3-{5-[4-(3-Methyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-butyl]-tetrazol-1-yl}-propionitrile

ID: ALA187788

Max Phase: Preclinical

Molecular Formula: C19H19N5O2

Molecular Weight: 349.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(CCCCc2nnnn2CCC#N)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C19H19N5O2/c1-13-14(19(26)16-9-3-2-8-15(16)18(13)25)7-4-5-10-17-21-22-23-24(17)12-6-11-20/h2-3,8-9H,4-7,10,12H2,1H3

Standard InChI Key:  YPNNFMWQOGXFLX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -1.2665    0.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2155    0.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6884   -0.3075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0119    1.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9181   -0.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3130   -1.0403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967   -0.9069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077    0.2760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3677   -0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017    0.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6504    0.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0584    2.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716   -1.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093   -1.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -2.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4827   -0.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5763    1.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6350    0.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3537   -0.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4386    1.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077    0.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9446   -0.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0947   -0.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1370    0.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  8  1  0
  4  1  1  0
  5  2  1  0
  6  7  1  0
  7  9  1  0
  8  9  2  0
  9 20  1  0
 10  4  1  0
 11 10  1  0
 12 13  3  0
 13 17  1  0
 14  4  2  0
 15  5  2  0
 16  7  1  0
 17 16  1  0
 18  2  1  0
 19  1  1  0
 20 24  1  0
 21 11  2  0
 22 10  2  0
 23 18  1  0
 24 23  1  0
 25 26  2  0
 26 22  1  0
  5 11  1  0
 25 21  1  0
  6  3  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA187788

   ---

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: 349.39

Molecular Weight (Monoisotopic): 349.1539

AlogP: 2.70

#Rotatable Bonds: 7

Polar Surface Area: 101.53

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.22

CX LogD: 2.22

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -0.90

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