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

ID: ALA422615

PubChem CID: 44354311

Max Phase: Preclinical

Molecular Formula: C23H19N3O5S

Molecular Weight: 449.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1nc2cc(C(=O)c3cc(CC(=O)OCc4ccccc4)cs3)ccc2[nH]1

Standard InChI:  InChI=1S/C23H19N3O5S/c1-30-23(29)26-22-24-17-8-7-16(11-18(17)25-22)21(28)19-9-15(13-32-19)10-20(27)31-12-14-5-3-2-4-6-14/h2-9,11,13H,10,12H2,1H3,(H2,24,25,26,29)

Standard InChI Key:  UPSZUFCDHDURFZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.0542   -5.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -6.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -7.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2750   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -5.8542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -5.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -6.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1917   -7.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -7.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -8.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7500   -6.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7750   -8.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125   -9.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3292   -5.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333   -9.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208  -10.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583  -11.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625  -10.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833  -11.1292    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 16  1  0
 24 10  1  0
 25 23  1  0
 26 25  1  0
 27 24  1  0
 28 26  2  0
 29 26  1  0
 30 29  2  0
 31 28  1  0
 32 30  1  0
 11  6  1  0
 12 18  2  0
 13 14  2  0
 32 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA422615

   [5-(2-Methoxycarbonylamino-1H-benzoimidazole-5-carbonyl)-thiophen-3-yl]-acetic acid benzyl 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: 449.49

Molecular Weight (Monoisotopic): 449.1045

AlogP: 4.32

#Rotatable Bonds: 7

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: 4.68

CX LogD: 4.67

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: -0.97

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