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

ID: ALA340993

PubChem CID: 136046108

Max Phase: Preclinical

Molecular Formula: C21H23FN6O4

Molecular Weight: 442.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC(NC(=O)c1ccc(CNc2ccc3nc(N)nc(O)c3c2F)cc1)C(=O)O

Standard InChI:  InChI=1S/C21H23FN6O4/c22-17-14(8-7-13-16(17)19(30)28-21(24)27-13)25-10-11-3-5-12(6-4-11)18(29)26-15(20(31)32)2-1-9-23/h3-8,15,25H,1-2,9-10,23H2,(H,26,29)(H,31,32)(H3,24,27,28,30)

Standard InChI Key:  BFFCUPVMMUQRMT-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
    4.1875   -8.3542    0.0000 N   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   -8.9542    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
    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
    4.7042   -7.4500    0.0000 O   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
    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
    3.6667   -9.2542    0.0000 N   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
   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  2  0
  3  1  1  0
  4  2  1  0
  5  6  1  0
  6  3  2  0
  7 14  1  0
  8  3  1  0
  9  7  1  0
 10 12  1  0
 11  8  2  0
 12  9  1  0
 13  1  1  0
 14 22  1  0
 15 11  1  0
 16  6  1  0
 17  7  2  0
 18 10  2  0
 19  4  1  0
 20 11  1  0
 21 27  1  0
 22 28  2  0
 23  8  1  0
 24 15  1  0
 25 10  1  0
 26 24  1  0
 27 26  2  0
 28 26  1  0
 29 31  1  0
 30 12  1  0
 31 32  1  0
 32 30  1  0
  4  5  2  0
 16 20  2  0
 21 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA340993

   ---

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: 442.45

Molecular Weight (Monoisotopic): 442.1765

AlogP: 1.59

#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: 9.88

CX LogP: -0.81

CX LogD: -0.81

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -0.65

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