levonorgestrel   Click here for help

GtoPdb Ligand ID: 2881

Synonyms: l-norgestrel | Norplant®
Approved drug PDB Ligand
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
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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
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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 Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1990))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(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 Click here for help
INN number INN
3475 levonorgestrel
2157 norgestrel
Synonyms Click here for help
l-norgestrel | Norplant®
Database Links Click here for help
CAS Registry No. 797-63-7 (source: Scifinder)
ChEMBL Ligand CHEMBL1389
DrugBank Ligand DB00367
DrugCentral Ligand 1572, 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
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Search PubMed titles/abstracts norgestrel
SynPHARM 6593 (in complex with Progesterone receptor)
UniChem Compound Search for chemical match using the InChIKey WWYNJERNGUHSAO-XUDSTZEESA-N
UniChem Connectivity Search for chemical match using the InChIKey WWYNJERNGUHSAO-XUDSTZEESA-N
Wikipedia Levonorgestrel

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Tocris
Levonorgestrel (links to external site)
Cat. No. 4833