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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:15:22 UTC
Update Date2017-12-07 03:26:36 UTC
HMDB IDHMDB0033518
Secondary Accession Numbers
  • HMDB33518
Metabolite Identification
Common NameS-(2-Aminoethyl)-L-cysteine
DescriptionS-(2-Aminoethyl)-L-cysteine, also known as 4-thialysine or thiosine, belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. S-(2-Aminoethyl)-L-cysteine is soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, S-(2-aminoethyl)-L-cysteine is primarily located in the cytoplasm. Outside of the human body, S-(2-aminoethyl)-L-cysteine can be found in mushrooms. This makes S-(2-aminoethyl)-L-cysteine a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
2-AminoethylcysteineHMDB
4-Thia-L-lysineHMDB
4-ThialysineHMDB
AminoethylcysteineHMDB
gamma-ThialysineHMDB
S-2-Aminoethyl cysteineHMDB
ThialysineHMDB
ThiosineHMDB
Chemical FormulaC5H12N2O2S
Average Molecular Weight164.226
Monoisotopic Molecular Weight164.061948328
IUPAC Name2-amino-3-[(2-aminoethyl)sulfanyl]propanoic acid
Traditional Name5-(2-aminoethyl)homocysteine
CAS Registry Number2936-69-8
SMILES
NCCSCC(N)C(O)=O
InChI Identifier
InChI=1S/C5H12N2O2S/c6-1-2-10-3-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)
InChI KeyGHSJKUNUIHUPDF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility40.3 g/LALOGPS
logP-3.3ALOGPS
logP-3.8ChemAxon
logS-0.61ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)9.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.03 m³·mol⁻¹ChemAxon
Polarizability17.21 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-9100000000-f8f6c2ee84a4a254b465View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00lv-9400000000-3be6e60123efd56d747cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-7900000000-1106b712954316d62fe4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-9300000000-c2ec537a5aae6720612aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-764c0b22ec650ecebcd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-6900000000-08c141e31190b7c22f7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9200000000-2b18c2f7f3297efd74e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-64dce75fc85357ca47beView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FoodDB IDFDB011573
KNApSAcK IDNot Available
Chemspider ID18889
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20049
PDB IDNot Available
ChEBI ID497734
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .