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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-04-04 16:09:12 UTC
Update Date2022-09-22 18:34:32 UTC
HMDB IDHMDB0240343
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetylmethionine sulfoxide
DescriptionN-Acetylmethionine sulfoxide (CAS: 3054-51-1), also known as N-ACMSO or 2-(acetylamino)-4-(methylsulfinyl)butanoic acid, belongs to the class of organic compounds known as N-acyl-L-alpha-amino acids. These are N-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-Acetylmethionine sulfoxide has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1573770469
Synonyms
ValueSource
(2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulfinylbutanoateGenerator
(2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulphinylbutanoateGenerator
(2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulphinylbutanoic acidGenerator
N-ACMSOMeSH
N-Acetylmethionine sulfoxideMeSH
(2S)-2-(Acetylamino)-4-(methylsulfinyl)butanoic acidHMDB
(2S)-2-Acetamido-4-(methylsulfinyl)butanoic acidHMDB
(2S)-2-Acetamido-4-methanesulfinylbutanoic acidHMDB
(2S)-2-Acetamido-4-methylsulfinylbutanoic acidHMDB
2-(Acetylamino)-4-(methylsulfinyl)butanoic acidHMDB
N-Acetyl-L-methionine sulfoxideHMDB
Chemical FormulaC7H13NO4S
Average Molecular Weight207.24
Monoisotopic Molecular Weight207.056529077
IUPAC Name(2S)-2-acetamido-4-methanesulfinylbutanoic acid
Traditional Name(2S)-2-acetamido-4-methanesulfinylbutanoic acid
CAS Registry Number108646-71-5
SMILES
CC(=O)N[C@@H](CCS(C)=O)C(O)=O
InChI Identifier
InChI=1S/C7H13NO4S/c1-5(9)8-6(7(10)11)3-4-13(2)12/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-,13?/m0/s1
InChI KeyNPIMMZJBURSMON-YLTHGKPTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Sulfoxide
  • Sulfinyl compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Carbonyl group
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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-0.96ALOGPS
logP-2.5ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity48.79 m³·mol⁻¹ChemAxon
Polarizability20.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+138.60730932474
DeepCCS[M-H]-135.72930932474
DeepCCS[M-2H]-172.18230932474
DeepCCS[M+Na]+147.7230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetylmethionine sulfoxideCC(=O)N[C@@H](CCS(C)=O)C(O)=O2940.3Standard polar33892256
N-Acetylmethionine sulfoxideCC(=O)N[C@@H](CCS(C)=O)C(O)=O1771.6Standard non polar33892256
N-Acetylmethionine sulfoxideCC(=O)N[C@@H](CCS(C)=O)C(O)=O1835.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetylmethionine sulfoxide,1TMS,isomer #1CC(=O)N[C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C1734.6Semi standard non polar33892256
N-Acetylmethionine sulfoxide,1TMS,isomer #2CC(=O)N([C@@H](CCS(C)=O)C(=O)O)[Si](C)(C)C1736.6Semi standard non polar33892256
N-Acetylmethionine sulfoxide,2TMS,isomer #1CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C1754.9Semi standard non polar33892256
N-Acetylmethionine sulfoxide,2TMS,isomer #1CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C2073.8Standard non polar33892256
N-Acetylmethionine sulfoxide,2TMS,isomer #1CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C2133.5Standard polar33892256
N-Acetylmethionine sulfoxide,1TBDMS,isomer #1CC(=O)N[C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C(C)(C)C1963.9Semi standard non polar33892256
N-Acetylmethionine sulfoxide,1TBDMS,isomer #2CC(=O)N([C@@H](CCS(C)=O)C(=O)O)[Si](C)(C)C(C)(C)C1967.9Semi standard non polar33892256
N-Acetylmethionine sulfoxide,2TBDMS,isomer #1CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2240.7Semi standard non polar33892256
N-Acetylmethionine sulfoxide,2TBDMS,isomer #1CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2615.3Standard non polar33892256
N-Acetylmethionine sulfoxide,2TBDMS,isomer #1CC(=O)N([C@@H](CCS(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2347.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylmethionine sulfoxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylmethionine sulfoxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 10V, Positive-QTOFsplash10-014i-0910000000-93ffaabee484f7cd67a42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 20V, Positive-QTOFsplash10-0f6t-7900000000-0ea877575dff1139e9612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 40V, Positive-QTOFsplash10-03di-9100000000-7b0e97a852e51236a59b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 10V, Negative-QTOFsplash10-03di-7950000000-3b5c400fe303c25511092021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 20V, Negative-QTOFsplash10-03di-9400000000-3b4399cf013a7bb288122021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmethionine sulfoxide 40V, Negative-QTOFsplash10-01ox-9000000000-87fb4d29772a0579d39c2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID19354090
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]