Thymidine - USP, Internal toxicity

CAS: 50-89-5 Cat. No.: GMP1527860 Formula: C₁₀H₁₄N₂O₅ Molecular Weight: 242.23 Beilstein Registry Number: 89285 EC Number: 200-070-4

GRADE & PURITY USP, Internal toxicity<200EU/g, microbial limit ≤ 100cfu/g

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Overview

Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication.

Specifications

Specifications & Purity

USP, Internal toxicity<200EU/g, microbial limit ≤ 100cfu/g

Biochemical and Physiological Mechanisms

Pyrimidine deoxynucleoside. Potent thymidine kinase substrate (IC 50 = 16 nM). Pairs with deoxyadenosine in double-stranded DNA. Synchronizes cells in S phase in vivo.

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

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

Grade

USP

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.

Names and Identifiers

Canonical Smiles

CC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)NC1=O

IUPAC Name

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

InChIKey

IQFYYKKMVGJFEH-XLPZGREQSA-N

INCHI

1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m0/s1

Isomeric SMILES

CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O

WGK Germany

3

RTECS

XP2071000

Molecular Weight

242.23

Beilstein

89285

Reaxy-Rn

889638

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=889638&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Pyrimidine nucleosides
      • Subclass Pyrimidine 2'-deoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Pyrimidine nucleosides
• Subclass: Pyrimidine 2'-deoxyribonucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrimidine 2'-deoxyribonucleosides
• Alternative Parents: Pyrimidones Hydroxypyrimidines Hydropyrimidines Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrimidine 2'-deoxyribonucleoside - Pyrimidone - Hydroxypyrimidine - Hydropyrimidine - Pyrimidine - Heteroaromatic compound - Tetrahydrofuran - Secondary alcohol - Oxacycle - Azacycle - Organoheterocyclic compound - Alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
• External Descriptors: Deoxyribonucleosides

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

• Solubility: Soluble in water, methanol, hot ethanol, hot acetone, hot ethyl acetate, pyridine, glacial acetic acid and hydrochloric acid. Slightly soluble in hot chloroform .
• Sensitivity: Light sensitive;Hygroscopic
• x_specific_rotation: 33 ° (C=1, 1mol/L NaOH)
• x_melt_point_char: 183-191°C
• Molecular Weight: 242.230 g/mol
• XLogP3: -1.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 242.09 Da
• Monoisotopic Mass: 242.09 Da
• Topological Polar Surface Area: 99.100 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 381.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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