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

ID: ALA41161

PubChem CID: 136056634

Max Phase: Preclinical

Molecular Formula: C21H23N5O4S

Molecular Weight: 441.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC(NC(=O)c1ccc(SCc2ccc3nc(N)nc(O)c3c2)cc1)C(=O)O

Standard InChI:  InChI=1S/C21H23N5O4S/c22-9-1-2-17(20(29)30)24-18(27)13-4-6-14(7-5-13)31-11-12-3-8-16-15(10-12)19(28)26-21(23)25-16/h3-8,10,17H,1-2,9,11,22H2,(H,24,27)(H,29,30)(H3,23,25,26,28)

Standard InChI Key:  TWMPDTBJNMXLSH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    2.4125   -6.7417    0.0000 N   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
    3.4500   -6.7417    0.0000 C   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
    2.9292   -7.6417    0.0000 N   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
    7.5917   -5.5250    0.0000 C   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
    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
    3.9625   -6.4417    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
    2.9292   -5.8417    0.0000 O   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
    8.1042   -4.6167    0.0000 O   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
    1.8875   -7.6375    0.0000 N   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
    6.5500   -5.5292    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
    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
    4.4792   -7.3417    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
    6.0292   -5.8375    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  2  0
  3  2  1  0
  4  1  1  0
  5  4  2  0
  6  5  1  0
  7 12  1  0
  8  7  1  0
  9 10  1  0
 10  8  1  0
 11  3  2  0
 12 19  1  0
 13  2  1  0
 14  7  2  0
 15  9  2  0
 16  6  2  0
 17  4  1  0
 18 24  1  0
 19 27  2  0
 20 26  1  0
 21 11  1  0
 22 18  1  0
 23  9  1  0
 24 21  1  0
 25 16  1  0
 26 22  2  0
 27 22  1  0
 28 30  1  0
 29 10  1  0
 30 31  1  0
 31 29  1  0
  6  3  1  0
 25 21  2  0
 20 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA41161

   ---

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: 441.51

Molecular Weight (Monoisotopic): 441.1471

AlogP: 2.13

#Rotatable Bonds: 9

Polar Surface Area: 164.45

Molecular Species: ZWITTERION

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.26

CX Basic pKa: 9.88

CX LogP: 0.10

CX LogD: 0.10

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: -0.78

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