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

ID: ALA84045

PubChem CID: 135529975

Max Phase: Preclinical

Molecular Formula: C19H23N5O6S

Molecular Weight: 449.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c(SCCCc2cccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)c2)c(O)n1

Standard InChI:  InChI=1S/C19H23N5O6S/c20-15-14(17(28)24-19(21)23-15)31-8-2-4-10-3-1-5-11(9-10)16(27)22-12(18(29)30)6-7-13(25)26/h1,3,5,9,12H,2,4,6-8H2,(H,22,27)(H,25,26)(H,29,30)(H5,20,21,23,24,28)/t12-/m0/s1

Standard InChI Key:  YHRWDSHFZKASFT-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  1  0  0  0  0  0999 V2000
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    1.0750   -3.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0750   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375   -3.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375   -3.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -3.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -2.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -2.9667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -4.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -3.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833   -4.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -5.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -4.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4625   -4.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -3.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -5.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -2.9667    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 10  1  0
  8  7  1  0
 11  9  1  6
 10 17  1  0
 11  8  1  0
 12  5  1  0
 13 22  1  0
 14  3  1  0
 15  7  2  0
 16  2  1  0
 17 25  2  0
 18  9  2  0
 19  6  1  0
 20 13  2  0
 21 11  1  0
 22 21  1  0
 23  9  1  0
 24 13  1  0
 25 30  1  0
 26 27  1  0
 27 29  2  0
 28 14  1  0
 29 25  1  0
 30 31  1  0
 31 28  1  0
  3  5  2  0
 10 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA84045

   ---

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: 3.37

CX Basic pKa: 4.34

CX LogP: 1.13

CX LogD: -4.85

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.21

Np Likeness Score: -0.43

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