US9253997, 32

ID: ALA3986052

PubChem CID: 71542641

Max Phase: Preclinical

Molecular Formula: C19H21Cl2N3O6S

Molecular Weight: 490.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCC(=O)Nc1cc(Cl)cc(S(=O)(=O)O)c1O)C(=O)NCCc1cccc(Cl)c1

Standard InChI:  InChI=1S/C19H21Cl2N3O6S/c20-12-3-1-2-11(8-12)6-7-23-19(27)14(22)4-5-17(25)24-15-9-13(21)10-16(18(15)26)31(28,29)30/h1-3,8-10,14,26H,4-7,22H2,(H,23,27)(H,24,25)(H,28,29,30)/t14-/m0/s1

Standard InChI Key:  MALJWUBSEFTRCS-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  1  0  0  0  0  0999 V2000
    7.8024   -2.6887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8003   -1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969    0.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5988   -1.5004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6384   -0.9011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -2.7004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377   -2.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0990   -0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0969    0.4636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4003   -1.4841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6990   -0.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0002   -1.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2989   -0.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6006   -1.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8971   -0.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8919    0.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5902    1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5861    2.7272    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.2938    0.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14  8  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 16 18  2  0
 16 19  1  0
  2 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986052

   3-[[(4S)-4-amino-5-[2-(3-chlorophenyl)ethylamino]-5-oxopentanoyl]amino]-5-chloro-2-hydroxybenzenesulfonic 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: 490.37

Molecular Weight (Monoisotopic): 489.0528

AlogP: 2.35

#Rotatable Bonds: 9

Polar Surface Area: 158.82

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -2.82

CX Basic pKa: 8.22

CX LogP: 1.66

CX LogD: 1.60

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -0.72

References

1.  (2016)  Alkylamine derivative, 

Source

Source(1):

• BindingDB Database