Bilirubin bisglucuronide

ID: ALA3038248

Chembl Id: CHEMBL3038248

PubChem CID: 73354261

Max Phase: Preclinical

Molecular Formula: C45H52N4O18

Molecular Weight: 936.92

Molecule Type: Small molecule

Names and Identifiers

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@@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

Standard InChI:  InChI=1S/C45H52N4O18/c1-7-20-19(6)40(58)49-27(20)14-25-18(5)23(10-12-31(51)65-45-37(57)33(53)35(55)39(67-45)43(62)63)29(47-25)15-28-22(17(4)24(46-28)13-26-16(3)21(8-2)41(59)48-26)9-11-30(50)64-44-36(56)32(52)34(54)38(66-44)42(60)61/h7-8,13-14,32-39,44-47,52-57H,1-2,9-12,15H2,3-6H3,(H,48,59)(H,49,58)(H,60,61)(H,62,63)/b26-13-,27-14-/t32-,33+,34+,35+,36-,37-,38-,39+,44+,45+/m0/s1

Standard InChI Key:  SCJLWMXOOYZBTH-VVYCZZSLSA-N

Alternative Forms

1. Parent:

   

   ALA3038248

   (2S,3R,4S,5S,6S)-6-[3-[2-[[3-[3-[(2S,3S,4R,5R,6R)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy-3-oxopropyl]-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-meth

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 936.92

Molecular Weight (Monoisotopic): 936.3277

AlogP: -0.77

#Rotatable Bonds: 16

Polar Surface Area: 356.82

Molecular Species: ACID

HBA: 16

HBD: 12

#RO5 Violations: 3

HBA (Lipinski): 22

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.97

CX Basic pKa:

CX LogP: -0.78

CX LogD: -7.64

Aromatic Rings: 2

Heavy Atoms: 67

QED Weighted: 0.09

Np Likeness Score: 1.03

References

1. 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]

2. Kamisako T, Leier I, Cui Y, König J, Buchholz U, Hummel-Eisenbeiss J, Keppler D..  (1999)  Transport of monoglucuronosyl and bisglucuronosyl bilirubin by recombinant human and rat multidrug resistance protein 2.,  30  (1): [PMID:10421658] [10.1002/hep.510300220]

3. Nishida T, Gatmaitan Z, Roy-Chowdhry J, Arias IM..  (1992)  Two distinct mechanisms for bilirubin glucuronide transport by rat bile canalicular membrane vesicles. Demonstration of defective ATP-dependent transport in rats (TR-) with inherited conjugated hyperbilirubinemia.,  90  (1): [PMID:1430236] [10.1172/jci116098]

4. Jedlitschky G, Leier I, Buchholz U, Hummel-Eisenbeiss J, Burchell B, Keppler D..  (1997)  ATP-dependent transport of bilirubin glucuronides by the multidrug resistance protein MRP1 and its hepatocyte canalicular isoform MRP2.,  327  (1): [PMID:9355767] [10.1042/bj3270305]

Source

Source(1):

• TP-search Transporter Database