5-(Hydroxymethyl)cytosine (5hmC) - Moligand™, ≥95% , CAS No.1123-95-1

CAS: 1123-95-1 Cat. No.: H302221 Molecular Weight: 141.13

GRADE & PURITY Moligand™, ≥95%

Synonyms

4-AMINO-2-HYDROXY-5-PYRIMIDINEMETHANOL | PD158492 | 5-(hydroxymethyl)cytosine | 2,4-Dioxopyrimidine | 4-amino-5-(hydroxymethyl)pyrimidin-2(1H)-one | ES-2013 | Ureaphil | DEMETHYLBACIMETHRIN | AKOS015854852 | 2-Hydroxy-5-hydroxymethyl-6-amino-pyrimidin | F

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

5-Hydroxymethylcytosine is a DNA pyrimidine nitrogen base and a nucleobase analogue of cytosine, where the hydrogen at position 5 is replaced by a hydroxymethyl group. Chemically, 5-hydroxymethylcytosine is an aminopyrimidine and an intermediate metabolite in active DNA demethylation. It plays a key role in gene expression, DNA methylation, and various critical cellular functions. 5-Hydroxymethylcytosine has been shown to be a potential biomarker of cellular transformation and is involved in axonal growth, transcriptional regulation, and the action of leukemia inhibitory factor.

Application：

5-Hydroxymethylcytosine finds application in metabolomics, biochemical, phytochemical, cell signaling and drug discovery research.

Specifications

Synonyms

4-AMINO-2-HYDROXY-5-PYRIMIDINEMETHANOL | PD158492 | 5-(hydroxymethyl)cytosine | 2, 4-Dioxopyrimidine | 4-amino-5-(hydroxymethyl)pyrimidin-2(1H)-one | ES-2013 | Ureaphil | DEMETHYLBACIMETHRIN | AKOS015854852 | 2-Hydroxy-5-hydroxymethyl-6-amino-pyrimidin | F

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

Novel DNA pyrimidine nitrogen base. Initiates DNA demethylation. 5-Methylcytosine oxidation product. Epigenetic modifier in vivo.

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504754567
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504754567
• Canonical Smiles: C1=NC(=O)NC(=C1CO)N
• IUPAC Name: 6-amino-5-(hydroxymethyl)-1H-pyrimidin-2-one
• InChIKey: RYVNIFSIEDRLSJ-UHFFFAOYSA-N
• INCHI: 1S/C5H7N3O2/c6-4-3(2-9)1-7-5(10)8-4/h1,9H,2H2,(H3,6,7,8,10)
• Isomeric SMILES: C1=NC(=O)NC(=C1CO)N
• Molecular Weight: 141.13
• Reaxy-Rn: 776230
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=776230&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrimidines and pyrimidine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrimidines and pyrimidine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydroxypyrimidines
• Alternative Parents: Imidolactams Hydropyrimidines Heteroaromatic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Hydroxypyrimidine - Imidolactam - Hydropyrimidine - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Aromatic alcohol - Primary alcohol - Organooxygen compound - Organonitrogen compound - Alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
• External Descriptors: aminopyrimidine - pyrimidone - aromatic primary alcohol - nucleobase analogue

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Refractive Index: 1.696
• Molecular Weight: 141.130 g/mol
• XLogP3: -1.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 141.054 Da
• Monoisotopic Mass: 141.054 Da
• Topological Polar Surface Area: 87.700 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 219.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1