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

ID: ALA2270680

PubChem CID: 44185110

Max Phase: Preclinical

Molecular Formula: C26H34N3O11PS2

Molecular Weight: 659.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOP(=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/C26H34N3O11PS2/c1-6-12-36-41(42,19-10-8-7-9-11-19)28-29-21(34)14-43-26(29)27-25-24(39-18(5)33)23(38-17(4)32)22(37-16(3)31)20(40-25)13-35-15(2)30/h7-11,20,22-25H,6,12-14H2,1-5H3,(H,28,42)/b27-26+/t20-,22-,23+,24-,25-,41?/m1/s1

Standard InChI Key:  RDMWKZXHQBANHU-NWVZUMQYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2270680

   [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(E)-[4-oxo-3-[[phenyl(propoxy)phosphinothioyl]amino]-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: 659.68

Molecular Weight (Monoisotopic): 659.1372

AlogP: 1.57

#Rotatable Bonds: 12

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: 2.32

CX LogD: 2.06

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.19

Np Likeness Score: 0.38

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