Methyl 4-(2-(benzo[d][1,3]dioxol-5-yl)-4-oxo-1,2-dihydroquinazolin-3(4H)-yl)butanoate

ID: ALA3585833

PubChem CID: 122179904

Max Phase: Preclinical

Molecular Formula: C20H20N2O5

Molecular Weight: 368.39

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H20N2O5/c1-25-18(23)7-4-10-22-19(13-8-9-16-17(11-13)27-12-26-16)21-15-6-3-2-5-14(15)20(22)24/h2-3,5-6,8-9,11,19,21H,4,7,10,12H2,1H3

Standard InChI Key:  UAFKHKMLMDSULZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -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
   -6.5121    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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 O   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 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
  2  3  1  0
  3  4  1  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  1 11  2  0
  2 12  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 23 13  1  0
  3 13  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 23 24  2  0
 16 25  1  0
 24 16  1  0
 24 27  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3585833

   ---

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): 368.1372

AlogP: 2.94

#Rotatable Bonds: 5

Polar Surface Area: 77.10

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: ┄

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -0.49

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