AFCDB: Adenosine (FDB003554)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:51 UTC

Update date

2020-09-17 15:38:13 UTC

Primary ID

FDB003554

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Adenosine

Description

Adenosine, also known as adenocard or ade-rib, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. Adenosine is a drug which is 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. Adenosine is a strong basic compound (based on its pKa). Adenosine exists in all living species, ranging from bacteria to humans. Within humans, adenosine participates in a number of enzymatic reactions. In particular, adenosine can be converted into inosine; which is mediated by the enzyme adenosine deaminase. In addition, adenosine can be converted into adenine and ribose 1-phosphate; which is mediated by the enzyme purine nucleoside phosphorylase. In humans, adenosine is involved in thioguanine action pathway. Outside of the human body, Adenosine is found, on average, in the highest concentration within beers and milk (cow). Adenosine has also been detected, but not quantified in, several different foods, such as capers, new zealand spinachs, welsh onions, hickory nuts, and pepper (spice). This could make adenosine a potential biomarker for the consumption of these foods. Adenosine is a potentially toxic compound.

CAS Number

58-61-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	14 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-2.1	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	3.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	139.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.2 m³·mol⁻¹	ChemAxon
Polarizability	25.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H13N5O4

IUPAC name

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

InChI Identifier

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

InChI Key

OIRDTQYFTABQOQ-KQYNXXCUSA-N

Isomeric SMILES

NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1

Average Molecular Weight

267.2413

Monoisotopic Molecular Weight

267.096753929

Classification

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monosaccharide
N-substituted imidazole
Pyrimidine
Imidolactam
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Organic oxygen compound
Organic nitrogen compound
Alcohol
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Amine
Primary alcohol
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenosines (CHEBI:16335 )
Ribonucleosides (C00212 )

Ontology

Physiological effect

Health effect:

Health condition:

Septic shock

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

All tissues

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Role

Indirect biological role:

Biological role:

Metabolite

Industrial application:

Personal care products

Pharmaceutical industry:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	235.5 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	-1.05	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	0
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Adenosine, 4 TMS, GC-MS Spectrum	splash10-0f7w-1890000000-5c70a5423faa5e8eceaf	Spectrum
GC-MS	Adenosine, 4 TMS, GC-MS Spectrum	splash10-001v-0691000000-8f88854b7d5adec5c558	Spectrum
GC-MS	Adenosine, non-derivatized, GC-MS Spectrum	splash10-001s-0790000000-cc3bcd977e11efd4ea25	Spectrum
GC-MS	Adenosine, 4 TMS, GC-MS Spectrum	splash10-00di-9460000000-3ae19bfaa5d2df72f9b1	Spectrum
GC-MS	Adenosine, 3 TMS, GC-MS Spectrum	splash10-0gc0-0590000000-05874cecded3009c1f4d	Spectrum
GC-MS	Adenosine, 4 TMS, GC-MS Spectrum	splash10-0fsv-1792000000-b37fd6826f28aaf9e825	Spectrum
GC-MS	Adenosine, non-derivatized, GC-MS Spectrum	splash10-0f7w-1890000000-5c70a5423faa5e8eceaf	Spectrum
GC-MS	Adenosine, non-derivatized, GC-MS Spectrum	splash10-001v-0691000000-8f88854b7d5adec5c558	Spectrum
GC-MS	Adenosine, non-derivatized, GC-MS Spectrum	splash10-001s-0790000000-cc3bcd977e11efd4ea25	Spectrum
GC-MS	Adenosine, non-derivatized, GC-MS Spectrum	splash10-00di-9460000000-3ae19bfaa5d2df72f9b1	Spectrum
GC-MS	Adenosine, non-derivatized, GC-MS Spectrum	splash10-0gc0-0590000000-05874cecded3009c1f4d	Spectrum
GC-MS	Adenosine, non-derivatized, GC-MS Spectrum	splash10-0fsv-1792000000-b37fd6826f28aaf9e825	Spectrum
Predicted GC-MS	Adenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4v-9560000000-986f3b1dfa5d898ed7a2	Spectrum
Predicted GC-MS	Adenosine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01c4-6912500000-ae103f43432726c1ad22	Spectrum
Predicted GC-MS	Adenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Adenosine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Adenosine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Adenosine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Adenosine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Adenosine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Adenosine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Adenosine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Adenosine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Adenosine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Adenosine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014r-0890000000-588861a9494ab4680698	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-1900000000-dd7cbed8e76c6e783831	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-2900000000-c6644520b5943b59403d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0090000000-3d4fd8ea211eaed10531	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-cb58ec56a5faa09c9a02	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-9559aa07ec13a688fb16	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-f7c1371d8e1058df3a32	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0940000000-da71247788bf1ba222e2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0920000000-f2e8ec028abdd674b5e3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-0910000000-815ed65588c07415cd65	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001i-1910000000-2780e737da8848411c4f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-053r-1900000000-c6c1128990661334c15b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0090000000-106e7131507fadd4befb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-0910000000-1c53823486cd2c23f90e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000i-0900000000-f0313435db4847490fd6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-000i-1900000000-dcd4c2972882dcd7535a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-000i-2900000000-5ee474864189cef6df64	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-17edf36faf6eb5750912	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-0591143763a0bad31c23	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014i-0290000000-f1d71a97ce39145c8e31	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00kr-0950000000-9bbdbb14aed287ad5ac8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0910000000-35f90965f1f3c2b3236b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-0900000000-f360cca994696d7ae735	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0940000000-42bee9785f9b55b32eea	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-c8cda6a661ace060572c	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16335

Phenol-Explorer ID

Not Available

DrugBank ID

DB00640

HMDB ID

HMDB00050

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Adenosine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anti aggregant			DUKE
anti arrhythmic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti diuretic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti endotoxic	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
anti hypertensive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti insomniac	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti lipolytic			DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti tachycardic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anxiolytic	35474	Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.	DUKE
arteriodilator			DUKE
glucogonogenic			DUKE
hypocholesterolemic			DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE
hypotensive			DUKE
immunomodulator	50846	Biologically active substance whose activity affects or plays a role in the functioning of the immune system.	DUKE
insulinic			DUKE
laxative	50503	An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.	DUKE
lipolytic			DUKE
myorelaxant			DUKE
platelet aggregation factor inhibitor	50427	A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.	DUKE
pyrogenic			DUKE
respirastimulant			DUKE
secretomotor			DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
vasodilator	35620	A drug used to cause dilation of the blood vessels.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Adenosine deaminase	ADA	P00813
Adenosine receptor A1	ADORA1	P30542
Adenosine receptor A2a	ADORA2A	P29274
Adenosine receptor A2b	ADORA2B	P29275
Purine nucleoside phosphorylase	PNP	P00491
Deoxycytidine kinase	DCK	P27707
Cytosolic 5'-nucleotidase 3	NT5C3	Q9H0P0
Adenosine receptor A3	ADORA3	P33765
Adenosine 3'-phospho 5'-phosphosulfate transporter 1	SLC35B2	Q8TB61

Pathways

Name	SMPDB Link	KEGG Link
Purine Metabolism	SMP00050	map00230

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Adenosine (FDB003554)

Structure for FDB003554 (Adenosine)