CAS 58-61-7|CAS 5536-17-4|Adenine-9-β-D-ribofuranoside|ADENOSINE, U.S.P.|Adenine Riboside|9-β-D-Ribofuranosyladenine|ADENOSINE FREE BASE|(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxym...

General Information

Structure

Molecular Formula

C₁₀H₁₃N₅O₄

Molecular Mass

267.24132

Exact Mass

267.09675392

Charge

0

InChI

InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

InChIKey

OIRDTQYFTABQOQ-KQYNXXCUSA-N

Canonic Smiles

OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N

Isomeric Smiles

O1[C@@H](n2c3ncnc(N)c3nc2)[C@H](O)[C@H](O)[C@H]1CO

Calculated Properties

JChem

LogD (pH = 7.4)

-2.09

LogD (pH = 5.5)

-2.21

Log P

-2.09

Rotatable Bonds

2

H Donor

4

H Acceptors

8

Lipinski's Rule of Five

true

Acid pKa

5.02

Polar Surface Area

139.54

Polarizability

25.17

Molar Refractivity

63.20

LOG S

-1.32

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

Adenine-9-β-D-ribofuranosideADENOSINE, U.S.P.Adenine Riboside9-β-D-RibofuranosyladenineADENOSINE FREE BASEAdenine riboside, Adenine-9-β-D-ribofuranosideADENINE-9-β-D-ARABINOFURANOSIDEAra-AVidarabine9-β-D-ArabinofuranosyladenineArabinosyl-adenineAdenocardAdenosine腺苷9-β-D-Ribofuranosyladenine腺嘌呤核苷腺嘌呤-9-β-D-呋喃核糖苷Adenine-9-β-D-ribofuranosideAdenosine9-β-D-呋喃核糖基腺嘌呤(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diolAdenoscanAdenocor2'-DeoxyadenosineDeoxyadenosineAdenine Deoxy NucleosideUSAF CB-10AdenyldeoxyribosideAdenine NucleosideDesoxyadenosineAdenine DeoxyriboseMEDR-640adenosineAdenine Deoxyribonucleoside9-beta-D-RibofuranosidoadenineAdenosinAde-RibAdenine DeoxyribonucleosideDeoxyadenosineadenosine9-beta-D-Ribofuranosyl-9H-purin-6-aminebeta-D-Adenosine6-Amino-9-beta-D-ribofuranosyl-9H-purineAdenyldeoxyribosideAdoADENOSINEAdenosineadenosine(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol9-beta-D-ribofuranosyl-9H-purin-6-amineDesoxyadenosine

IUPAC name

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

IUPAC Traditional name

adenosine (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Brand Name

AdenocardAdenoscanMyocolPallacorAdenosinAdensoineBonitonAdenocorSandesinNucleocardyl

API Name

Adenosine

Names and Identifiers

Registration numbers

CAS Number

EC Number

MDL Number

IUPHAR ligand ID

Chemspider ID

Wikipedia Title

Unique Ingredient Identifier

K72T3FS567

DrugBank ID

DB00640

CHEBI ID

16335CHEBI:40825CHEBI:40558CHEBI:16335CHEBI:13734CHEBI:22237CHEBI:2472CHEBI:40911CHEBI:40906

Beilstein Number

PubChem CID

KEGG ID

CHEMBL

ATC CODE

PubChem SID

2427768546508728248907391609639858143428

Reaxys Registry

93029

BKMS React Database

99843122

BRENDA Database

2.7.1.903.2.2.42.7.11.133.2.2.22.7.6.11.11.1.93.1.3.23.1.4.373.2.2.302.1.1.772.7.1.321.7.2.31.1.3.281.1.1.441.6.1.2

MetaboLights Database

MTBLS570MTBLS4967MTBLS4463MTBLS5148MTBLS457MTBLS606MTBLS1407MTBLS1410MTBLS208MTBLS2295MTBLS23MTBLS1402MTBLS4722MTBLS4495MTBLS2870

BRENDA Ligand Database

12299843

CompTox Database

DTXSID1022558

PubMed Citation Links

11820865171908523238541800097416183671112132371691709311978011

KNApSAcK Database

LINCS Database

ACToR Database

MetaCyc Database

Protein Data Bank

1dgm2b8j3qgz3g1u5hji4xdr2kqe2w034dta6bq46ttp1q973uaw6fbp4kal1xwf

SABIO-RK Database

81191104473819569156925144192523057839668013413310734

UniProt Database

A1IRY3Q7A018Q2W3L4E1WTS4Q5HAN0B4ESU3Q5PA14Q3A4K3A9W8M8Q4UM45Q8E6Q1A9C2R2B5ELR8A9VG53Q02196

SureChEMBL Database

SCHEMBL731

Patent number

US2007254853EP1443041EP1579873WO2007121917US2006135566US2005222153US2006058304US2007010522US2007225335WO2006044504WO2006091898US2006025453EP1903044US2008248012

Golm Database

584527e7-e896-4b45-a5ee-86212c5c1084693bbb97-c55c-4b6d-a071-89200eab867fc733f27b-d6a9-47e1-9a50-5fcb14c18dd18d203204-dbe9-436b-a0c0-f0f62e289d497c8d70a8-3373-4fc5-9575-d22223dccb4ace161672-4891-4abe-97c7-747cddcabf2a4e26e390-4158-460c-bf3d-e98a8b5d31b15888a42e-aa39-479c-ab2a-45fc8ab6dd8209a78a03-b80a-42be-966e-f71c416ab9732b125d07-b9d6-4e63-8451-032c313f1f3bd959577e-edcd-4f2a-a193-f18c990c77e6c546a666-1780-41ed-b243-26ad40ce8eeb2d390070-06c8-43aa-a5e4-a38cbd700c1f43679853-9844-4629-882f-63f148f53b1f

Rhea Database

RHEA:69596RHEA:15489RHEA:27898RHEA:24408RHEA:37343RHEA:18185RHEA:18669RHEA:52532RHEA:52536RHEA:56140RHEA:20824RHEA:14913RHEA:29987RHEA:46000RHEA:27642RHEA:67896

VirtualMetabolicHuman Database

adn

PDBeChem Database

ADN

EnzymePortal Database

A3PFB5B2AGG2P32112B8ZQE9Q62G22Q57AG3A9KD88B7V419Q8FXZ7P55264Q13T36B1XSH8A3NER1Q04WX0P58855

BioModels Database

BIOMD0000000636BIOMD0000000470BIOMD0000000469BIOMD0000000497BIOMD0000000473BIOMD0000001061BIOMD0000000015BIOMD0000000471BIOMD0000000496BIOMD0000000472

IntEnz Database

EC 2.7.1.20EC 2.4.2.1EC 2.7.1.114EC 1.1.3.39EC 3.2.2.7EC 3.3.1.1EC 3.5.4.4EC 3.13.1.8EC 2.5.1.153

HMDB Database

HMDB0000050

Reactom Database

R-HSA-744887R-HSA-109539R-HSA-109624R-HSA-379044R-HSA-418904R-HSA-5628807R-HSA-5684862R-HSA-727740R-HSA-9660829R-HSA-109278R-HSA-380073R-HSA-109387R-HSA-2161193R-HSA-2408532R-HSA-5693346

Drug Central Database

90

BindingDB Database

14487

YMDB Database

YMDB00058

GeneOntology Database

GO:0006169GO:0006154GO:0046085GO:0001609GO:0032238GO:0046086

KEGG DRUG Database

D00045

Gmelin ID

53385

ArrayExpress (Gene Expression Altlas)

E-MTAB-5007

ECMDB Database

ECMDB00050

Registration numbers

Properties

Physical Property

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00640

Drug Groups

approved; investigational

Description

A nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. [PubChem]

Indication

Used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (PVST), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (SVT). Also used as an adjunct to thallous chloride TI 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex SVT.

Pharmacology

Adenosine is an endogenous nucleoside occurring in all cells of the body and is not chemically related to other antiarrhythmic drugs. Adenosine may exert its pharmacologic effects by activation of purine (cell surface A₁ and A₂ adenosine) receptors, as well as relax vascular smooth muscles through the reduction in calcium uptake by inhibition of slow inward calcium current and activation of adenylate cyclase in smooth muscle cells. Adenosine may reduce vascular tone by modulation of sympathetic neurotransmission. The drug also has negative chronotropic, dromotropic, and inotropic effects on the heart by slowing conduction time throught he AV node and interrupting AV nodal reentry pathways. Adenosine is a potent vasodilator in most vascular beds, but vasoconstriction is produced in renal afferent arterioles and hepatic veins. The drug produces a net mild to moderate reduction in systolic, diastolic, and mean arterial blood pressure and a reflex increase in heart rate. Adenosine is antagonized competitively by methylxanthines such as caffeine and theophylline, and potentiated by blockers of nucleoside transport such as dipyridamole. Adenosine is not blocked by atropine.

Affected Organisms

Humans and other mammals

Biotransformation

Intracellular adenosine is rapidly metabolized either via phosphorylation to adenosine monophosphate by adenosine kinase, or via deamination to inosine by adenosine deaminase in the cytosol.

Half Life

Less than 10 secs

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1647

Biological Activity:
Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a β-N9-glycosidic bond. [1] Extracellular adenosine concentrations from normal cells are approximately 300 nM; however, in response to cellular damage (e.g. in inflammatory or ischemic tissue), these concentrations are quickly elevated (600–1,200 nM). Thus, in regard to stress or injury, the function of adenosine is primarily that of cytoprotection preventing tissue damage during instances of hypoxia, ischemia, and seizure activity. Activation of A2A receptors produces a constellation of responses that in general can be classified as anti-inflammatory. [2]

MP Biomedicals

02100070

Crystalline
Reported to possess antiviral activity¹ and useful for metabolism studies²

02100199

Free Base
Crystalline

02194609

Free Base
Cell Culture Reagent

05212443

MP Biomedicals Rare Chemical collection

Wikipedia

Adenosine

Sigma Aldrich

A9251

包装
1, 5, 25, 100 g in poly bottle
Biochem/physiol Actions
腺苷受体处的内源性神经递质。心肌保护作用可能与 A1 腺苷受体的激活有关。通过 A2 腺苷受体可介导腺苷的抗血小板和抗炎作用。相比之下，腺苷在哮喘和慢性阻塞性肺部疾病 (COPD) 中起促炎介质作用。

A4036

Biochem/physiol Actions
腺苷受体处的内源性神经递质。心肌保护作用可能与 A1 腺苷受体的激活有关。通过 A2 腺苷受体可介导腺苷的抗血小板和抗炎作用。相比之下，腺苷在哮喘和慢性阻塞性肺部疾病 (COPD) 中起促炎介质作用。

146595

Biochem/physiol Actions
Endogenous neurotransmitter at adenosine receptors. Cardioprotective effects may relate to activation of A1 adenosine receptors. The antiplatelet and anti-inflammatory actions of adenosine appear to be mediated via the A2 adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).

PHR1138

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Biochem/physiol Actions
Endogenous neurotransmitter at adenosine receptors. Cardioprotective effects may relate to activation of A1 adenosine receptors. The antiplatelet and anti-inflammatory actions of adenosine appear to be mediated via the A2 adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).

ChEBI

CHEBI:16335

A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Adenosine

• de Rudder, Privat de Garilhe, Antimicrob. Ag. Chemother. , 578 (1965).

• Cancer Res. , 24 : 1042 (1964).

• Pinski, S.L. et al., Cleveland Clin. J. Med., 1990, 57, 383, (use)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 222A; 224A; 227B; 229B, (nmr)

• Sarma, R.H. et al., J.A.C.S., 1974, 96, 7337-7348, (pmr, conformn)

• Wilson, C.C. et al., Acta Cryst. C, 1986, 42, 697-700, (cryst struct, triacetyl)

• Earl, R.A. et al., J.O.C., 1975, 40, 1822-1828, (cmr)

• Puech, P. et al., Handb. Exp. Pharmacol., 1989, 89, 453-460, (rev, metab, props, use)

• Reddy, A.M. et al., J. Het. Chem., 1990, 27, 1297-1305, (ms)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AEH750

• Shikata, K. et al., Acta Cryst. B, 1973, 29, 31-38, (cryst struct)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 57

• Brown, D.M. et al., J.C.S., 1950, 3299-3304, (synth)

• Morgan, J.M. et al., Circulation, 1991, 84, 1145, (use)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 719C; 720A; 721A; 722C; 725B, (ir)

• Davoll, J. et al., J.C.S., 1948, 967-969, (synth)

• Biemann, K. et al., J.A.C.S., 1962, 84, 2005-2007, (ms)

• Adenosine and Adenosine Receptors, Williams, M., ed., Chapman and Hall, 1990, (book)

• Mahler, G.S., Anal. Profiles Drug Subst., 1998, 25, 1-37, (rev)

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:522