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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 10:04:19 UTC
Update Date2021-09-24 10:04:19 UTC
HMDB IDHMDB0304476
Secondary Accession NumbersNone
Metabolite Identification
Common NameS-adenosyl-L-methioninamine
DescriptionDecarboxy-sam, also known as S-adenosyl 3-(methylthio)propylamine or dcsam, is a member of the class of compounds known as 5'-deoxy-5'-thionucleosides. 5'-deoxy-5'-thionucleosides are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. Decarboxy-sam is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Decarboxy-sam can be found in a number of food items such as caraway, celeriac, prunus (cherry, plum), and sparkleberry, which makes decarboxy-sam a potential biomarker for the consumption of these food products. Decarboxy-sam may be a unique E.coli metabolite.
Structure
Thumb
Synonyms
ValueSource
S-Adenosyl 3-(methylsulfanyl)propylamineChEBI
S-Adenosyl 3-(methylsulphanyl)propylamineGenerator
S-Adenosyl 3-(methylthio)propylamineChEBI
Chemical FormulaC14H24N6O3S
Average Molecular Weight356.444
Monoisotopic Molecular Weight356.163059354
IUPAC Name{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-azaniumylpropyl)methylsulfanium
Traditional NameS-adenosylmethioninaminium
CAS Registry NumberNot Available
SMILES
[H][C@]1(C[S+](C)CCC[NH3+])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O
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/p+1/t8-,10-,11-,14-,24?/m1/s1
InChI KeyZUNBITIXDCPNSD-LSRJEVITSA-O
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
Not Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-1.7ALOGPS
logP-2.8ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)10.09ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area146.95 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.7 m³·mol⁻¹ChemAxon
Polarizability37.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+179.50532859911
AllCCS[M+H-H2O]+177.08232859911
AllCCS[M+Na]+182.37132859911
AllCCS[M+NH4]+181.73432859911
AllCCS[M-H]-178.53132859911
AllCCS[M+Na-2H]-178.37532859911
AllCCS[M+HCOO]-178.34232859911
DeepCCS[M-2H]-208.54330932474
DeepCCS[M+Na]+183.61130932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
S-adenosyl-L-methioninamine,3TMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3146.5Semi standard non polar33892256
S-adenosyl-L-methioninamine,3TMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3081.5Standard non polar33892256
S-adenosyl-L-methioninamine,3TMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C4110.8Standard polar33892256
S-adenosyl-L-methioninamine,3TMS,isomer #2C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O3128.0Semi standard non polar33892256
S-adenosyl-L-methioninamine,3TMS,isomer #2C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O3112.8Standard non polar33892256
S-adenosyl-L-methioninamine,3TMS,isomer #2C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O3896.6Standard polar33892256
S-adenosyl-L-methioninamine,3TMS,isomer #3C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C3137.4Semi standard non polar33892256
S-adenosyl-L-methioninamine,3TMS,isomer #3C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C3099.8Standard non polar33892256
S-adenosyl-L-methioninamine,3TMS,isomer #3C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C3871.5Standard polar33892256
S-adenosyl-L-methioninamine,4TMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3130.1Semi standard non polar33892256
S-adenosyl-L-methioninamine,4TMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3132.0Standard non polar33892256
S-adenosyl-L-methioninamine,4TMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3589.1Standard polar33892256
S-adenosyl-L-methioninamine,3TBDMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3681.7Semi standard non polar33892256
S-adenosyl-L-methioninamine,3TBDMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3682.0Standard non polar33892256
S-adenosyl-L-methioninamine,3TBDMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C4161.0Standard polar33892256
S-adenosyl-L-methioninamine,3TBDMS,isomer #2C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3647.8Semi standard non polar33892256
S-adenosyl-L-methioninamine,3TBDMS,isomer #2C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3732.4Standard non polar33892256
S-adenosyl-L-methioninamine,3TBDMS,isomer #2C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3957.2Standard polar33892256
S-adenosyl-L-methioninamine,3TBDMS,isomer #3C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3654.1Semi standard non polar33892256
S-adenosyl-L-methioninamine,3TBDMS,isomer #3C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3715.7Standard non polar33892256
S-adenosyl-L-methioninamine,3TBDMS,isomer #3C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3932.2Standard polar33892256
S-adenosyl-L-methioninamine,4TBDMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3779.8Semi standard non polar33892256
S-adenosyl-L-methioninamine,4TBDMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3867.6Standard non polar33892256
S-adenosyl-L-methioninamine,4TBDMS,isomer #1C[S+](CCC[NH3+])C[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3732.4Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031151
KNApSAcK IDNot Available
Chemspider ID26330790
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID57443
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available