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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:19 UTC
Update Date2020-02-26 21:43:36 UTC
HMDB IDHMDB0029422
Secondary Accession Numbers
  • HMDB29422
Metabolite Identification
Common NameL-Histidine trimethylbetaine
DescriptionL-Histidine trimethylbetaine, also known as hercynine, 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. L-Histidine trimethylbetaine is a very strong basic compound (based on its pKa). Outside of the human body, L-Histidine trimethylbetaine has been detected, but not quantified in, several different foods, such as wild rices, corns, triticales, millets, and red rices. This could make L-histidine trimethylbetaine a potential biomarker for the consumption of these foods.
Structure
Data?1582753416
Synonyms
ValueSource
HercynineHMDB
Nalpha,nalpha,nalpha-trimethyl-L-histidineHMDB
3-(1H-Imidazol-5-yl)-2-(trimethylazaniumyl)propanoic acidGenerator
Chemical FormulaC9H15N3O2
Average Molecular Weight197.2343
Monoisotopic Molecular Weight197.116426739
IUPAC Name3-(1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate
Traditional Name3-(3H-imidazol-4-yl)-2-(trimethylammonio)propanoate
CAS Registry Number534-30-5
SMILES
C[N+](C)(C)C(CC1=CN=CN1)C([O-])=O
InChI Identifier
InChI=1S/C9H15N3O2/c1-12(2,3)8(9(13)14)4-7-5-10-6-11-7/h5-6,8H,4H2,1-3H3,(H-,10,11,13,14)
InChI KeyGPPYTCRVKHULJH-UHFFFAOYSA-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
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Azole
  • Tetraalkylammonium salt
  • Imidazole
  • Heteroaromatic compound
  • Quaternary ammonium salt
  • Carboxylic acid salt
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point237 - 238 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.21 g/LALOGPS
logP-1.8ALOGPS
logP-4.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.03ChemAxon
pKa (Strongest Basic)6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.81 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.88 m³·mol⁻¹ChemAxon
Polarizability20.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-8900000000-23e837c0bc53b9793f1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-6f49d5f6fc28676113b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uea-0900000000-d1901140fb27057067f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9300000000-925a8659f4b4a9b8a016Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-01825853cb11cac69d2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-1900000000-a2afc86184c1f3923d7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-2136d232e21b4b12147eSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000520
KNApSAcK IDNot Available
Chemspider ID2340795
KEGG Compound IDC05575
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3083620
PDB IDNot Available
ChEBI ID15781
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .