(S)-2-{4-[3-(2,4-Diamino-6-oxo-1,6-dihydro-pyrimidin-5-ylsulfanyl)-propyl]-benzoylamino}-pentanedioic acid

ID: ALA84904

PubChem CID: 135493624

Max Phase: Preclinical

Molecular Formula: C19H23N5O6S

Molecular Weight: 449.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c(SCCCc2ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc2)c(O)n1

Standard InChI:  InChI=1S/C19H23N5O6S/c20-15-14(17(28)24-19(21)23-15)31-9-1-2-10-3-5-11(6-4-10)16(27)22-12(18(29)30)7-8-13(25)26/h3-6,12H,1-2,7-9H2,(H,22,27)(H,25,26)(H,29,30)(H5,20,21,23,24,28)/t12-/m0/s1

Standard InChI Key:  GCOANCQEKIHPTN-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  1  0  0  0  0  0999 V2000
    0.6292   -3.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -2.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292   -1.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -1.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9042   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750   -1.9125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750   -3.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -0.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4000   -3.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9042   -1.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3875   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -0.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4250   -1.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  6  2  0
  5  4  1  0
  6  1  1  0
  7 11  1  0
  8  7  1  0
 10  9  1  6
 10  8  1  0
 11 21  1  0
 12  5  1  0
 13 23  1  0
 14  3  1  0
 15  7  2  0
 16  2  1  0
 17  9  2  0
 18  6  1  0
 19 13  2  0
 20 10  1  0
 21 27  2  0
 22 26  1  0
 23 20  1  0
 24  9  1  0
 25 13  1  0
 26 28  2  0
 27 28  1  0
 28 30  1  0
 29 14  1  0
 30 31  1  0
 31 29  1  0
  3  5  2  0
 22 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA84904

   ---

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: 449.49

Molecular Weight (Monoisotopic): 449.1369

AlogP: 1.12

#Rotatable Bonds: 11

Polar Surface Area: 201.75

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.34

CX Basic pKa: 4.37

CX LogP: 1.12

CX LogD: -4.82

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.21

Np Likeness Score: -0.36

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