5-(3-Methyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-pentanoic acid (2-cyano-ethyl)-amide

ID: ALA190592

Max Phase: Preclinical

Molecular Formula: C19H20N2O3

Molecular Weight: 324.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(CCCCC(=O)NCCC#N)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C19H20N2O3/c1-13-14(7-4-5-10-17(22)21-12-6-11-20)19(24)16-9-3-2-8-15(16)18(13)23/h2-3,8-9H,4-7,10,12H2,1H3,(H,21,22)

Standard InChI Key:  TUTOGQXXTPQLAF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -1.0458    0.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0458   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917    0.1208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583   -1.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    1.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -1.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -0.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333    0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083    0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    0.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  6  1  0
  6  3  1  0
  7  8  3  0
  8 14  1  0
  9  4  2  0
 10  3  2  0
 11 20  1  0
 12 11  2  0
 13 11  1  0
 14 19  1  0
 15  2  1  0
 16  1  1  0
 17  5  2  0
 18  6  2  0
 19 13  1  0
 20 22  1  0
 21 15  1  0
 22 21  1  0
 23 24  2  0
 24 18  1  0
  4  5  1  0
 23 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA190592

   ---

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: 324.38

Molecular Weight (Monoisotopic): 324.1474

AlogP: 2.97

#Rotatable Bonds: 7

Polar Surface Area: 87.03

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.93

CX LogD: 1.93

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: 0.12

References

1. Biot C, Bauer H, Schirmer RH, Davioud-Charvet E..  (2004)  5-substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials.,  47  (24): [PMID:15537352] [10.1021/jm0497545]

Source

Source(1):

• Scientific Literature