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Showing metabocard for S-Adenosylmethioninamine (HMDB0000988)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:49 UTC
HMDB IDHMDB0000988
Secondary Accession Numbers
  • HMDB00988
Metabolite Identification
Common NameS-Adenosylmethioninamine
DescriptionS-Adenosylmethioninamine, also known as decarboxy-adomet or dadomet, 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. S-Adenosylmethioninamine is a very strong basic compound (based on its pKa). S-Adenosylmethioninamine exists in all living species, ranging from bacteria to humans. Within humans, S-adenosylmethioninamine participates in a number of enzymatic reactions. In particular, S-adenosylmethioninamine can be biosynthesized from S-adenosylmethionine through its interaction with the enzyme S-adenosylmethionine decarboxylase proenzyme. In addition, S-adenosylmethioninamine and putrescine can be converted into 5'-methylthioadenosine and spermidine through the action of the enzyme spermidine synthase. S-Adenosylmethioninamine (decarboxylated S-adenosyl methionine) is a substrate that is involved in the biosynthesis of polyamines including spermidine, spermine, and thermospermine. In humans, S-adenosylmethioninamine is involved in the metabolic disorder called homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblg complementation type.
Structure
Data?1582752169
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfoniumChEBI
(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium cationChEBI
(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium saltChEBI
[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfoniumChEBI
S-Adenosyl-(5')-3-methylthiopropylamineChEBI
S-Adenosyl-3-methylthiopropylamineChEBI
S-Adenosyl 3-(methylthio)propylamineKegg
S-Adenosyl 3-(methylsulfanyl)propylamineKegg
Decarboxy-adometKegg
(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulphoniumGenerator
(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulphonium cationGenerator
(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulphonium saltGenerator
[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfoniumGenerator
[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulphoniumGenerator
[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulphoniumGenerator
[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfoniumGenerator
[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulphoniumGenerator
S-Adenosyl 3-(methylsulphanyl)propylamineGenerator
S--AdenosylmethioninamineHMDB
(5-Deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium saltHMDB
DAdoMetHMDB
Decarboxylated adometHMDB
Decarboxylated S-adenosylmethionineHMDB
Decarboxylated samHMDB
S-Adenosyl-L-methioninamineHMDB
S-5'-Deoxyadenosyl-(5')-3-methylthiopropylamineHMDB
S-Adenosyl(5')-3-methylthiopropylamineHMDB
Chemical FormulaC14H23N6O3S
Average Molecular Weight355.436
Monoisotopic Molecular Weight355.155234322
IUPAC Name{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-aminopropyl)methylsulfanium
Traditional Namedecarboxylated sam
CAS Registry Number22365-13-5
SMILES
C[S+](CCCN)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1
InChI KeyZUNBITIXDCPNSD-LSRJEVITSA-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
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.27 g/LALOGPS
logP0.28ALOGPS
logP-2.8ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)10.09ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.33 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.4 m³·mol⁻¹ChemAxon
Polarizability36.97 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06wi-7923000000-45e056b479c0e2cba364Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ai-8291700000-8e1b09746b1c704e209fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0904000000-5a1b6a3a878c0630e6eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-70103a635ebc7c51a985Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3900000000-65b9306b33b0ffc5e9fcSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    		 details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022353
    KNApSAcK IDNot Available
    Chemspider ID388529
    KEGG Compound IDC01137
    BioCyc IDNot Available
    BiGG ID36895
    Wikipedia LinkS-Adenosylmethioninamine
    METLIN ID3501
    PubChem Compound439415
    PDB IDNot Available
    ChEBI ID15625
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferencePegg, Anthony E. Assay of aminopropyltransferases. Methods in Enzymology (1983), 94(Polyamines), 260-5.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Fontecave M, Atta M, Mulliez E: S-adenosylmethionine: nothing goes to waste. Trends Biochem Sci. 2004 May;29(5):243-9. [PubMed:15130560 ]

    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
    Reactions
    S-Adenosylmethioninamine + Spermidine → 5'-Methylthioadenosine + Sperminedetails
    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
    Reactions
    S-Adenosylmethioninamine + Putrescine → 5'-Methylthioadenosine + Spermidinedetails
    S-Adenosylmethioninamine + Spermidine → 5'-Methylthioadenosine + Sperminedetails
    S-Adenosylmethioninamine + Cadaverine → 5'-Methylthioadenosine + Aminopropylcadaverinedetails
    Enzyme Details
    3. S-adenosylmethionine decarboxylase proenzyme
    General function:
    Involved in adenosylmethionine decarboxylase activity
    Specific function:
    Not Available
    Gene Name:
    AMD1
    Uniprot ID:
    P17707
    Molecular weight:
    21301.015
    Reactions
    S-Adenosylmethionine + Hydrogen Ion → S-Adenosylmethioninamine + Carbon dioxidedetails