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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 22:15:19 UTC
Update Date2017-12-07 01:53:49 UTC
HMDB IDHMDB0004611
Secondary Accession Numbers
  • HMDB04611
Metabolite Identification
Common Name7a-Hydroxydehydroepiandrosterone
Description7a-Hydroxydehydroepiandrosterone is a major metabolite of dehydroepiandrosterone (DHEA), which is is 7alpha-hydroxylated by the cytochrome P450 7B1 (EC 1.14.13.100, 25-hydroxycholesterol 7alpha-hydroxylase, CYP7B1) in the human brain and liver microsomes. Exposure to the proinflammatory cytokines TNFalpha, IL-1alpha, IL-1beta, and IL-17 increases CYP7B activity in synovial tissue. Increased CYP7B activity leads to higher levels of the DHEA metabolite 7alpha-OH-DHEA in synovial fluid, which may contribute to the maintenance of the chronic inflammation observed in rheumatoid arthritis patients. The glucocorticoid dhydrocorticosterone inhibits the conversion of DHEA to 7a-Hydroxydehydroepiandrosterone. The total levels of 7a-Hydroxydehydroepiandrosterone are increased in serum of patients with Alzheimer's disease. (PMID: 17467270 , 15751070 , 12667489 , 9520908 ).
Structure
Thumb
Synonyms
ValueSource
7alpha-OH-DHEAKegg
3beta,7alpha-Dihydroxy-5-androstene-17-oneKegg
7a-OH-DHEAGenerator
7α-OH-dheaGenerator
3b,7a-Dihydroxy-5-androstene-17-oneGenerator
3β,7α-dihydroxy-5-androstene-17-oneGenerator
(-)-7a-HydroxydehydroepiandrosteroneHMDB
(3b,7a)-3,7-Dihydroxy-androst-5-en-17-oneHMDB
3b,7a-Dihydroxy-5-androsten-17-oneHMDB
3b,7a-Dihydroxy-androst-5-en-17-oneHMDB
7-a-OH-DHEAHMDB
7-alpha-OH-DHEAHMDB
7a-Hydroxy-dheaHMDB
7a-HydroxydehydroisoandrosteroneHMDB
7 alpha-HydroxydehydroepiandrosteroneMeSH
7-Hydroxydehydroepiandrosterone, (3beta,7beta)-isomerMeSH
7-Hydroxydehydroepiandrosterone, (3beta)-isomerMeSH
7beta-HydroxydehydroepiandrosteroneMeSH
7beta-OH-DHEAMeSH
7-HydroxydehydroepiandrosteroneMeSH
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one
Traditional Name7β-oh-dhea
CAS Registry Number53-00-9
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1
InChI KeyOLPSAOWBSPXZEA-JIEICEMKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point182 - 183 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.84ALOGPS
logP2.21ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.1 m³·mol⁻¹ChemAxon
Polarizability34.78 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-0390000000-5b84fc74cc8c3d885c1bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-003r-5204900000-bdb069dd8202b45f9ea3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0092000000-003d307a3c381597e38bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0190000000-7563041720b768705389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-3190000000-8012f9fad41969d73d46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-3459db2d82d83321802fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0098000000-6a1aaf578c3c1719798aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-2090000000-85d4a8001358a115f59bView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB023382
KNApSAcK IDNot Available
Chemspider ID58963
KEGG Compound IDC18045
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound65517
PDB IDNot Available
ChEBI ID712194
References
Synthesis ReferenceIshidate, Morizo; Okada, Masashi. Steroids. (1963), 2 pp. JP 38023170 19631031 Showa. CAN 60:12972 AN 1964:12972
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hennebert O, Chalbot S, Alran S, Morfin R: Dehydroepiandrosterone 7alpha-hydroxylation in human tissues: possible interference with type 1 11beta-hydroxysteroid dehydrogenase-mediated processes. J Steroid Biochem Mol Biol. 2007 May;104(3-5):326-33. Epub 2007 Mar 24. [PubMed:17467270 ]
  2. Robinzon B, Michael KK, Ripp SL, Winters SJ, Prough RA: Glucocorticoids inhibit interconversion of 7-hydroxy and 7-oxo metabolites of dehydroepiandrosterone: a role for 11beta-hydroxysteroid dehydrogenases? Arch Biochem Biophys. 2003 Apr 15;412(2):251-8. [PubMed:12667489 ]
  3. Dulos J, van der Vleuten MA, Kavelaars A, Heijnen CJ, Boots AM: CYP7B expression and activity in fibroblast-like synoviocytes from patients with rheumatoid arthritis: regulation by proinflammatory cytokines. Arthritis Rheum. 2005 Mar;52(3):770-8. [PubMed:15751070 ]
  4. Attal-Khemis S, Dalmeyda V, Michot JL, Roudier M, Morfin R: Increased total 7 alpha-hydroxy-dehydroepiandrosterone in serum of patients with Alzheimer's disease. J Gerontol A Biol Sci Med Sci. 1998 Mar;53(2):B125-32. [PubMed:9520908 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:
CYP7A1
Uniprot ID:
P22680
Molecular weight:
57660.155
Reactions
Dehydroepiandrosterone + Oxygen + NADPH + Hydrogen Ion → 7a-Hydroxydehydroepiandrosterone + NADP + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:
HSD11B1
Uniprot ID:
P28845
Molecular weight:
32400.665
References
  1. Hennebert O, Chalbot S, Alran S, Morfin R: Dehydroepiandrosterone 7alpha-hydroxylation in human tissues: possible interference with type 1 11beta-hydroxysteroid dehydrogenase-mediated processes. J Steroid Biochem Mol Biol. 2007 May;104(3-5):326-33. Epub 2007 Mar 24. [PubMed:17467270 ]
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325
References
  1. Hennebert O, Chalbot S, Alran S, Morfin R: Dehydroepiandrosterone 7alpha-hydroxylation in human tissues: possible interference with type 1 11beta-hydroxysteroid dehydrogenase-mediated processes. J Steroid Biochem Mol Biol. 2007 May;104(3-5):326-33. Epub 2007 Mar 24. [PubMed:17467270 ]