(1R*,2R*)-2-(Pyridin-2-yl)cyclopropanecarboxylic Acid [(2R,3R)-2-Amino-3-methoxybutyl]-[4'-(methoxymethyl)biphenyl-4-yl]-amide dihydrochloride

ID: ALA4452474

PubChem CID: 137628671

Max Phase: Preclinical

Molecular Formula: C28H35Cl2N3O3

Molecular Weight: 459.59

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COCc1ccc(-c2ccc(N(C[C@@H](N)[C@@H](C)OC)C(=O)[C@@H]3C[C@H]3c3ccccn3)cc2)cc1.Cl.Cl

Standard InChI:  InChI=1S/C28H33N3O3.2ClH/c1-19(34-3)26(29)17-31(28(32)25-16-24(25)27-6-4-5-15-30-27)23-13-11-22(12-14-23)21-9-7-20(8-10-21)18-33-2;;/h4-15,19,24-26H,16-18,29H2,1-3H3;2*1H/t19-,24-,25-,26-;;/m1../s1

Standard InChI Key:  YEUXFGDNARDKIP-DBJQVROASA-N

Molfile:  

     RDKit          2D

 36 37  0  0  0  0  0  0  0  0999 V2000
   19.2875  -25.4998    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.7779  -28.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7767  -29.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4917  -30.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2084  -29.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2055  -28.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4899  -28.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9156  -28.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6322  -28.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3448  -28.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3421  -27.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6209  -27.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9112  -27.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0547  -27.1911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7674  -27.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0505  -26.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7715  -28.4265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4799  -27.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3338  -25.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6212  -26.3737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3012  -27.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8873  -26.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0182  -27.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0203  -28.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7365  -28.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4498  -28.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4424  -27.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7256  -27.1669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3295  -25.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0422  -24.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6128  -24.7246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6087  -23.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0575  -30.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3515  -29.6786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6365  -30.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3705  -25.4701    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  6  8  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 15 17  2  0
 18 15  1  6
 16 19  1  0
 19 20  1  1
 21 18  1  0
 22 21  1  0
 18 22  1  0
 21 23  1  1
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 19 29  1  0
 29 30  1  6
 29 31  1  0
 31 32  1  0
  3 33  1  0
 33 34  1  0
 34 35  1  0
M  END

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: 459.59

Molecular Weight (Monoisotopic): 459.2522

AlogP: 4.39

#Rotatable Bonds: 10

Polar Surface Area: 77.68

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.59

CX LogP: 3.34

CX LogD: 2.13

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.49

Np Likeness Score: -0.61

References

1. Jin C, Decker AM, Makhijani VH, Besheer J, Darcq E, Kieffer BL, Maitra R..  (2018)  Discovery of a Potent, Selective, and Brain-Penetrant Small Molecule that Activates the Orphan Receptor GPR88 and Reduces Alcohol Intake.,  61  (15): [PMID:30011199] [10.1021/acs.jmedchem.8b00566]

2. Jin C, Decker AM, Makhijani VH, Besheer J, Darcq E, Kieffer BL, Maitra R..  (2018)  Discovery of a Potent, Selective, and Brain-Penetrant Small Molecule that Activates the Orphan Receptor GPR88 and Reduces Alcohol Intake.,  61  (15): [PMID:30011199] [10.1021/acs.jmedchem.8b00566]

Source

Source(1):

• Scientific Literature