2-[4-(2-Amino-4-oxo-3,4a,7,8a-tetrahydro-4H-pyrimido[4,5-b][1,4]oxazin-6-yl)-benzoylamino]-pentanedioic acid

ID: ALA17116

PubChem CID: 44270892

Max Phase: Preclinical

Molecular Formula: C18H19N5O7

Molecular Weight: 417.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC1=NC(=O)C2N=C(c3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)COC2N1

Standard InChI:  InChI=1S/C18H19N5O7/c19-18-22-15(27)13-16(23-18)30-7-11(20-13)8-1-3-9(4-2-8)14(26)21-10(17(28)29)5-6-12(24)25/h1-4,10,13,16H,5-7H2,(H,21,26)(H,24,25)(H,28,29)(H3,19,22,23,27)

Standard InChI Key:  FMDCGKMELCGRDQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.4042   -4.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -2.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -3.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -3.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -3.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -3.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250   -1.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -4.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8417   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8417   -1.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -3.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2625   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -1.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4167   -0.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1292   -0.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -4.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2542   -3.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9750   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5542   -1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5500   -2.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5542   -0.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9792   -2.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  2  1  0
  4  6  2  0
  5  2  1  0
  6  1  1  0
  7  1  1  0
  8 16  1  0
  9 14  1  0
 10  9  1  0
 11  7  1  0
 12 13  1  0
 13 10  1  0
 14 24  1  0
 15  8  1  0
 16 11  1  0
 17 28  1  0
 18  5  2  0
 19  9  2  0
 20 12  2  0
 21  6  1  0
 22 17  2  0
 23 25  1  0
 24 26  2  0
 25 15  2  0
 26 15  1  0
 27 13  1  0
 28 27  1  0
 29 12  1  0
 30 17  1  0
  5  4  1  0
  8  3  2  0
 14 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA17116

   2-[[4-(2-Amino-4-oxo-3,4a,7,8a-tetrahydropyrimido[4,5-b][1,4]oxazin-6-yl)benzoyl]amino]pentanedioic acid

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: 417.38

Molecular Weight (Monoisotopic): 417.1284

AlogP: -1.31

#Rotatable Bonds: 7

Polar Surface Area: 192.77

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.10

CX Basic pKa: 6.35

CX LogP: -2.58

CX LogD: -6.75

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: 0.03

References

1. Nair MG, Salter OC, Kisliuk RL, Gaumont Y, North G..  (1983)  Folate analogues. 22. Synthesis and biological evaluation of two analogues of dihydrofolic acid possessing a 7,8-dihydro-8-oxapterin ring system.,  26  (8): [PMID:6410065] [10.1021/jm00362a015]

Source

Source(1):

• Scientific Literature