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

ID: ALA2270687

PubChem CID: 44185048

Max Phase: Preclinical

Molecular Formula: C16H28N3O9PS2

Molecular Weight: 501.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H28N3O9PS2/c1-6-24-29(31,25-7-2)19-18-16(30)17-15-14(28-11(5)22)13(27-10(4)21)12(8-23-15)26-9(3)20/h12-15H,6-8H2,1-5H3,(H,19,31)(H2,17,18,30)/t12-,13+,14-,15-/m1/s1

Standard InChI Key:  XLBBYYQMBWXSCD-LXTVHRRPSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   10.2738  -12.2798    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.6729  -11.5621    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.8519  -11.5754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9961  -14.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9961  -15.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7014  -15.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4067  -15.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4067  -14.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7014  -13.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1141  -13.9966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1058  -13.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3940  -12.7781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8093  -12.7637    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3857  -11.9609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6655  -10.7440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1138  -15.6350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8221  -15.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5292  -15.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8233  -14.4102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7014  -16.4470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4091  -16.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4091  -17.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1168  -16.4470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2890  -15.6350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5807  -15.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8736  -15.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5795  -14.4102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4319  -10.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3695  -10.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8291  -10.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3622   -9.5118    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
 28 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270687

   [(3R,4S,5R,6R)-4,5-diacetyloxy-6-[(diethoxyphosphinothioylamino)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: 501.52

Molecular Weight (Monoisotopic): 501.1005

AlogP: 0.40

#Rotatable Bonds: 10

Polar Surface Area: 142.68

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.01

CX Basic pKa: ┄

CX LogP: 0.49

CX LogD: 0.49

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.12

Np Likeness Score: 0.43

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