TRETINOIN

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC D10AD01 L01XF01
UNII 5688UTC01R
EPA CompTox DTXSID7021239

Structure

InChI Key SHGAZHPCJJPHSC-YCNIQYBTSA-N
Smiles CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1
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+

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H28O2
Molecular Weight 300.44
AlogP 5.6
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 37.3
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 22.0

Pharmacology

Mechanism of Action Action Reference
Retinoic acid receptor agonist AGONIST DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Fatty acid binding protein family
- - - - 100
Enzyme Hydrolase
- - - - -0.7-9.3
Enzyme Isomerase
- 820 800 820 -
Enzyme Lyase
- - - - 87-92
Enzyme Oxidoreductase
- - - - 9
Membrane receptor
- 180 - - -
Other cytosolic protein
- 370-600 0.4-2 - 100
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 1
1-563 0.78-15 2.3-16 0.1-187 100-100
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 2
0.52-105 0.9-13 0.4-17 0.4-17.4 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 3
0.2-50.12 0.5-18 0.2-19 0.04-18.5 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group F Nuclear hormone receptor subfamily 1 group F member 1
- 199.53 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group F Nuclear hormone receptor subfamily 1 group F member 3
- 199.53 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group F
- 0.15-125.89 280 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 1
54-900 - 9-53 0.4-350 10
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 2
4.5 - 306 0.5-881 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 3
2-961 350 306-350 1.4-288 -
Unclassified protein
- - - - 72-86
EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Agaricus bisporus
- - - - 9
Cercopithecidae
10-900 - - - -
Cricetinae
- 0.01 - - -
Cricetulus griseus
- - - - 88.4
Electrophorus electricus
- - - - 9.3
Equus caballus
- - - -
Escherichia coli
- - - - 72-86
Gallus gallus
- 370-600 - - 67-100
Homo sapiens
0.2-900 0.15-820 0.2-800 0.04-820 3.1-100
Human herpesvirus 4
- 15.4 - - 21.6-100
Mus musculus
0.22-961 0.1-31 0.4-350 - 10-100
Rattus norvegicus
- - - - 11

Target Conservation

Protein: Retinoic acid receptor
Description: Retinoic acid receptor alpha
Organism : Homo sapiens
P10276 ENSG00000131759
Protein: Retinoic acid receptor
Description: Retinoic acid receptor beta
Organism : Homo sapiens
P10826 ENSG00000077092
Protein: Retinoic acid receptor
Description: Retinoic acid receptor gamma
Organism : Homo sapiens
P13631 ENSG00000172819

Related Entries

Cross References

Resources Reference
ChEBI 15367
ChEMBL CHEMBL38
DrugBank DB00755
DrugCentral 2722
FDA SRS 5688UTC01R
Human Metabolome Database HMDB0001852
Guide to Pharmacology 2644
KEGG C00777
PDB REA
PharmGKB PA164746900
PubChem 444795
SureChEMBL SCHEMBL19091395
ZINC ZINC000012358651
CONTENTS