1-Dimethoxythiophosphoryl-4-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)thiosemicarbazide

ID: ALA2270688

PubChem CID: 44185047

Max Phase: Preclinical

Molecular Formula: C14H24N3O9PS2

Molecular Weight: 473.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=S)(NNC(=S)N[C@@H]1OC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)OC

Standard InChI:  InChI=1S/C14H24N3O9PS2/c1-7(18)24-10-6-23-13(12(26-9(3)20)11(10)25-8(2)19)15-14(28)16-17-27(29,21-4)22-5/h10-13H,6H2,1-5H3,(H,17,29)(H2,15,16,28)/t10-,11+,12-,13-/m1/s1

Standard InChI Key:  WKMGSKXNMAAQII-YVECIDJPSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
    2.9975  -11.6896    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3966  -10.9719    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.5756  -10.9852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198  -13.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198  -14.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251  -15.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304  -14.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1304  -13.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251  -13.4052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378  -13.4064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8295  -12.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1177  -12.1879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5330  -12.1735    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093  -11.3707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3892  -10.1538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375  -15.0448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5458  -14.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2529  -15.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5470  -13.8200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251  -15.8568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1328  -16.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1328  -17.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8405  -15.8568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0127  -15.0448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3044  -14.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5973  -15.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3032  -13.8200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1556  -10.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932   -9.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  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
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14  2  1  0
  2 15  1  0
  7 16  1  6
 16 17  1  0
 17 18  1  0
 17 19  2  0
  6 20  1  1
 20 21  1  0
 21 22  1  0
 21 23  2  0
  5 24  1  6
 24 25  1  0
 25 26  1  0
 25 27  2  0
  3 28  1  0
 15 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270688

   [(3R,4S,5R,6R)-4,5-diacetyloxy-6-[(dimethoxyphosphinothioylamino)carbamothioylamino]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: 473.47

Molecular Weight (Monoisotopic): 473.0692

AlogP: -0.38

#Rotatable Bonds: 8

Polar Surface Area: 142.68

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.15

CX Basic pKa: ┄

CX LogP: -0.22

CX LogD: -0.22

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.14

Np Likeness Score: 0.46

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