x(1S,3R)-3-[(1-Mercaptomethyl-cyclopentanecarbonyl)-amino]-cyclohexanecarboxylic acid(1S,3R)-3-[(1-Mercaptomethyl-cyclohexanecarbonyl)-amino]-cyx(1S,3R)-3-[(1-Mercaptomethyl-cyclopentanecarbonyl)-amino]-cyclohexanecarboxylic acidclohexanecarboxylic acid

ID: ALA167249

PubChem CID: 44380510

Max Phase: Preclinical

Molecular Formula: C15H25NO3S

Molecular Weight: 299.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CCC[C@@H](NC(=O)C2(CS)CCCCC2)C1

Standard InChI:  InChI=1S/C15H25NO3S/c17-13(18)11-5-4-6-12(9-11)16-14(19)15(10-20)7-2-1-3-8-15/h11-12,20H,1-10H2,(H,16,19)(H,17,18)/t11-,12+/m0/s1

Standard InChI Key:  XBBDRTXWJGOWFH-NWDGAFQWSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  1  0  0  0  0  0999 V2000
    5.2417   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8167   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1042   -6.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -5.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8167   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6792   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5292   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -5.7750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -7.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -4.1250    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  7  1  0
  6  1  2  0
  7  9  1  0
  8  4  2  0
  9  3  1  1
 10  2  1  0
 11  4  1  0
 12 10  1  0
 13  2  1  0
 14  2  1  0
 15 16  1  0
 16 17  1  0
 17  9  1  0
 18 13  1  0
 19 14  1  0
 20 19  1  0
 18 20  1  0
  5 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA167249

   (1S,3R)-3-[[1-(sulfanylmethyl)cyclohexanecarbonyl]amino]cyclohexane-1-carboxylic 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: 299.44

Molecular Weight (Monoisotopic): 299.1555

AlogP: 2.63

#Rotatable Bonds: 4

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: 4.54

CX Basic pKa: 0.22

CX LogP: 2.86

CX LogD: 0.07

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.70

Np Likeness Score: 0.02

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