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

ID: ALA130090

PubChem CID: 44354290

Max Phase: Preclinical

Molecular Formula: C15H13N3O4S

Molecular Weight: 331.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H13N3O4S/c1-22-15(21)18-14-16-10-3-2-9(5-11(10)17-14)13(20)12-4-8(6-19)7-23-12/h2-5,7,19H,6H2,1H3,(H2,16,17,18,21)

Standard InChI Key:  PRMSXBKAEWYKDJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   12.0500   -1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5625   -0.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5625   -1.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8750   -1.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7792   -0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1750   -0.3917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6417   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8417   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4542   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7792   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3542   -0.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0625   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2417    0.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3542   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6375    0.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0625   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2542   -0.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8375   -0.1792    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 13  1  0
 22 21  1  0
 23 20  1  0
 11  6  1  0
 12 17  2  0
 13 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA130090

   [5-(4-Hydroxymethyl-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: 331.35

Molecular Weight (Monoisotopic): 331.0627

AlogP: 2.53

#Rotatable Bonds: 4

Polar Surface Area: 104.31

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.11

CX Basic pKa: 3.34

CX LogP: 2.41

CX LogD: 2.40

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.64

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