(S)-2-[(1-Mercaptomethyl-cyclopentanecarbonyl)-amino]-3-phenyl-propionic acid

ID: ALA355221

PubChem CID: 44380497

Max Phase: Preclinical

Molecular Formula: C16H21NO3S

Molecular Weight: 307.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H](Cc1ccccc1)NC(=O)C1(CS)CCCC1

Standard InChI:  InChI=1S/C16H21NO3S/c18-14(19)13(10-12-6-2-1-3-7-12)17-15(20)16(11-21)8-4-5-9-16/h1-3,6-7,13,21H,4-5,8-11H2,(H,17,20)(H,18,19)/t13-/m0/s1

Standard InChI Key:  YPOMPHXPLUEVBA-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  1  0  0  0  0  0999 V2000
    5.0167   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -2.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167   -4.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -4.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -4.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -2.9167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8792   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5917   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3042   -3.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5792   -4.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3042   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  4  1  0
  6  1  2  0
  4  7  1  1
  8  5  2  0
  9  2  1  0
 10  5  1  0
 11  9  1  0
 12  7  1  0
 13  2  1  0
 14  2  1  0
 15 12  2  0
 16 12  1  0
 17 14  1  0
 18 13  1  0
 19 16  2  0
 20 15  1  0
 21 19  1  0
 17 18  1  0
 20 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA355221

   (S)-2-[(1-Mercaptomethyl-cyclopentanecarbonyl)-amino]-3-phenyl-propionic 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: 307.42

Molecular Weight (Monoisotopic): 307.1242

AlogP: 2.29

#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: 4.12

CX Basic pKa: ┄

CX LogP: 3.09

CX LogD: 0.01

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.71

Np Likeness Score: 0.08

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