Livestock Metabolome Database: Showing metabocard for 5'-Methylthioadenosine (LMDB00304)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:53 UTC

Update Date

2016-09-23 18:45:07 UTC

Lmdb

LMDB00304

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5'-Methylthioadenosine

Description

5'-Methylthioadenosine (MTA) is a naturally occurring sulfur-containing nucleoside present in all mammalian tissues. It is produced from S-adenosylmethionine mainly through the polyamine biosynthetic pathway, where it behaves as a powerful inhibitory product. MTA is metabolized solely by MTA-phosphorylase, to yield 5-methylthioribose-1-phosphate and adenine, a crucial step in the methionine and purine salvage pathways, respectively. Evidence suggests that MTA can affect cellular processes in many ways. For instance, MTA has been shown to influence regulation of gene expression, proliferation, differentiation and apoptosis (PMID 15313459 ). 5-Methylthioadenosine can be found in animal urine. Elevated excretion appears in children with severe combined immunodeficiency syndrome (PMID 3987052 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5'-Deoxy-5'-(methylthio)adenosine	ChEBI
5-Methylthioadenosine	ChEBI
9-(5-S-Methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine	ChEBI
Methylthioadenosine	ChEBI
MTA	ChEBI
S-Methyl-5'-thioadenosine	ChEBI
Thiomethyladenosine	ChEBI
9-(5-S-Methyl-5-thio-b-D-ribofuranosyl)-9H-purin-6-amine	Generator
9-(5-S-Methyl-5-thio-β-D-ribofuranosyl)-9H-purin-6-amine	Generator
1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-ribofuranose	HMDB
1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-ribofuranose	HMDB
5'-(Methylthio)-5'-deoxyadenosine	HMDB
5'-(Methylthio)adenosine	HMDB
5'-S-Methyl-5'-thio-adenosine	HMDB
5'-S-Methyl-5'-thioadenosine	HMDB
S-Methyl-5-thioadenosine	HMDB
Adenine(5'-deoxy-5'-methylthio)9-beta-D-furanoriboside	HMDB
5-MTDA	HMDB
5'-Methylthio-5'-deoxyadenosine	HMDB
5'-Deoxy-5'-methylthioadenosine	HMDB
5'-Methylthioadenosine, methyl-(14)C-labeled	HMDB
5'-Methylthioadenosine	ChEBI

Chemical Formula

C₁₁H₁₅N₅O₃S

Average Molecular Weight

297.334

Monoisotopic Molecular Weight

297.089560061

IUPAC Name

(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol

Traditional Name

methylthioadenosine

CAS Registry Number

2457-80-9

SMILES

CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1

InChI Key

WUUGFSXJNOTRMR-IOSLPCCCSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

5'-deoxyribonucleosides

Sub Class

5'-deoxy-5'-thionucleosides

Direct Parent

5'-deoxy-5'-thionucleosides

Alternative Parents

Substituents

5'-deoxy-5'-thionucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monosaccharide
N-substituted imidazole
Pyrimidine
Imidolactam
Azole
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Dialkylthioether
Sulfenyl compound
Thioether
Azacycle
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Amine
Primary amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

thioadenosine (CHEBI:17509 )

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	-0.14	ALOGPS
logP	-0.61	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	3.92	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	3	ChemAxon
Refractivity	74.03 m³·mol⁻¹	ChemAxon
Polarizability	29.26 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) (Non-derivatized)	splash10-000i-0940000000-16b1106966ac98c7a107	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-0940000000-16b1106966ac98c7a107	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-0940000000-30fc68e7b5ff7576069b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01ti-0900000000-312bd8eec3c461e919f9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9530000000-5fbf6b1a856ad3827980	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0h70-9636300000-67e425eba97fe420c464	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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000j-0940000000-55655e7a0a6c8acba0f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-1900000000-f37865ca2029a623ace7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-2900000000-ae0e3df9bf25c100940d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-0090000000-72139812c5b2ede077ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-0910000000-0c3d173f36272e3271eb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000i-0900000000-f3443ca133811f52c5d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-000i-1900000000-49cc299525d7fca27818	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-000i-3900000000-39bebdcaa7ce2695465b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-76b935f4f0a78c15ca0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0002-4900000000-d8c0df43305b934d71dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-0900000000-d3bfbeb6fb95e3768ef6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0910000000-56784be58ef9065f21f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0910000000-56784be58ef9065f21f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-0090000000-72139812c5b2ede077ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0910000000-0c3d173f36272e3271eb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0900000000-f3443ca133811f52c5d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-1900000000-6ec86a11bf8ad7331bd2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-3900000000-39bebdcaa7ce2695465b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-0900000000-b9006ef8eecdaefc89a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0940000000-eb168427f389d7079abf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-714e20a3376683008e65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900000000-cb0adab85341c49ced5b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9220000000-14da12fd68bc6d33eed9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4910000000-324b5daf65bdaa0d2bdb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-4900000000-14e9c89fcdd488f204aa	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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details

External Links

DrugBank ID

DB02282

HMDB ID

HMDB0001173

FooDB ID

FDB031156

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

34127

BioCyc ID

5-METHYLTHIOADENOSINE

METLIN ID

3425

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Avila MA, Garcia-Trevijano ER, Lu SC, Corrales FJ, Mato JM: Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30. [15313459 ]
Mills GC, Mills JS: Urinary excretion of methylthioadenosine in immunodeficient children. Clin Chim Acta. 1985 Mar 30;147(1):15-23. [3987052 ]

Showing metabocard for 5'-Methylthioadenosine (LMDB00304)

Structure for LMDB00304 (5'-Methylthioadenosine)