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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEMBL501680
CAS Number: 635-65-4
TTD ID: D0O8ZV
VARIDT ID: DR00252
INTEDE ID: DR1980

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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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]
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]
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]
CAP-Gly domain-containing linker protein 1 (CLIP1)	OTTGAEJE	CLIP1_HUMAN	Gene/Protein Processing	[7]
Carboxypeptidase D (CPD)	OT2CS64Y	CBPD_HUMAN	Gene/Protein Processing	[7]
CD302 antigen (CD302)	OTX580VU	CD302_HUMAN	Gene/Protein Processing	[7]

Molecular Interaction Atlas (MIA)

MIA Detail

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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.