(2S)-N-((1R)-2-amino-1-(4-(2-methylpentyloxy)-phenyl)ethyl)-2-phenylpropanamide hydrochloride

ID: ALA3884102

PubChem CID: 134130378

Max Phase: Preclinical

Molecular Formula: C23H33ClN2O2

Molecular Weight: 368.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(C)COc1ccc([C@H](CN)NC(=O)[C@@H](C)c2ccccc2)cc1.Cl

Standard InChI:  InChI=1S/C23H32N2O2.ClH/c1-4-8-17(2)16-27-21-13-11-20(12-14-21)22(15-24)25-23(26)18(3)19-9-6-5-7-10-19;/h5-7,9-14,17-18,22H,4,8,15-16,24H2,1-3H3,(H,25,26);1H/t17?,18-,22-;/m0./s1

Standard InChI Key:  DSMKQJRFZUULOL-NCNOEJATSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   14.3196   -8.5446    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.2107   -6.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9190   -6.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9175   -7.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2121   -5.5242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5050   -6.7487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6288   -6.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3372   -6.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0429   -6.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0444   -5.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3360   -5.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6303   -5.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7966   -6.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7981   -5.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0909   -6.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3826   -6.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6714   -6.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6702   -7.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3785   -7.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0855   -7.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9603   -7.9672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9630   -8.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2531   -9.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5448   -8.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8350   -9.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1307   -8.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2517  -10.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5079   -5.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  6
  2  5  2  0
  2  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  3  7  1  0
 13 14  1  6
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 22  1  0
 23 27  1  0
 18 21  1  0
 13 15  1  0
 14 28  1  0
  6 13  1  0
M  END

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: 368.52

Molecular Weight (Monoisotopic): 368.2464

AlogP: 4.42

#Rotatable Bonds: 10

Polar Surface Area: 64.35

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.60

CX Basic pKa: 8.76

CX LogP: 4.53

CX LogD: 3.16

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: -0.28

References

1. Jin C, Decker AM, Langston TL..  (2017)  Design, synthesis and pharmacological evaluation of 4-hydroxyphenylglycine and 4-hydroxyphenylglycinol derivatives as GPR88 agonists.,  25  (2): [PMID:27956039] [10.1016/j.bmc.2016.11.058]

2. Rahman MT,Decker AM,Langston TL,Mathews KM,Laudermilk L,Maitra R,Ma W,Darcq E,Kieffer BL,Jin C.  (2020)  Design, Synthesis, and Structure-Activity Relationship Studies of (4-Alkoxyphenyl)glycinamides and Bioisosteric 1,3,4-Oxadiazoles as GPR88 Agonists.,  63  (23): [PMID:33205975] [10.1021/acs.jmedchem.0c01581]

Source

Source(1):

• Scientific Literature