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221287-92-9 molecular structure
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methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-{2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenoxy}oxane-2-carboxylate

ChemBase ID: 174064
Molecular Formular: C23H23N3O13S
Molecular Mass: 581.50602
Monoisotopic Mass: 581.09515881
SMILES and InChIs

SMILES:
c1c(c(ccc1)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)C(=O)Nc1ncc(s1)[N+](=O)[O-]
Canonical SMILES:
COC(=O)[C@H]1O[C@H](Oc2ccccc2C(=O)Nc2ncc(s2)[N+](=O)[O-])[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
InChI:
InChI=1S/C23H23N3O13S/c1-10(27)35-16-17(36-11(2)28)19(37-12(3)29)22(39-18(16)21(31)34-4)38-14-8-6-5-7-13(14)20(30)25-23-24-9-15(40-23)26(32)33/h5-9,16-19,22H,1-4H3,(H,24,25,30)/t16-,17-,18-,19+,22+/m1/s1
InChIKey:
JZMCAGQTKJRRDM-DIGZUXTDSA-N

Cite this record

CBID:174064 http://www.chembase.cn/molecule-174064.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-{2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenoxy}oxane-2-carboxylate
IUPAC Traditional name
methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-{2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenoxy}oxane-2-carboxylate
Synonyms
2-[[(5-Nitro-2-thiazolyl)amino]carbonyl]phenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate
Methyl 1-[[2-N-(5-Nitrothiazolyl)carboxamido]phenyl]-2,3,4- tri-O-acetyl-β-D-glucopyranuronate
CAS Number
221287-92-9
PubChem SID
164229974
PubChem CID
71750504

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC M325820 external link Add to cart
PubChem 71750504 external link
Data Source Data ID Price
TRC
M325820 external link Add to cart Please log in.
Data Source Data ID
PubChem 71750504 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 8.422701  H Acceptors 10 
H Donor LogD (pH = 5.5) 1.7315723 
LogD (pH = 7.4) 1.6947365  Log P 1.732065 
Molar Refractivity 128.9741 cm3 Polarizability 50.851044 Å3
Polar Surface Area 211.47 Å2 Rotatable Bonds 13 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
Yellow Solid expand Show data source
Melting Point
268-270°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - M325820 external link
An intermediate in the synthesis of the metabolite of Nitazoxanide.

REFERENCES

REFERENCES

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  • • Honma, K., et al.: Chem. Pharm. Bull., 24, 394 (1976)
  • • Dubreuil, L., et al.: Antimicrob. Agents Chemother., 40, 2266 (1976)
  • • Stockis, A., et al.: Int. J. Clin. Pharmacol. Ther., 34, 349 (1976)
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PATENTS

PATENTS

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INTERNET

INTERNET

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