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Record Information
Version1.0
Creation Date2016-09-30 22:31:20 UTC
Update Date2020-06-04 20:20:16 UTC
MCDB ID BMDB0000479
Secondary Accession Numbers
  • BMDB00479
Metabolite Identification
Common Name3-Methylhistidine
DescriptionN(pros)-Methyl-L-histidine, also known as 3-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. N(pros)-Methyl-L-histidine is possibly soluble (in water) and a very strong basic compound (based on its pKa). N(pros)-Methyl-L-histidine exists in all eukaryotes, ranging from yeast to humans.
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 NameNot Available
Traditional NameNot Available
CAS Registry Number368-16-1
SMILESNot Available
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility200 mg/mL at 25 °CBEILSTEIN
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected and Quantified103 - 151 uM details
HMDB IDHMDB0000479
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093613
KNApSAcK IDNot Available
Chemspider ID58494
KEGG Compound IDC01152
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylhistidine
METLIN ID5466
PubChem Compound64969
PDB IDNot Available
ChEBI ID27596
References
Synthesis ReferenceOhba, Masashi; Mukaihira, Takafumi; Fujii, Tozo. Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines. Chemical & Pharmaceutical Bulletin (1994), 42(9), 1784-90.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]