Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1941)
Drug Name
Curcumin
Synonyms
Curcuma; Curcuma oil; Curcumin I; Curcumine; Diferaloylmethane; Diferuloylmethane; Gelbwurz; Golden seal; Haldar; Hydrastis; Indian saffron; Indian turmeric; Kacha haldi; Kurkumin [Czech]; Merita earth; Natural yellow 3; Oils, curcuma; Orange Root; Safran d'Inde; Souchet; Terra Merita; Tumeric yellow; Turmeric; Turmeric extract; Turmeric oil; Turmeric yellow; Yellow Ginger; Yellow Root; Yellow puccoon; Yo-Kin; curcumin; (1E,6E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione; 458-37-7; C.I. Natural Yellow 3; Haidr; Halad; Halud
Indication Stomach cancer [ICD11: 2B72] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 368.4 Topological Polar Surface Area 93.1
Heavy Atom Count 27 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
969516
PubChem SID
91276 ; 521754 ; 616319 ; 806710 ; 855880 ; 3139269 ; 7979963 ; 8136975 ; 8145866 ; 8719722 ; 10319004 ; 12013839 ; 12055808 ; 14803853 ; 17389087 ; 24892408 ; 24892983 ; 29203996 ; 44256039 ; 46493764 ; 48184781 ; 48414613 ; 48414614 ; 48423182 ; 48424998 ; 49854349 ; 49856278 ; 50104137 ; 50104138 ; 53788771 ; 56312449 ; 56313017 ; 56422380 ; 57288615 ; 57408903 ; 75735540 ; 81040856 ; 81054961 ; 81093229 ; 85286188 ; 85789755 ; 87565556 ; 87565557 ; 88806667 ; 92126156 ; 92709887 ; 93165931 ; 103961572 ; 104171337 ; 105852703
ChEBI ID
CHEBI:3962
CAS Number
458-37-7
TTD Drug ID
D07SDQ
Formula
C21H20O6
Canonical SMILES
COC1=C(C=CC(=C1)C=CC(=O)CC(=O)C=CC2=CC(=C(C=C2)O)OC)O
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Curcumin bate-O-glucuronide DM016428
92024088
Conjugation - Glucuronidation 1 [4] , [5]
Dihydrocurcumin DM015461
5469426
Oxidation - Sulfonation 1 [6] , [5]
Dihydrocurcumin DM015461
5469426
Oxidation - O-dealkylation 1 [4]
Dihydrocurcumin DM015461
5469426
Reduction - Reduction 1 [4] , [6] , [5]
Dihydrocurcumin bate-O-glucuronide DM017957 N. A. Reduction - Reduction 2 [4]
Dihydrocurcumin bate-O-glucuronide DM017957 N. A. Conjugation - Glucuronidation 2 [4]
Tetrahydrocurcumin DM015146
124072
Reduction - Reduction 2 [4] , [6] , [5]
Hexahydrocurcumin DM015443
5318039
Reduction - Reduction 3 [4] , [6] , [5]
Tetrahydrocurcumin bate-O-glucuronide DM016808
156028092
Reduction - Reduction 3 [4]
Tetrahydrocurcumin bate-O-glucuronide DM016808
156028092
Conjugation - Glucuronidation 3 [4]
Hexahydrocurcumin bate-O-glucuronide DM016038
24968347
Reduction - Reduction 4 [4]
Hexahydrocurcumin bate-O-glucuronide DM016038
24968347
Conjugation - Glucuronidation 4 [4]
Octahydrocurcumin DM015732
11068834
Reduction - Reduction 4 [7] , [5]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009669 Curcumin Dihydrocurcumin Reduction - Reduction curA [4], [6], [5]
MR009678 Curcumin Curcumin bate-O-glucuronide Conjugation - Glucuronidation UGT [4], [5]
MR009679 Curcumin bate-O-glucuronide Dihydrocurcumin bate-O-glucuronide Reduction - Reduction Unclear [4]
MR009670 Dihydrocurcumin Dihydrocurcumin bate-O-glucuronide Conjugation - Glucuronidation UGT [4]
MR009673 Dihydrocurcumin Tetrahydrocurcumin Reduction - Reduction curA [4], [6], [5]
MR009671 Dihydrocurcumin bate-O-glucuronide Tetrahydrocurcumin bate-O-glucuronide Reduction - Reduction Unclear [4]
MR009674 Tetrahydrocurcumin Tetrahydrocurcumin bate-O-glucuronide Conjugation - Glucuronidation UGT [4]
MR009675 Tetrahydrocurcumin Hexahydrocurcumin Reduction - Reduction Unclear [4], [6], [5]
MR009676 Hexahydrocurcumin Hexahydrocurcumin bate-O-glucuronide Conjugation - Glucuronidation UGT [4]
MR009677 Hexahydrocurcumin Octahydrocurcumin Reduction - Reduction Unclear [7], [5]
MR009672 Tetrahydrocurcumin bate-O-glucuronide Hexahydrocurcumin bate-O-glucuronide Reduction - Reduction Unclear [4]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
NADPH-dependent curcumin reductase (curA) DME1077 Escherichia coli
CURA_ECOLI
1.3.1.-
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DME0065 Homo sapiens
UD17_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Km = 0.1 microM
UD11_HUMAN
[3]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DME0065 Km = 0.1 microM
UD17_HUMAN
[3]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Km = 0.1 microM
UD18_HUMAN
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Km = 0.1 microM
UD19_HUMAN
[3]
References
1 Nanocurcumin: a promising therapeutic advancement over native curcumin. Crit Rev Ther Drug Carrier Syst. 2013;30(4):331-68.
2 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.
3 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.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 Curcumin and Weight Loss: Does It Work?
6 Curcumin, Gut Microbiota, and Neuroprotection
7 Biological and pharmacological effects of hexahydrocurcumin, a metabolite of curcumin

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.