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

ID: ALA2270692

PubChem CID: 44184991

Max Phase: Preclinical

Molecular Formula: C22H30N3O10PS2

Molecular Weight: 591.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COP(=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)c1ccccc1

Standard InChI:  InChI=1S/C22H30N3O10PS2/c1-12(26)31-11-17-18(32-13(2)27)19(33-14(3)28)20(34-15(4)29)21(35-17)23-22(37)24-25-36(38,30-5)16-9-7-6-8-10-16/h6-10,17-21H,11H2,1-5H3,(H,25,38)(H2,23,24,37)/t17-,18-,19+,20-,21-,36?/m1/s1

Standard InChI Key:  IQLLVDRDYLWOPI-LGYNLNHPSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2270692

   [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[[methoxy(phenyl)phosphinothioyl]amino]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: 591.60

Molecular Weight (Monoisotopic): 591.1110

AlogP: 0.32

#Rotatable Bonds: 10

Polar Surface Area: 159.75

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.46

CX Basic pKa: ┄

CX LogP: 1.12

CX LogD: 1.12

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.11

Np Likeness Score: 0.44

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