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

General Information of Drug (ID: DR1980)
Drug Name
Bilirubin
Synonyms
Bilirubin IX-alpha; Bilirubin IXalpha; Bilirubin, 99%; Disodium bilirubinate IXalpha; Hematoidin; Hemetoidin; PHEOPHYTIN; Principal bile pigment; RFM9X3LJ49; bilirubin; 21H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-; 635-65-4; 93891-87-3; AI3-23078; BPYKTIZUTYGOLE-IFADSCNNSA-N; BRN 0074376; Biline-8,12-dipropionic acid, 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-; CHEBI:16990; EINECS 211-239-7; MFCD00005499; NSC 26685; UNII-RFM9X3LJ49
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 584.7 Topological Polar Surface Area 164
Heavy Atom Count 43 Rotatable Bond Count 12
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5280352
PubChem SID
3769 ; 8144728 ; 8616233 ; 10319019 ; 11537670 ; 14935827 ; 24848604 ; 24891751 ; 25630735 ; 26612105 ; 26681048 ; 26749657 ; 39289522 ; 47348442 ; 47868681 ; 47942824 ; 49746883 ; 49834296 ; 49893925 ; 50096481 ; 50096483 ; 53789017 ; 57357704 ; 57647150 ; 80330271 ; 85245571 ; 85248032 ; 85248034 ; 87563495 ; 88266590 ; 92718032 ; 99455424 ; 99455426 ; 103619919 ; 111677770 ; 113853139 ; 117636345 ; 124636399 ; 126522981 ; 126628628 ; 127269546 ; 127269547 ; 127269548 ; 127269549 ; 134977906 ; 135252701 ; 135253133 ; 137144061 ; 138836811 ; 144072300
ChEBI ID
CHEBI:16990
CAS Number
635-65-4
TTD Drug ID
D0O8ZV
Formula
C33H36N4O6
Canonical SMILES
CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)C=C3C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)C=C4C(=C(C(=O)N4)C=C)C
InChI
1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-
InChIKey
BPYKTIZUTYGOLE-IFADSCNNSA-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
Bilirubin monoglucuronide DM006943
134820148
Conjugation - Conjugation 1 [3] , [4]
Bilirubin diglucuronide DM006944
5280817
Conjugation - Conjugation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007558 Bilirubin Bilirubin monoglucuronide Conjugation - Conjugation UGT1A1 [3], [4]
MR007559 Bilirubin monoglucuronide Bilirubin diglucuronide Conjugation - Conjugation UGT1A1 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Homo sapiens
UD16_HUMAN
2.4.1.17
[2]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Km = 0.024 microM
UD16_HUMAN
[2]
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 4577).
2 Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev. 1999 Nov;31(4):817-99.
3 UGT1A1 dysfunction increases liver burden and aggravates hepatocyte damage caused by long-term bilirubin metabolism disorder
4 Monthly variation in the plasma copper and zinc concentration of pregnant and non-pregnant mares

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