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134680-32-3 molecular structure
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4-amino-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

ChemBase ID: 172176
Molecular Formular: C8H11N3O3S
Molecular Mass: 229.25624
Monoisotopic Mass: 229.05211223
SMILES and InChIs

SMILES:
S1C[C@@H](O[C@@H]1CO)n1c(=O)nc(cc1)N
Canonical SMILES:
Nc1ccn(c(=O)n1)[C@H]1CS[C@H](O1)CO
InChI:
InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m1/s1
InChIKey:
JTEGQNOMFQHVDC-RQJHMYQMSA-N

Cite this record

CBID:172176 http://www.chembase.cn/molecule-172176.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-amino-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
IUPAC Traditional name
2'3' dideoxy 3' thiacytidine
Synonyms
4-Amino-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone
(2S-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone
(+)-BCH 189
2',3'-Dideoxy-3'-thiacytidine
2'-Deoxy-3'-thiacytidine
3TC
NSC 620753
cis(+)-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane
ent-Lamivudine
4-amino-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
CAS Number
134680-32-3
MDL Number
MFCD00870542
PubChem SID
164228086
PubChem CID
73339

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 73339 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.294606  H Acceptors
H Donor LogD (pH = 5.5) -1.0951098 
LogD (pH = 7.4) -1.0951077  Log P -1.0951076 
Molar Refractivity 55.1645 cm3 Polarizability 21.351086 Å3
Polar Surface Area 88.15 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
Off-White to Pale Yellow Solid expand Show data source
Melting Point
164-166°C expand Show data source
176 - 178°C expand Show data source
Hydrophobicity(logP)
-1.462 expand Show data source
Storage Condition
Hygroscopic, Refrigerator, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Purity
95% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - L172505 external link
An enantiomer of Lamivudine (L172500); an antiviral that inhibits HIV-reverse transcriptase.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Pepe, G. et al.: Eur. J. Med. Chem., 31, 775 (1996)
  • • Marr, E. et al.: Antiviral Res., 28, 1 (1996)
  • • Parikh, U.M. et al.: Antimicrob. Agents Chemother., 49, 1139 (1996)
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PATENTS

PATENTS

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INTERNET

INTERNET

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