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

ID: ALA2270674

PubChem CID: 44185228

Max Phase: Preclinical

Molecular Formula: C22H28N3O9PS2

Molecular Weight: 573.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=S)(NN1C(=O)CS/C1=N/[C@@H]1OC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)c1ccccc1

Standard InChI:  InChI=1S/C22H28N3O9PS2/c1-5-31-35(36,16-9-7-6-8-10-16)24-25-18(29)12-37-22(25)23-21-20(34-15(4)28)19(33-14(3)27)17(11-30-21)32-13(2)26/h6-10,17,19-21H,5,11-12H2,1-4H3,(H,24,36)/b23-22+/t17-,19+,20-,21-,35?/m1/s1

Standard InChI Key:  RWLXGXIBSBMYMQ-UYIUDEFXSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
   25.6631  -11.2838    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.2421  -10.7018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5971  -13.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5971  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3024  -14.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0076  -14.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0076  -13.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3024  -12.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7150  -12.8740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7147  -14.5124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4230  -14.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1302  -14.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4242  -13.2876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3024  -15.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0101  -15.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0101  -16.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7178  -15.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8900  -14.5124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1817  -14.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4745  -14.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1805  -13.2876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7123  -12.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3728  -11.5719    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.1177  -10.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3005  -10.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0507  -11.5763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2739  -11.8303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8889  -11.5386    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.0248   -9.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8179  -10.1388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9558  -10.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9693  -10.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2628   -9.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5438  -10.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5357  -10.8479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2428  -11.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5987   -9.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  3  8  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
  6 10  1  6
 10 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  1
 14 15  1  0
 15 16  1  0
 15 17  2  0
  4 18  1  6
 18 19  1  0
 19 20  1  0
 19 21  2  0
  9 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
 26 27  1  0
 27  1  1  0
  1 28  2  0
  2 29  1  0
 25 30  2  0
  1 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
 29 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270674

   [(3R,4S,5R,6R)-4,5-diacetyloxy-6-[(E)-[3-[[ethoxy(phenyl)phosphinothioyl]amino]-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: 573.59

Molecular Weight (Monoisotopic): 573.1005

AlogP: 1.25

#Rotatable Bonds: 9

Polar Surface Area: 142.06

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.48

CX Basic pKa: ┄

CX LogP: 2.09

CX LogD: 1.83

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.26

Np Likeness Score: 0.23

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