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1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-5-(pyrrolidin-1-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HCID 178787692
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Basic information

CAS
89845-82-9
Standard SMILES
CC1(C)O[C@@H]2[C@H](O1)[C@@H](CO)O[C@H]2n1cc(CN2CCCC2)c(=O)[nH]c1=S
InChIKey
IFJTVPASSJKUFD-RGCMKSIDSA-N
Molecular formula
C17H25N3O5S
Average molar mass
383.5 g/mol

Names & identifiers

Preferred name
1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-5-(pyrrolidin-1-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
IUPAC
1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-(pyrrolidin-1-ylmethyl)-2-sulfanylidenepyrimidin-4-one
English name
2',3'-O-Isopropylidene-5-pyrrolidinoMethyl-2-thiouridine
Molecular formula
C17H25N3O5S
Molecular weight
383.46

Names & synonyms

89845-82-91-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-5-(pyrrolidin-1-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one2',3'-o-isopropylidene-5-pyrrolidinomethyl-2-thiouridine1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-(pyrrolidin-1-ylmethyl)-2-sulfanylidenepyrimidin-4-oneorb1908298SCHEMBL3700730TNU06981-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-5-[(pyrrolidin-1-yl)methyl]-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-oneDA-69650F128162’,3’-O-Isopropylidene-5-pyrrolidinomethyl-2-thiouridine2',3'-Di-O-isopropylidene-5-pyrrolidinomethyl-2-thiouridine
Show more names
2’,3’-Di-O-isopropylidene-5-pyrrolidinomethyl-2-thiouridine2',3'-O-(1-Methylethylidene)-5-(1-pyrrolidinylmethyl)-2-thiouridineUridine, 2',3'-O-(1-methylethylidene)-5-(1-pyrrolidinylmethyl)-2-thio-

Database identifiers

CAS
89845-82-9

Properties

Computed structural propertiesFilling in

XLogP
-0.4
Topological polar surface area
116 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
7
Rotatable bonds
4
Heavy atoms
26
Formal charge
0
Complexity
634

Physicochemical properties

Density
1.43 · 1.43±0.1 g/cm3(Predicted)
pka
6.45 · 6.45±0.23(Predicted)

Chemistry & industry

Applications · 1 item

Uses2',3'-O-Isopropylidene-5-pyrrolidinomethyl-2-thiouridine is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].

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