7alpha-Hydroxy-DHEA
Basic information
- CAS
53-00-9- Standard SMILES
C[C@]12CC[C@H](O)CC1=C[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12- InChIKey
OLPSAOWBSPXZEA-JIEICEMKSA-N- Molecular formula
- C19H28O3
- Average molar mass
- 304.4 g/mol
- Monoisotopic mass
- 304.20384475
Overview
7alpha-hydroxydehydroepiandrosterone is an androstanoid that is dehydroepiandrosterone carrying an additional hydroxy substituent at the 7alpha-position. It has a role as an antioxidant, an estrogen, an anti-inflammatory agent, a human xenobiotic metabolite and a rat metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a 17-oxo steroid, a 7alpha-hydroxy steroid and an androstanoid. It is functionally related to a dehydroepiandrosterone.
Names & identifiers
- Preferred name
- 7alpha-Hydroxy-DHEA
- IUPAC
- (3S,7S,8R,9S,10R,13S,14S)-3,7-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
- English name
- 7-alpha-Hydroxydehydroepiandrosterone
- Molecular formula
- C19H28O3
- Molecular weight
- 304.43
Names & synonyms
53-00-97alpha-Hydroxydehydroepiandrosterone7alpha-Hydroxy-DHEA7alpha-OH-DHEA7-HydroxydehydroepiandrosteroneCL15H93XTM3beta,7alpha-Dihydroxy-5-androstene-17-one(3S,7S,8R,9S,10R,13S,14S)-3,7-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-oneCHEBI:81471(3beta,7alpha)-3,7-dihydroxyandrost-5-en-17-oneAndrost-5-en-17-one, 3,7-dihydroxy-, (3beta,7alpha)-(3S,7S,8R,9S,10R,13S,14S)-3,7-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta(a)phenanthren-17-one
Show more names
7α-hydroxy-DHEA7-OH-DHEA7A-HYDROXY DHEA7 ALPHA-HYDROXY DHEAHYDROXYDEHYDROEPIANDROSTERONE7alpha-Hydroxydehydroepiandros5-ANDROSTEN-3β, 7α-DIOL-17-ONE7a-hydroxydehydroisoandrosterone7α-Hydroxydehydroisoandrosterone7α-Hydroxydehydroepiandrosterone
RefChem:9144287-alpha-Hydroxydehydroepiandrosterone3beta,7alpha-dihydroxy-5-androsten-17-one7?-Hydroxy Dehydro Epiandrosterone3BETA,7ALPHA-DIHYDROXYANDROST-5-EN-17-ONE7|A-Hydroxy-DHEAUNII-CL15H93XTM7alpha-Hydroxy Dehydro Epiandrosterone (1mg/ml in Acetonitrile)
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 539
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202]
Melting Point182 - 183 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 181.5 · 181.5-183.5 °C(Solv: acetone (67-64-1))
- Boiling point
- 473.3 · 473.3±45.0 °C(Predicted)
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Ethanol: soluble
- form
- A solid
- pka
- 14.06 · 14.06±0.70(Predicted)
- CAS DataBase Reference
- 53 · 53-00-9(CAS DataBase Reference)
- FDA UNII
- 15 H93XTM · CL15H93XTM
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesCarc. 2 (100%)
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
Uses7α-Hydroxydehydroepiandrosterone (7α-OH DHEA) is the main metabolite of Dehydroepiandrosterone (DHEA) (D229585).
Additional notes
DefinitionChEBI: 7alpha-hydroxydehydroepiandrosterone is an androstanoid that is dehydroepiandrosterone carrying an additional hydroxy substituent at the 7alpha-position. It has a role as an estrogen, an anti-inflammatory agent, an antioxidant, a rat metabolite and a human xenobiotic metabolite. It is a 17-oxo steroid, a 3beta-hydroxy-Delta(5)-steroid, an androstanoid and a 7alpha-hydroxy steroid. It is functionally related to a dehydroepiandrosterone.
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