CC9

curcumin

Created: 2013-04-19
Last modified:  2021-03-13

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Chemical Details

Formal Charge0
Atom Count47
Chiral Atom Count0
Bond Count48
Aromatic Bond Count12
2D diagram of CC9
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Chemical Component Summary

Namecurcumin
Synonyms(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
Systematic Name (OpenEye OEToolkits)(1E,6E)-1,7-bis(3-methoxy-4-oxidanyl-phenyl)hepta-1,6-diene-3,5-dione
FormulaC21 H20 O6
Molecular Weight368.38
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C(\C=C\c1ccc(O)c(OC)c1)CC(=O)\C=C\c2cc(OC)c(O)cc2
SMILESCACTVS3.370COc1cc(C=CC(=O)CC(=O)C=Cc2ccc(O)c(OC)c2)ccc1O
SMILESOpenEye OEToolkits1.7.6COc1cc(ccc1O)C=CC(=O)CC(=O)C=Cc2ccc(c(c2)OC)O
Canonical SMILESCACTVS3.370 COc1cc(\C=C\C(=O)CC(=O)\C=C\c2ccc(O)c(OC)c2)ccc1O
Canonical SMILESOpenEye OEToolkits1.7.6 COc1c(ccc(c1)/C=C/C(=O)CC(=O)/C=C/c2cc(c(cc2)O)OC)O
InChIInChI1.03 InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+
InChIKeyInChI1.03 VFLDPWHFBUODDF-FCXRPNKRSA-N

Drug Info: DrugBank

DrugBank IDDB11672 
NameCurcumin
Groups
  • investigational
  • approved
DescriptionCurcumin, also known as diferuloylmethane, is an active component in the golden spice turmeric (Curcuma longa) and in [Curcuma xanthorrhiza oil]. It is a highly pleiotropic molecule that exhibits antibacterial, anti-inflammatory, hypoglycemic, antioxidant, wound-healing, and antimicrobial activities [A33166]. Due to these properties, curcumin has been investigated for the treatment and supportive care of clinical conditions including proteinuria, breast cancer, multiple myeloma, depression, and Non Small Cell Lung Cancer (NSCLC). Despite proven efficacy against numerous experimental models, poor bioavailability due to poor absorption, rapid metabolism, and rapid systemic elimination have been shown to limit the therapeutic efficacy of curcumin [A33166]. Curcumin is under investigation for the treatment and supportive care of various clinical conditions including mucositis, rectal cancer, prostate cancer, chronic schizophrenia, and Mild Cognitive Impairment (MCI) [A33166].
Synonyms
  • Curcumin
  • Diferuloylmethane
Brand Names
  • Melittin Joint Soothing
  • Gel
  • Medical Grade High Performance Joint Repair
  • Kaydia Patch
  • Victory 19 Virus Out
IndicationNo approved therapeutic indications.
Categories
  • Alkanes
  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents
  • Antineoplastic Agents
CAS number458-37-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknowninhibitor
Nitric oxide synthase, inducibleMACPWKFLFKTKFHQYAMNGEKDINNNVEKAPCATSSPVTQDDLQYHNLS...unknowninhibitor
Carbonic anhydrase 14MLFSALLLEVIWILAADGGQHWTYEGPHGQDHWPASYPECGNNAQSPIDI...unknowninhibitor
Carbonic anhydrase 1MASPDWGYDDKNGPEQWSKLYPIANGNNQSPVDIKTSETKHDTSLKPISV...unknowninhibitor
Collagenase 3MHPGVLAAFLFLSWTHCRALPLPSGGDEDDLSEEDLQFAERYLRSYYHPT...unknowninhibitor
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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 CHEMBL140
PubChem 969516
ChEMBL CHEMBL140
ChEBI CHEBI:3962
CCDC/CSD QUMDIN