Basic information
- CAS
156126-12-4- Standard SMILES
Cc1cn([C@H]2C[C@H](O)[C@]3(CO)C[C@H]23)c(=O)[nH]c1=O- InChIKey
NOWRLNPOENZFHP-ARHDFHRDSA-N- Molecular formula
- C12H16N2O4
- Average molar mass
- 252.27 g/mol
- Monoisotopic mass
- 252.111007
Overview
1-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo[3.1.0]hexan-2-yl]thymine is a carbobicyclic compound that is bicyclo[3.1.0]hexane which is substituted at the 2-pro-S, 4-pro-S and 5-pro-R positions by thymin-1-yl, hydroxy, and hydroxymethyl groups, respectively. It is a primary alcohol, a secondary alcohol, a carbobicyclic compound, a C-glycosyl pyrimidine and a pyrimidone. It is functionally related to a thymine.
Names & identifiers
- Preferred name
- (North)-methanocarbathymidine
- IUPAC
- 1-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-bicyclo[3.1.0]hexanyl]-5-methylpyrimidine-2,4-dione
- English name
- 1-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo[3.1.0]hexan-2-yl]thymine
- Molecular formula
- C12H16N2O4
- Molecular weight
- 252.27
Names & synonyms
(North)-methanocarbathymidineLTM5S02010CHEBI:460261-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-bicyclo[3.1.0]hexanyl]-5-methylpyrimidine-2,4-dione1-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo[3.1.0]hex-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione1-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo[3.1.0]hexan-2-yl]thymine1-((1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo(3.1.0)hexan-2-yl)thymine1-((1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-bicyclo(3.1.0)hexanyl)-5-methylpyrimidine-2,4-dione1-((1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo(3.1.0)hex-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dioneRefChem:70185(N)-MCTnorth-methanocarbathymidine
Show more names
2,4(1H,3H)-Pyrimidinedione, 1-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo[3.1.0]hex-2-yl]-5-methyl-
N-MCTN-Methanocarbathymidine156126-12-4UNII-LTM5S020101-[4-HYDROXY-5-(HYDROXYMETHYL)BICYCLO[3.1.0]HEX-2-YL]-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONECHEMBL1466732,4(1H,3H)-Pyrimidinedione, 1-(4-hydroxy-5-(hydroxymethyl)bicyclo(3.1.0)hex-2-yl)-5-methyl-, (1S-(1alpha,2alpha,4beta,5alpha))-1-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
Properties
Computed structural properties
- XLogP
- -0.5
- Topological polar surface area
- 89.9 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 461
Physicochemical properties
- Density
- 1.49 · 1.490±0.06 g/cm3(Predicted)
- pka
- 9.82 · 9.82±0.10(Predicted)
- FDA UNII
- 5 S02010 · LTM5S02010
Chemistry & industry
Applications
Usesn-MCT is an antiviral agent that is used against herpesvirus and orthopoxvirus infections.
Suppliers1 total
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
Additional notes
DefinitionChEBI: 1-[(1S,2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)bicyclo[3.1.0]hexan-2-yl]thymine is a carbobicyclic compound that is bicyclo[3.1.0]hexane which is substituted at the 2-pro-S, 4-pro-S and 5-pro-R positions by thymin-1-yl, hydroxy, and hydroxymethyl groups, respectively. It is a carbobicyclic compound, a primary alcohol, a secondary alcohol, a C-glycosyl pyrimidine and a pyrimidone. It is functionally related to a thymine.
Related reactions
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Compound notes
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