3-Methoxy(phenyl)thiophosphorylamido-2-(2',3',4'-tri-O-acetyl-beta-D-xylopyranosyl-1'-imino)thiazolidine-4-one

ID: ALA2270675

PubChem CID: 44185171

Max Phase: Preclinical

Molecular Formula: C21H26N3O9PS2

Molecular Weight: 559.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=S)(NN1C(=O)CS/C1=N/[C@@H]1OC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)c1ccccc1

Standard InChI:  InChI=1S/C21H26N3O9PS2/c1-12(25)31-16-10-30-20(19(33-14(3)27)18(16)32-13(2)26)22-21-24(17(28)11-36-21)23-34(35,29-4)15-8-6-5-7-9-15/h5-9,16,18-20H,10-11H2,1-4H3,(H,23,35)/b22-21+/t16-,18+,19-,20-,34?/m1/s1

Standard InChI Key:  QUDPCGOTVPODJH-SAUMSYQASA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2270675

   [(3R,4S,5R,6R)-4,5-diacetyloxy-6-[(E)-[3-[[methoxy(phenyl)phosphinothioyl]amino]-4-oxo-1,3-thiazolidin-2-ylidene]amino]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: 559.56

Molecular Weight (Monoisotopic): 559.0848

AlogP: 0.86

#Rotatable Bonds: 8

Polar Surface Area: 142.06

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.48

CX Basic pKa: ┄

CX LogP: 1.75

CX LogD: 1.49

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.27

Np Likeness Score: 0.26

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