(4S,7S,12bR)-6-oxo-7-[(2-sulfanylacetyl)amino]-2,3,4,7,8,12b-hexahydro-1H-pyrido[2,1-a][2]benzazepine-4-carboxylic acid

ID: ALA5281720

Max Phase: Preclinical

Molecular Formula: C17H20N2O4S

Molecular Weight: 348.42

Names and Identifiers

Canonical SMILES:  O=C(CS)N[C@H]1Cc2ccccc2[C@H]2CCC[C@@H](C(=O)O)N2C1=O

Standard InChI:  InChI=1S/C17H20N2O4S/c20-15(9-24)18-12-8-10-4-1-2-5-11(10)13-6-3-7-14(17(22)23)19(13)16(12)21/h1-2,4-5,12-14,24H,3,6-9H2,(H,18,20)(H,22,23)/t12-,13+,14-/m0/s1

Standard InChI Key:  CZDSEQUNZGMJPF-MJBXVCDLSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    1.8018    1.1316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5883    0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852    0.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685   -0.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550   -0.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581   -1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446   -1.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9477   -2.0558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280   -2.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747   -0.4620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150   -0.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150   -1.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1108   -0.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2525    0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923    1.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0859    1.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3559    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1738    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5579    1.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142    1.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251   -0.8032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -0.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2540   -0.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9685   -0.3907    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    0.4343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  6  7  1  1
  7  8  2  0
  7  9  1  0
 10  6  1  0
 10  2  1  0
 11 10  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 15 20  2  0
 20  2  1  0
 13 21  1  1
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281720

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 348.42

Molecular Weight (Monoisotopic): 348.1144

AlogP: 1.16

#Rotatable Bonds: 3

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: 3.83

CX Basic pKa: ┄

CX LogP: 1.11

CX LogD: -2.14

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -0.17

References

1. Van der Poorten O, Knuhtsen A, Sejer Pedersen D, Ballet S, Tourwé D..  (2016)  Side Chain Cyclized Aromatic Amino Acids: Great Tools as Local Constraints in Peptide and Peptidomimetic Design.,  59  (24): [PMID:27690430] [10.1021/acs.jmedchem.6b01029]

Source

Source(1):

• Scientific Literature