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

ID: ALA133900

PubChem CID: 44354712

Max Phase: Preclinical

Molecular Formula: C20H21N3O5S

Molecular Weight: 415.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H21N3O5S/c1-20(2,3)28-16(24)8-11-7-15(29-10-11)17(25)12-5-6-13-14(9-12)22-18(21-13)23-19(26)27-4/h5-7,9-10H,8H2,1-4H3,(H2,21,22,23,26)

Standard InChI Key:  XZBCJXRKHAFCOB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    8.6292   -5.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1417   -5.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -5.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1417   -6.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4542   -5.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -5.0500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -4.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -6.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0417   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -6.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -6.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -7.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -5.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -7.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8250   -4.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -7.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -6.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -4.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -6.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417   -6.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125   -8.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8292   -5.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -8.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -7.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -8.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4167   -4.8375    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 16  1  0
 13  9  1  0
 14 19  1  0
 15  7  1  0
 16  6  2  0
 17 14  1  0
 18 10  2  0
 19 13  1  0
 20 23  1  0
 21  8  2  0
 22 14  2  0
 23 11  2  0
 24 17  1  0
 25 10  1  0
 26 24  1  0
 27 24  1  0
 28 24  1  0
 29 25  1  0
 11  6  1  0
 12 20  2  0
 13 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA133900

   [5-(2-Methoxycarbonylamino-1H-benzoimidazole-5-carbonyl)-thiophen-3-yl]-acetic acid tert-butyl 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: 415.47

Molecular Weight (Monoisotopic): 415.1202

AlogP: 3.92

#Rotatable Bonds: 5

Polar Surface Area: 110.38

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.11

CX Basic pKa: 3.34

CX LogP: 4.01

CX LogD: 4.00

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: -1.04

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