Livestock Metabolome Database: Showing metabocard for Deoxyadenosine (LMDB00754)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-30 18:16:18 UTC

Update Date

2016-08-01 19:17:07 UTC

Lmdb

LMDB00754

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Deoxyadenosine

Description

Deoxyadenosine, also known as dA, belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2. Deoxyadenosine is a strong basic compound (based on its pKa). Deoxyadenosine exists in all living species, ranging from bacteria to humans. Within humans, deoxyadenosine participates in a number of enzymatic reactions. In particular, deoxyadenosine can be converted into adenine and deoxyribose 1-phosphate through its interaction with the enzyme purine nucleoside phosphorylase. In addition, deoxyadenosine can be converted into deoxyinosine through its interaction with the enzyme adenosine deaminase. A purine 2'-deoxyribonucleoside having adenine as the nucleobase. In humans, deoxyadenosine is involved in mercaptopurine action pathway. Outside of the human body, Deoxyadenosine is found, on average, in the highest concentration within beers. Deoxyadenosine has also been detected, but not quantified in, milk (cow). This could make deoxyadenosine a potential biomarker for the consumption of these foods. Deoxyadenosine is a potentially toxic compound. Deoxyadenosine, with regard to humans, has been found to be associated with several diseases such as colorectal cancer and eosinophilic esophagitis; deoxyadenosine has also been linked to several inborn metabolic disorders including adenosine deaminase deficiency and adenylosuccinate lyase deficiency.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol	ChEBI
5-(6-AMINO-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol	ChEBI
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine	ChEBI
9-(2-Deoxy-beta-D-ribofuranosyl)-9H-purin-6-amine	ChEBI
Adenine deoxyribonucleoside	ChEBI
Adenyldeoxyriboside	ChEBI
dA	ChEBI
2'-Deoxyadenosine	Kegg
9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenine	Generator
9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenine	Generator
9-(2-Deoxy-b-D-ribofuranosyl)-9H-purin-6-amine	Generator
9-(2-Deoxy-β-D-ribofuranosyl)-9H-purin-6-amine	Generator
1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-b-D-ribofuranose	HMDB
1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-ribofuranose	HMDB
1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-ribofuranose	HMDB
2-Deoxyadenosine	HMDB
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-amine	HMDB
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-9H-purin-6-amine	HMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-9H-purin-6-amine	HMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adenine	HMDB
9-(2-Deoxy-beta-delta-ribofuranosyl)-9H-purin-6-amine	HMDB
Adenine deoxyribose	HMDB
Adenine-9 2-deoxy-b-D-erythro-pentofuranoside	HMDB
Adenine-9 2-deoxy-beta-D-erythro-pentofuranoside	HMDB
Adenine-9 2-deoxy-beta-delta-erythro-pentofuranoside	HMDB
Desoxyadenosine	HMDB
Deoxyadenosine	ChEBI

Chemical Formula

C₁₀H₁₃N₅O₃

Average Molecular Weight

251.2419

Monoisotopic Molecular Weight

251.101839307

IUPAC Name

(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

Traditional Name

2-deoxyadenosine

CAS Registry Number

Not Available

SMILES

NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1

InChI Identifier

InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1

InChI Key

OLXZPDWKRNYJJZ-RRKCRQDMSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 2'-deoxyribonucleosides

Direct Parent

Purine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
N-substituted imidazole
Pyrimidine
Imidolactam
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Amine
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine 2'-deoxyribonucleoside (CHEBI:17256 )
Deoxyribonucleosides (C00559 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.95	ALOGPS
logP	-1.2	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	3.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.68 m³·mol⁻¹	ChemAxon
Polarizability	24.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0pbc-1950000000-892b755b10f34bcfa1c7	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-05fr-9750000000-34ebf7e59598c6551f52	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0pbc-2950000000-9d52e7dcd83de5a30aef	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0pbc-1950000000-892b755b10f34bcfa1c7	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05fr-9750000000-34ebf7e59598c6551f52	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0pbc-2950000000-9d52e7dcd83de5a30aef	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9550000000-219c39ab05ecbebb53ee	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0ge9-6917000000-51808985bdc9abeb3cb3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udr-1790000000-c0d4c0cc085cab7c2dcf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-1900000000-e2abd19062db64ff67be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000i-2900000000-1b8d5c847c2b1955056e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-000i-5900000000-845c20e0f6bd5494b6dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004r-8900000000-484d9f08e4e28fab1f70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-e852451e7253e0de72be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0390000000-fba17d1430b371138db2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-000i-0930000000-931c7b084c33f9122af4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0900000000-66ae7ac8bd510a173402	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-001i-0900000000-c71d67857e2136dc7666	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udr-1790000000-cfbdf2e3950e7987b94b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-1900000000-a3c367588a28d36cf5f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-2900000000-1b8d5c847c2b1955056e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-5900000000-f950493ce420caae6a66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004r-8900000000-61ed5b4b3e748a449803	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-0900000000-31d03c242f14d91a718c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0390000000-fba17d1430b371138db2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0930000000-931c7b084c33f9122af4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0900000000-81ac782a59b2ca52f52b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0920000000-2e897a458cf4c7af381c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-f52b5322fde2e3722903	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-fcb0a5032b8607fd8b11	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0290000000-bec96a9658c683fa0d9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0910000000-b504aa725d20d6213b20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-2900000000-d09551db93d558a5aed7	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum