dehydroepiandrosterone   

GtoPdb Ligand ID: 2370

Abbreviated name: DHEA
Synonyms: androstenolone | dehydroepiandrostenedione | DHA | Intrarosa®
dehydroepiandrosterone is an approved drug (FDA (2016), EMA (2018))
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 37.3
Molecular weight 288.21
XLogP 3.04
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OC1CCC2(C(=CCC3C2CCC2(C3CCC2=O)C)C1)C
Isomeric SMILES O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CCC2=O)C)C1)C
InChI InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
InChI Key FMGSKLZLMKYGDP-USOAJAOKSA-N
Classification
Compound class Metabolite or derivative
Approved drug? Yes (FDA (2016), EMA (2018))
IUPAC Name
(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
International Nonproprietary Names
INN number INN
2869 prasterone
Synonyms
androstenolone | dehydroepiandrostenedione | DHA | Intrarosa®
Database Links
BindingDB Ligand 50223368
CAS Registry No. 53-43-0
ChEBI CHEBI:28689
ChEMBL Ligand CHEMBL90593
DrugBank Ligand DB01708
DrugCentral Ligand 795
GtoPdb PubChem SID 135651466
NURSA Ligand 10.1621/PNXJ6CHX7S
PubChem CID 5881
RCSB PDB Ligand AND
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Wikipedia Dehydroepiandrosterone