norgestimate   

GtoPdb Ligand ID: 7091

Synonyms: dexnorgestrel | ORF-10131 | RWJ-10131
norgestimate is an approved drug (FDA (1989))
Comment: Norgestimate is an acetylated progestin (synthelic progesterone-like compound). It is converted to the primary active metabolite norelgestromin (17-deacetylnorgestimate or levonorgestrel 3-oxime) in vivo. 17-deacetylnorgestimate does not cause the androgenic side effects associated with other 19-nortestosterone progestins.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 58.89
Molecular weight 369.23
XLogP 4.8
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES ON=C1CCC2C(=C1)CCC1C2CCC2(C1CCC2(C#C)OC(=O)C)CC
Isomeric SMILES O/N=C/1\CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C#C)OC(=O)C)CC
InChI InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1
InChI Key KIQQMECNKUGGKA-NMYWJIRASA-N
Classification
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1989))
IUPAC Name
[(3E,8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
International Nonproprietary Names
INN number INN
3942 norgestimate
Synonyms
dexnorgestrel | ORF-10131 | RWJ-10131
Database Links
CAS Registry No. 35189-28-7
ChEBI CHEBI:50815
ChEMBL Ligand CHEMBL1200934
DrugBank Ligand DB00957
DrugCentral Ligand 1968
GtoPdb PubChem SID 178103669
PubChem CID 6540478
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