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isotretinoin   Click here for help

GtoPdb Ligand ID: 7600

Synonyms: 13-cis retinoic acid
Approved drug
isotretinoin is an approved drug (FDA (1982))
Compound class: Synthetic organic
Comment: Isotretinoin is a retinoid type drug ie it is a vitamin A-like molecule. It is the endogenous agonist for retinoic acid receptors (RARs).
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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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 5
Topological polar surface area 37.3
Molecular weight 300.21
XLogP 6.25
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(=CC=CC(=CC(=O)O)C)C=CC1=C(C)CCCC1(C)C
Isomeric SMILES C/C(=C\C=C\C(=C/C(=O)O)\C)/C=C/C1=C(C)CCCC1(C)C
InChI InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
InChI Key SHGAZHPCJJPHSC-XFYACQKRSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1982)
IUPAC Name Click here for help
(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
International Nonproprietary Names Click here for help
INN number INN
4617 isotretinoin
Synonyms Click here for help
13-cis retinoic acid
Database Links Click here for help
CAS Registry No. 4759-48-2
ChEMBL Ligand CHEMBL547
DrugBank Ligand DB00982
DrugCentral Ligand 1508
GtoPdb PubChem SID 223365935
LIPID MAPS LMPR01090021
PubChem CID 5282379
Search Google for chemical match using the InChIKey SHGAZHPCJJPHSC-XFYACQKRSA-N
Search Google for chemicals with the same backbone SHGAZHPCJJPHSC
Search PubMed clinical trials isotretinoin
Search PubMed titles isotretinoin
Search PubMed titles/abstracts isotretinoin
UniChem Compound Search for chemical match using the InChIKey SHGAZHPCJJPHSC-XFYACQKRSA-N
UniChem Connectivity Search for chemical match using the InChIKey SHGAZHPCJJPHSC-XFYACQKRSA-N
Wikipedia Isotretinoin

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MedChemExpress
Isotretinoin (links to external site)
Cat. No. HY-15127