(4S,6S,9aS)-6-((S)-2-Mercapto-3-phenyl-propionylamino)-5-oxo-octahydro-1-thia-4a-aza-benzocycloheptene-4-carboxylic acid

ID: ALA165953

PubChem CID: 44377613

Max Phase: Preclinical

Molecular Formula: C19H24N2O4S2

Molecular Weight: 408.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1CCC[C@@H]2SCC[C@@H](C(=O)O)N2C1=O)[C@@H](S)Cc1ccccc1

Standard InChI:  InChI=1S/C19H24N2O4S2/c22-17(15(26)11-12-5-2-1-3-6-12)20-13-7-4-8-16-21(18(13)23)14(19(24)25)9-10-27-16/h1-3,5-6,13-16,26H,4,7-11H2,(H,20,22)(H,24,25)/t13-,14-,15-,16-/m0/s1

Standard InChI Key:  HSNXSUNHPADRNW-VGWMRTNUSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  1  0  0  0  0  0999 V2000
    6.6125   -2.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9917   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250   -2.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8250   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -1.7417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -3.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -1.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -3.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -3.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4625   -2.2542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -3.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4625   -3.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1250   -1.3167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  5  1  0
  7  5  1  1
  6  1  1  0
  7  2  1  0
  3  8  1  1
  9  6  1  0
 10  4  1  0
 11  2  2  0
 12  4  2  0
 13  8  2  0
 10 14  1  6
 15  3  1  0
 16 10  1  0
 17  9  1  0
 18  8  1  0
 19 14  1  0
 20  7  1  0
 21  6  1  0
 22 21  1  0
 23 19  2  0
 24 19  1  0
 25 24  2  0
 26 23  1  0
 27 25  1  0
  6 28  1  1
 22 20  1  0
 17 15  1  0
 27 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA165953

   (4S,7S,10aS)-6-oxo-7-[[(2S)-3-phenyl-2-sulfanylpropanoyl]amino]-2,3,4,7,8,9,10,10a-octahydro-[1,3]thiazino[3,2-a]azepine-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: 408.55

Molecular Weight (Monoisotopic): 408.1177

AlogP: 1.94

#Rotatable Bonds: 5

Polar Surface Area: 86.71

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.77

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: -1.22

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: -0.10

References

1. Slusarchyk WA, Robl JA, Taunk PC, Assad MM, Bird J, DiMarco J, Pan Y.  (1995)  Dual metalloprotease inhibitors.v. Utilization of bicyclic azepinonethiazolidines and azepinonetetrahydrothiazines in constrained peptidomimetics of mercaptoacyl dipeptides,  5  (7): [10.1016/0960-894X(95)00109-7]

Source

Source(1):

• Scientific Literature