3-Dimethoxythiophosphorylamido-2-(2',3',4'-tri-O-acetyl-beta-D-xylopyranosyl-1'-imino)thiazolidine-4-one

ID: ALA2270677

PubChem CID: 44185169

Max Phase: Preclinical

Molecular Formula: C16H24N3O10PS2

Molecular Weight: 513.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=S)(NN1C(=O)CS/C1=N/[C@@H]1OC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)OC

Standard InChI:  InChI=1S/C16H24N3O10PS2/c1-8(20)27-11-6-26-15(14(29-10(3)22)13(11)28-9(2)21)17-16-19(12(23)7-32-16)18-30(31,24-4)25-5/h11,13-15H,6-7H2,1-5H3,(H,18,31)/b17-16+/t11-,13+,14-,15-/m1/s1

Standard InChI Key:  MXVVCHWUWKVTCN-WWBGHNHMSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    2.6744   -9.6247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8891  -10.4171    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.4680   -9.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8230  -12.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8230  -13.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5283  -13.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2336  -13.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2336  -12.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5283  -12.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9410  -12.0073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9407  -13.6456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6490  -13.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3561  -13.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6502  -12.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5283  -14.4577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360  -14.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360  -15.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9437  -14.4577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1159  -13.6456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4076  -13.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005  -13.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064  -12.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9382  -11.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5988  -10.7052    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3437   -9.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5264   -9.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2766  -10.7096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4999  -10.9636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1149  -10.6719    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2507   -9.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845   -9.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438   -9.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  1
  7 11  1  6
 11 12  1  0
 12 13  1  0
 12 14  2  0
  6 15  1  1
 15 16  1  0
 16 17  1  0
 16 18  2  0
  5 19  1  6
 19 20  1  0
 20 21  1  0
 20 22  2  0
 10 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 27 28  1  0
 28  2  1  0
  2 29  2  0
  3 30  1  0
  1 31  1  0
 26 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270677

   [(3R,4S,5R,6R)-4,5-diacetyloxy-6-[(E)-[3-(dimethoxyphosphinothioylamino)-4-oxo-1,3-thiazolidin-2-ylidene]amino]oxan-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: 513.49

Molecular Weight (Monoisotopic): 513.0641

AlogP: 0.09

#Rotatable Bonds: 8

Polar Surface Area: 151.29

Molecular Species: NEUTRAL

HBA: 13

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.45

CX Basic pKa: ┄

CX LogP: -0.01

CX LogD: -0.28

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.27

Np Likeness Score: 0.39

References

1. Li YX, Wang HA, Yang XP, Cheng HY, Wang ZH, Li YM, Li ZM, Wang SH, Yan DW..  (2009)  Regioselective synthesis of novel 3-alkoxy (phenyl) thiophosphorylamido-2-(per-O-acetylglycosyl-1'-imino)thiazolidine-4-one derivatives from O-alkyl N4-glycosyl(thiosemicarbazido)phosphonothioates.,  344  (10): [PMID:19450796] [10.1016/j.carres.2009.03.027]

Source

Source(1):

• Scientific Literature