1-Methoxy(phenyl)thiophosphoryl-4-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)thiosemicarbazide

ID: ALA2270686

PubChem CID: 44185049

Max Phase: Preclinical

Molecular Formula: C19H26N3O8PS2

Molecular Weight: 519.54

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)c1ccccc1

Standard InChI:  InChI=1S/C19H26N3O8PS2/c1-11(23)28-15-10-27-18(17(30-13(3)25)16(15)29-12(2)24)20-19(32)21-22-31(33,26-4)14-8-6-5-7-9-14/h5-9,15-18H,10H2,1-4H3,(H,22,33)(H2,20,21,32)/t15-,16+,17-,18-,31?/m1/s1

Standard InChI Key:  CZDNPYXGBMGXKQ-LSXCGXKBSA-N

Molfile:  

     RDKit          2D

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   18.0895  -11.5332    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.2685  -11.5465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4128  -14.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4128  -15.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.1181  -13.9665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5307  -13.9677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5224  -13.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8106  -12.7492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2259  -12.7348    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.8023  -11.9320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5305  -15.6061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   20.2399  -14.3813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8258  -16.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8258  -17.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5335  -16.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7057  -15.6061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9974  -15.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2902  -15.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9962  -14.3813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8485  -10.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4989  -10.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3138  -10.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7233  -10.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3156   -9.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4941   -9.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0884  -10.1236    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
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  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  1
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 11 13  2  0
 12 14  1  0
 14  2  1  0
  7 15  1  6
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 16 17  1  0
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  6 19  1  1
 19 20  1  0
 20 21  1  0
 20 22  2  0
  5 23  1  6
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 24 25  1  0
 24 26  2  0
  3 27  1  0
  2 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270686

   [(3R,4S,5R,6R)-4,5-diacetyloxy-6-[[[methoxy(phenyl)phosphinothioyl]amino]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: 519.54

Molecular Weight (Monoisotopic): 519.0899

AlogP: 0.39

#Rotatable Bonds: 8

Polar Surface Area: 133.45

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.46

CX Basic pKa: ┄

CX LogP: 1.37

CX LogD: 1.37

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.14

Np Likeness Score: 0.28

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