2′-Deoxycytidine - ≥99% , CAS No.951-77-9

CAS: 951-77-9 Cat. No.: D104773 Formula: C₉H₁₃N₃O₄ Molecular Weight: 227.22 Beilstein Registry Number: 87567 EC Number: 213-454-1

GRADE & PURITY ≥99%

Synonyms

CYTIDINE, 2'-DEOXY- | Desoxycytidin [German] | MFCD00006547 | Doxecitine | 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one | C00881 | 1-(2-Deoxy-b-D-ribofuranosyl)cytosine | Deoxyribose cytidine | Cytidine, 2'-deox

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

application：

2′-Deoxycytidine (deoxyC) is one of the deoxynucleosides which after phosphorylation to dCTP is used to synthesis DNA via various DNA polymerases or reverse transcriptases. 2′-Deoxycytidine (deoxyC) is the substrate for deoxycytidine deaminase (EC 3.5.4.14) which converts it into 2′-deoxyuridine. 2′-Deoxycytidine is phosphorylated to the nucleotide dCMP by the enzyme deoxycytidine kinase (DCK).

product description：

2′-Deoxycytidine (deoxyC) is one of the deoxynucleosides containing cytosine as the nucleobase. It is found in the blood, feces, and urine.

application：

2′-Deoxycytidine has been used:

as a substrate for Trypanosoma brucei cytidine deaminase (TbCDA) to measure its activity

as a standard in the isolation and quantification of metabolite levels in murine tumor interstitial fluid by liquid chromatography-mass spectrometry (LC–MS)

to study the role of autophagy in response to oncogenes and DNA replication stress 

Specifications

Synonyms

CYTIDINE, 2'-DEOXY- | Desoxycytidin [German] | MFCD00006547 | Doxecitine | 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one | C00881 | 1-(2-Deoxy-b-D-ribofuranosyl)cytosine | Deoxyribose cytidine | Cytidine, 2'-deox

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

2′-Deoxycytidine (deoxyC) forms dCTP upon phosphorylation which is used to synthesis DNA via various DNA polymerases or reverse transcriptases. DeoxyC is the substrate for deoxycytidine deaminase (EC 3.5.4.14) which converts it into 2′-deoxyuridine. Deoxy

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥99%

Names and Identifiers

Pubchem Sid

504752485

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504752485

Canonical Smiles

C1C(C(OC1N2C=CC(=NC2=O)N)CO)O

IUPAC Name

4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

InChIKey

CKTSBUTUHBMZGZ-SHYZEUOFSA-N

INCHI

1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1

Isomeric SMILES

C1[C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)N)CO)O

WGK Germany

3

RTECS

HA3800000

Alternate CAS

652157-52-3

Molecular Weight

227.22

Beilstein

87567

Reaxy-Rn

14609546

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=14609546&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 Aminopyrimidines and derivatives Imidolactams Hydropyrimidines Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary amines Primary alcohols Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrimidine 2'-deoxyribonucleoside - Aminopyrimidine - Pyrimidone - Hydropyrimidine - Pyrimidine - Imidolactam - Heteroaromatic compound - Tetrahydrofuran - Secondary alcohol - Azacycle - Oxacycle - Organoheterocyclic compound - Alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Primary amine - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Amine - 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

Associated Targets(Human)

DCK Tchem Deoxycytidine kinase (530 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TK1 Tchem Thymidine kinase, cytosolic (627 Activities)

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CCRF-CEM (65223 Activities)

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DU-145 (51482 Activities)

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MCF7 (126967 Activities)

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MT4 (17854 Activities)

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ATH-8 cell line (300 Activities)

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HaCaT (4069 Activities)

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HCT-116 (91556 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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Associated Targets(non-human)

TK Thymidine kinase (276 Activities)

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pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

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Deoxycytidylate deaminase (6 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cda Cytidine deaminase (37 Activities)

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dnk Deoxynucleoside kinase (95 Activities)

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deoA Thymidine phosphorylase (531 Activities)

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Uck1 Uridine-cytidine kinase 1 (5 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Tk2 Thymidine kinase 2 (53 Activities)

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Enterococcus faecium (13803 Activities)

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Human immunodeficiency virus (3636 Activities)

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L1210 (27553 Activities)

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C6 (2371 Activities)

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L6 (7924 Activities)

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LM (36 Activities)

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dak Deoxyadenosine kinase (12 Activities)

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Perknaster fuscus (7 Activities)

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Woodchuck hepatitis virus (122 Activities)

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Ileum (29 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water, DMSO.
• x_specific_rotation: 59 ° (C=1, H2O)
• x_melt_point_char: 209-211°C
• Molecular Weight: 227.220 g/mol
• XLogP3: -1.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 227.091 Da
• Monoisotopic Mass: 227.091 Da
• Topological Polar Surface Area: 108.000 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 355.000
• 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

Frequently Asked Questions

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 951-77-9, the molecular formula is C9H13N3O4, and the molecular weight is 227.22 g/mol. InChIKey CKTSBUTUHBMZGZ-SHYZEUOFSA-N.

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.