Compound: Dehydroepiandrosterone
SMILES: O=C1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(C[C@@H](O)CC4)=CC3)C)CC2)CC1)C
InChIKey: FMGSKLZLMKYGDP-USOAJAOKSA-N
Synonyms: Dehydroepiandrosterone, DHEA, PRASTERONE, 53-43-0, Dehydroisoandrosterone, Androstenolone, Diandron, 3beta-hydroxyandrost-5-en-17-one, 17-Hormoforin, Intrarosa, Prasterona, 3-beta-Hydroxy-5-androsten-17-one, Prasteronum, Vaginorm, 5,6-Dehydroisoandrosterone, Biolaif, EM-760, NSC-9896, Androst-5-en-17-one, 3-hydroxy-, (3beta)-, DTXSID4020379, NSC9896, 459AG36T1B, (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one, DTXCID40379, CHEBI:28689, Fidelin, Prastera, Natrol dhea, Enzymatic therapy, GL701, (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta(a)phenanthren-17-one, Prasterone, 3 alpha, prasterone and ibuprofen, RefChem:55906, 5 Androsten 3 ol 17 one, DHEA (Dehydroepiandrosterone), Therapeutic Dehydroepiandrosterone, A14AA07, G03XX01, 5 Androsten 3 beta hydroxy 17 one, 5-Androsten-3-beta-hydroxy-17-one, 200-175-5, trans-Dehydroandrosterone, Diandrone, Psicosterone, 17-Chetovis, Prestara, Andrestenol, 5-Dehydroepiandrosterone, Dehydro-epi-androsterone, Siscelar plus, (+)-Dehydroisoandrosterone, 5,6-Didehydroisoandrosterone, dehydroepiandrosterone (dhea), Epiandrosterone, 5-dehydro-, Caswell No. 051F, 5,6-Dehydroisoandrostorone, 3beta-hydroxy-5-androsten-17-one, Astenile, CCRIS 3277, Deandros, (3-beta)-3-Hydroxyandrost-5-en-17-one, DEHYDROISOANDOSTERONE, GL 701, dehydroepiandosterone, EPA Pesticide Chemical Code 126510, 5-Androsten-3beta-ol-17-one, NSC 9896, MFCD00003613, Androst-5-en-17-one, 3-hydroxy-, (3.beta.)-, (3beta)-3-hydroxyandrost-5-en-17-one, Androst-5-en-17-one, 3-beta-hydroxy-, CHEMBL90593, D5-Androsten-3beta-ol-17-one, Androst-5-ene-3beta-ol-17-one, 3beta-Hydroxy-D5-androsten-17-one, 3-beta-hydroxyandrost-5-en-17-one, (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one, Dehydro Epiandrosterone, AND, Prasterone [INN], Prasteronum [INN-Latin], Prasterona [INN-Spanish], CAS-53-43-0, (1S,5S,11S,15S,2R,10R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0<2,7>.0<11,15> ]heptadec-7-en-14-one, SMR000059075, Androst-5-en-17-one, 3.beta.-hydroxy-, SR-01000075815, Prasterone [USAN:INN], EINECS 200-175-5, Dehydro Epiandrosterone (1.0 mg/mL in Acetonitrile), BRN 2058110, 5-Androsten-3.beta.-ol-17-one, Anastar, Inflabloc, Aslera, UNII-459AG36T1B, Fidelin T, Androst-5-en-17-one, 3-hydroxy-, (3b)-, DHEA; Prasterone, NCGC00093802-04, NCGC00093802-06, Biolaif (TN), Androst-5-en-17-one, 3beta-hydroxy-, dehydroepiandrostenedione, 5-dehydro-Epiandrosterone, Prasterone (USAN/INN), trans-de-hydroandrosterone, PRASTERONE [USAN], bmse000665, EC 200-175-5, Dehydroisoandrosterone(Dhea), PRASTERONE [MART.], Prasterone, (3.alpha.)-, Androsten-3beta-ol-17-one, PRASTERONE [WHO-DD], Androst-5-en-17-one, 3-hydroxy-, (3-beta)-, BIDD:PXR0080, Lopac0_000368, SCHEMBL24156, 4-08-00-00994 (Beilstein Handbook Reference), MLS001066350, MLS001333231, MLS001333232, MLS001424274, orb180847, 5-Androsten-3B-ol-17-one, D5-Androsten-3b-ol-17-one, GTPL2370, Androst-5-ene-3b-ol-17-one, PRASTERONE [ORANGE BOOK], SCHEMBL27464949, 3b-Hydroxyandrost-5-en-17-one, 5-Androsten-3-beta-ol-17-one, MSK2264, 3b-Hydroxy-D5-androsten-17-one, 3beta-Hyroxyandrost-5-en-17-one, DEHYDROEPIANDROSTERONE [MI], EL-10, HMS2052P11, HMS2090C04, HMS2232K11, IM 28, trans-Dehydroandrosterone, >=99%, 3-beta-hydroxy-5-androsten-17-on, IPL-1001, 3beta-hydroxy-androst-5-en-17-one, 3beta-Hydroxyandrost-5-ene-17-one, Tox21_111222, Tox21_201996, Tox21_302761, Androst-5-en-3.alpha.-ol-17-one, BDBM50223368, CMC_13435, Delta5-androsten-3-beta-ol-17-one, DL-373, GL-701, LMST02020021, MSK2264-100A, PB-007, s2604, SBB012501, DEHYDROEPIANDROSTERONE [VANDF], 3.beta.-Hydroxyandrost-5-en-17-one, 5-Androsten-3beta-ol-17-one; DHEA, AKOS007930299, AKOS015951378, MSK2264-1000A, Tox21_111222_1, CCG-101190, CS-1667, DB01708, FD12003, GS-0906, IP-1001, NC00440, SH-K-04828, NCGC00093802-09, NCGC00256412-01, NCGC00259545-01, (3beta)-3-Hydroxyandrost-5-ene-17-one, AC-28716, HY-14650, NCI60_042215, Prasterone (DHEA; Dehydroepiandrosterone), ST069381, (3beta)-3-hydroxy-Androst-5-en-17-one, D0044, EU-0100368, NS00000508, Androst-5-en-17-one, 3beta-hydroxy- (8CI), C01227, D 4000, D-0340, D08409, (3alpha,8alpha)-3-hydroxyandrost-5-en-17-one, AB00375810-06, AB00375810_09, Dehydroepiandrosterone (DHEA), 1mg/ml in Methanol, Q408376, SR-01000075815-1, SR-01000075815-4, BRD-K41256143-001-12-7, (3beta,16alpha)-3,16-dihydroxy-androst-5-en-17-one, Androst-5-en-17-one, 3-hydroxy-, (3beta)- (9CI), 1A9D2040-240C-427D-ADE4-0CB700B785CB, Dehydroepiandrosterone Solution in Acetonitrile, 1000ug/mL, Dehydroepiandrosterone Solution in Acetonitrile, 100ug/mL, Prasterone (DHEA; Dehydroepiandrosterone) 1.0 mg/ml in Acetonitrile, (1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one, (3S,8R,10R,13S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one, 105597-37-3
Theoretical properties:
molecular_formula: C19H28O2
molecular_weight: 288.4 g/mol
exact_mass: 288.208930132 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 21
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 140-141 °C
Descriptions:
pubchem: Dehydroepiandrosterone is an androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands. It has a role as an androgen, a mouse metabolite and a human metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a 17-oxo steroid and an androstanoid.
chebi: An androstanoid that is androst-5-ene substituted by a β-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.
chembl: PRASTERONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It functions as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids both in the gonads and in various other tissues. However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors, and acting as a neurosteroid and modulator of neurotrophic factor receptors.
In the United States, DHEA is sold as an over-the-counter supplement, and medication called prasterone.