2-{4-[2-(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid

ID: ALA352444

PubChem CID: 136055863

Max Phase: Preclinical

Molecular Formula: C22H26N4O6

Molecular Weight: 442.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2c(n1)CCC(CCc1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1)C2

Standard InChI:  InChI=1S/C22H26N4O6/c23-22-25-16-8-5-13(11-15(16)20(30)26-22)2-1-12-3-6-14(7-4-12)19(29)24-17(21(31)32)9-10-18(27)28/h3-4,6-7,13,17H,1-2,5,8-11H2,(H,24,29)(H,27,28)(H,31,32)(H3,23,25,26,30)

Standard InChI Key:  TXHRVJYDANXEGJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.5958   -6.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0208   -6.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -5.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -7.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0208   -7.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -5.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833   -5.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -5.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -5.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958   -7.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -3.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -3.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7333   -7.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -6.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -6.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -4.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -3.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -6.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4042   -4.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -6.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -6.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  1  1  0
  4  1  2  0
  5  4  1  0
  6  5  2  0
  7 12  1  0
  8  7  1  0
  9 10  1  0
 10  8  1  0
 11  1  1  0
 12 22  1  0
 13  3  1  0
 14 23  1  0
 15  4  1  0
 16  7  2  0
 17  9  2  0
 18  6  1  0
 19 14  2  0
 20 10  1  0
 21 28  1  0
 22 29  2  0
 23 20  1  0
 24  9  1  0
 25 11  1  0
 26 31  1  0
 27 14  1  0
 28 26  2  0
 29 26  1  0
 30 25  1  0
 31 32  1  0
 32 25  1  0
 15 30  1  0
  6  2  1  0
 12 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA352444

   ---

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: 442.47

Molecular Weight (Monoisotopic): 442.1852

AlogP: 1.55

#Rotatable Bonds: 9

Polar Surface Area: 175.73

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.34

CX Basic pKa: 2.89

CX LogP: 2.25

CX LogD: -3.93

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: 0.02

References

1. Rosowsky A, Forsch RA, Moran RG..  (1989)  (6R,6S)-5,8,10-trideaza-5,6,7,8-tetrahydrofolate and 6(R,6S)-5,8,10-trideaza-5,6,7,8-tetrahydropteroyl-L-ornithine as potential antifolates and antitumor agents.,  32  (3): [PMID:2918520] [10.1021/jm00123a037]

Source

Source(1):

• Scientific Literature