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

ID: ALA3559468

PubChem CID: 4186380

Max Phase: Preclinical

Molecular Formula: C16H15N3O2

Molecular Weight: 281.32

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H15N3O2/c17-16-18(10-12-6-2-1-3-7-12)13-8-4-5-9-14(13)19(16)11-15(20)21/h1-9,17H,10-11H2,(H,20,21)

Standard InChI Key:  GIDZNHVCAQXMGZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    4.0407   -7.0650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2784   -7.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535   -6.7276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9990   -6.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2034   -6.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7406   -7.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9287   -6.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4862   -7.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -8.1773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5279   -6.3152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -6.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1777   -7.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5781   -5.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9868   -5.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8538   -5.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -6.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5659   -4.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3657   -4.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -5.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4039   -4.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5791   -4.7031    0.0000 C   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  3  1  0
  8  6  1  0
  9  2  1  0
 10  8  2  0
 11  7  1  0
 12  8  1  0
 13  4  1  0
 14  5  1  0
 15 11  2  0
 16 11  1  0
 17 18  1  0
 18 13  2  0
 19 16  2  0
 20 15  1  0
 21 19  1  0
  3  5  1  0
 14 17  2  0
 21 20  2  0
M  CHG  2   1   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559468

   2-(2-Amino-3-benzylbenzimidazol-3-ium-1-yl)acetate

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: 281.32

Molecular Weight (Monoisotopic): 281.1164

AlogP: 0.31

#Rotatable Bonds: 4

Polar Surface Area: 74.96

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.30

CX Basic pKa: ┄

CX LogP: -1.85

CX LogD: -2.08

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.70

Np Likeness Score: -0.80

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