Details of the Drug

General Information of Drug (ID: DMI0V4O)

Drug Name
bilirubin
Synonyms
bilirubin; 635-65-4; Hematoidin; Hemetoidin; Principal bile pigment; UNII-RFM9X3LJ49; Bilirubin IXalpha; Bilirubin IX-alpha; EINECS 211-239-7; NSC 26685; BRN 0074376; RFM9X3LJ49; AI3-23078; 21H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-; CHEBI:16990; BPYKTIZUTYGOLE-IFADSCNNSA-N; PHEOPHYTIN; MFCD00005499; Bilirubin, 99%; Biline-8,12-dipropionic acid, 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 584.7
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 12
Hydrogen Bond Donor Count (hbonddonor) 6
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C33H36N4O6
IUPAC Name
3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
Canonical SMILES
CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)/C=C\\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/C=C\\4/C(=C(C(=O)N4)C=C)C
InChI
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
Cross-matching ID
PubChem CID
5280352
ChEBI ID
CHEBI:16990
CAS Number
635-65-4
TTD ID
D0O8ZV
VARIDT ID
DR00252
INTEDE ID
DR1980

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [2]
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [3]
Organic anion transporting polypeptide 1B3 (SLCO1B3) DT9C1TS SO1B3_HUMAN Substrate [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A6 (UGT1A6)
Main DME 		DESD26P UD16_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Albumin (ALB) OTVMM513 ALBU_HUMAN Drug Response [5]
Amino acid transporter heavy chain SLC3A2 (SLC3A2) OTBR33M9 4F2_HUMAN Gene/Protein Processing [6]
Amphiregulin (AREG) OTJFOR67 AREG_HUMAN Gene/Protein Processing [7]
AN1-type zinc finger protein 2A OTTG7P8R ZFN2A_HUMAN Gene/Protein Processing [7]
Ankyrin repeat and SOCS box protein 13 (ASB13) OTTONRCH ASB13_HUMAN Gene/Protein Processing [7]
Annexin A1 (ANXA1) OT5OFDJC ANXA1_HUMAN Gene/Protein Processing [7]
Aspartyl aminopeptidase (DNPEP) OT3UQXXV DNPEP_HUMAN Gene/Protein Processing [7]
Axin-2 (AXIN2) OTRMGQNU AXIN2_HUMAN Gene/Protein Processing [7]
Biogenesis of lysosome-related organelles complex 1 subunit 1 (BLOC1S1) OT123376 BL1S1_HUMAN Gene/Protein Processing [7]
C-X-C motif chemokine 10 (CXCL10) OTTLQ6S0 CXL10_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction 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: 4577).
2 Transport of monoglucuronosyl and bisglucuronosyl bilirubin by recombinant human and rat multidrug resistance protein 2. Hepatology. 1999 Aug;30(2):485-90.
3 Role of organic anion-transporting polypeptides, OATP-A, OATP-C and OATP-8, in the human placenta-maternal liver tandem excretory pathway for foetal bilirubin. Biochem J. 2003 May 1;371(Pt 3):897-905.
4 Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev. 1999 Nov;31(4):817-99.
5 Folic acid alleviates jaundice of phenylhydrazine (PHA)-induced neonatal rats by reducing Lys-homocysteinylation of albumin. Cell Biol Toxicol. 2021 Oct;37(5):679-693. doi: 10.1007/s10565-021-09602-3. Epub 2021 Mar 31.
6 Functional induction of the cystine-glutamate exchanger system Xc(-) activity in SH-SY5Y cells by unconjugated bilirubin. PLoS One. 2011;6(12):e29078. doi: 10.1371/journal.pone.0029078. Epub 2011 Dec 27.
7 Global changes in gene regulation demonstrate that unconjugated bilirubin is able to upregulate and activate select components of the endoplasmic reticulum stress response pathway. J Biochem Mol Toxicol. 2010 Mar-Apr;24(2):73-88.