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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 22:15:19 UTC
Update Date2021-09-14 15:41:23 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
Data?1582752309
Synonyms
ValueSource
(3beta,7alpha)-3,7-Dihydroxyandrost-5-en-17-oneChEBI
3beta,7alpha-Dihydroxy-5-androstene-17-oneChEBI
3beta,7alpha-Dihydroxyandrost-5-en-17-oneChEBI
7alpha-Hydroxy-dheaChEBI
7alpha-OH-DHEAChEBI
(3b,7a)-3,7-Dihydroxyandrost-5-en-17-oneGenerator
(3Β,7α)-3,7-dihydroxyandrost-5-en-17-oneGenerator
3b,7a-Dihydroxy-5-androstene-17-oneGenerator
3Β,7α-dihydroxy-5-androstene-17-oneGenerator
3b,7a-Dihydroxyandrost-5-en-17-oneGenerator
3Β,7α-dihydroxyandrost-5-en-17-oneGenerator
7a-Hydroxy-dheaGenerator
7Α-hydroxy-dheaGenerator
7a-OH-DHEAGenerator
7Α-OH-dheaGenerator
(-)-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-HydroxydehydroisoandrosteroneHMDB
7 alpha-HydroxydehydroepiandrosteroneHMDB
7-Hydroxydehydroepiandrosterone, (3beta,7beta)-isomerHMDB
7-Hydroxydehydroepiandrosterone, (3beta)-isomerHMDB
7beta-HydroxydehydroepiandrosteroneHMDB
7beta-OH-DHEAHMDB
7-HydroxydehydroepiandrosteroneHMDB
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
Description 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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point182 - 183 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP10(1.84) g/LALOGPS
logP10(2.21) g/LChemAxon
logS10(-3.4) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.63131661259
DarkChem[M-H]-166.20531661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7a-Hydroxydehydroepiandrosterone,1TMS,#1C[C@]12CC[C@H]3[C@@H]([C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CCC2=O2735.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,1TMS,#2C[C@]12CC[C@H]3[C@@H]([C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2723.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,1TMS,#3C[C@]12CC[C@H]3[C@@H]([C@H](O)C=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2702.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,2TMS,#1C[C@]12CC[C@H]3[C@@H]([C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2689.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,2TMS,#2C[C@]12CC[C@H]3[C@@H]([C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2731.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,2TMS,#3C[C@]12CC[C@H]3[C@@H]([C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2717.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@@H]1C=C2C[C@@H](O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]122993.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,1TBDMS,#2CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=C[C@@H](O)[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C12993.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2998.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,2TBDMS,#1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C13211.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,2TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C3295.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
7a-Hydroxydehydroepiandrosterone,2TBDMS,#3CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3252.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7a-Hydroxydehydroepiandrosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-0390000000-5b84fc74cc8c3d885c1b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a-Hydroxydehydroepiandrosterone GC-MS (2 TMS) - 70eV, Positivesplash10-003r-5204900000-bdb069dd8202b45f9ea32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a-Hydroxydehydroepiandrosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 10V, Positive-QTOFsplash10-00kr-0092000000-003d307a3c381597e38b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 20V, Positive-QTOFsplash10-0ap0-0190000000-7563041720b7687053892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 40V, Positive-QTOFsplash10-0a6u-3190000000-8012f9fad41969d73d462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 10V, Negative-QTOFsplash10-0udi-0049000000-3459db2d82d83321802f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 20V, Negative-QTOFsplash10-0udr-0098000000-6a1aaf578c3c1719798a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 40V, Negative-QTOFsplash10-059f-2090000000-85d4a8001358a115f59b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 10V, Negative-QTOFsplash10-0udi-0009000000-93986d59045cc7fce5512021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 20V, Negative-QTOFsplash10-0udi-0019000000-8b3060136e49afe5a3362021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 40V, Negative-QTOFsplash10-0uy0-0093000000-e42b11a1c3c059294db32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 10V, Positive-QTOFsplash10-0a4i-0069000000-61a09d88b13611d21a892021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 20V, Positive-QTOFsplash10-0670-1981000000-b0f1410f207bdaec9fa12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 40V, Positive-QTOFsplash10-05dl-3910000000-4b2efd9d887548375fc02021-09-25Wishart LabView Spectrum
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
FooDB IDFDB023382
KNApSAcK IDNot Available
Chemspider ID58963
KEGG Compound IDC18045
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link7alpha-Hydroxy-DHEA
METLIN IDNot Available
PubChem Compound65517
PDB IDNot Available
ChEBI ID712194
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]