tretinoin   

GtoPdb Ligand ID: 2644

Synonyms: all-trans-retinoic acid (ATRA) | Altreno® (0.05% lotion) | Avita® (0.025% gel) | Renova® (0.02% cream)
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
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
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
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
3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
International Nonproprietary Names
INN number INN
2875 tretinoin
Synonyms
all-trans-retinoic acid (ATRA) | Altreno® (0.05% lotion) | Avita® (0.025% gel) | Renova® (0.02% cream)
Database Links
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
NURSA Ligand 10.1621/3ZT36894UZ
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

Product suppliers

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Tocris
Retinoic acid
Cat. No. 0695