Details of the Drug

General Information of Drug (ID: DMQPH29)

Drug Name
Curcumin
Synonyms
curcumin; 458-37-7; Diferuloylmethane; Natural yellow 3; Turmeric yellow; Turmeric; Curcuma; Kacha haldi; Gelbwurz; Indian saffron; Curcumin I; Souchet; Halud; Halad; Haidr; Haldar; Merita earth; Yellow Ginger; Terra Merita; Yellow Root; Safran d'Inde; Yo-Kin; Golden seal; Curcuma oil; Orange Root; Oils, curcuma; CI Natural Yellow 3; Curcumine; Hydrastis; Indian turmeric; Yellow puccoon; Turmeric extract; Diferaloylmethane; Kurkumin [Czech]; (1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione; Tumeric yellow; Turmeric oil
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 368.4
Logarithm of the Partition Coefficient (xlogp) 3.2
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
Elimination
Following oral administration of curcumin to rats at a dose of 1 g/kg bw, about 75% of dose was excreted in the faeces and only traces of the compound was detected in the urine []
Metabolism
The drug is metabolized via O-conjugation []
Chemical Identifiers
Formula
C21H20O6
IUPAC Name
(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
Canonical SMILES
COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC(=C(C=C2)O)OC)O
InChI
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+
InChIKey
VFLDPWHFBUODDF-FCXRPNKRSA-N
Cross-matching ID
PubChem CID
969516
ChEBI ID
CHEMBL140
CAS Number
458-37-7
UNII
ZW3Z11D0JV
DrugBank ID
DB16594
TTD ID
D07SDQ
VARIDT ID
DR00559
INTEDE ID
DR1941
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Albendazole monooxygenase (CYP3A4) TTXV4FI CP3A4_HUMAN Inhibitor [2]
Amyloid beta A4 protein (APP) TTE4KHA A4_HUMAN Inhibitor [3]
Carbonic anhydrase (CA) TTUNARX NOUNIPROTAC Inhibitor [4]
Carbonic anhydrase I (CA-I) TTHQPL7 CAH1_HUMAN Inhibitor [4]
Carbonic anhydrase II (CA-II) TTANPDJ CAH2_HUMAN Inhibitor [4]
Carbonic anhydrase IV (CA-IV) TTZHA0O CAH4_HUMAN Inhibitor [4]
Carbonic anhydrase IX (CA-IX) TT2LVK8 CAH9_HUMAN Inhibitor [4]
Carbonic anhydrase VI (CA-VI) TTCFSPE CAH6_HUMAN Inhibitor [4]
Carbonic anhydrase XII (CA-XII) TTSYM0R CAH12_HUMAN Inhibitor [4]
Carbonic anhydrase XIV (CA-XIV) TTEYTKG CAH14_HUMAN Inhibitor [4]
DNA [cytosine-5]-methyltransferase (DNMT) TTHVCUP NOUNIPROTAC Inhibitor [5]
DNA [cytosine-5]-methyltransferase 3B (DNMT3B) TT6VZ78 DNM3B_HUMAN Inhibitor [5]
Matrix metalloproteinase-13 (MMP-13) TTHY57M MMP13_HUMAN Inhibitor [6]
Matrix metalloproteinase-9 (MMP-9) TT6X50U MMP9_HUMAN Inhibitor [7]
Multidrug resistance protein (MDR) TT0JLSD NOUNIPROTAC Inhibitor [8]
Nitric-oxide synthase inducible (NOS2) TTF10I9 NOS2_HUMAN Inhibitor [9]
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Inhibitor [10]
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [10]
Xanthine dehydrogenase/oxidase (XDH) TT7RJY8 XDH_HUMAN Inhibitor [11]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [12]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [13]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [13]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DE2GB8N UD18_HUMAN Substrate [13]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DEZO4N3 UD17_HUMAN Substrate [13]
NADPH-dependent curcumin reductase (curA) DEZWDKE CURA_ECOLI Substrate [14]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (CYP24A1) OTG2T749 CP24A_HUMAN Gene/Protein Processing [15]
14-3-3 protein epsilon OT3WQXNA 1433E_HUMAN Gene/Protein Processing [16]
5'-AMP-activated protein kinase catalytic subunit alpha-1 (PRKAA1) OT7TNF0L AAPK1_HUMAN Post-Translational Modifications [17]
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4 (PFKFB4) OTQYEXL2 F264_HUMAN Gene/Protein Processing [18]
A disintegrin and metalloproteinase with thrombospondin motifs 4 (ADAMTS4) OT4CA13K ATS4_HUMAN Gene/Protein Processing [19]
A-kinase anchor protein 6 (AKAP6) OTN59BZS AKAP6_HUMAN Gene/Protein Processing [20]
Acetyl-CoA carboxylase 1 (ACACA) OT5CQPZY ACACA_HUMAN Post-Translational Modifications [17]
Adenomatous polyposis coli protein (APC) OTKV0TIK APC_HUMAN Gene/Protein Processing [21]
Adenylate cyclase type 9 (ADCY9) OT1IZT5K ADCY9_HUMAN Gene/Protein Processing [21]
Alanine--tRNA ligase, cytoplasmic (AARS1) OTW8D813 SYAC_HUMAN Gene/Protein Processing [18]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Solid tumour/cancer
ICD Disease Classification 2A00-2F9Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin G/H synthase 2 (COX-2) DTT PTGS2 7.93E-04 -0.29 -0.34
Amyloid beta A4 protein (APP) DTT APP 1.60E-02 -0.07 -0.31
Prostaglandin G/H synthase 1 (COX-1) DTT PTGS1 3.97E-03 0.16 0.43
P-glycoprotein 1 (ABCB1) DTP P-GP 9.39E-02 1.07E-01 2.80E-01
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 1.10E-01 -5.91E-02 -3.60E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7000).
2 Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues. Eur J Med Chem. 2008 Aug;43(8):1621-31.
3 Curcumin and dehydrozingerone derivatives: synthesis, radiolabeling, and evaluation for beta-amyloid plaque imaging. J Med Chem. 2006 Oct 5;49(20):6111-9.
4 Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3.
5 Novel and selective DNA methyltransferase inhibitors: Docking-based virtual screening and experimental evaluation. Bioorg Med Chem. 2010 Jan 15;18(2):822-9.
6 High throughput screening of potentially selective MMP-13 exosite inhibitors utilizing a triple-helical FRET substrate. Bioorg Med Chem. 2009 Feb 1;17(3):990-1005.
7 Synthesis and biological evaluation of curcuminoid pyrazoles as new therapeutic agents in inflammatory bowel disease: effect on matrix metalloprote... Bioorg Med Chem. 2009 Feb 1;17(3):1290-6.
8 Thiazolides: a new class of antiviral drugs. Expert Opin Drug Metab Toxicol. 2009 Jun;5(6):667-74.
9 A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases. Proc Natl Acad Sci U S A. 2007 Dec 18;104(51):20523-8.
10 Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammator... Bioorg Med Chem Lett. 2005 Apr 1;15(7):1793-7.
11 Inhibition studies of bovine xanthine oxidase by luteolin, silibinin, quercetin, and curcumin. J Nat Prod. 2009 Apr;72(4):725-31.
12 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
13 Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake. J Biol Chem. 2004 Jan 9;279(2):1429-41.
14 Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism. Proc Natl Acad Sci U S A. 2011 Apr 19;108(16):6615-20.
15 Curcumin: a novel nutritionally derived ligand of the vitamin D receptor with implications for colon cancer chemoprevention. J Nutr Biochem. 2010 Dec;21(12):1153-61.
16 Curcumin suppresses PPARdelta expression and related genes in HT-29 cells. World J Gastroenterol. 2009 Mar 21;15(11):1346-52. doi: 10.3748/wjg.15.1346.
17 Curcumin inhibits Akt/mammalian target of rapamycin signaling through protein phosphatase-dependent mechanism. Mol Cancer Ther. 2008 Sep;7(9):2609-20. doi: 10.1158/1535-7163.MCT-07-2400.
18 Gene-expression profiling during curcumin-induced apoptosis reveals downregulation of CXCR4. Exp Hematol. 2007 Jan;35(1):84-95.
19 Comparison between chondroprotective effects of glucosamine, curcumin, and diacerein in IL-1beta-stimulated C-28/I2 chondrocytes. Osteoarthritis Cartilage. 2008 Oct;16(10):1205-12. doi: 10.1016/j.joca.2008.01.013. Epub 2008 Mar 5.
20 Curcumin restores corticosteroid function in monocytes exposed to oxidants by maintaining HDAC2. Am J Respir Cell Mol Biol. 2008 Sep;39(3):312-23. doi: 10.1165/rcmb.2008-0012OC. Epub 2008 Apr 17.
21 Gene expression profiling identifies activating transcription factor 3 as a novel contributor to the proapoptotic effect of curcumin. Mol Cancer Ther. 2005 Feb;4(2):233-41.