2-Amino-3-benzyl-1-phenylcarbamoylmethyl-3H-benzoimidazol-1-ium

ID: ALA3559459

PubChem CID: 118753782

Max Phase: Preclinical

Molecular Formula: C24H22N4O5

Molecular Weight: 357.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1n(Cc2ccccc2)c2ccccc2[n+]1CC(=O)Nc1ccccc1.O=C([O-])C(=O)O

Standard InChI:  InChI=1S/C22H20N4O.C2H2O4/c23-22-25(15-17-9-3-1-4-10-17)19-13-7-8-14-20(19)26(22)16-21(27)24-18-11-5-2-6-12-18;3-1(4)2(5)6/h1-14,23H,15-16H2,(H,24,27);(H,3,4)(H,5,6)

Standard InChI Key:  MSZTWDZQFPLPMY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    1.4943   -7.0163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7340   -7.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2105   -6.6798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444   -6.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6550   -5.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1923   -7.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277   -7.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6122   -6.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257   -7.5440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5345   -8.1174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9775   -6.2685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3569   -7.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0609   -6.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303   -5.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4348   -5.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0466   -7.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3985   -6.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -6.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -5.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184   -4.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165   -4.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399   -4.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7820   -7.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1339   -5.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322   -5.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583   -4.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8194   -6.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6568   -2.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3698   -3.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9438   -3.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0828   -2.9063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6568   -2.0765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3698   -4.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  4  2  0
  6  1  1  0
  7  6  1  0
  8  3  1  0
  9  7  1  0
 10  2  1  0
 11  7  2  0
 12  9  1  0
 13  8  1  0
 14  4  1  0
 15  5  1  0
 16 12  2  0
 17 12  1  0
 18 13  1  0
 19 13  2  0
 20 14  2  0
 21 20  1  0
 22 19  1  0
 23 16  1  0
 24 17  2  0
 25 18  2  0
 26 22  2  0
 27 24  1  0
  3  5  1  0
 15 21  2  0
 27 23  2  0
 26 25  1  0
 29 28  1  0
 30 28  1  0
 31 29  1  0
 32 28  2  0
 33 29  2  0
M  CHG  2   1   1  30  -1
M  END

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: 357.44

Molecular Weight (Monoisotopic): 357.1710

AlogP: 3.20

#Rotatable Bonds: 5

Polar Surface Area: 63.93

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.96

CX Basic pKa: ┄

CX LogP: -0.41

CX LogD: -0.41

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: -1.10

References

1. Ramström H, Bourotte M, Philippe C, Schmitt M, Haiech J, Bourguignon JJ..  (2004)  Heterocyclic bis-cations as starting hits for design of inhibitors of the bifunctional enzyme histidine-containing protein kinase/phosphatase from Bacillus subtilis.,  47  (9): [PMID:15084125] [10.1021/jm021043o]

Source

Source(1):

• Scientific Literature