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

ID: ALA315076

PubChem CID: 136035748

Max Phase: Preclinical

Molecular Formula: C20H23N5O6S

Molecular Weight: 461.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2c(n1)NCC(CCc1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1)S2

Standard InChI:  InChI=1S/C20H23N5O6S/c21-20-24-16-15(18(29)25-20)32-12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,12-13H,3,6-9H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)

Standard InChI Key:  KXVFDIDJQOTBSL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    3.5125   -7.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -7.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -7.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -7.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -6.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -7.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -6.7000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0250   -7.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6750   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1917   -6.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7167   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7125   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -6.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -6.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2667   -6.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6750   -5.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2375   -4.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -7.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7917   -5.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2292   -6.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6292   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1500   -6.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5417   -7.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7500   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1917   -4.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -6.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2667   -6.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6292   -7.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -6.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  5  1  0
  5  1  2  0
  6  4  2  0
  7  1  1  0
  8  2  1  0
  9 13  1  0
 10  9  1  0
 11 12  1  0
 12 10  1  0
 13 22  1  0
 14  5  1  0
 15 25  1  0
 16  9  2  0
 17 11  2  0
 18  6  1  0
 19 15  2  0
 20  7  1  0
 21 12  1  0
 22 30  2  0
 23 29  1  0
 24 20  1  0
 25 21  1  0
 26 11  1  0
 27 31  1  0
 28 15  1  0
 29 27  2  0
 30 27  1  0
 31 32  1  0
 32 20  1  0
  8 24  1  0
  6  3  1  0
 23 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA315076

   ---

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: 461.50

Molecular Weight (Monoisotopic): 461.1369

AlogP: 1.33

#Rotatable Bonds: 9

Polar Surface Area: 187.76

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.34

CX Basic pKa: 3.78

CX LogP: 1.20

CX LogD: -4.81

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: 0.01

References

1. Varney MD, Palmer CL, Romines WH, Boritzki T, Margosiak SA, Almassy R, Janson CA, Bartlett C, Howland EJ, Ferre R..  (1997)  Protein structure-based design, synthesis, and biological evaluation of 5-thia-2,6-diamino-4(3H)-oxopyrimidines: potent inhibitors of glycinamide ribonucleotide transformylase with potent cell growth inhibition.,  40  (16): [PMID:9258357] [10.1021/jm9607459]

Source

Source(1):

• Scientific Literature