1-Methylpseudouridine

HCID 99543

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Basic information

CAS: 13860-38-3
Standard SMILES: Cn1cc([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O
InChIKey: UVBYMVOUBXYSFV-XUTVFYLZSA-N
Molecular formula: C10H14N2O6
Average molar mass: 258.23 g/mol
Monoisotopic mass: 258.08518617

Overview

1-methylpseudouridine is a methylpseudouridine in which the methyl group is located at position N-1 on the uracil ring.

Names & identifiers

Preferred name: 1-Methylpseudouridine
IUPAC: 5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methylpyrimidine-2,4-dione
English name: 1-methylpseudouridine
Molecular formula: C10H14N2O6
Molecular weight: 258.229

Names & synonyms

1-Methylpseudouridine13860-38-3N1-MethylpseudouridineN1-methyl-pseudouridine09RAD4M6WFCHEBI:190682,4(1H,3H)-Pyrimidinedione, 1-methyl-5-beta-D-ribofuranosyl-DTXSID50160724U-50228(1S)-1,4-anhydro-1-(1-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-D-ribitolNSC-240023U 50228

Show more names

N1-Me-PseudouridineN1-MePseUAntibiotic U-502281-N-ME-PSEUDOURIDINEN1-methylpseudourineNl-methylpseudourine1-MethyipseudouridineN1-methylpeudouridine

5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methylpyrimidine-2,4-dione5-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1-methylpyrimidine-2,4-dioneRefChem:831470DTXCID90832155-((2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1-methylpyrimidine-2,4(1H,3H)-dionem1psiMFCD106870171-methyl-pseudouridine

Database identifiers

CAS: 13860-38-3
PubChem CID: 99543
DTXSID: DTXSID50160724
ChEBI: CHEBI:19068
UNII: 09RAD4M6WF
EC Number: 974-126-8
Nikkaji: J13.862B

Properties

Computed structural properties

XLogP: -2.6
Topological polar surface area: 119 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 6
Rotatable bonds: 2
Heavy atoms: 18
Formal charge: 0
Complexity: 409

Physicochemical properties

Density: 1.576 · 1.576±0.06 g/cm3(Predicted)
storage temp.: -20 °C · Store at -20°C
solubility: 20 mg/mL · >20 mg/mL in EtOH; >20.65 mg/mL in DMSO
pka: 9.43 · 9.43±0.10(Predicted)
form: A solid
color: White to off-white
Water Solubility: insoluble in Water;
InChI: InChI=1/C10H14N2O6/c1-12-2-4(9(16)11-10(12)17)8-7(15)6(14)5(3-13)18-8/h2,5-8,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,8+/s3
InChIKey: UVBYMVOUBXYSFV-CAYFCZNJNA-N
SMILES: [C@@H]1(O)[C@@H](CO)O[C@@H](C2C(=O)NC(=O)N(C)C=2)[C@@H]1O |&1:0,2,6,16,r|
FDA UNII: 9 RAD4M6WF · 09RAD4M6WF
UNSPSC Code: 41106305 · 41106305
NACRES: 21 · NA.21
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
WGK Germany: 3 · WGK 3
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS ClassificationNot Classified

Hazard information

Hazard Classes and CategoriesNot Classified

Safety data

wgk: WGK 3
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 1 item

DescriptionN1-Methylpseudouridine is a modified nucleoside used for enhancing mRNA translation. Incorporation of N1-Methylpseudouridine into mRNA turns off the immune/eIF2α phosphorylation-dependent inhibition of translation, and increases ribosome pausing and density on the mRNA, thus dramatically facilitating the translation process. N1-Methylpseudouridine outperforms several other modified nucleosides (e.g. 5-Methylcytidine) and corresponding combinations in terms of translation capacity.

Upstream & downstream products

Upstream raw materials

2,4(1H,3H)-Pyrimidinedione, 1-methyl-5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione, 5-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione, 5-[5-O-[(1,1-dimethylethyl)diphenylsilyl]-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl]-1-methyl-

Suppliers100 total

常州帝通化工有限公司+86-0519-88298848 · [email protected]

苏州华赛生物工程技术有限公司0512-89581819; 18915732708 · [email protected]

武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]

上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]

Additional notes

DefinitionChEBI: 1-methylpseudouridine is a methylpseudouridine in which the methyl group is located at position N-1 on the uracil ring.

Related reactions

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Compound notes

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