated steroidogenesis with the activation of protein kinase. Eur J Biochem. 1976 Nov 15;70(2):427-33. [PubMed:188647 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular weight:
60101.87
Reactions
Cholesterol + Oxygen + Hydrogen Ion + Reduced adrenal ferredoxin → 20alpha-Hydroxycholesterol + Water + Oxidized adrenal ferredoxindetails
20alpha-Hydroxycholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion → 20a,22b-Dihydroxycholesterol + Water + Oxidized adrenal ferredoxindetails
General function:
Involved in monooxygenase activity
Specific function:
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:
CYP17A1
Uniprot ID:
P05093
Molecular weight:
57369.995
Reactions
20alpha-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 17a,20a-Dihydroxycholesterol + NADP + Waterdetails