3-(4-(6-(5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl)-1H-benzo[d]imidazol-2-yl)-3,5-dimethylphenyl)-2,2-dimethylpropanoic Acid sodium

ID: ALA4098214

PubChem CID: 137661810

Max Phase: Preclinical

Molecular Formula: C29H28N4NaO4+

Molecular Weight: 496.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2nnc(-c3ccc4nc(-c5c(C)cc(CC(C)(C)C(=O)O)cc5C)[nH]c4c3)o2)cc1.[Na+]

Standard InChI:  InChI=1S/C29H28N4O4.Na/c1-16-12-18(15-29(3,4)28(34)35)13-17(2)24(16)25-30-22-11-8-20(14-23(22)31-25)27-33-32-26(37-27)19-6-9-21(36-5)10-7-19;/h6-14H,15H2,1-5H3,(H,30,31)(H,34,35);/q;+1

Standard InChI Key:  CDJLBSTYCHKNOF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 38 41  0  0  0  0  0  0  0  0999 V2000
   26.9564  -17.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9605  -17.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2505  -17.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7313  -16.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9830  -16.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5551  -16.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7547  -18.1224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9878  -16.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3833  -16.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0875  -17.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0768  -17.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3220  -17.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7679  -15.7948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4974  -17.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2350  -18.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2578  -16.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8390  -17.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5352  -17.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0831  -16.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5633  -16.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9473  -18.2934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4868  -15.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4160  -18.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5540  -16.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3099  -15.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7756  -17.1326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2674  -15.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0670  -15.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2691  -17.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2559  -17.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7144  -17.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0879  -16.9653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9230  -16.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5487  -16.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7800  -17.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1939  -17.8455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1837  -16.4295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7419  -19.2481    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
 11 23  1  0
 23 15  2  0
 16 13  2  0
 11 30  1  0
 32 18  1  0
 15 31  1  0
 18 21  2  0
 27  6  1  0
 31  9  2  0
 22 19  1  0
 20 11  2  0
  6 24  2  0
  5  8  1  0
 14 10  1  0
 29  8  2  0
 14 12  1  0
 24 29  1  0
 16 19  1  0
 24 17  1  0
 17 32  1  0
 21  7  1  0
  4 25  1  0
  7 17  2  0
 26 16  1  0
  9 20  1  0
 19 14  2  0
 22 28  1  0
  5 27  2  0
  8 26  1  0
 12  4  2  0
 13  5  1  0
 25 22  2  0
 18 31  1  0
 30 33  1  0
  4 34  1  0
 34  2  1  0
  2 35  1  0
 35 36  1  0
 35 37  2  0
M  CHG  1  38   1
M  END

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: 496.57

Molecular Weight (Monoisotopic): 496.2111

AlogP: 6.23

#Rotatable Bonds: 7

Polar Surface Area: 114.13

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.07

CX Basic pKa: 4.42

CX LogP: 5.82

CX LogD: 3.85

Aromatic Rings: 5

Heavy Atoms: 37

QED Weighted: 0.27

Np Likeness Score: -0.51

References

1. Nakajima K, Chatelain R, Clairmont KB, Commerford R, Coppola GM, Daniels T, Forster CJ, Gilmore TA, Gong Y, Jain M, Kanter A, Kwak Y, Li J, Meyers CD, Neubert AD, Szklennik P, Tedesco V, Thompson J, Truong D, Yang Q, Hubbard BK, Serrano-Wu MH..  (2017)  Discovery of an Orally Bioavailable Benzimidazole Diacylglycerol Acyltransferase 1 (DGAT1) Inhibitor That Suppresses Body Weight Gain in Diet-Induced Obese Dogs and Postprandial Triglycerides in Humans.,  60  (11): [PMID:28498655] [10.1021/acs.jmedchem.7b00173]

Source

Source(1):

• Scientific Literature