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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:21 UTC
Update Date2020-02-26 21:37:17 UTC
HMDB IDHMDB0012286
Secondary Accession Numbers
  • HMDB12286
Metabolite Identification
Common NameS-Prenyl-L-cysteine
DescriptionS-Prenyl-L-cysteine, also known as prenisteine, 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-Prenyl-L-cysteine is a very strong basic compound (based on its pKa). Outside of the human body, S-Prenyl-L-cysteine has been detected, but not quantified in, several different foods, such as soft-necked garlics, spinachs, black elderberries, cucumbers, and mango. This could make S-prenyl-L-cysteine a potential biomarker for the consumption of these foods. This reaction may represent the final. step in the degradation of prenylated proteins in mammalian tissues. S-Prenyl-L-cysteine is catalysed by prenylcysteine oxidase to form L-cysteine. Cleaves the thioether bond of S-prenyl-L-cysteines, such as S-farnesylcysteine and S-geranylgeranylcysteine. The enzyme is originally thought to be a simple lyase so it had been classified as. A flavoprotein (FAD). prenylcysteinyl peptides are not substrates.
Structure
Data?1582753037
Synonyms
ValueSource
2-Amino-3-prenylmercaptopropionic acidHMDB
2-Amino-3-prenylthiopropionic acidHMDB
3-((3-Methyl-2-butenyl)thio)-L-alanineHMDB
PrenisteineHMDB
Prenyl-L-cysteineHMDB
S-(3-Methyl-2-butenyl-L-cysteine)HMDB
2-Amino-3-[(3-methylbut-2-en-1-yl)sulfanyl]propanoateGenerator
2-Amino-3-[(3-methylbut-2-en-1-yl)sulphanyl]propanoateGenerator
2-Amino-3-[(3-methylbut-2-en-1-yl)sulphanyl]propanoic acidGenerator
Chemical FormulaC8H15NO2S
Average Molecular Weight189.275
Monoisotopic Molecular Weight189.082349419
IUPAC Name2-amino-3-[(3-methylbut-2-en-1-yl)sulfanyl]propanoic acid
Traditional Name2-amino-3-[(3-methylbut-2-en-1-yl)sulfanyl]propanoic acid
CAS Registry Number5287-46-7
SMILES
CC(C)=CCSCC(N)C(O)=O
InChI Identifier
InChI=1S/C8H15NO2S/c1-6(2)3-4-12-5-7(9)8(10)11/h3,7H,4-5,9H2,1-2H3,(H,10,11)
InChI KeyULHWZNASVJIOEM-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

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 Solubility3.75 g/LALOGPS
logP-1.3ALOGPS
logP-1.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.66ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity52.04 m³·mol⁻¹ChemAxon
Polarizability21.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bc-9100000000-6b9d4986c5053a3e2ef2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01ba-9500000000-306fa7aff9ba79e09a2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-4900000000-c9a250834ea0193407f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi0-9700000000-605b4578ccaf5e63f1d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tf-9000000000-d5655710f0e8d8eaeb7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fe0-1900000000-a8bb9e73942a6263088cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3900000000-915ec040bc628baa6cf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fz0-9100000000-203be232579639567f67Spectrum
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
FoodDB IDFDB028916
KNApSAcK IDNot Available
Chemspider ID4295950
KEGG Compound IDNot Available
BioCyc IDS-PRENYL-L-CYSTEINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5121218
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available