(S)-2-{[6-(2,4-Diamino-6-oxo-1,6-dihydro-pyrimidin-5-ylsulfanylmethyl)-4,5,6,7-tetrahydro-benzo[b]thiophene-2-carbonyl]-amino}-pentanedioic acid

ID: ALA309415

PubChem CID: 135497378

Max Phase: Preclinical

Molecular Formula: C19H23N5O6S2

Molecular Weight: 481.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c(SCC2CCc3cc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)sc3C2)c(O)n1

Standard InChI:  InChI=1S/C19H23N5O6S2/c20-15-14(17(28)24-19(21)23-15)31-7-8-1-2-9-6-12(32-11(9)5-8)16(27)22-10(18(29)30)3-4-13(25)26/h6,8,10H,1-5,7H2,(H,22,27)(H,25,26)(H,29,30)(H5,20,21,23,24,28)/t8?,10-/m0/s1

Standard InChI Key:  ZGMCQEIDLHETAQ-HTLJXXAVSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
    0.0417   -4.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -2.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5875   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -2.7625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -2.4917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8250   -2.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0625   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6500   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -1.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2875   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -1.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -4.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875   -2.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -4.1417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8750   -4.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8750   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -1.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1125   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  2  0
  4  6  2  0
  5  4  1  0
  6  1  1  0
  7  8  1  0
  8  9  1  0
  9 19  1  0
 10 22  1  0
 11  7  1  0
 12 10  1  0
 13  2  1  0
 14 11  1  0
 16 15  1  6
 16 14  1  0
 17  5  1  0
 18 28  1  0
 19 30  1  0
 20 11  2  0
 21  3  1  0
 22 32  1  0
 23 15  2  0
 24  6  1  0
 25 18  2  0
 26 16  1  0
 27 13  1  0
 28 26  1  0
 29 15  1  0
 30 27  1  0
 31 18  1  0
 32 30  1  0
  2  5  2  0
 10  9  2  0
  7 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA309415

   ---

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: 481.56

Molecular Weight (Monoisotopic): 481.1090

AlogP: 1.35

#Rotatable Bonds: 9

Polar Surface Area: 201.75

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.73

CX Basic pKa: 4.04

CX LogP: 1.70

CX LogD: -4.03

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: -0.51

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