2-(4-Ethylsulfanyl-3-methyl-pyridin-2-ylmethanesulfinyl)-benzoimidazole-1-carboxylic acid 4-nitro-benzyl ester

ID: ALA275283

PubChem CID: 14877913

Max Phase: Preclinical

Molecular Formula: C24H22N4O5S2

Molecular Weight: 510.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSc1ccnc(C[S+]([O-])c2nc3ccccc3n2C(=O)OCc2ccc([N+](=O)[O-])cc2)c1C

Standard InChI:  InChI=1S/C24H22N4O5S2/c1-3-34-22-12-13-25-20(16(22)2)15-35(32)23-26-19-6-4-5-7-21(19)27(23)24(29)33-14-17-8-10-18(11-9-17)28(30)31/h4-13H,3,14-15H2,1-2H3

Standard InChI Key:  XHVRBDKLEAIHJP-UHFFFAOYSA-N

Molfile:  

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M  CHG  4   4   1   6   1  14  -1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA275283

   2-(4-Ethylsulfanyl-3-methyl-pyridin-2-ylmethanesulfinyl)-benzoimidazole-1-carboxylic acid 4-nitro-benzyl ester

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: 510.60

Molecular Weight (Monoisotopic): 510.1032

AlogP: 5.25

#Rotatable Bonds: 8

Polar Surface Area: 123.21

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.37

CX Basic pKa: 2.86

CX LogP: 4.72

CX LogD: 4.72

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.14

Np Likeness Score: -1.05

References

1. Sih JC, Im WB, Robert A, Graber DR, Blakeman DP..  (1991)  Studies on (H(+)-K+)-ATPase inhibitors of gastric acid secretion. Prodrugs of 2-[(2-pyridinylmethyl)sulfinyl]benzimidazole proton-pump inhibitors.,  34  (3): [PMID:1848293] [10.1021/jm00107a026]

Source

Source(1):

• Scientific Literature