1-Diethoxythiophosphoryl-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)thiosemicarbazide

ID: ALA2270693

PubChem CID: 44184990

Max Phase: Preclinical

Molecular Formula: C19H32N3O11PS2

Molecular Weight: 573.58

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H32N3O11PS2/c1-7-28-34(36,29-8-2)22-21-19(35)20-18-17(32-13(6)26)16(31-12(5)25)15(30-11(4)24)14(33-18)9-27-10(3)23/h14-18H,7-9H2,1-6H3,(H,22,36)(H2,20,21,35)/t14-,15-,16+,17-,18-/m1/s1

Standard InChI Key:  BKKJLPUWENANDV-UYTYNIKBSA-N

Molfile:  

     RDKit          2D

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    3.3474   -2.7348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -5.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0750   -5.5697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  6 20  1  1
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  5 29  1  6
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  3 33  1  0
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 15 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270693

   [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(diethoxyphosphinothioylamino)carbamothioylamino]oxan-2-yl]methyl 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: 573.58

Molecular Weight (Monoisotopic): 573.1216

AlogP: 0.34

#Rotatable Bonds: 12

Polar Surface Area: 168.98

Molecular Species: NEUTRAL

HBA: 13

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.01

CX Basic pKa: ┄

CX LogP: 0.31

CX LogD: 0.31

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.10

Np Likeness Score: 0.58

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