5-Amino-2-[4-(4-oxo-3,4-dihydro-quinazolin-6-ylmethylsulfanyl)-benzoylamino]-pentanoic acid

ID: ALA43288

PubChem CID: 136056635

Max Phase: Preclinical

Molecular Formula: C21H22N4O4S

Molecular Weight: 426.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC(NC(=O)c1ccc(SCc2ccc3ncnc(O)c3c2)cc1)C(=O)O

Standard InChI:  InChI=1S/C21H22N4O4S/c22-9-1-2-18(21(28)29)25-19(26)14-4-6-15(7-5-14)30-11-13-3-8-17-16(10-13)20(27)24-12-23-17/h3-8,10,12,18H,1-2,9,11,22H2,(H,25,26)(H,28,29)(H,23,24,27)

Standard InChI Key:  XVWYIOMVJJDIKK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.4500   -6.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -6.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -5.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -6.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1125   -5.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -7.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -7.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -7.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -5.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -6.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -4.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -5.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1042   -4.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -6.7292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -7.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -6.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5500   -5.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -6.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375   -6.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1417   -4.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -6.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -5.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -6.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -7.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6792   -7.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1542   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6792   -6.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1542   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 11  1  0
  4  2  2  0
  5  3  1  0
  6  8  1  0
  7  6  2  0
  8  1  2  0
  9 10  1  0
 10  5  1  0
 11 18  2  0
 12  1  1  0
 13  3  2  0
 14  2  1  0
 15  9  2  0
 16 23  1  0
 17  8  1  0
 18 25  1  0
 19 24  2  0
 20 12  2  0
 21 16  1  0
 22  9  1  0
 23 20  1  0
 24 21  1  0
 25 21  2  0
 26 20  1  0
 27 29  1  0
 28 10  1  0
 29 30  1  0
 30 28  1  0
 17 26  2  0
  4  7  1  0
 11 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA43288

   ---

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: 426.50

Molecular Weight (Monoisotopic): 426.1362

AlogP: 2.55

#Rotatable Bonds: 9

Polar Surface Area: 138.43

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.25

CX Basic pKa: 9.84

CX LogP: 0.25

CX LogD: 0.25

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -0.82

References

1. Patil SA, Shane B, Freisheim JH, Singh SK, Hynes JB..  (1989)  Inhibition of mammalian folylpolyglutamate synthetase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin bearing a terminal L-ornithine.,  32  (7): [PMID:2738891] [10.1021/jm00127a026]

Source

Source(1):

• Scientific Literature