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103882-85-5 molecular structure
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4-amino-1-[(2R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

ChemBase ID: 168055
Molecular Formular: C9H11F2N3O4
Molecular Mass: 263.1981464
Monoisotopic Mass: 263.07176229
SMILES and InChIs

SMILES:
n1c(=O)n(ccc1N)[C@H]1C(C(O)[C@@H](CO)O1)(F)F
Canonical SMILES:
OC[C@H]1O[C@H](C(C1O)(F)F)n1ccc(nc1=O)N
InChI:
InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6?,7-/m1/s1
InChIKey:
SDUQYLNIPVEERB-ZJXFTUPMSA-N

Cite this record

CBID:168055 http://www.chembase.cn/molecule-168055.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-amino-1-[(2R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
IUPAC Traditional name
4-amino-1-[(2R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Synonyms
4-Amino-1-(deoxy-2,2-difluoro-D-threo-pentofuranosyl)-2(1H)-pyrimidinone
(Gemcitabine Impurity
3'-Epi Gemcitabine (Gemcitabine Impurity)
CAS Number
103882-85-5
PubChem SID
162262187
PubChem CID
46705350

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC E588520 external link Add to cart
PubChem 46705350 external link
Data Source Data ID Price
TRC
E588520 external link Add to cart Please log in.
Data Source Data ID
PubChem 46705350 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.51707  H Acceptors
H Donor LogD (pH = 5.5) -1.4665402 
LogD (pH = 7.4) -1.4665728  Log P -1.4665396 
Molar Refractivity 53.2503 cm3 Polarizability 20.563793 Å3
Polar Surface Area 108.38 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
102-104°C expand Show data source
Storage Condition
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - E588520 external link
An impurity from the synthesis of Gemcitabine.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Haufman, et al.: Science, 145, 585 (1964)
  • • Prusoff, et al.: Biochim. Biophys. Acta, 32, 295 (1959)
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PATENTS

PATENTS

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INTERNET

INTERNET

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