[5-(2-Methoxycarbonylamino-1H-benzoimidazole-5-carbonyl)-thiophen-3-yl]-acetic acid

ID: ALA130169

PubChem CID: 44354334

Max Phase: Preclinical

Molecular Formula: C16H13N3O5S

Molecular Weight: 359.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1nc2cc(C(=O)c3cc(CC(=O)O)cs3)ccc2[nH]1

Standard InChI:  InChI=1S/C16H13N3O5S/c1-24-16(23)19-15-17-10-3-2-9(6-11(10)18-15)14(22)12-4-8(7-25-12)5-13(20)21/h2-4,6-7H,5H2,1H3,(H,20,21)(H2,17,18,19,23)

Standard InChI Key:  XEOMNHSYWULZPF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    6.4542   -8.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -7.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -8.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -9.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2750   -8.5625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -8.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -7.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -7.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -8.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8625   -7.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -8.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -8.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -9.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -8.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -7.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -9.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -7.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -8.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -6.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -9.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -9.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000   -9.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6542   -8.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500  -10.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417   -7.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  8  1  0
  4  1  1  0
  5  1  1  0
  6  2  1  0
  7  3  1  0
  8 12  1  0
  9  3  2  0
 10  5  1  0
 11  4  1  0
 12 15  1  0
 13  9  1  0
 14  7  1  0
 15  6  2  0
 16 21  1  0
 17 10  2  0
 18 20  1  0
 19  8  2  0
 20 11  2  0
 21 13  1  0
 22 16  2  0
 23 10  1  0
 24 16  1  0
 25 23  1  0
 11  6  1  0
 12 18  2  0
 13 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA130169

   [5-(2-Methoxycarbonylamino-1H-benzoimidazole-5-carbonyl)-thiophen-3-yl]-acetic 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: 359.36

Molecular Weight (Monoisotopic): 359.0576

AlogP: 2.66

#Rotatable Bonds: 5

Polar Surface Area: 121.38

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.13

CX Basic pKa: 3.24

CX LogP: 2.43

CX LogD: -0.34

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: -1.00

References

1. Kruse LI, Ladd DL, Harrsch PB, McCabe FL, Mong SM, Faucette L, Johnson R..  (1989)  Synthesis, tubulin binding, antineoplastic evaluation, and structure-activity relationship of oncodazole analogues.,  32  (2): [PMID:2913301] [10.1021/jm00122a020]

Source

Source(1):

• Scientific Literature