(2E)-2-(2-ethyl-5-methyl-pyrazole-3-carbonyl)imino-1-[(2S)-2-hydroxy-2-phenyl-ethyl]-3H-benzimidazole-5-carboxamide

ID: ALA4522871

PubChem CID: 138976714

Max Phase: Preclinical

Molecular Formula: C23H24N6O3

Molecular Weight: 432.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCn1nc(C)cc1C(=O)/N=c1\[nH]c2cc(C(N)=O)ccc2n1C[C@@H](O)c1ccccc1

Standard InChI:  InChI=1S/C23H24N6O3/c1-3-29-19(11-14(2)27-29)22(32)26-23-25-17-12-16(21(24)31)9-10-18(17)28(23)13-20(30)15-7-5-4-6-8-15/h4-12,20,30H,3,13H2,1-2H3,(H2,24,31)(H,25,26,32)/t20-/m1/s1

Standard InChI Key:  NMXJYHHOVIHSBO-HXUWFJFHSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   33.6281  -15.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3416  -15.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3416  -14.3383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0554  -15.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7695  -15.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4838  -15.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4838  -16.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7720  -16.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0554  -16.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9144  -15.1643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1575  -15.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6056  -14.8841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0204  -14.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8243  -14.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3794  -13.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1208  -12.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3180  -12.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7660  -13.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1044  -11.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3067  -11.7636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6883  -11.3931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9437  -16.2966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1495  -16.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9357  -17.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4530  -17.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0022  -18.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2086  -18.4263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1636  -17.6023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4504  -17.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7372  -17.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2158  -19.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5649  -15.9259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  5  4  2  0
  6  5  1  0
  7  6  2  0
  8  7  1  0
  9  8  2  0
  4  9  1  0
  1 10  1  0
 11 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 13 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 11 22  2  0
 22 23  1  0
 23 24  1  0
 25 24  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  1  0
 28 29  1  0
 29 30  1  0
 26 31  1  0
 23 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4522871

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 432.48

Molecular Weight (Monoisotopic): 432.1910

AlogP: 2.07

#Rotatable Bonds: 6

Polar Surface Area: 131.29

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.83

CX LogP: 1.35

CX LogD: 1.35

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -1.67

References

1. Zhang H, You QD, Xu XL..  (2020)  Targeting Stimulator of Interferon Genes (STING): A Medicinal Chemistry Perspective.,  63  (8): [PMID:31820978] [10.1021/acs.jmedchem.9b01039]

2. Liu Y, Lu X, Qin N, Qiao Y, Xing S, Liu W, Feng F, Liu Z, Sun H..  (2021)  STING, a promising target for small molecular immune modulator: A review.,  211  [PMID:33360799] [10.1016/j.ejmech.2020.113113]

3. Niu J, Bai H, Li Z, Gao Y, Zhang Y, Wang X, Yang Y, Xu Y, Geng M, Xie Z, Zhou B..  (2022)  Discovery of novel Thieno[2,3-d]imidazole derivatives as agonists of human STING for antitumor immunotherapy using systemic administration.,  238  [PMID:35671593] [10.1016/j.ejmech.2022.114482]

4. Jeon MJ, Lee H, Lee J, Baek SY, Lee D, Jo S, Lee JY, Kang M, Jung HR, Han SB, Kim NJ, Lee S, Kim H..  (2022)  Development of Potent Immune Modulators Targeting Stimulator of Interferon Genes Receptor.,  65  (7.0): [PMID:35315650] [10.1021/acs.jmedchem.1c01795]

Source

Source(1):

• Scientific Literature