3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

ID: ALA501680

Cas Number: 635-65-4

PubChem CID: 5280352

Product Number: np005740, Order Now?

Max Phase: Phase

Molecular Formula: C33H36N4O6

Molecular Weight: 584.67

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (4z,15z)-bilirubin ix.alpha. | Bilirubin | Bilirubin ix.alpha. | Bilirubin test | Cholerythrin | Hematoidin | NSC-26685 | bilirubin|635-65-4|Hematoidin|Hemetoidin|Bilirubin IX-alpha|Cholerythrin|Bilibubin|Bilirubin IX.alpha.|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|Bilirubin IXalpha|MFCD00005499|RFM9X3LJ49|21H-Biline-8,12-dipropShow More⌵

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

Molfile:  

     RDKit          2D

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   -1.2095   -2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -1.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3483   -4.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5094   -5.1339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3273   -5.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6334   -8.4908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4054   -7.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6867   -5.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4559   -6.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7898   -7.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801   -8.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2472   -9.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0568   -8.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
  5  1  2  0
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  9 11  1  0
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  1  2  1  0
  1 24  1  0
  3 12  1  0
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  5  6  1  0
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 27 28  1  0
 28 29  1  0
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  4  7  1  0
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  2  3  1  0
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  7  8  1  0
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 15 16  2  0
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 16 17  1  0
 34 35  2  0
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 17 13  2  0
  3  4  2  0
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  8  9  1  0
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 38 39  2  0
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 17 19  1  0
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  4  5  1  0
 38 41  1  0
 19 20  1  0
 41 42  2  0
  9 10  2  0
 37 43  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA501680

   BILIRUBIN

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

Calculated 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):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• TP-search Transporter Database
• Patent Bioactivity Data
• IMI-CARE SARS-CoV-2 Data