[5-(4-Aminomethyl-thiophene-2-carbonyl)-1H-benzoimidazol-2-yl]-carbamic acid methyl ester

ID: ALA336324

PubChem CID: 44354347

Max Phase: Preclinical

Molecular Formula: C15H14N4O3S

Molecular Weight: 330.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H14N4O3S/c1-22-15(21)19-14-17-10-3-2-9(5-11(10)18-14)13(20)12-4-8(6-16)7-23-12/h2-5,7H,6,16H2,1H3,(H2,17,18,19,21)

Standard InChI Key:  XGSRCSPKGNSPMJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    6.5417   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    7.3667   -6.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    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
    5.2750   -7.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -7.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -6.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7375   -5.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -7.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -7.4292    0.0000 C   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
    1.6792   -8.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917   -7.9375    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
  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 10  2  0
 17 19  1  0
 18  8  2  0
 19 11  2  0
 20 10  1  0
 21 22  1  0
 22 13  1  0
 23 20  1  0
 11  6  1  0
 12 17  2  0
 13 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA336324

   [5-(4-Aminomethyl-thiophene-2-carbonyl)-1H-benzoimidazol-2-yl]-carbamic acid methyl 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: 330.37

Molecular Weight (Monoisotopic): 330.0787

AlogP: 2.49

#Rotatable Bonds: 4

Polar Surface Area: 110.10

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.22

CX Basic pKa: 8.44

CX LogP: 1.96

CX LogD: 1.12

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: -1.15

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