(S)-7-((R)-2-Mercapto-3-phenyl-propionylamino)-6-oxo-1,2,3,4,6,7,8,12b-octahydro-benzo[c]pyrido[1,2-a]azepine-4-carboxylic acid

ID: ALA353341

PubChem CID: 44385210

Max Phase: Preclinical

Molecular Formula: C24H26N2O4S

Molecular Weight: 438.55

Molecule Type: Small molecule

Names and Identifiers

Synonyms: MDL-101628 | CHEMBL353341

Canonical SMILES:  O=C(O)C1CCCC2c3ccccc3C[C@H](NC(=O)[C@H](S)Cc3ccccc3)C(=O)N12

Standard InChI:  InChI=1S/C24H26N2O4S/c27-22(21(31)13-15-7-2-1-3-8-15)25-18-14-16-9-4-5-10-17(16)19-11-6-12-20(24(29)30)26(19)23(18)28/h1-5,7-10,18-21,31H,6,11-14H2,(H,25,27)(H,29,30)/t18-,19?,20?,21+/m0/s1

Standard InChI Key:  RIWRWPXUDHZKIO-GKYDQMIMSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  1  0  0  0  0  0999 V2000
    7.3125   -3.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7000   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9375   -3.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -3.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -4.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -2.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -2.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -4.6292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8667   -2.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5792   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8625   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2500   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -4.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6625   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -5.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -4.6042    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
  5  1  1  0
  4  6  1  1
  7  6  1  0
  8  3  1  0
  9  8  2  0
 10  5  1  0
 11  4  1  0
 12  7  1  0
 13  2  2  0
 14  7  2  0
 15 10  2  0
 16 12  1  0
 12 17  1  6
 18 10  1  0
 19  3  1  0
 20 16  1  0
 21  5  1  0
 22  8  1  0
 23  9  1  0
 24 21  1  0
 25 20  1  0
 26 20  2  0
 27 22  2  0
 28 27  1  0
 29 26  1  0
 30 25  2  0
 31 29  2  0
 19 24  1  0
  9 11  1  0
 28 23  2  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA353341

   (7S)-6-oxo-7-[[(2R)-3-phenyl-2-sulfanylpropanoyl]amino]-2,3,4,7,8,12b-hexahydro-1H-pyrido[2,1-a][2]benzazepine-4-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: 438.55

Molecular Weight (Monoisotopic): 438.1613

AlogP: 2.78

#Rotatable Bonds: 5

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: 3.81

CX Basic pKa: ┄

CX LogP: 3.34

CX LogD: 0.08

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.63

Np Likeness Score: -0.05

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