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BILIRUBIN
ID: ALA501680
Max Phase: Phase
Molecular Formula: C33H36N4O6
Molecular Weight: 584.67
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (7): (4z,15z)-bilirubin ix.alpha. | Bilirubin | Bilirubin ix.alpha. | Bilirubin test | Cholerythrin | Hematoidin | NSC-26685
Synonyms from Alternative Forms(7):
Canonical SMILES: 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
Standard 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-
Standard InChI Key: BPYKTIZUTYGOLE-IFADSCNNSA-N
Associated Targets(Human)
Caco-2 (12174 Activities)
MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
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LMNA Tbio Prelamin-A/C (36751 Activities)
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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)
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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
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CASP7 Tchem Caspase-7 (3146 Activities)
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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
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MAPT Tclin Microtubule-associated protein tau (95507 Activities)
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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
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CASP1 Tchem Caspase-1 (6235 Activities)
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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
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UGT1A1 Tchem UDP-glucuronosyltransferase 1-1 (448 Activities)
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VDR Tclin Vitamin D receptor (26531 Activities)
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POLK Tbio DNA polymerase kappa (8653 Activities)
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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)
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UGT1A4 Tbio UDP-glucuronosyltransferase 1A4 (288 Activities)
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UGT1A6 Tbio UDP-glucuronosyltransferase 1-6 (221 Activities)
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UGT1A9 Tbio UDP-glucuronosyltransferase 1-9 (343 Activities)
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UGT2B17 Tbio UDP-glucuronosyltransferase 2B17 (197 Activities)
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UGT2B7 Tchem UDP-glucuronosyltransferase 2B7 (787 Activities)
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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
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SLCO1A2 Tchem Solute carrier organic anion transporter family member 1A2 (104 Activities)
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MRGPRX4 Tchem Mas-related G-protein coupled receptor member X4 (415 Activities)
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Associated Targets(non-human)
Cruzipain (33337 Activities)
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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
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Impa1 Inositol monophosphatase 1 (16203 Activities)
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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)
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Slco1a1 Solute carrier organic anion transporter family member 1A1 (265 Activities)
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Salmonella typhimurium (15756 Activities)
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SARS-CoV-2 (38078 Activities)
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: Yes | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 584.67 | Molecular Weight (Monoisotopic): 584.2635 | AlogP: 4.53 | #Rotatable Bonds: 12 |
| Polar Surface Area: 164.38 | Molecular Species: ACID | HBA: 4 | HBD: 6 |
| #RO5 Violations: 2 | HBA (Lipinski): 10 | HBD (Lipinski): 6 | #RO5 Violations (Lipinski): 2 |
| CX Acidic pKa: 4.03 | CX Basic pKa: | CX LogP: 3.12 | CX LogD: -2.76 |
| Aromatic Rings: 2 | Heavy Atoms: 43 | QED Weighted: 0.21 | Np Likeness Score: 0.91 |
References
| 1. Bulmer AC, Blanchfield JT, Coombes JS, Toth I.. (2008) In vitro permeability and metabolic stability of bile pigments and the effects of hydrophilic and lipophilic modification of biliverdin., 16 (7): [PMID:18304823] [10.1016/j.bmc.2008.02.008] |
| 2. PubChem BioAssay data set, |
| 3. Lowe R, Glen RC, Mitchell JB.. (2010) Predicting phospholipidosis using machine learning., 7 (5): [PMID:20799726] [10.1021/mp100103e] |
| 4. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF.. (2008) Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models., 18 (2): [PMID:20020916] [10.1080/15376510701857262] |
| 5. International Transporter Consortium, Giacomini KM, Huang SM, Tweedie DJ, Benet LZ, Brouwer KL, Chu X, Dahlin A, Evers R, Fischer V, Hillgren KM, Hoffmaster KA, Ishikawa T, Keppler D, Kim RB, Lee CA, Niemi M, Polli JW, Sugiyama Y, Swaan PW, Ware JA, Wright SH, Yee SW, Zamek-Gliszczynski MJ, Zhang L.. (2010) Membrane transporters in drug development., 9 (3): [PMID:20190787] [10.1038/nrd3028] |
| 6. (2008) Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, |
| 7. Tukey RH, Strassburg CP.. (2000) Human UDP-glucuronosyltransferases: metabolism, expression, and disease., 40 (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581] |
| 8. Briz O, Serrano MA, MacIas RI, Gonzalez-Gallego J, Marin JJ.. (2003) 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., 371 (1): [PMID:12568656] [10.1042/bj20030034] |
| 9. Kullak-Ublick GA, Hagenbuch B, Stieger B, Wolkoff AW, Meier PJ.. (1994) Functional characterization of the basolateral rat liver organic anion transporting polypeptide., 20 (1): [PMID:8045503] [10.1016/0270-9139(94)90194-5] |
| 10. Cui Y, König J, Leier I, Buchholz U, Keppler D.. (2001) Hepatic uptake of bilirubin and its conjugates by the human organic anion transporter SLC21A6., 276 (1): [PMID:11134001] [10.1074/jbc.m004968200] |
| 11. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP.. (2013) Structure-based identification of OATP1B1/3 inhibitors., 83 (6): [PMID:23571415] [10.1124/mol.112.084152] |
| 12. Mölzer C, Huber H, Steyrer A, Ziesel GV, Wallner M, Hong HT, Blanchfield JT, Bulmer AC, Wagner KH.. (2013) Bilirubin and related tetrapyrroles inhibit food-borne mutagenesis: a mechanism for antigenotoxic action against a model epoxide., 76 (10): [PMID:24156291] [10.1021/np4005807] |
| 13. Unpublished dataset, |
| 14. Ellen Van Damme. (2021) Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity, [10.6019/CHEMBL4651402] |
| 15. (2020) Modulators of mas-related g-protein receptor x4 and related products and methods, |
Source
Source(6):