Basic information
- Standard SMILES
Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O- InChIKey
DWRXFEITVBNRMK-JXOAFFINSA-N- Molecular formula
- C10H14N2O6
- Average molar mass
- 258.23 g/mol
- Monoisotopic mass
- 258.08518617
Overview
Ribothymidine is a methyluridine having a single methyl substituent at the 5-position on the uracil ring. It has a role as an antigen, an Escherichia coli metabolite and a human metabolite.
Names & identifiers
- Preferred name
- 5-Methyluridine
- IUPAC
- 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
- English name
- 5-Methyluridine
- Molecular formula
- C10H14N2O6
- Molecular weight
- 258.23
Names & synonyms
5-Methyluridine1463-10-1RibothymidineThymine ribosideRibosylthymineribosylthymidine1-(beta-D-ribofuranosyl)thymineCHEBI:45996ZS1409014ADTXSID201633481-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
Show more names
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dione5-Me-U5-Me-UrMethyluridine5-methyuridine5-methyl-uridinTHYMINERIBOSIDE
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-5-methylpyrimidine-2,4-dioneRefChem:898086DTXCID9085839215-973-9Uridine, 5-methyl-5-Methyl UridineThymine ribofuranoside
Database identifiers
- CAS
1463-10-1- PubChem CID
- 445408
- DTXSID
DTXSID20163348- ChEMBL
CHEMBL106175- ChEBI
CHEBI:45996- UNII
- ZS1409014A
- EC Number
- 215-973-9
- Nikkaji
- J32.354C
Properties
Computed structural properties
- XLogP
- -1.6
- Topological polar surface area
- 119 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 409
Experimental & physicochemical properties
Melting Point183 - 187 °C
Physical DescriptionSolid
Collision Cross Section153.52 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 183 · 183-184 °C(lit.)
- Density
- 1.576 · 1.576±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Methanol (Slightly, Heated, Sonicated), Water (Sparingly, Sonicated)
- pka
- 9.55 · 9.55±0.10(Predicted)
- form
- powder
- color
- white
- PH
- 9.7 · 9.7
- optical activity
- -8.9 ° · -8.9°(C=1 g/100ml H2O)
- λmax
- 267 · 267 (pH 1)；268 (pH 13)
- InChI
- InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1
- InChIKey
- DWRXFEITVBNRMK-JXOAFFINSA-N
- SMILES
- OC[C@H]1O[C@@H](N2C=C(C)C(=O)NC2=O)[C@H](O)[C@@H]1O
- CAS DataBase Reference
- 1463 · 1463-10-1(CAS DataBase Reference)
- FDA UNII
- 1409014 A · ZS1409014A
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- T+
- Risk Statements
- 26 · 26/27/28
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- HS Code
- 29349990 · 29349990
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.
Warning
H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 09-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/31788
Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29349990
- risk_code
- 26/27/28
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- T+
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
Applications
Description5-Methyluridine is a pyrimidine nucleoside and methylated form of uridine. It is the ribonucleoside counterpart to the deoxyribonucleoside thymidine, which lacks a hydroxyl group at the 2' position. 5-Methyluridine contains a thymine base joined to a ribose pentose sugar. It is an endogenous methylated nucleoside found in human fluids. In cells, 5-methyluridine is present in tRNA, formed during its post-transcriptional modification by the methylation of uridine.
UsesA primary degradation product of tRNA, an urinary nucleoside as biological marker for patients with colorectal cancer.It enhances the antitumor activity of 5-fluorouracil in a mouse Erlich solid carcinoma model and a P388 murine leukemia model. It has been used to characterize the activity of a variety of enzymes, including uridine nucleosidase.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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Syntechem Co.,Ltd[email protected]
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武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
杭州东帆化学有限公司86-0571-85151182
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Additional notes
DefinitionChEBI: Ribothymidine is a methyluridine having a single methyl substituent at the 5-position on the uracil ring. It has a role as a human metabolite, an Escherichia coli metabolite and an antigen.
Related reactions
12 records
Linked notes
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