Showing Compound Card for Methionine-sulfoxide (CDB006323)

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Record Information
Version1.0
Created at2020-09-11 15:49:04 UTC
Updated at2022-12-13 23:36:24 UTC
CannabisDB IDCDB006323
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethionine-sulfoxide
DescriptionMethionine sulfoxide 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). In humans, methionine sulfoxide is involved in the metabolic disorder called hypermethioninemia. Methionine sulfoxide is found, on average, in the highest concentration within a few different foods, such as barleys (Hordeum vulgare), green beans (Phaseolus vulgaris), and broccolis (Brassica oleracea var. italica) and in a lower concentration in red beetroots (Beta vulgaris var. rubra), red bell peppers (Capsicum annuum), and yellow bell peppers (Capsicum annuum). Methionine sulfoxide has also been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make methionine sulfoxide a potential biomarker for the consumption of these foods. Methionine sulfoxide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Methionine sulfoxide.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Methionine sulphoxideGenerator
Methionine sulfoxide, (+-)-isomerMeSH
Methionine sulfoxide, (2R)-isomerMeSH
Methionine sulfoxide, (2S)-isomerMeSH
Methionine sulfoxide, (R-(r*,s*))-isomerMeSH
Methionine sulfoxide, (S-(r*,s*))-isomerMeSH
Methionine sulfoxide, 35S-labeled, (+-)-isomerMeSH
2-amino-4-(Methylsulfinyl)-butanoateHMDB
2-amino-4-(Methylsulfinyl)-butanoic acidHMDB
alpha-amino-gamma-(Methylsulfinyl)-butyric acidHMDB
DL-Methionine sulfoxideHMDB
L-Methionine (S)-S-oxideHMDB
L-Methionine R-oxideHMDB
L-Methionine sulfoxideHMDB
Met-soHMDB
S-Oxide-methionineHMDB
Chemical FormulaC5H11NO3S
Average Molecular Weight165.211
Monoisotopic Molecular Weight165.045963913
IUPAC Name2-amino-4-methanesulfinylbutanoic acid
Traditional NameDL-methionine sulfoxide
CAS Registry NumberNot Available
SMILES
CS(=O)CCC(N)C(O)=O
InChI Identifier
InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)
InChI KeyQEFRNWWLZKMPFJ-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Thia fatty acid
  • Fatty acyl
  • Fatty acid
  • Sulfoxide
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfinyl compound
  • 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 Descriptors
Ontology
Not Available
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
logP-2.4ALOGPS
logP-4.6ChemAxon
logS-0.49ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.34 m³·mol⁻¹ChemAxon
Polarizability16.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSMethionine-sulfoxide, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-6639ef576db5a01f8ee5Spectrum
GC-MSMethionine-sulfoxide, non-derivatized, GC-MS Spectrumsplash10-004i-0910000000-4231d540eda02eebe871Spectrum
GC-MSMethionine-sulfoxide, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-f0849e8acf9a3e1e2763Spectrum
GC-MSMethionine-sulfoxide, 3 TMS, GC-MS Spectrumsplash10-004i-1910000000-b7a64800b9e577e219d4Spectrum
GC-MSMethionine-sulfoxide, non-derivatized, GC-MS Spectrumsplash10-004i-1910000000-b7a64800b9e577e219d4Spectrum
GC-MSMethionine-sulfoxide, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-a5138c4f03667c81645cSpectrum
GC-MSMethionine-sulfoxide, non-derivatized, GC-MS Spectrumsplash10-004i-0910000000-b8f17a35f754f6a2adffSpectrum
GC-MSMethionine-sulfoxide, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-40d23196cb4ee1cad23fSpectrum
Predicted GC-MSMethionine-sulfoxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kmi-9300000000-40502e78936db0335f4aSpectrum
Predicted GC-MSMethionine-sulfoxide, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fs-9600000000-b39ca26ddac3482e7cc5Spectrum
Predicted GC-MSMethionine-sulfoxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethionine-sulfoxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethionine-sulfoxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethionine-sulfoxide, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethionine-sulfoxide, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethionine-sulfoxide, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9400000000-cac8577601b69f1b723a2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-43361da834d0b07907fd2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-6090b56aa5a22d72fb4f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-9300000000-fccbb5a2836a564cd61c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-74770a100fb96d6b77182021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-b39a3e60167512e828392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-01ot-9000000000-7a9db4277879a8bd920b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-1900000000-f7bdaacb8f4c8c0ecac82016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-3900000000-0dbf2b087d6505b4b8202016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-00dc8b47e3cb0dc2e3212016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9600000000-9032163b7ca7799d7c432016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-562e35acb4f9e5564a692016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-2125dfc28681bc1d4c2e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9400000000-7375ade3d9a2e79890d42021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-4fa3654466563449190c2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-375f7404d6c31bdf96b32021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9500000000-a4583e8c3a4365d330e22021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-433cb4a770ae8f69c6152021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ff3de228e84a6b4470bc2021-10-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.00634 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.0540 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.0171 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.0296 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.00753 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.0174 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0253902
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022789
KNApSAcK IDC00051545
Chemspider ID824
KEGG Compound IDNot Available
BioCyc IDCPD0-1959
BiGG IDNot Available
Wikipedia LinkMethionine sulfoxide
METLIN IDNot Available
PubChem Compound847
PDB IDNot Available
ChEBI ID49033
References
General ReferencesNot Available