(1S,3R)-3-(2-Mercaptomethyl-3-phenyl-propionylamino)-cyclohexanecarboxylic acid

ID: ALA170555

PubChem CID: 44380511

Max Phase: Preclinical

Molecular Formula: C17H23NO3S

Molecular Weight: 321.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H]1CCC[C@H](C(=O)O)C1)C(CS)Cc1ccccc1

Standard InChI:  InChI=1S/C17H23NO3S/c19-16(14(11-22)9-12-5-2-1-3-6-12)18-15-8-4-7-13(10-15)17(20)21/h1-3,5-6,13-15,22H,4,7-11H2,(H,18,19)(H,20,21)/t13-,14?,15+/m0/s1

Standard InChI Key:  VSWXQPZVYYPRIX-ZHDDOTHNSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
    5.6500   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -3.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -3.5875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2167   -3.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -4.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2167   -2.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9292   -4.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -3.5875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2250   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7792   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9250   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5750   -1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  5  4  1  1
  5  8  1  0
  6  2  1  0
  7  1  2  0
  8 10  1  0
  9  4  2  0
 10  3  1  1
 11  4  1  0
 12 14  1  0
 13  6  1  0
 14  2  1  0
 15 16  1  0
 16 17  1  0
 17 10  1  0
 18 13  2  0
 19 13  1  0
 20 19  2  0
 21 18  1  0
 22 20  1  0
  5 15  1  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA170555

   (1S,3R)-3-(2-Mercaptomethyl-3-phenyl-propionylamino)-cyclohexanecarboxylic acid

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: 321.44

Molecular Weight (Monoisotopic): 321.1399

AlogP: 2.53

#Rotatable Bonds: 6

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.40

CX Basic pKa: ┄

CX LogP: 3.01

CX LogD: 0.12

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.71

Np Likeness Score: -0.18

References

1. James K, Palmer MJ.  (1993)  Gem-cycloalkyl substituted thiol inhibitors of neutral endopeptidase 24.11. Synthesis via nucleophilic opening of 2,2-spiro--lactones,  3  (5): [10.1016/S0960-894X(00)80674-5]

Source

Source(1):

• Scientific Literature