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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:01:52 UTC
Update Date2021-09-16 15:45:22 UTC
HMDB IDHMDB0060424
Secondary Accession Numbers
  • HMDB60424
Metabolite Identification
Common Name7alpha-Hydroxypregnenolone
Description7alpha-Hydroxypregnenolone 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. 7alpha-Hydroxypregnenolone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866058
Synonyms
ValueSource
(3beta,7alpha)-3,7-Dihydroxypregn-5-en-20-oneChEBI
3beta,7alpha-Dihydroxy-5-pregnen-20-oneChEBI
(3b,7a)-3,7-Dihydroxypregn-5-en-20-oneGenerator
(3Β,7α)-3,7-dihydroxypregn-5-en-20-oneGenerator
3b,7a-Dihydroxy-5-pregnen-20-oneGenerator
3Β,7α-dihydroxy-5-pregnen-20-oneGenerator
7a-HydroxypregnenoloneGenerator
7Α-hydroxypregnenoloneGenerator
7-HydroxypregnenoloneHMDB
Chemical FormulaC21H32O3
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
IUPAC Name1-[(1S,2R,5S,9S,10S,11S,14S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one
Traditional Name1-[(1S,2R,5S,9S,10S,11S,14S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethanone
CAS Registry NumberNot Available
SMILES
CC(=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI Identifier
InChI=1S/C21H32O3/c1-12(22)15-4-5-16-19-17(7-9-21(15,16)3)20(2)8-6-14(23)10-13(20)11-18(19)24/h11,14-19,23-24H,4-10H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21+/m0/s1
InChI KeyUEWNVBNIVGLQPG-XXHSLLPRSA-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-oxosteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • 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 Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.061 g/LALOGPS
logP2.45ALOGPS
logP2.43ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.2 m³·mol⁻¹ChemAxon
Polarizability38.71 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available176.15231661259
DarkChem[M-H]-PredictedNot Available172.87731661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
7alpha-Hydroxypregnenolone,1TMS,#12925.074https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,1TMS,#22896.24https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,1TMS,#32909.2217https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,1TMS,#42880.1157https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,2TMS,#12857.6003https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,2TMS,#22976.35https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,2TMS,#32914.5981https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,2TMS,#42932.738https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,2TMS,#52890.75https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,1TBDMS,#13171.7656https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,1TBDMS,#23154.697https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,1TBDMS,#33187.4517https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,1TBDMS,#43140.654https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,2TBDMS,#13354.8103https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,2TBDMS,#23495.5974https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,2TBDMS,#33406.1416https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,2TBDMS,#43457.1375https://arxiv.org/abs/1905.12712
7alpha-Hydroxypregnenolone,2TBDMS,#53367.624https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gi9-0395000000-a3839fafe16d86fbf21e2017-09-20View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-3204900000-728186ec5f2f45d6d61e2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0039000000-3dc8e28e52ac056e99ab2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0295000000-53f09e66cf959f46c84c2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-3190000000-5d54c45ae9a68081d5792017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-98e075661a5168c917a92017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0019000000-3e15d7b43b23e67061a42017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00rj-1095000000-efe56e3900b7c1c313882017-10-06View Spectrum
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC18038
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9967418
PDB IDNot Available
ChEBI ID81467
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB 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 monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325
Reactions
Pregnenolone + NADPH + Hydrogen Ion + Oxygen → 7alpha-Hydroxypregnenolone + NADP + Waterdetails