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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL705
CHEMBL705
Compound Name ALITRETINOIN
ChEMBL Synonyms LGD-1057 | LG-100057 | AGN 192013 | TOCTINO | PANRETIN | ALRT1057 | ALRT-1057 | LG100057 | ALITRETINOIN | LGD1057
Max Phase 4 (Approved)
Trade Names PANRETIN | TOCTINO
Molecular Formula C20H28O2

Additional synonyms for CHEMBL705 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-ZVCIMWCZSA-N

Sources

  • British National Formulary
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL705

Molecule Features

CHEMBL705 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:Y Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Retinoid receptor agonist Retinoid receptor DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Hand DermatosesD006229EFO:1000706hand dermatosis3ClinicalTrials
EczemaD004485HP:0000964Eczema4ATC
ClinicalTrials
Lupus Erythematosus, CutaneousD008178EFO:0003834cutaneous lupus erythematosus2ClinicalTrials
Lichen PlanusD008010EFO:1000726lichen planus2ClinicalTrials
PsoriasisD011565EFO:0000676psoriasis2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC

Clinical Data

ClinicalTrials.gov ALITRETINOIN
The Cochrane Collaboration ALITRETINOIN

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 CHEMBL705. 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
CHEMBL2055 Retinoic acid receptor alpha 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
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 1.000
CHEMBL3100 Plasma retinol-binding protein Homo sapiens 1.000
CHEMBL2073709 Monocarboxylate transporter 1 Rattus norvegicus 0.998
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 0.954
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.922
CHEMBL4521 Cytochrome P450 24A1 Homo sapiens 0.843
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.739
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.445
CHEMBL4681 Aldo-keto-reductase family 1 member C3 Homo sapiens 0.286
CHEMBL5192 Botulinum neurotoxin type A Clostridium botulinum 0.273



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2055 Retinoic acid receptor alpha 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
CHEMBL1870 Retinoid X receptor beta Homo sapiens 1.000
CHEMBL4402 Retinoid X receptor gamma Mus musculus 1.000
CHEMBL4047 Retinoid X receptor beta Mus musculus 1.000
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 1.000
CHEMBL3100 Plasma retinol-binding protein Homo sapiens 1.000
CHEMBL1743121 Solute carrier organic anion transporter family member 1B3 Homo sapiens 1.000
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 1.000
CHEMBL1697668 Solute carrier organic anion transporter family member 1B1 Homo sapiens 0.999
CHEMBL3775 Dual specificity phosphatase Cdc25A Homo sapiens 0.995
CHEMBL2073709 Monocarboxylate transporter 1 Rattus norvegicus 0.995
CHEMBL1075315 C-X-C chemokine receptor type 5 Homo sapiens 0.883
CHEMBL4521 Cytochrome P450 24A1 Homo sapiens 0.881
CHEMBL3091268 Nuclear receptor ROR-beta Homo sapiens 0.874
CHEMBL4804 Dual specificity phosphatase Cdc25B Homo sapiens 0.678
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.637

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
300.4 300.2089 5.6 5 37.3 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
1 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 3.62 0 22 0.53

Structural Alerts

There are 9 structural alerts for CHEMBL705. To view alerts please click here.

Compound Cross References

ATC D - DERMATOLOGICALS
D11 - OTHER DERMATOLOGICAL PREPARATIONS
D11A - OTHER DERMATOLOGICAL PREPARATIONS
D11AH - Agents for dermatitis, excluding corticosteroids
D11AH04 - alitretinoin

L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XX - Other antineoplastic agents
L01XX22 - alitretinoin

ChemSpider ChemSpider:SHGAZHPCJJPHSC-ZVCIMWCZSA-N
DailyMed alitretinoin
PubChem SID: 144212512 SID: 26755228 SID: 26755229 SID: 26755230
Wikipedia Alitretinoin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL705



ACToR 5300-03-8
BindingDB 31892
Brenda 9774 62226 32134
CarotenoidDB CA01035
ChEBI 50648
ChemicalBook CB3222630
DrugBank DB00523
DrugCentral 3862
eMolecules 594075
EPA CompTox Dashboard DTXSID6040404
FDA SRS 1UA8E65KDZ
Guide to Pharmacology 5383 2645
Human Metabolome Database HMDB0002369
KEGG Ligand C15493
LINCS LSM-42856
LipidMaps LMPR01090022
Metabolights MTBLC50648
MolPort MolPort-002-507-281
PDBe 9CR
PubChem 449171
PubChem: Drugs of the Future 12014910
PubChem: Thomson Pharma 14898408
SureChEMBL SCHEMBL18666
ZINC ZINC000012661824

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