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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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) (23rd List, 2023). 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
LIPID MAPS LMST02030119
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
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