2-(2,3,4-tri-O-acetyl-alpha-L-arabinopyranosyl)-6-(4-chlorophenyl)-2H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-3-thione

ID: ALA241930

PubChem CID: 23584875

Max Phase: Preclinical

Molecular Formula: C20H19ClN4O7S2

Molecular Weight: 526.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](n2nc3sc(-c4ccc(Cl)cc4)nn3c2=S)OC[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C20H19ClN4O7S2/c1-9(26)30-14-8-29-18(16(32-11(3)28)15(14)31-10(2)27)24-20(33)25-19(23-24)34-17(22-25)12-4-6-13(21)7-5-12/h4-7,14-16,18H,8H2,1-3H3/t14-,15-,16+,18+/m0/s1

Standard InChI Key:  ABJGRSBOSOPVMR-LISAXSMJSA-N

Molfile:  

     RDKit          2D

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   12.8562  -11.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5707  -12.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2898  -11.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2898  -11.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5707  -10.6654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4273  -13.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8562  -13.5621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5696  -13.1496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2835  -13.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2823  -14.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9985  -13.1516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0037  -12.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7187  -11.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.7199  -11.0891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1408  -10.6717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0508   -9.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3862  -11.0088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6620   -9.2971    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.8327  -10.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2441   -9.6773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6866   -9.0636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9306   -9.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0210  -10.2282    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2144   -8.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2111   -8.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4956   -7.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7819   -8.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7882   -9.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042   -9.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0652   -7.7686    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  1  6  1  0
 16 18  2  0
  8  9  1  0
  1 19  1  6
 19 20  1  0
  2  3  1  0
  8 10  2  0
 20 24  1  0
 23 21  2  0
 21 19  1  0
  3  4  1  0
 20 22  2  0
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  3 11  1  6
  4  5  1  0
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  5  6  1  0
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 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 23  1  0
 26 28  1  0
 12 14  2  0
 28 29  2  0
  2  7  1  1
 29 30  1  0
  4 15  1  6
 30 31  2  0
  1  2  1  0
 31 32  1  0
 15 16  1  0
 32 33  2  0
 33 28  1  0
  7  8  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA241930

   [(3S,4S,5R,6R)-4,5-diacetoxy-6-[6-(4-chlorophenyl)-3-thioxo-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-2-yl]tetrahydropyran-3-yl] acetate

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: 526.98

Molecular Weight (Monoisotopic): 526.0384

AlogP: 2.97

#Rotatable Bonds: 5

Polar Surface Area: 123.25

Molecular Species: NEUTRAL

HBA: 13

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.28

Np Likeness Score: -0.43

References

1. Khalil NS..  (2007)  N- and S-alpha-l-arabinopyranosyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles. First synthesis and biological evaluation.,  42  (9): [PMID:17408811] [10.1016/j.ejmech.2007.01.025]

Source

Source(1):

• Scientific Literature