5-Amino-2-{4-[(2-amino-4-oxo-5-trifluoromethyl-3,4-dihydro-quinazolin-6-ylamino)-methyl]-benzoylamino}-pentanoic acid

ID: ALA133637

PubChem CID: 136046110

Max Phase: Preclinical

Molecular Formula: C22H23F3N6O4

Molecular Weight: 492.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC(NC(=O)c1ccc(CNc2ccc3nc(N)nc(O)c3c2C(F)(F)F)cc1)C(=O)O

Standard InChI:  InChI=1S/C22H23F3N6O4/c23-22(24,25)17-14(8-7-13-16(17)19(33)31-21(27)30-13)28-10-11-3-5-12(6-4-11)18(32)29-15(20(34)35)2-1-9-26/h3-8,15,28H,1-2,9-10,26H2,(H,29,32)(H,34,35)(H3,27,30,31,33)

Standard InChI Key:  JZBLZTRTDODFAU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
    5.2250   -8.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -8.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -8.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -8.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -8.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -9.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -8.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -7.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3792   -7.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000   -7.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4167   -6.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -8.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4167   -7.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -7.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875   -8.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3750   -6.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2667   -8.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -6.9042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -7.0542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -7.0542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8625   -8.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -7.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3042   -8.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9292   -6.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8250   -8.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8167   -7.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417   -8.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4917   -7.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9375   -7.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9792   -7.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4542   -7.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  2  0
  5  6  2  0
  6  7  1  0
  7  1  1  0
  8  4  1  0
  9 16  1  0
 10  9  1  0
 11 13  1  0
 12  4  1  0
 13 10  1  0
 14  2  1  0
 15 12  1  0
 16 25  2  0
 17  7  2  0
 18  9  2  0
 19 11  2  0
 20  5  1  0
 21 17  1  0
 22  8  1  0
 23  8  1  0
 24  8  1  0
 25 31  1  0
 26 30  2  0
 27 15  1  0
 28 11  1  0
 29 27  1  0
 30 29  1  0
 31 29  2  0
 32 34  1  0
 33 13  1  0
 34 35  1  0
 35 33  1  0
 21 12  2  0
  3  5  1  0
 16 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA133637

   ---

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: 492.46

Molecular Weight (Monoisotopic): 492.1733

AlogP: 2.47

#Rotatable Bonds: 9

Polar Surface Area: 176.48

Molecular Species: ZWITTERION

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.47

CX Basic pKa: 9.89

CX LogP: -0.08

CX LogD: -0.08

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.26

Np Likeness Score: -0.55

References

1. Hynes JB, Singh SK, Fetzer O, Shane B..  (1992)  Inhibition of hog liver folylpolyglutamate synthetase by 5-substituted 5,8-dideaza analogues of folic acid bearing a terminal L-ornithine residue.,  35  (22): [PMID:1433214] [10.1021/jm00100a013]

Source

Source(1):

• Scientific Literature