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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:00:29 UTC
Update Date2019-07-23 07:14:16 UTC
HMDB IDHMDB0060408
Secondary Accession Numbers
  • HMDB60408
Metabolite Identification
Common Name5alpha-Pregnan-20alpha-ol-3-one
Description5alpha-Pregnan-20alpha-ol-3-one, also known as 5α-pregnan-20α-ol-3-one or 20 beta-hydroxy-5 alpha-pregnan-3-one, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. 5alpha-Pregnan-20alpha-ol-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866056
Synonyms
ValueSource
Allopregnan-20alpha-ol-3-oneKegg
Allopregnan-20a-ol-3-oneGenerator
Allopregnan-20α-ol-3-oneGenerator
5a-Pregnan-20a-ol-3-oneGenerator
5Α-pregnan-20α-ol-3-oneGenerator
20 beta-Hydroxy-5 alpha-pregnan-3-oneHMDB
Allopregnan-20 alpha-ol-3-one, (5alpha)-isomerHMDB
Allopregnan-20 alpha-ol-3-one, (5beta,20S)-isomerHMDB
20 alpha-Hydroxy-5 alpha-pregnan-3-oneHMDB
Allopregnan-20 alpha-ol-3-one, (5beta,17alpha,20S)-isomerHMDB
Allopregnan-20 beta-ol-3-oneHMDB
20-AHAPOHMDB
Allopregnan-20 alpha-ol-3-oneHMDB
Allopregnan-20 alpha-ol-3-one, (20S)-isomerHMDB
Allopregnan-20 alpha-ol-3-one, (5alpha,20R)-isomerHMDB
Allopregnan-20 alpha-ol-3-one, (5beta,20R)-isomerHMDB
Chemical FormulaC21H34O2
Average Molecular Weight318.4935
Monoisotopic Molecular Weight318.255880332
IUPAC Name(1S,2S,7S,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Name(1S,2S,7S,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
CAS Registry NumberNot Available
SMILES
C[C@H](O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI Identifier
InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h13-14,16-19,22H,4-12H2,1-3H3/t13-,14-,16-,17+,18-,19-,20-,21+/m0/s1
InChI KeyDYVGYXXLXQESJE-SKLBOBKVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-hydroxysteroid
  • 3-oxosteroid
  • Hydroxysteroid
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • Cyclic ketone
  • Ketone
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP3.88ALOGPS
logP3.99ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)19ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.91 m³·mol⁻¹ChemAxon
Polarizability38.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k95-0192000000-b00561a2208d4cb0b913Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2129000000-5c43699af1fc715c5869Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0019000000-3506e9f182ec12c5aed0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0395000000-c801058bbfa1f2c4f099Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-0290000000-fd24da59e508c11cc6a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-df9503094940704a35bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0079000000-1254a079d1defaae9337Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kmm-1091000000-bebd195b92650838516fSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC18041
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3080558
PDB IDNot Available
ChEBI ID81469
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91
Reactions
5alpha-Pregnan-20alpha-ol-3-one + NADPH + Hydrogen Ion → 5alpha-Pregnane-3alpha,20alpha-diol + NADPdetails
General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
Reactions
5alpha-Pregnan-20alpha-ol-3-one + NADPH + Hydrogen Ion → 5alpha-Pregnane-3alpha,20alpha-diol + NADPdetails
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
AKR1C2
Uniprot ID:
P52895
Molecular weight:
15747.91
Reactions
5alpha-Pregnan-20alpha-ol-3-one + NADPH + Hydrogen Ion → 5alpha-Pregnane-3alpha,20alpha-diol + NADPdetails