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

ID: ALA2270681

PubChem CID: 44185109

Max Phase: Preclinical

Molecular Formula: C24H30N3O11PS2

Molecular Weight: 631.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=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)c1ccccc1

Standard InChI:  InChI=1S/C24H30N3O11PS2/c1-13(28)34-11-18-20(35-14(2)29)21(36-15(3)30)22(37-16(4)31)23(38-18)25-24-27(19(32)12-41-24)26-39(40,33-5)17-9-7-6-8-10-17/h6-10,18,20-23H,11-12H2,1-5H3,(H,26,40)/b25-24+/t18-,20-,21+,22-,23-,39?/m1/s1

Standard InChI Key:  HUWHIYILOYTEMM-OCKTXSBOSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2270681

   [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(E)-[3-[[methoxy(phenyl)phosphinothioyl]amino]-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: 631.62

Molecular Weight (Monoisotopic): 631.1059

AlogP: 0.79

#Rotatable Bonds: 10

Polar Surface Area: 168.36

Molecular Species: NEUTRAL

HBA: 14

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.48

CX Basic pKa: ┄

CX LogP: 1.51

CX LogD: 1.25

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.22

Np Likeness Score: 0.42

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