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

ID: ALA339240

PubChem CID: 136046109

Max Phase: Preclinical

Molecular Formula: C22H24FN5O4

Molecular Weight: 441.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(O)c2c(F)c(NCc3ccc(C(=O)NC(CCCN)C(=O)O)cc3)ccc2n1

Standard InChI:  InChI=1S/C22H24FN5O4/c1-12-26-15-8-9-16(19(23)18(15)21(30)27-12)25-11-13-4-6-14(7-5-13)20(29)28-17(22(31)32)3-2-10-24/h4-9,17,25H,2-3,10-11,24H2,1H3,(H,28,29)(H,31,32)(H,26,27,30)

Standard InChI Key:  BETGUEQQQUIULC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    4.7042   -8.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -8.3542    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
    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
    4.1875   -8.9542    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
    5.7417   -8.0542    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
    8.8625   -7.4417    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
    5.7417   -9.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3750   -6.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8917   -6.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -8.9542    0.0000 C   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
    5.7417   -7.4542    0.0000 F   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
    8.3417   -8.3417    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
   12.4917   -7.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -9.2542    0.0000 C   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  1  2  0
  4  6  2  0
  5  2  2  0
  6  3  1  0
  7 13  1  0
  8  2  1  0
  9  7  1  0
 10 12  1  0
 11  8  2  0
 12  9  1  0
 13 21  1  0
 14  1  1  0
 15 11  1  0
 16  5  1  0
 17  7  2  0
 18 10  2  0
 19 11  1  0
 20 26  1  0
 21 27  2  0
 22  8  1  0
 23 15  1  0
 24 10  1  0
 25 23  1  0
 26 25  2  0
 27 25  1  0
 28 31  1  0
 29  6  1  0
 30 12  1  0
 31 32  1  0
 32 30  1  0
  4  5  1  0
 16 19  2  0
 20 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA339240

   ---

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: 441.46

Molecular Weight (Monoisotopic): 441.1812

AlogP: 2.32

#Rotatable Bonds: 9

Polar Surface Area: 150.46

Molecular Species: ZWITTERION

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.47

CX Basic pKa: 9.88

CX LogP: -0.32

CX LogD: -0.32

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: -0.80

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