levonorgestrel   

GtoPdb Ligand ID: 2881

Synonyms: l-norgestrel | Norplant®
levonorgestrel is an approved drug (FDA (1990))
Compound class: Synthetic organic
Comment: Levonorgestrel is the name for the active isomer in norgestrel, a racemic mixture
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 37.3
Molecular weight 312.21
XLogP 3.81
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES C#CC1(O)CCC2C1(CC)CCC1C2CCC2=CC(=O)CCC12
Isomeric SMILES C#C[C@]1(O)CC[C@@H]2[C@]1(CC)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
InChI InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChI Key WWYNJERNGUHSAO-XUDSTZEESA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1990))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
International Nonproprietary Names
INN number INN
3475 levonorgestrel
2157 norgestrel
Synonyms
l-norgestrel | Norplant®
Database Links
CAS Registry No. 797-63-7 (source: Scifinder)
ChEMBL Ligand CHEMBL1389
DrugBank Ligand DB00367
DrugCentral Ligand 1572
GtoPdb PubChem SID 135650516
PubChem CID 13109
RCSB PDB Ligand NOG
Search Google for chemical match using the InChIKey WWYNJERNGUHSAO-XUDSTZEESA-N
Search Google for chemicals with the same backbone WWYNJERNGUHSAO
Search PubMed clinical trials norgestrel
Search PubMed titles norgestrel
Search PubMed titles/abstracts norgestrel
Search UniChem for chemical match using the InChIKey WWYNJERNGUHSAO-XUDSTZEESA-N
Search UniChem for chemicals with the same backbone WWYNJERNGUHSAO
SynPHARM 6593 (in complex with Progesterone receptor)
Wikipedia Levonorgestrel

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Levonorgestrel
Cat. No. 4833