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Record Information
Version1.0
Creation Date2016-09-30 22:07:14 UTC
Update Date2020-05-21 16:28:38 UTC
BMDB IDBMDB0000001
Secondary Accession Numbers
  • BMDB00001
Metabolite Identification
Common Name1-Methylhistidine
Description1-Methylhistidine, also known as 1-mhis, 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. 1-Methylhistidine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 1-Methylhistidine exists in all living organisms, ranging from bacteria to humans. 1-Methylhistidine participates in a number of enzymatic reactions, within cattle. In particular, 1-Methylhistidine and beta-alanine can be converted into anserine through its interaction with the enzyme carnosine synthase 1. In addition, beta-Alanine and 1-methylhistidine can be biosynthesized from anserine; which is mediated by the enzyme cytosolic non-specific dipeptidase. In cattle, 1-methylhistidine is involved in the metabolic pathway called the histidine metabolism pathway. 1-Methylhistidine has been found to be associated with several diseases known as eosinophilic esophagitis, early preeclampsia, and obesity; also 1-methylhistidine has been linked to several inborn metabolic disorders including maple syrup urine disease and propionic acidemia.
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acidChEBI
Pi-methylhistidineChEBI
(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoateGenerator
1 MethylhistidineHMDB
1-Methyl histidineHMDB
1-Methyl-histidineHMDB
1-Methyl-L-histidineHMDB
1-MHisHMDB
1-N-Methyl-L-histidineHMDB
L-1-MethylhistidineHMDB
N1-Methyl-L-histidineHMDB
1-Methylhistidine dihydrochlorideHMDB
1-MethylhistidineChEBI
Chemical FormulaC7H11N3O2
Average Molecular Weight169.1811
Monoisotopic Molecular Weight169.085126611
IUPAC Name(2S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid
Traditional Name1 methylhistidine
CAS Registry Number332-80-9
SMILES
CN1C=NC(C[C@H](N)C(O)=O)=C1
InChI Identifier
InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
InChI KeyBRMWTNUJHUMWMS-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
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point249http://download.cappchem.com/data/Properties-of-Amino-Acids.pdf
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3ALOGPS
logP-3.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)9.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.39 m³·mol⁻¹ChemAxon
Polarizability17.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-9610000000-d0147d3e28362f91174aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gbd-4941000000-cee19577c72eecd95aecView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-9610000000-d0147d3e28362f91174aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gbd-4941000000-cee19577c72eecd95aecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-9500000000-e50450f2dc8a5d4b3655View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9310000000-d6f7eb07e6f5ecb74263View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0900000000-037d24a7d65676b7e356View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-0900000000-03e99316bd6c098f5d11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00ea-9800000000-a33c82a1c91f56d372feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-695bcc2d0a01df2d7521View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-4eea9cf6f12f18d06f98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05us-9300000000-072d6fe7a7a03cd7390bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-57f1e30ae8b606ea5f5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-5900000000-ff71b6d300a9ee595b3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adj-9300000000-e045823003ab541d5b1eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Colostrum
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Placenta
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
    • Jiyuan Li, Everes...
details
BloodDetected and Quantified14+/-2 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
BloodDetected and Quantified2-12 uMNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified25+/-5 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Longissimus Thoracis MuscleDetected and Quantified35+/-8 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified2+/-1 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Semimembranosus MuscleDetected and Quantified35+/-9 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
TestisDetected and Quantified19+/-4 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Fed pasture vs barley-based concentrate
details
HMDB IDHMDB0000001
DrugBank IDDB04151
Phenol Explorer Compound IDNot Available
FooDB IDFDB093588
KNApSAcK IDNot Available
Chemspider ID83153
KEGG Compound IDC01152
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylhistidine
METLIN ID3741
PubChem Compound92105
PDB IDNot Available
ChEBI ID50599
References
Synthesis ReferenceJain, Rahul; Cohen, Louis A. Regiospecific alkylation of histidine and histamine at N-1 (t).Tetrahedron (1996), 52(15), 5363-70.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Hydrolyzes a variety of dipeptides including L-carnosine but has a strong preference for Cys-Gly. Catalyzes the production of N-lactoyl-amino acids from lactate and amino acids by reverse proteolysis.
Gene Name:
CNDP2
Uniprot ID:
Q3ZC84
Molecular weight:
52655.0
Reactions
Anserine + Water → Beta-Alanine + 1-Methylhistidinedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
A5PJL9
Molecular weight:
54461.0
Reactions
Adenosine triphosphate + 1-Methylhistidine + Beta-Alanine → ADP + Hydrogen phosphate + Anserinedetails