ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL38
CHEMBL38
Compound Name TRETINOIN
ChEMBL Synonyms RETIN-A | TRETINOIN | RENOVA | VESANOID | Retin-A Micro | Atralin | AVITA | Tretin-X
Max Phase 4 (Approved)
Trade Names RENOVA | RETIN-A | Tretin-X | AVITA | Atralin | Retin-A Micro | Tretinoin | VESANOID
Molecular Formula C20H28O2

Additional synonyms for CHEMBL38 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES C\C(=C/C=C/C(=C/C(=O)O)/C)\C=C\C1=C(C)CCCC1(C)C
Standard InChI InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3 ...
Download InChI
Standard InChI Key SHGAZHPCJJPHSC-YCNIQYBTSA-N

Sources

  • British National Formulary
  • Curated Drug Pharmacokinetic Data
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL38

Molecule Features

CHEMBL38 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Retinoic acid receptor agonist Retinoic acid receptor DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
NEOPLASMSD009369EFO:0000616NEOPLASM4ATC
ACNE VULGARISD000152EFO:0003894ACNE4ATC
ClinicalTrials
ATC
LYMPHOMAD008223EFO:0000574LYMPHOMA2ClinicalTrials
MULTIPLE MYELOMAD009101EFO:0001378MULTIPLE MYELOMA1ClinicalTrials
ROSACEAD012393EFO:1000760ROSACEA3ClinicalTrials
LEUKEMIA, MYELOID, ACUTED015470EFO:0000222ACUTE MYELOID LEUKEMIA3ClinicalTrials

Clinical Data

ClinicalTrials.gov TRETINOIN
The Cochrane Collaboration TRETINOIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL38. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL2055 Retinoic acid receptor alpha Homo sapiens 1.000
CHEMBL2004 Retinoid X receptor gamma Homo sapiens 1.000
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 1.000
CHEMBL2061 Retinoid X receptor alpha Homo sapiens 1.000
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL3100 Plasma retinol-binding protein Homo sapiens 1.000
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 1.000
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.924
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 0.775
CHEMBL4521 Cytochrome P450 24A1 Homo sapiens 0.641
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.501
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.281



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL2003 Retinoic acid receptor gamma Homo sapiens 1.000
CHEMBL2004 Retinoid X receptor gamma Homo sapiens 1.000
CHEMBL2008 Retinoic acid receptor beta Homo sapiens 1.000
CHEMBL2061 Retinoid X receptor alpha Homo sapiens 1.000
CHEMBL2055 Retinoic acid receptor alpha Homo sapiens 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL3100 Plasma retinol-binding protein Homo sapiens 1.000
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 1.000
CHEMBL1743121 Solute carrier organic anion transporter family member 1B3 Homo sapiens 1.000
CHEMBL1697668 Solute carrier organic anion transporter family member 1B1 Homo sapiens 0.999
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.999
CHEMBL3775 Dual specificity phosphatase Cdc25A Homo sapiens 0.996
CHEMBL5868 Nuclear receptor ROR-alpha Homo sapiens 0.908
CHEMBL4521 Cytochrome P450 24A1 Homo sapiens 0.771
CHEMBL4804 Dual specificity phosphatase Cdc25B Homo sapiens 0.693
CHEMBL3091268 Nuclear receptor ROR-beta Homo sapiens 0.646
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.478
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.390

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
300.4 300.2089 5.55 5 37.29 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 1 1 2 1 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.73 - 6.26 3.63 0 22 0.53

Structural Alerts

There are 9 structural alerts for CHEMBL38. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XX - Other antineoplastic agents
L01XX14 - tretinoin

D - DERMATOLOGICALS
D10 - ANTI-ACNE PREPARATIONS
D10A - ANTI-ACNE PREPARATIONS FOR TOPICAL USE
D10AD - Retinoids for topical use in acne
D10AD51 - tretinoin, combinations

D - DERMATOLOGICALS
D10 - ANTI-ACNE PREPARATIONS
D10A - ANTI-ACNE PREPARATIONS FOR TOPICAL USE
D10AD - Retinoids for topical use in acne
D10AD01 - tretinoin

ChemSpider ChemSpider:SHGAZHPCJJPHSC-YCNIQYBTSA-N
DailyMed tretinoin
PubChem SID: 104171346 SID: 124882949 SID: 124882951 SID: 124882956 SID: 124882957 SID: 144204363 SID: 144209528 SID: 144210625 SID: 170465045 SID: 26746936 SID: 29214999 SID: 416403 SID: 50103969 SID: 50103970 SID: 50126361 SID: 50126362 SID: 56422209 SID: 85231340 SID: 855632 SID: 90341365
Wikipedia Retinoic_acid Tretinoin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL38



ACToR 187175-63-9 302-79-4 4759-48-2
Atlas retinoic acid tretinoin 9-cis retinoic-acid all-trans retinoic acid
BindingDB 31883
Brenda 12679 6481 193381 5126 21231 2354
CarotenoidDB CA01036
ChEBI 15367
DrugCentral 2722
eMolecules 1934590
EPA CompTox Dashboard DTXSID7021239
FDA SRS 5688UTC01R
Guide to Pharmacology 2644
IBM Patent System 5AD93E60FC59B124ECE547DE667E3738
KEGG Ligand C00777
LINCS LSM-42854
LipidMaps LMPR01090019
Metabolights MTBLC15367
NIH Clinical Collection SAM002264647
Nikkaji J690.379G J1.313.469C J1.518K J2.378.058E J646.157C J970.183D J494.243D J627.166I J646.158A J623.910B J528.606I
PDBe REA
PharmGKB PA164746900
PubChem 444795
PubChem: Drugs of the Future 12014646
PubChem: Thomson Pharma 14849563 14825303
Selleck Tretinoin(Aberela)
SureChEMBL SCHEMBL19091395 SCHEMBL3145
ZINC ZINC000012358651

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/SHGAZHPCJJPHSC-YCNIQYBTSA-N spacer
spacer