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Showing metabocard for 1-Methylhistidine (BMDB0000001)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:07:14 UTC
Update Date2020-06-04 20:10:20 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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acidChEBI
(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
Tau methylhistidineHMDB
N(Tau)-methylhistidineHMDB
Tau-methyl-L-histidineHMDB
N Tau-methylhistidineHMDB
Chemical FormulaC7H11N3O2
Average Molecular Weight169.1811
Monoisotopic Molecular Weight169.085126611
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number332-80-9
SMILESNot Available
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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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 QuantifiedNot SpecifiedNot Specified
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Jiyuan Li, Everes...
 details
BloodDetected and Quantified14 +/- 2 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
BloodDetected and Quantified2-12 uMNot SpecifiedNot Specified
Normal		 details
LiverDetected and Quantified25 +/- 5 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified35 +/- 8 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified2 +/- 1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Semimembranosus MuscleDetected and Quantified35 +/- 9 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified19 +/- 4 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Fed pasture vs barley-based concentrate		 details
HMDB IDHMDB0000001
DrugBank IDDB04151
Phenol Explorer Compound IDNot Available
FooDB IDFDB093588
KNApSAcK IDC00052105
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

Enzyme Details
1. Cytosolic non-specific dipeptidase
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
Enzyme Details
2. ATP-grasp domain-containing protein
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