9CR

(9cis)-retinoic acid

Created: 2012-12-18
Last modified:  2012-12-21

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Chemical Details

Formal Charge0
Atom Count50
Chiral Atom Count0
Bond Count50
Aromatic Bond Count0
2D diagram of 9CR
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Chemical Component Summary

Name(9cis)-retinoic acid
Systematic Name (OpenEye OEToolkits)(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
FormulaC20 H28 O2
Molecular Weight300.435
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C(O)\C=C(\C=C\C=C(/C=C/C1=C(C)CCCC1(C)C)C)C
SMILESCACTVS3.370CC1=C(C=CC(C)=CC=CC(C)=CC(O)=O)C(C)(C)CCC1
SMILESOpenEye OEToolkits1.7.6CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
Canonical SMILESCACTVS3.370 CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C(O)=O)C(C)(C)CCC1
Canonical SMILESOpenEye OEToolkits1.7.6 CC1=C(C(CCC1)(C)C)/C=C/C(=C\C=C\C(=C\C(=O)O)\C)/C
InChIInChI1.03 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+
InChIKeyInChI1.03 SHGAZHPCJJPHSC-ZVCIMWCZSA-N

Drug Info: DrugBank

DrugBank IDDB00523 
NameAlitretinoin
Groups
  • investigational
  • approved
DescriptionAn important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth; and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).
Synonyms
  • Alitrétinoïne
  • (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
  • 9-cis-retinoic acid
  • Alitretinoin
  • 9-cis-Tretinoin
Brand Names
  • Clindamycin 1% / Niacinamide 4% / Tretinoin 0.05%
  • Hanzema
  • Toctino
  • Panretin
IndicationFor topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma.
Categories
  • Agents for Dermatitis, Excluding Corticosteroids
  • Alkenes
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Biological Factors
ATC-Code
  • L01XF02
  • D11AH04
CAS number5300-03-8

Drug Targets

NameTarget SequencePharmacological ActionActions
Retinoic acid receptor alphaMASNSSSCPTPGGGHLNGYPVPPYAFFFPPMLGGLSPPGALTTLQHQLPV...unknownagonist
Retinoic acid receptor RXR-alphaMDTKHFLPLDFSTQVNSSLTSPTGRGSMAAPSLHPSLGPGIGSPGQLHSP...unknownagonist
Retinoic acid receptor betaMTTSGHACPVPAVNGHMTHYPATPYPLLFPPVIGGLSLPPLHGLHGHPPP...unknownagonist
Retinoic acid receptor RXR-betaMSWAARPPFLPQRHAAGQCGPVGVRKEMHCGVASRWRRRRPWLDPAAAAA...unknownagonist
Retinoic acid receptor gammaMATNKERLFAAGALGPGSGYPGAGFPFAFPGALRGSPPFEMLSPSFRGLG...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL705
PubChem 449171
ChEMBL CHEMBL705
ChEBI CHEBI:50648