N-((1S,2S)-2-hydroxycyclohexyl)-1-(4-methoxybenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide

ID: ALA4546244

PubChem CID: 117937668

Max Phase: Preclinical

Molecular Formula: C22H25N3O3

Molecular Weight: 379.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(Cn2cc(C(=O)N[C@H]3CCCC[C@@H]3O)c3ncccc32)cc1

Standard InChI:  InChI=1S/C22H25N3O3/c1-28-16-10-8-15(9-11-16)13-25-14-17(21-19(25)6-4-12-23-21)22(27)24-18-5-2-3-7-20(18)26/h4,6,8-12,14,18,20,26H,2-3,5,7,13H2,1H3,(H,24,27)/t18-,20-/m0/s1

Standard InChI Key:  KQYFNYPILBBWOB-ICSRJNTNSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   28.1683   -2.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7319   -3.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7307   -4.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4388   -4.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4370   -3.1364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1456   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1504   -4.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9304   -4.6087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4078   -3.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9227   -3.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1874   -5.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9878   -5.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2396   -6.3254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0390   -6.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5832   -5.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3224   -5.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5235   -4.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3838   -6.0442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6418   -6.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6163   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9662   -2.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8621   -1.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6657   -0.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9123   -0.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3631    0.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5639    0.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3139   -0.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5157   -0.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
 10  1  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  2  0
 22 20  1  6
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4546244

   US10072005, Example 93

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: 379.46

Molecular Weight (Monoisotopic): 379.1896

AlogP: 3.13

#Rotatable Bonds: 5

Polar Surface Area: 76.38

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.48

CX LogP: 2.83

CX LogD: 2.83

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -0.79

References

1. Wold EA, Chen J, Cunningham KA, Zhou J..  (2018)  Allosteric Modulation of Class A GPCRs: Targets, Agents, and Emerging Concepts.,  62  (1): [PMID:30106578] [10.1021/acs.jmedchem.8b00875]

Source

Source(1):

• Scientific Literature