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Record Information
Version1.0
Creation Date2016-07-13 19:43:44 UTC
Update Date2016-07-20 20:27:44 UTC
LmdbLMDB00163
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Methylhistidine
Description3-Methylhistidine belongs to the class of organic compounds known as histidine and derivatives. Histidine 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. 3-Methylhistidine is a very strong basic compound (based on its pKa). 3-Methylhistidine exists in all eukaryotes, ranging from yeast to humans. In humans, 3-methylhistidine is involved in methylhistidine metabolism. A L-histidine derivative that is L-histidine substituted by a methyl group at position 3 on the imidazole ring.
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acidChEBI
3-Methyl-L-histidineChEBI
N-pros-Methyl-L-histidineChEBI
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoateGenerator
3-N-Methyl-L-histidineHMDB
L-3-MethylhistidineHMDB
N(pros)-Methyl-L-histidineHMDB
N3-Methyl-L-histidineHMDB
3-Methylhistidine hydrideHMDB
3-Methylhistidine dihydrochlorideHMDB
3-MethylhistidineChEBI
Pi methylhistidineHMDB
N(Pi)-methylhistidineHMDB
N Pi-methylhistidineHMDB
Chemical FormulaC7H11N3O2
Average Molecular Weight169.1811
Monoisotopic Molecular Weight169.085126611
IUPAC Name(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Traditional Name3,methylhistidine
CAS Registry Number368-16-1
SMILES
CN1C=NC=C1C[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
InChI KeyJDHILDINMRGULE-LURJTMIESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as histidine and derivatives. Histidine 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 ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot 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-2.9ALOGPS
logP-3.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.96 m³·mol⁻¹ChemAxon
Polarizability16.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-9500000000-ab7d6324146b8775fe50Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9400000000-42443c78fdfca9db1926Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-2900000000-15f0e43eb0d06e7f3ef3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9200000000-5a1ab4d052e6ba4a76e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0002-9000000000-c1951c88c84885804fb6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-4e0fea0fe9b1142db07bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0592-4900000000-ee1bce969d650e9fcfbeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0002-9200000000-1ad733cdcfa4db4fe3b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0002-9000000000-a87ff5cc0642ea3af69cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0002-9000000000-28a73708493f968c2ac6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9800000000-6565ccf96757ef3bc08fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-3cbd02f5b6c4e6e64eb9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-0900000000-e6ce7548fd6f09e2098fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-3cbd02f5b6c4e6e64eb9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-2d351351f285b2188710Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0592-4900000000-ee1bce969d650e9fcfbeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9200000000-1ad733cdcfa4db4fe3b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-2ed34e7b458d9f8c092fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-9000000000-c1b8a62adc15b80955c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9800000000-6565ccf96757ef3bc08fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-6900000000-acc4a08855924a8bf5a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-1ca24429b22e547d10d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-4cafc4698b6e3649ce7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9300000000-ef0c8b716935df30c508Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-8a91a6a64bb07285c36dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-4900000000-4ad91c6f55caf69120e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05di-9300000000-ea67f38340a4b7ef8e11Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Follicular Fluid
  • Milk
  • Plasma
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Follicular FluidDetected and Quantified44 +/- 1-5+/-2 uMNot AvailablePorcine details
MilkDetected and Quantified103-151 uMNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected and Quantified5 +/- 0-9+/-2 uMNot AvailablePorcine details
PlasmaDetected and Quantified6 +/- 1-8+/-1 uMNot AvailablePorcine details
PlasmaDetected and Quantified7 +/- 0-6+/-0 uMNot AvailablePorcine details
SerumDetected and Quantified2.187 uMNot AvailablePorcine details
SerumDetected and Quantified2.483 uMNot AvailablePorcine details
SerumDetected and Quantified2.00968 uMNot AvailablePorcine details
SerumDetected and Quantified2.719 uMNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified46 +/- 6 uMNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0000479
FooDB IDFDB093613
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5466
PDB IDNot Available
Wikipedia Link3-Methylhistidine
Chemspider ID58494
ChEBI ID27596
PubChem Compound ID64969
Kegg Compound IDC01152
YMDB IDYMDB00703
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available