(S)-2-[(S)-4-((R)-2-Mercapto-3-phenyl-propionylamino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-pentanoic acid

ID: ALA366495

PubChem CID: 9825199

Max Phase: Preclinical

Molecular Formula: C25H30N2O4S

Molecular Weight: 454.59

Molecule Type: Small molecule

Names and Identifiers

Synonyms: MDL-100407 | CHEMBL366495|MDL-100407|BDBM50289194|(S)-2-[(S)-4-((R)-2-Mercapto-3-phenyl-propionylamino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-pentanoic acid

Canonical SMILES:  CC(C)C[C@@H](C(=O)O)N1Cc2ccccc2C[C@H](NC(=O)[C@H](S)Cc2ccccc2)C1=O

Standard InChI:  InChI=1S/C25H30N2O4S/c1-16(2)12-21(25(30)31)27-15-19-11-7-6-10-18(19)14-20(24(27)29)26-23(28)22(32)13-17-8-4-3-5-9-17/h3-11,16,20-22,32H,12-15H2,1-2H3,(H,26,28)(H,30,31)/t20-,21-,22+/m0/s1

Standard InChI Key:  MVSZLSBZJCTXKA-FDFHNCONSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  1  0  0  0  0  0999 V2000
    6.9167   -3.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125   -3.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3125   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -3.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2875   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9375   -2.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -3.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4917   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -2.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0667   -2.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -4.4042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750   -3.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7125   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5042   -5.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -4.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -4.6125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5  1  1  0
  3  6  1  1
  7  6  1  0
  8  4  1  0
  9  3  1  0
 10  5  1  0
 11 10  2  0
 12  7  1  0
 13  2  2  0
  4 14  1  6
 15  7  2  0
 16  8  2  0
 17 12  1  0
 12 18  1  6
 19  8  1  0
 20 17  1  0
 21 14  1  0
 22 10  1  0
 23 11  1  0
 24 20  2  0
 25 20  1  0
 26 21  1  0
 27 21  1  0
 28 29  1  0
 29 22  2  0
 30 25  2  0
 31 24  1  0
 32 30  1  0
  4 33  1  1
 11  9  1  0
 28 23  2  0
 31 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA366495

   (S)-2-[(S)-4-((R)-2-Mercapto-3-phenyl-propionylamino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-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: 454.59

Molecular Weight (Monoisotopic): 454.1926

AlogP: 3.10

#Rotatable Bonds: 8

Polar Surface Area: 86.71

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.95

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 0.85

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -0.17

References

1. Warshawsky AM, Flynn GA, Koehl JR, Mehdi S, Vaz RJ.  (1996)  The synthesis of aminobenzazepinones as anti-phenylalanine dipeptide mimics and their use in nep inhibition,  6  (8): [10.1016/0960-894X(96)00149-7]

Source

Source(1):

• Scientific Literature