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

ID: ALA16681

PubChem CID: 44270910

Max Phase: Preclinical

Molecular Formula: C19H21N5O7

Molecular Weight: 431.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC1=NC(=O)C2N=C(Cc3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)COC2N1

Standard InChI:  InChI=1S/C19H21N5O7/c20-19-23-16(28)14-17(24-19)31-8-11(21-14)7-9-1-3-10(4-2-9)15(27)22-12(18(29)30)5-6-13(25)26/h1-4,12,14,17H,5-8H2,(H,22,27)(H,25,26)(H,29,30)(H3,20,23,24,28)

Standard InChI Key:  RDGQBRHIWMVSEW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    1.3792   -5.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -3.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -3.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -5.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -5.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -3.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -5.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -6.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -4.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -8.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -2.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -4.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4917   -5.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -5.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2875   -8.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -4.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417   -7.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -3.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0250   -7.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1875   -6.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -3.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -8.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -4.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  5  2  0
  4  2  1  0
  5  1  1  0
  6  1  1  0
  7  2  1  0
  8 14  1  0
  9  8  1  0
 10  6  1  0
 11 21  1  0
 12 13  1  0
 13  9  1  0
 14 24  2  0
 15 26  1  0
 16  4  2  0
 17  8  2  0
 18 12  2  0
 19  5  1  0
 20 15  2  0
 21 10  1  0
 22 13  1  0
 23 30  2  0
 24 31  1  0
 25 11  1  0
 26 22  1  0
 27 12  1  0
 28 25  1  0
 29 15  1  0
 30 28  1  0
 31 28  2  0
  4  3  1  0
  7 11  2  0
 23 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA16681

   2-[[4-[(2-Amino-4-oxo-3,4a,7,8a-tetrahydropyrimido[4,5-b][1,4]oxazin-6-yl)methyl]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: 431.41

Molecular Weight (Monoisotopic): 431.1441

AlogP: -1.11

#Rotatable Bonds: 8

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: 3.32

CX Basic pKa: 6.33

CX LogP: -2.22

CX LogD: -6.29

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.34

Np Likeness Score: 0.12

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