Showing Compound Card for 5'-Methylthioadenosine (CDB004887)

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Record Information
Version1.0
Created at2020-04-17 18:47:06 UTC
Updated at2020-11-18 16:38:56 UTC
CannabisDB IDCDB004887
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name5'-Methylthioadenosine
Description5'-Methylthioadenosine, also known as MTA or thiomethyladenosine, 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. 5'-Methylthioadenosine is a strong basic compound (based on its pKa). 5'-Methylthioadenosine exists in all living species, ranging from bacteria to humans. Within humans, 5'-methylthioadenosine participates in a number of enzymatic reactions. In particular, 5'-methylthioadenosine and spermidine can be biosynthesized from S-adenosylmethioninamine and putrescine through its interaction with the enzyme spermidine synthase. In addition, 5'-methylthioadenosine can be converted into 5-methylthioribose 1-phosphate and L-methionine; which is catalyzed by the enzyme S-methyl-5'-thioadenosine phosphorylase. In humans, 5'-methylthioadenosine is involved in the metabolic disorder called hypermethioninemia. Outside of the human body, 5'-Methylthioadenosine has been detected, but not quantified in, several different foods, such as chia, black elderberries, kumquats, jew's ears, and pine nuts. This could make 5'-methylthioadenosine a potential biomarker for the consumption of these foods. Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group. 5'-Methylthioadenosine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC11H15N5O3S
Average Molecular Weight297.33
Monoisotopic Molecular Weight297.0896
IUPAC Name(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
Traditional Namemethylthioadenosine
CAS Registry Number2457-80-9
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 KeyWUUGFSXJNOTRMR-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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class5'-deoxyribonucleosides
Sub Class5'-deoxy-5'-thionucleosides
Direct Parent5'-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.14ALOGPS
logP-0.61ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.31 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.03 m³·mol⁻¹ChemAxon
Polarizability29.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS5'-Methylthioadenosine, non-derivatized, GC-MS Spectrumsplash10-000i-0940000000-16b1106966ac98c7a107Spectrum
GC-MS5'-Methylthioadenosine, non-derivatized, GC-MS Spectrumsplash10-000i-0940000000-16b1106966ac98c7a107Spectrum
GC-MS5'-Methylthioadenosine, non-derivatized, GC-MS Spectrumsplash10-000i-0940000000-30fc68e7b5ff7576069bSpectrum
GC-MS5'-Methylthioadenosine, non-derivatized, GC-MS Spectrumsplash10-01ti-0900000000-312bd8eec3c461e919f9Spectrum
Predicted GC-MS5'-Methylthioadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-9530000000-5fbf6b1a856ad3827980Spectrum
Predicted GC-MS5'-Methylthioadenosine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0h70-9636300000-67e425eba97fe420c464Spectrum
Predicted GC-MS5'-Methylthioadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5'-Methylthioadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Spermine synthaseSMSXp22.1P52788 details
Spermidine synthaseSRM1p36-p22P19623 details
S-methyl-5'-thioadenosine phosphorylaseMTAP9p21Q13126 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001173
DrugBank IDDB02282
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031156
KNApSAcK IDNot Available
Chemspider ID388321
KEGG Compound IDC00170
BioCyc ID5-METHYLTHIOADENOSINE
BiGG ID34127
Wikipedia LinkNot Available
METLIN ID3425
PubChem Compound439176
PDB IDNot Available
ChEBI ID17509
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Spermine synthase
General function:
Involved in spermine synthase activity
Specific function:
Catalyzes the production of spermine from spermidine and decarboxylated S-adenosylmethionine (dcSAM).
Gene Name:
SMS
Uniprot ID:
P52788
Molecular weight:
35278.2
Enzyme Details
2. Spermidine synthase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM). Has a strong preference for putrescine as substrate, and has very low activity towards 1,3-diaminopropane. Has extremely low activity towards spermidine.
Gene Name:
SRM
Uniprot ID:
P19623
Molecular weight:
33824.455
Enzyme Details
3. S-methyl-5'-thioadenosine phosphorylase
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
Catalyzes the reversible phosphorylation of S-methyl-5'-thioadenosine (MTA) to adenine and 5-methylthioribose-1-phosphate. Involved in the breakdown of MTA, a major by-product of polyamine biosynthesis. Responsible for the first step in the methionine salvage pathway after MTA has been generated from S-adenosylmethionine. Has broad substrate specificity with 6-aminopurine nucleosides as preferred substrates.
Gene Name:
MTAP
Uniprot ID:
Q13126
Molecular weight:
31235.76