5′-Deoxyadenosine - ≥98% , CAS No.4754-39-6

CAS: 4754-39-6 Cat. No.: D350076 Molecular Weight: 251.24

GRADE & PURITY ≥98%

Synonyms

5′-dAdo

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

5′-Deoxyadenosine is an analog of adenosin. In the degradation reaction of S-adenosylmethionine (SAM), 5′-Deoxyadenosine is an intermediate. 5′-Deoxyadenosine is used to study the enzyme kinematics of phosphomethylpyrimidine synthase, glutamate mutase, and 5′-methylthioadenosine phosphorylase. In addition, 5′-Deoxyadenosine has been used as a mass spectroscopy standard, and a thymidine phosphorylase activity screening inhibitor. Finally, 5′-Deoxyadenosine functions as a substrate if 5′-Deoxyadenosine deaminase (DadD) assay.

Specifications

Synonyms

5′-dAdo

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

5 '- deoxyadenosine is a substrate of methylthioadenosine/S-adenosine homocysteine (MTA/SAH) nucleosidase in microorganisms. 5 '- deoxyadenosine is a byproduct of S-adenosylmethionine (SAM) cleavage. High levels of deoxyadenosine inhibit SAM dependent enz

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.

Action Type

INHIBITOR

Purity

≥98%

Product Properties

• pKa: pKa: 13.29 (Predicted), pKa: 3.82 (Predicted)
• Ki Data: Adenosine A1 receptor: Ki= 269 nM (rat); Adenosine A2a receptor: Ki= 596 nM (rat); Adenosine A3 receptor: Ki= 2.83 μM (rat)

Names and Identifiers

• Canonical Smiles: CC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• IUPAC Name: (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-methyloxolane-3,4-diol
• InChIKey: XGYIMTFOTBMPFP-KQYNXXCUSA-N
• INCHI: 1S/C10H13N5O3/c1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15/h2-4,6-7,10,16-17H,1H3,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
• Isomeric SMILES: C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
• WGK Germany: 3
• RTECS: AU7358650
• Molecular Weight: 251.24
• Reaxy-Rn: 24731656
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24731656&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class 5'-deoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: 5'-deoxyribonucleosides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: 5'-deoxyribonucleosides
• Alternative Parents: Glycosylamines 6-aminopurines Aminopyrimidines and derivatives N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary alcohols 1,2-diols Oxacyclic compounds Azacyclic compounds Primary amines Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 5'-deoxyribonucleoside - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Purine - Imidazopyrimidine - Aminopyrimidine - Imidolactam - Pyrimidine - N-substituted imidazole - Azole - Heteroaromatic compound - Imidazole - Tetrahydrofuran - 1,2-diol - Secondary alcohol - Oxacycle - Azacycle - Organoheterocyclic compound - Alcohol - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Amine - Primary amine - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.
• External Descriptors: adenosines - 5'-deoxyribonucleoside

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)

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

Discover Target: ADORA1

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

ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

Discover Target: ADORA2A

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

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

Discover Target: ADORA3

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

MTAP Tchem S-methyl-5-thioadenosine phosphorylase (233 Activities)

Discover Target: MTAP

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

HeLa (62764 Activities)

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Associated Targets(non-human)

Rattus norvegicus (775804 Activities)

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Vero (26788 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (19.60 - 20.40 m mg/ml).
• Refractive Index: n20D1.87 (Predicted)
• Boil Point(°C): 595.0° C at 760 mmHg (Predicted)
• Melt Point(°C): 203-205° C
• Molecular Weight: 251.240 g/mol
• XLogP3: -0.600
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 251.102 Da
• Monoisotopic Mass: 251.102 Da
• Topological Polar Surface Area: 119.000 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 320.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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