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

ID: ALA85436

PubChem CID: 136035747

Max Phase: Preclinical

Molecular Formula: C18H21N5O6S2

Molecular Weight: 467.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(O)c2c(n1)NCC(CCc1ccc(C(=O)N[C@H](CCC(=O)O)C(=O)O)s1)S2

Standard InChI:  InChI=1S/C18H21N5O6S2/c19-18-22-14-13(16(27)23-18)31-9(7-20-14)2-1-8-3-5-11(30-8)15(26)21-10(17(28)29)4-6-12(24)25/h3,5,9-10H,1-2,4,6-7H2,(H,21,26)(H,24,25)(H,28,29)(H4,19,20,22,23,27)/t9?,10-/m1/s1

Standard InChI Key:  HHKAOUMVRGSKLS-QVDQXJPCSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
    3.8250   -5.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250   -6.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -6.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -5.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -6.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3750   -5.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -5.5750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667   -5.8292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -6.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2125   -6.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -4.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -5.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1625   -5.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042   -6.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4875   -4.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -4.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8875   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3250   -4.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7542   -5.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -6.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4792   -7.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -5.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0500   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -6.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6417   -6.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -5.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9167   -5.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5292   -7.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -5.5792    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 10  1  0
  8  1  1  0
  9  7  1  0
 10 14  1  0
 11  2  1  0
 12  9  1  0
 13 17  1  0
 14 28  1  0
 16 15  1  1
 16 12  1  0
 17 14  2  0
 18  5  1  0
 19 27  1  0
 20  9  2  0
 21 15  2  0
 22  6  1  0
 23 19  2  0
 24  8  1  0
 25 16  1  0
 26 24  1  0
 27 25  1  0
 28 31  1  0
 29 15  1  0
 30 19  1  0
 31 24  1  0
 11 26  1  0
  6  3  1  0
  7 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA85436

   ---

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: 467.53

Molecular Weight (Monoisotopic): 467.0933

AlogP: 1.39

#Rotatable Bonds: 9

Polar Surface Area: 187.76

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.67

CX Basic pKa: 3.44

CX LogP: 1.35

CX LogD: -4.49

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: -0.33

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