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Bilirubin

AlkaPlorer ID: AK319708

Synonym: None

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

Structure

SMILES: C=CC1=C(C)/C(=C/C2=C(C)C(CCC(=O)O)=C(CC3=C(CCC(=O)O)C(C)=C(/C=C4\NC(=O)C(C)=C4C=C)N3)N2)NC1=O

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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-

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InChIKey: BPYKTIZUTYGOLE-IFADSCNNSA-N

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Reference

PubChem CID: 5280352

LOTUS: LTS0037862

NPASS: NPC325481

Properties Information

Molecule Weight: 584.6730000000003

TPSA？: 164.37999999999997

MolLogP？: 4.531240000000001

Number of H-Donors: 6

Number of H-Acceptors: 4

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 39810.7 nM None
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 14091.9 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 28183.8 nM None
Homo sapiens Caco-2 Papp 0.2 10'-7 cm/s 10.1016/j.bmc.2008.02.008
Homo sapiens Caco-2 Papp 10.4 10'-7 cm/s 10.1016/j.bmc.2008.02.008
Homo sapiens Caspase-1 Potency 25118.9 nM None
Homo sapiens Caspase-7 Potency 19952.6 nM None
Homo sapiens DNA polymerase kappa Potency 39810.7 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 25118.9 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 31622.8 nM None
Homo sapiens Mas-related G-protein coupled receptor member X4 Activity nan None None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 28183.8 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 39810.7 nM None
Homo sapiens Microtubule-associated protein tau Potency 10000.0 nM None
Homo sapiens Microtubule-associated protein tau Potency 14125.4 nM None
Homo sapiens Microtubule-associated protein tau Potency 31622.8 nM None
Homo sapiens Prelamin-A/C Potency 17782.8 nM None
Homo sapiens Solute carrier organic anion transporter family member 1A2 Activity nan None 10.1042/bj20030034
Homo sapiens Solute carrier organic anion transporter family member 1B1 Activity nan None 10.1038/nrd3028
Homo sapiens Solute carrier organic anion transporter family member 1B1 Activity nan None 10.1042/bj20030034
Homo sapiens Solute carrier organic anion transporter family member 1B1 Activity nan None 10.1074/jbc.m004968200
Homo sapiens Solute carrier organic anion transporter family member 1B1 IC50 1318.26 nM 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 15.29 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B1 Ki 720.0 nM 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B1 Km 7.6 nM 10.1042/bj20030034
Homo sapiens Solute carrier organic anion transporter family member 1B3 Activity nan None 10.1042/bj20030034
Homo sapiens Solute carrier organic anion transporter family member 1B3 IC50 3388.44 nM 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 32.05 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Ki 2630.0 nM 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Km 39.1 nM 10.1042/bj20030034
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 31622.8 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 79432.8 nM None
Homo sapiens UDP-glucuronosyltransferase 1-1 Activity 400.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1-1 Activity nan None None
Homo sapiens UDP-glucuronosyltransferase 1-6 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1-9 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 1A4 Activity 2.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B17 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens UDP-glucuronosyltransferase 2B7 Activity 0.0 pm/min/mg 10.1146/annurev.pharmtox.40.1.581
Homo sapiens Vitamin D receptor Potency 22387.2 nM None
Rattus norvegicus Inositol monophosphatase 1 Potency 10000.0 nM None
Rattus norvegicus Solute carrier organic anion transporter family member 1A1 Inhibition 43.0 % 10.1016/0270-9139(94)90194-5
Salmonella enterica subsp. enterica serovar Typhimurium Salmonella typhimurium Activity 352.0 % 10.1021/np4005807
Salmonella enterica subsp. enterica serovar Typhimurium Salmonella typhimurium Activity nan None 10.1021/np4005807
Salmonella enterica subsp. enterica serovar Typhimurium Salmonella typhimurium Inhibition 54.0 % 10.1021/np4005807
Salmonella enterica subsp. enterica serovar Typhimurium Salmonella typhimurium Inhibition 82.0 % 10.1021/np4005807
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Trypanosoma cruzi Cruzipain Potency 39810.7 nM None
None ADMET Activity nan None 10.1016/j.bmc.2008.02.008
None ADMET Stability 0.33 %/min 10.1016/j.bmc.2008.02.008
None ADMET Stability 44.0 % None
None ADMET Stability nan % None
None Phospholipidosis Phospholipidosis nan None 10.1021/mp100103e
None Phospholipidosis Phospholipidosis nan None 10.1080/15376510701857262
None Unchecked Potency 5623.4 nM None
None Unchecked Potency 25118.9 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT001771 C=CC1=C(C)/C(=C/C2=N/C(=C\c3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)C(CCC(=O)O)=C2C)NC1=O>>C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)c(CCC(=O)O)c2C)NC1=O BILIVERDIN-REDUCTASE-RXN
AKRT001775 C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)c(CCC(=O)O)c2C)NC1=O.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c(CCC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c2C)NC1=O R02389
AKRT001776 C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)c(CCC(=O)O)c2C)NC1=O.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)c(CCC(=O)O[C@H]3[C@H](O)[C@@H](C(=O)O)O[C@@H](O)[C@@H]3O)c2C)NC1=O RXN-19359
AKRT001777 C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)c(CCC(=O)O)c2C)NC1=O.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)OC3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c(CCC(=O)O)c2C)NC1=O enzymemap_34619
AKRT001778 C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)c(CCC(=O)O)c2C)NC1=O.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c(CCC(=O)O)c2C)NC1=O enzymemap_34578
AKRT001779 C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)c(CCC(=O)O)c2C)NC1=O.O=C(O)[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O>>C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O[C@H]3[C@H](O)[C@@H](C(=O)O)O[C@@H](O)[C@@H]3O)c(CCC(=O)O)c2C)NC1=O RXN-19358
AKRT001780 C=CC1=C(C)/C(=C/c2[nH]c(Cc3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)c(CCC(=O)O)c2C)NC1=O>>C=CC1=C(C)/C(=C/C2=N/C(=C\c3[nH]c(/C=C4\NC(=O)C(C)=C4C=C)c(C)c3CCC(=O)O)C(CCC(=O)O)=C2C)NC1=O R02394