4-(2-(Benzo[d][1,3]dioxol-5-yl)-1,2-dihydro-4-oxoquinazolin-3(4H)-yl)butanehydrazide

ID: ALA3585842

PubChem CID: 122179913

Max Phase: Preclinical

Molecular Formula: C19H20N4O4

Molecular Weight: 368.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NNC(=O)CCCN1C(=O)c2ccccc2NC1c1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C19H20N4O4/c20-22-17(24)6-3-9-23-18(12-7-8-15-16(10-12)27-11-26-15)21-14-5-2-1-4-13(14)19(23)25/h1-2,4-5,7-8,10,18,21H,3,6,9,11,20H2,(H,22,24)

Standard InChI Key:  NUJBATKKAFINQJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -7.8109    0.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1121    1.4882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8090   -0.4597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1506    0.8868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5121    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928    2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122    1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086   -1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010   -2.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2102   -3.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5081   -3.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109    0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2240   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5149   -1.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9281   -3.4731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8088   -2.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9391   -1.0665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  1  0
  1  3  2  0
  2  4  1  0
 10  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  6 16  2  0
  7 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 23 18  1  0
  8 18  1  0
 17 22  1  0
 22  5  1  0
 23 24  2  0
 21 25  1  0
 24 21  1  0
 24 27  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3585842

   ---

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: 368.39

Molecular Weight (Monoisotopic): 368.1485

AlogP: 1.75

#Rotatable Bonds: 5

Polar Surface Area: 105.92

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.03

CX Basic pKa: 3.27

CX LogP: 1.80

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.42

Np Likeness Score: -0.89

References

1. Khattab SN, Haiba NS, Asal AM, Bekhit AA, Amer A, Abdel-Rahman HM, El-Faham A..  (2015)  Synthesis and evaluation of quinazoline amino acid derivatives as mono amine oxidase (MAO) inhibitors.,  23  (13): [PMID:25922182] [10.1016/j.bmc.2015.04.021]

Source

Source(1):

• Scientific Literature