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

ID: ALA84605

PubChem CID: 135501119

Max Phase: Preclinical

Molecular Formula: C19H25N5O6S2

Molecular Weight: 483.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cc(CCCSc2c(N)nc(N)nc2O)sc1C(=O)N[C@@H](CCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C19H25N5O6S2/c1-2-9-8-10(4-3-7-31-14-15(20)23-19(21)24-17(14)28)32-13(9)16(27)22-11(18(29)30)5-6-12(25)26/h8,11H,2-7H2,1H3,(H,22,27)(H,25,26)(H,29,30)(H5,20,21,23,24,28)/t11-/m0/s1

Standard InChI Key:  YBDNVGJNYGPGFB-NSHDSACASA-N

Molfile:  

     RDKit          2D

 32 33  0  0  1  0  0  0  0  0999 V2000
    1.2750   -3.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -2.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625   -2.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -2.8417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -3.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -2.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -1.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -2.6000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -3.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292   -2.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2417   -3.8000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5125   -4.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0250   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8875   -2.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4625   -4.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2875   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792   -1.2667    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
  9 12  1  0
 10 13  1  0
 11  8  1  0
 12 13  2  0
 13 29  1  0
 15 14  1  6
 15 11  1  0
 16  5  1  0
 17 25  1  0
 18  8  2  0
 19  3  1  0
 20  2  1  0
 21 14  2  0
 22  6  1  0
 23 17  2  0
 24 15  1  0
 25 24  1  0
 26 14  1  0
 27 17  1  0
 28  9  1  0
 29 31  1  0
 30 19  1  0
 31 30  1  0
 32 28  1  0
  3  5  2  0
  7  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA84605

   ---

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: 483.57

Molecular Weight (Monoisotopic): 483.1246

AlogP: 1.74

#Rotatable Bonds: 12

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: 3.85

CX Basic pKa: 3.61

CX LogP: 2.26

CX LogD: -3.34

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.19

Np Likeness Score: -0.57

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