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

ID: ALA2270691

PubChem CID: 44184992

Max Phase: Preclinical

Molecular Formula: C24H34N3O10PS2

Molecular Weight: 619.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOP(=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/C24H34N3O10PS2/c1-6-12-33-38(40,18-10-8-7-9-11-18)27-26-24(39)25-23-22(36-17(5)31)21(35-16(4)30)20(34-15(3)29)19(37-23)13-32-14(2)28/h7-11,19-23H,6,12-13H2,1-5H3,(H,27,40)(H2,25,26,39)/t19-,20-,21+,22-,23-,38?/m1/s1

Standard InChI Key:  FVLQQNMEMDPNBK-OZGSANRRSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2270691

   [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[[phenyl(propoxy)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: 619.66

Molecular Weight (Monoisotopic): 619.1423

AlogP: 1.10

#Rotatable Bonds: 12

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: 1.93

CX LogD: 1.93

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.10

Np Likeness Score: 0.40

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