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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-21 17:57:37 UTC
HMDB IDHMDB0000988
Secondary Accession Numbers
  • HMDB00988
Metabolite Identification
Common NameS-Adenosylmethioninamine
DescriptionS-Adenosylmethioninamine is a biological sulfonium compound known as the major biological methyl donor. It is also a donor of methylene groups, amino groups, ribosyl groups and aminopropyl groups (PMID 15130560 ). S-Adenosylmethioninamine is a prodcut of enzyme adenosylmethionine decarboxylase [EC 4.1.1.50] in methionine metabolism pathway (KEGG).
Structure
Thumb
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--AdenosylmethioninamineChEBI
S-Adenosyl-(5')-3-methylthiopropylamineChEBI
S-Adenosyl-3-methylthiopropylamineChEBI
(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
(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-methylthiopropylamineMeSH
S-Adenosyl(5')-3-methylthiopropylamineMeSH
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub Class5'-deoxyribonucleosides
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
  • Primary aromatic amine
  • Pyrimidine
  • Imidolactam
  • Oxolane
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organosulfur compound
  • Amine
  • Primary amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
  • Component of beta-Alanine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.4 m3·mol-1ChemAxon
Polarizability36.97 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Cystathionine Beta-Synthase DeficiencyPw000100Pw000100 greyscalePw000100 simpleNot Available
Glycine N-methyltransferase DeficiencyPw000103Pw000103 greyscalePw000103 simpleNot Available
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typePw000546Pw000546 greyscalePw000546 simpleNot Available
HypermethioninemiaPw000101Pw000101 greyscalePw000101 simpleNot Available
Methionine Adenosyltransferase DeficiencyPw000105Pw000105 greyscalePw000105 simpleNot Available
Displaying entries 1 - 5 of 9 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    Cerebrospinal Fluid (CSF)Detected and Quantified0.207 +/- 0.037 uMAdult (>18 years old)Not SpecifiedNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    Cerebrospinal Fluid (CSF)Detected and Quantified0.193 +/- 0.031 uMAdult (>18 years old)Not SpecifiedAlzheimer's disease details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022353
    KNApSAcK IDNot Available
    Chemspider ID388529
    KEGG Compound IDC01137
    BioCyc IDS-ADENOSYLMETHIONINAMINE
    BiGG ID36895
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0000988
    METLIN ID3501
    PubChem Compound439415
    PDB IDNot Available
    ChEBI ID15625
    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

    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
    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
    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