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Bovine Metabolome Database



Showing metabocard for 1-Methylhistidine (BMDB00001)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-10-16 12:18:01
Accession Number BMDB00001
Common Name 1-Methylhistidine
Description One-methylhistidine (1-MHis) is derived mainly from the anserine of dietary flesh sources, especially poultry. The enzyme, carnosinase, splits anserine into b-alanine and 1-MHis. High levels of 1-MHis tend to inhibit the enzyme carnosinase and increase anserine levels. Conversely, genetic variants with deficient carnosinase activity in plasma show increased 1-MHis excretions when they consume a high meat diet. Reduced serum carnosinase activity is also found in patients with Parkinson's disease and multiple sclerosis and patients following a cerebrovascular accident. Vitamin E deficiency can lead to 1-methylhistidinuria from increased oxidative effects in skeletal muscle.
Synonyms
  1. 1 methylhistidine
  2. 1-methyl histidine
  3. 1-MHis
  4. 1-Methyl-Histidine
  5. 1-Methyl-L-histidine
  6. 1-N-Methyl-L-histidine
  7. L-1-Methylhistidine
  8. N1-Methyl-L-histidine
  9. pi-methylhistidine
Chemical IUPAC Name (2S)-2-amino-3-(1-methylimidazol-4-yl)propanoic acid
Chemical Formula C7H11N3O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • primary amine; primary aliphatic amine (alkylamine); carboxylic acid; aromatic compound; heterocyclic compound; alpha-aminoacid
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application
Source
  • Endogenous
Average Molecular Weight 169.181
Monoisotopic Molecular Weight 169.085129
Isomeric SMILES CN1C=NC(C[C@H](N)C(O)=O)=C1
Canonical SMILES CN1C=NC(CC(N)C(O)=O)=C1
KEGG Compound ID C01152 Link Image
BioCyc ID CPD-1823 Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 3741 Link Image
PubChem Compound 92105 Link Image
PubChem Substance 10225185 Link Image
ChEBI ID 50599 Link Image
CAS Registry Number 332-80-9
InChI Identifier InChI=1/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
Synthesis Reference Jain, Rahul; Cohen, Louis A. Regiospecific alkylation of histidine and histamine at N-1 (t).Tetrahedron (1996), 52(15), 5363-70.
Melting Point (Experimental) 246-248 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 6.93 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.8 [Predicted by PubChem via XLOGP]; -2.95 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location
Tissue References
Muscle
Skeletal Muscle
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Histidine Metabolism
HMDB Pathways
Name Histidine Metabolism
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KEGG Pathways
Name Histidine Metabolism
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SimCell Pathways
Name Histidine Metabolism
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Graph
SBML
General References Not Available