3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid

ID: ALA2063284

PubChem CID: 60150582

Max Phase: Preclinical

Molecular Formula: C29H31N3O3

Molecular Weight: 469.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(CCC(=O)O)cc(C)c1-c1nc2ccc(C(=O)Nc3ccc(C(C)(C)C)cc3)cc2[nH]1

Standard InChI:  InChI=1S/C29H31N3O3/c1-17-14-19(6-13-25(33)34)15-18(2)26(17)27-31-23-12-7-20(16-24(23)32-27)28(35)30-22-10-8-21(9-11-22)29(3,4)5/h7-12,14-16H,6,13H2,1-5H3,(H,30,35)(H,31,32)(H,33,34)

Standard InChI Key:  LDGXQPOCIGRAMC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.2349  -14.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497  -14.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9479  -13.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6633  -13.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6636  -14.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4540  -14.6256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424  -13.9531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9964  -13.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1735  -13.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799  -14.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7632  -15.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6222  -14.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3365  -14.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3376  -15.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184  -16.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9071  -15.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0519  -16.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2385  -13.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6522  -14.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4772  -14.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8909  -15.3771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8885  -13.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7666  -15.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0514  -16.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7708  -16.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 16 18  2  0
  8  9  2  0
 17 19  1  0
  9  5  1  0
 15 20  1  0
  4  1  1  0
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  5  6  1  0
 19 22  2  0
 10 11  2  0
 22 23  1  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
  2  3  1  0
 25 26  2  0
 26 19  1  0
 12 13  2  0
 24 27  1  0
  3  6  2  0
 13 28  1  0
 13 14  1  0
 28 29  1  0
  1  2  2  0
 29 30  1  0
 14 15  2  0
 30 31  1  0
 15 10  1  0
 30 32  2  0
  8 10  1  0
 27 33  1  0
  5  4  2  0
 27 34  1  0
  2 16  1  0
 27 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2063284

   3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid

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: 469.59

Molecular Weight (Monoisotopic): 469.2365

AlogP: 6.41

#Rotatable Bonds: 6

Polar Surface Area: 95.08

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.12

CX Basic pKa: 4.49

CX LogP: 6.46

CX LogD: 4.53

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.30

Np Likeness Score: -0.95

References

1. Serrano-Wu MH, Coppola GM, Gong Y, Neubert AD, Chatelain R, Clairmont KB, Commerford R, Cosker T, Daniels T, Hou Y, Jain M, Juedes M, Li L, Mullarkey T, Rocheford E, Sung MJ, Tyler A, Yang Q, Yoon T, Hubbard BK..  (2012)  Intestinally Targeted Diacylglycerol Acyltransferase 1 (DGAT1) Inhibitors Robustly Suppress Postprandial Triglycerides.,  3  (5): [PMID:24900485] [10.1021/ml3000512]

2. 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