2'-O-Methylcytidine

HCID 150971

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Basic information

CAS: 2140-72-9
Standard SMILES: CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(N)nc1=O
InChIKey: RFCQJGFZUQFYRF-ZOQUXTDFSA-N
Molecular formula: C10H15N3O5
Average molar mass: 257.24 g/mol
Monoisotopic mass: 257.10117058

Overview

2'-O-methylcytidine is a methylcytidine.

Names & identifiers

Preferred name: 2'-O-Methylcytidine
IUPAC: 4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]pyrimidin-2-one
English name: 2'-O-Methylcytidine
Molecular formula: C10H15N3O5
Molecular weight: 257.24

Names & synonyms

2'-O-Methylcytidine2140-72-9Cytidine, 2'-O-methyl-O(2')-Methylcytidine5XD9IH2G27CHEBI:19228RefChem:804262'-O-Methyl cytidine4-amino-1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)pyrimidin-2(1H)-oneMFCD115190764-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]pyrimidin-2-one2 inverted exclamation marka-O-methylcytidine

Show more names

2'-OMe-C2'-OMe-rC2'-O-Me-rC2′-0-Methylcytidine2'-OMe-Cr2'-O-Me-dC2'-OMe Cytidine2'-OMe-cytidine

2'-O-METHYL-CYTIDINE4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl]pyrimidin-2-oneO-2-MethylcytidineO2'-methylycytidineOMe-rC2 -O-MethylcytidineUNII-5XD9IH2G27SCHEMBL64632

Database identifiers

CAS: 2140-72-9、58970-16-4
PubChem CID: 150971
DTXSID: DTXSID50943958
ChEMBL: CHEMBL176605
ChEBI: CHEBI:19228
UNII: 5XD9IH2G27
Nikkaji: J120.782B

Properties

Computed structural properties

XLogP: -1.6
Topological polar surface area: 118 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 3
Heavy atoms: 18
Formal charge: 0
Complexity: 397

Physicochemical properties

Melting point: 252 · 252-253 C
Boiling point: 506 · 506.0±60.0 °C(Predicted)
Density: 1.68 · 1.68±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility: Soluble in DMSO.
pka: 13.37 · 13.37±0.70(Predicted)
form: Powder
color: White to Off-white
PH: 4.2 · 4.2
optical activity: 70.902 ° · 70.902° (C=0.01 g/ml, H2O)
λmax: 281 · 281 (pH 1)；273 (EtOH)
Major Application: pharmaceutical
InChI: InChI=1S/C10H15N3O5/c1-17-8-7(15)5(4-14)18-9(8)13-3-2-6(11)12-10(13)16/h2-3,5,7-9,14-15H,4H2,1H3,(H2,11,12,16)/t5-,7-,8-,9-/m1/s1
InChIKey: RFCQJGFZUQFYRF-ZOQUXTDFSA-N
SMILES: OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](OC)[C@@H]1O
CAS DataBase Reference: 2140 · 2140-72-9(CAS DataBase Reference)
FDA UNII: 5 XD9IH2G27 · 5XD9IH2G27
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36-24/25
WGK Germany: 3 · 3
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

wgk: 3
hs_code: 29349990
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36-24/25
Storage Class: 11 - Combustible Solids

Chemistry & industry

Applications · 3 items

Description2'-O-Methylcytidine is a nucleoside with a hydroxyl group on the 2' carbon, making it an effective viral replication inhibitor. 2'-O-Methylcytidine is also metabolized by nucleotide salvage pathways and may be able to bind to the response element on DNA, which could inhibit protein synthesis in cancer cells. It is an inhibitor of hepatitis C virus (HCV) non-structural protein 5B (NS5B; IC50 = 3.8 μM). It inhibits HCV replication in a replicon assay (IC50 = 21.2 μM).

Uses2'-O-Methylcytidine is used in the preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.

UsesCytidine analog.