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

ID: ALA4550415

PubChem CID: 155555151

Max Phase: Preclinical

Molecular Formula: C27H33Cl2N3O3

Molecular Weight: 445.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(-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/C27H31N3O3.2ClH/c1-18(32-2)25(28)17-30(27(31)24-16-23(24)26-6-4-5-15-29-26)21-11-7-19(8-12-21)20-9-13-22(33-3)14-10-20;;/h4-15,18,23-25H,16-17,28H2,1-3H3;2*1H/t18-,23-,24-,25-;;/m1../s1

Standard InChI Key:  DWZQZUULIDASJG-NXMUYZBISA-N

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
   10.0333  -25.2164    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9006  -28.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995  -29.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149  -29.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3319  -29.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290  -28.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6131  -28.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394  -28.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521  -28.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4651  -28.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4625  -27.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7410  -26.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0350  -27.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1754  -26.9143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8926  -27.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1713  -26.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8967  -28.1502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6055  -26.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542  -25.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7412  -26.0965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4272  -26.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0090  -26.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1446  -27.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1467  -28.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8632  -28.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5727  -28.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5653  -27.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8523  -26.8901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4499  -24.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1628  -24.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7328  -24.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7286  -23.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1841  -29.8182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4694  -29.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9086  -25.1571    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
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: 445.56

Molecular Weight (Monoisotopic): 445.2365

AlogP: 4.26

#Rotatable Bonds: 9

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: 3.31

CX LogD: 2.10

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.53

Np Likeness Score: -0.59

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]

Source

Source(1):

• Scientific Literature