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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:24:33 UTC
Update Date2022-03-07 03:17:45 UTC
HMDB IDHMDB0060490
Secondary Accession Numbers
  • HMDB60490
Metabolite Identification
Common NameMethylselenopyruvate
DescriptionMethylselenopyruvate belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Methylselenopyruvate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866067
Synonyms
ValueSource
beta-MethylselenopyruvateKegg
b-MethylselenopyruvateGenerator
b-Methylselenopyruvic acidGenerator
beta-Methylselenopyruvic acidGenerator
Β-methylselenopyruvateGenerator
Β-methylselenopyruvic acidGenerator
Methylselenopyruvic acidGenerator
Chemical FormulaC4H6O3Se
Average Molecular Weight181.05
Monoisotopic Molecular Weight181.948215886
IUPAC Name3-(methylselanyl)-2-oxopropanoic acid
Traditional Name3-(methylselanyl)-2-oxopropanoic acid
CAS Registry NumberNot Available
SMILES
C[Se]CC(=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O3Se/c1-8-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
InChI KeyKCHPIRYOQIGZLW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassAlpha-keto acids and derivatives
Direct ParentAlpha-keto acids and derivatives
Alternative Parents
Substituents
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Selenoether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organoselenium compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
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
Water Solubility54.9 g/LALOGPS
logP-0.47ALOGPS
logP0.33ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)2.16ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.79 m³·mol⁻¹ChemAxon
Polarizability11.35 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]+128.81330932474
DeepCCS[M-H]-126.0430932474
DeepCCS[M-2H]-162.62630932474
DeepCCS[M+Na]+137.32130932474
AllCCS[M+H]+135.532859911
AllCCS[M+H-H2O]+131.732859911
AllCCS[M+NH4]+139.132859911
AllCCS[M+Na]+140.132859911
AllCCS[M-H]-141.532859911
AllCCS[M+Na-2H]-144.732859911
AllCCS[M+HCOO]-148.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethylselenopyruvateC[Se]CC(=O)C(O)=O1776.2Standard polar33892256
MethylselenopyruvateC[Se]CC(=O)C(O)=O1421.6Standard non polar33892256
MethylselenopyruvateC[Se]CC(=O)C(O)=O1602.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methylselenopyruvate,1TMS,isomer #1C[Se]CC(=O)C(=O)O[Si](C)(C)C1307.3Semi standard non polar33892256
Methylselenopyruvate,1TMS,isomer #2C[Se]C=C(O[Si](C)(C)C)C(=O)O1428.4Semi standard non polar33892256
Methylselenopyruvate,2TMS,isomer #1C[Se]C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1464.6Semi standard non polar33892256
Methylselenopyruvate,2TMS,isomer #1C[Se]C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1277.8Standard non polar33892256
Methylselenopyruvate,2TMS,isomer #1C[Se]C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1269.8Standard polar33892256
Methylselenopyruvate,1TBDMS,isomer #1C[Se]CC(=O)C(=O)O[Si](C)(C)C(C)(C)C1557.3Semi standard non polar33892256
Methylselenopyruvate,1TBDMS,isomer #2C[Se]C=C(O[Si](C)(C)C(C)(C)C)C(=O)O1662.9Semi standard non polar33892256
Methylselenopyruvate,2TBDMS,isomer #1C[Se]C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1911.8Semi standard non polar33892256
Methylselenopyruvate,2TBDMS,isomer #1C[Se]C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1682.2Standard non polar33892256
Methylselenopyruvate,2TBDMS,isomer #1C[Se]C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1600.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methylselenopyruvate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-fa55d8e35020dfc887a42017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylselenopyruvate GC-MS (1 TMS) - 70eV, Positivesplash10-00y0-9400000000-98006ffbe7b5b9a8b9092017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylselenopyruvate 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 - Methylselenopyruvate 10V, Positive-QTOFsplash10-001i-0900000000-fae31832f2765d747cfd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 20V, Positive-QTOFsplash10-001i-1900000000-d110db3043cda5cbbad92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 40V, Positive-QTOFsplash10-0006-7900000000-96ecb93529b1619adc722017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 10V, Negative-QTOFsplash10-01q9-3900000000-69f35542a7e43f206be72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 20V, Negative-QTOFsplash10-001r-4900000000-9d8eb9021a2d7a73f6492017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 40V, Negative-QTOFsplash10-0a4i-3900000000-11e14dce33b249382c682017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 10V, Positive-QTOFsplash10-03e9-0900000000-d55bb7006418fa7374f22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 20V, Positive-QTOFsplash10-052r-2900000000-72df6f77cd3868f8d98f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 40V, Positive-QTOFsplash10-0a4i-1900000000-84d6244c31320d88b12d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 10V, Negative-QTOFsplash10-001i-0900000000-46769265e5f64f4995e02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 20V, Negative-QTOFsplash10-0006-9000000000-a8e4ff3068cf371558042021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylselenopyruvate 40V, Negative-QTOFsplash10-0006-9100000000-2110439293c25484af822021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC18904
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53297415
PDB IDNot Available
ChEBI ID82049
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:
CCBL1
Uniprot ID:
Q16773
Molecular weight:
47874.765
Reactions
Se-Methylselenocysteine + 2-Oxo-4-methylthiobutanoic acid → Methylselenopyruvate + L-Methioninedetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:
CCBL2
Uniprot ID:
Q6YP21
Molecular weight:
51399.855
Reactions
Se-Methylselenocysteine + 2-Oxo-4-methylthiobutanoic acid → Methylselenopyruvate + L-Methioninedetails