5-Bromo-3-[(5-chloro-2-pyridyl)carbamoyl]-2-[(1-isopropylpiperidine-4-carbonyl)amino]phenyl b-D-glucopyranosiduronic acid

ID: ALA3354240

PubChem CID: 57594784

Max Phase: Preclinical

Molecular Formula: C27H32BrClN4O9

Molecular Weight: 671.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)N1CCC(C(=O)Nc2c(O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)cc(Br)cc2C(=O)Nc2ccc(Cl)cn2)CC1

Standard InChI:  InChI=1S/C27H32BrClN4O9/c1-12(2)33-7-5-13(6-8-33)24(37)32-19-16(25(38)31-18-4-3-15(29)11-30-18)9-14(28)10-17(19)41-27-22(36)20(34)21(35)23(42-27)26(39)40/h3-4,9-13,20-23,27,34-36H,5-8H2,1-2H3,(H,32,37)(H,39,40)(H,30,31,38)/t20-,21-,22+,23-,27+/m0/s1

Standard InChI Key:  FBJRMUJFXZHZGF-XJYXAJQWSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3354240

   (2S,3S,4S,5R,6S)-6-[5-bromo-3-[(5-chloropyridin-2-yl)carbamoyl]-2-[(1-propan-2-ylpiperidine-4-carbonyl)amino]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

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: 671.93

Molecular Weight (Monoisotopic): 670.1041

AlogP: 2.08

#Rotatable Bonds: 8

Polar Surface Area: 190.78

Molecular Species: ZWITTERION

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.42

CX Basic pKa: 9.37

CX LogP: -0.67

CX LogD: -0.67

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.24

Np Likeness Score: -0.60

References

1. Ishihara T, Koga Y, Mori K, Sugasawa K, Iwatsuki Y, Hirayama F..  (2014)  Novel strategy to boost oral anticoagulant activity of blood coagulation enzyme inhibitors based on biotransformation into hydrophilic conjugates.,  22  (22): [PMID:25438755] [10.1016/j.bmc.2014.09.059]

Source

Source(1):

• Scientific Literature