(E)-3-(1H-benzo[d]imidazol-2-yl)-4-(4-bromophenyl)but-3-enoic acid

ID: ALA4865698

PubChem CID: 94364702

Max Phase: Preclinical

Molecular Formula: C17H13BrN2O2

Molecular Weight: 357.21

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)C/C(=C\c1ccc(Br)cc1)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C17H13BrN2O2/c18-13-7-5-11(6-8-13)9-12(10-16(21)22)17-19-14-3-1-2-4-15(14)20-17/h1-9H,10H2,(H,19,20)(H,21,22)/b12-9+

Standard InChI Key:  JRLYJZRWIKEQPA-FMIVXFBMSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   19.0540  -22.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0529  -23.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7609  -24.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7591  -22.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4677  -22.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4680  -23.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2466  -24.0193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7277  -23.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2462  -22.6947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5449  -23.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9537  -24.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9532  -22.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7704  -22.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1748  -23.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9913  -23.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4004  -22.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9872  -21.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1721  -21.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5454  -24.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9542  -25.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7282  -24.7722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2176  -22.6474    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
 16 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4865698

   (E)-3-(1H-benzimidazol-2-yl)-4-(4-bromophenyl)but-3-enoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 357.21

Molecular Weight (Monoisotopic): 356.0160

AlogP: 4.34

#Rotatable Bonds: 4

Polar Surface Area: 65.98

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.56

CX Basic pKa: 5.22

CX LogP: 2.81

CX LogD: 0.95

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.73

Np Likeness Score: -0.57

References

1. Azuma M, Inoue M, Nishida A, Akahane H, Kitajima M, Natani S, Chimori R, Yoshimori A, Mano Y, Uchiro H, Tanuma SI, Takasawa R..  (2021)  Addition of hydrophobic side chains improve the apoptosis inducibility of the human glyoxalase I inhibitor, TLSC702.,  40  [PMID:33711442] [10.1016/j.bmcl.2021.127918]

Source

Source(1):

• Scientific Literature