1-Ethoxy(phenyl)thiophosphoryl-4-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)thiosemicarbazide

ID: ALA2270684

PubChem CID: 44185050

Max Phase: Preclinical

Molecular Formula: C20H28N3O8PS2

Molecular Weight: 533.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOP(=S)(NNC(=S)N[C@@H]1OC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)c1ccccc1

Standard InChI:  InChI=1S/C20H28N3O8PS2/c1-5-28-32(34,15-9-7-6-8-10-15)23-22-20(33)21-19-18(31-14(4)26)17(30-13(3)25)16(11-27-19)29-12(2)24/h6-10,16-19H,5,11H2,1-4H3,(H,23,34)(H2,21,22,33)/t16-,17+,18-,19-,32?/m1/s1

Standard InChI Key:  BVLMHWCUKNENLI-UHFKPTSJSA-N

Molfile:  

     RDKit          2D

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   24.4623  -11.4433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6065  -14.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.4197  -12.6316    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   23.8994  -15.5029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1911  -15.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.1899  -14.2781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0423  -10.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6926  -10.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5076  -10.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9170  -10.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5093   -9.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6879   -9.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 20 21  1  0
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  5 23  1  6
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 24 25  1  0
 24 26  2  0
  3 27  1  0
  2 28  1  0
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 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 27 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2270684

   [(3R,4S,5R,6R)-4,5-diacetyloxy-6-[[[ethoxy(phenyl)phosphinothioyl]amino]carbamothioylamino]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: 533.57

Molecular Weight (Monoisotopic): 533.1055

AlogP: 0.78

#Rotatable Bonds: 9

Polar Surface Area: 133.45

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.46

CX Basic pKa: ┄

CX LogP: 1.71

CX LogD: 1.71

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.14

Np Likeness Score: 0.25

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