(R,R) 2-(1-Mercaptomethyl-2-phenyl-ethylcarbamoyl)-4-methyl-pentanoic acid

ID: ALA164955

PubChem CID: 44377696

Max Phase: Preclinical

Molecular Formula: C16H23NO3S

Molecular Weight: 309.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](C(=O)O)C(=O)N[C@H](CS)Cc1ccccc1

Standard InChI:  InChI=1S/C16H23NO3S/c1-11(2)8-14(16(19)20)15(18)17-13(10-21)9-12-6-4-3-5-7-12/h3-7,11,13-14,21H,8-10H2,1-2H3,(H,17,18)(H,19,20)/t13-,14-/m0/s1

Standard InChI Key:  IFDBSSIZDWPRKI-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  1  0  0  0  0  0999 V2000
    6.5417   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -3.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -4.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -4.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -3.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -3.5792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -4.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -5.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -6.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -4.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -5.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  1  5  1  6
  6  2  2  0
  7  3  2  0
  8  4  1  0
  9  3  1  0
  8 10  1  1
 11 14  1  0
 12 10  1  0
 13  5  1  0
 14  8  1  0
 15 12  2  0
 16 12  1  0
 17 13  1  0
 18 13  1  0
 19 16  2  0
 20 15  1  0
 21 19  1  0
 20 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA164955

   (R,R) 2-(1-Mercaptomethyl-2-phenyl-ethylcarbamoyl)-4-methyl-pentanoic 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: 309.43

Molecular Weight (Monoisotopic): 309.1399

AlogP: 2.39

#Rotatable Bonds: 8

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: 4.28

CX Basic pKa: ┄

CX LogP: 3.28

CX LogD: 0.30

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.51

Np Likeness Score: 0.08

References

1. Fournié-Zaluski MC, Lucas-Soroca E, Devin J, Roques BP..  (1986)  1H NMR configurational correlation for retro-inverso dipeptides: application to the determination of the absolute configuration of "enkephalinase" inhibitors. Relationships between stereochemistry and enzyme recognition.,  29  (5): [PMID:3517331] [10.1021/jm00155a027]

Source

Source(1):

• Scientific Literature