tretinoin   Click here for help

GtoPdb Ligand ID: 2644

Synonyms: all-trans-retinoic acid (ATRA) | Altreno® (0.05% lotion) | Avita® (0.025% gel) | Renova® (0.02% cream)
Approved drug PDB Ligand
tretinoin is an approved drug (FDA (1995))
Comment: Tretinoin is a naturally occurring derivative of vitamin A (retinoic acid) and as such is an agonist at the retinoic acid receptors. Tretinoin binds to α, β, and γ isoforms of the retinoic acid receptor. Retionoids are important regulators of cell reproduction, proliferation, and differentiation.
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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 5
Topological polar surface area 37.3
Molecular weight 300.21
XLogP 6.25
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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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-YCNIQYBTSA-N
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1995))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
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
2875 tretinoin
Synonyms Click here for help
all-trans-retinoic acid (ATRA) | Altreno® (0.05% lotion) | Avita® (0.025% gel) | Renova® (0.02% cream)
Database Links Click here for help
BindingDB Ligand 31883
CAS Registry No. 302-79-4 (source: Scifinder)
ChEBI CHEBI:15367
ChEMBL Ligand CHEMBL38
DrugBank Ligand DB00755
DrugCentral Ligand 2722
GtoPdb PubChem SID 135651435
PubChem CID 444795
RCSB PDB Ligand REA, 3KV
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Search UniChem for chemical match using the InChIKey SHGAZHPCJJPHSC-YCNIQYBTSA-N
Search UniChem for chemicals with the same backbone SHGAZHPCJJPHSC
SynPHARM 79003 (in complex with Retinoic acid receptor-α)
6287 (in complex with Retinoic acid receptor-β)
79006 (in complex with Retinoic acid receptor-β)
6288 (in complex with Retinoic acid receptor-γ)
79008 (in complex with Retinoic acid receptor-γ)
Wikipedia Tretinoin

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Tocris
Retinoic acid
Cat. No. 0695