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

ID: ALA2270689

PubChem CID: 44184994

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-MQUFJNKCSA-N

Molfile:  

     RDKit          2D

 38 39  0  0  0  0  0  0  0  0999 V2000
   35.3509   -3.3608    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.7499   -2.6432    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   34.9289   -2.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0732   -5.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0732   -6.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7785   -6.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4837   -6.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4837   -5.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7785   -5.0765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.1911   -5.0777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1828   -4.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4710   -3.8591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.8863   -3.8448    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.4627   -3.0420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7426   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1909   -6.7160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8992   -6.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6063   -6.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9003   -5.4913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7785   -7.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4862   -7.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4862   -8.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1939   -7.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3643   -5.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3619   -4.2655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6530   -3.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6506   -3.0418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9465   -4.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4530   -1.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4460   -0.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7332   -0.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0261   -0.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0366   -1.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5090   -1.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3661   -6.7160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6578   -6.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9507   -6.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6566   -5.4913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  1
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14  2  1  0
  2 15  1  0
  7 16  1  6
 16 17  1  0
 17 18  1  0
 17 19  2  0
  6 20  1  1
 20 21  1  0
 21 22  1  0
 21 23  2  0
  4 24  1  1
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 15 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 15  1  0
  3 34  1  0
  5 35  1  1
 35 36  1  0
 36 37  1  0
 36 38  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270689

   [(2R,3S,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