3-Diethoxythiophosphorylamido-2-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl-1'-imino)thiazolidine-4-one

ID: ALA2270682

PubChem CID: 44185108

Max Phase: Preclinical

Molecular Formula: C21H32N3O12PS2

Molecular Weight: 613.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=S)(NN1C(=O)CS/C1=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/C21H32N3O12PS2/c1-7-31-37(38,32-8-2)23-24-16(29)10-39-21(24)22-20-19(35-14(6)28)18(34-13(5)27)17(33-12(4)26)15(36-20)9-30-11(3)25/h15,17-20H,7-10H2,1-6H3,(H,23,38)/b22-21+/t15-,17-,18+,19-,20-/m1/s1

Standard InChI Key:  WRMRXXBZXIXCAR-RKAXHSGFSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2270682

   [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(E)-[3-(diethoxyphosphinothioylamino)-4-oxo-1,3-thiazolidin-2-ylidene]amino]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: 613.60

Molecular Weight (Monoisotopic): 613.1165

AlogP: 0.80

#Rotatable Bonds: 12

Polar Surface Area: 177.59

Molecular Species: NEUTRAL

HBA: 15

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.45

CX Basic pKa: ┄

CX LogP: 0.51

CX LogD: 0.24

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: 0.52

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