You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2019-07-23 07:12:36 UTC
HMDB IDHMDB0059617
Secondary Accession Numbers
  • HMDB59617
Metabolite Identification
Common Name2-(3-carboxy-3-(trimethylammonio)propyl)-L-histidine
Description2-(3-carboxy-3-(trimethylammonio)propyl)-L-histidine 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. 2-(3-carboxy-3-(trimethylammonio)propyl)-L-histidine is a very strong basic compound (based on its pKa).
Structure
Data?1563865956
SynonymsNot Available
Chemical FormulaC13H23N4O4
Average Molecular Weight299.3461
Monoisotopic Molecular Weight299.171930244
IUPAC Name(3-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}-1-carboxypropyl)trimethylazanium
Traditional Name(3-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}-1-carboxypropyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@](N)(CC1=CN=C(CCC([H])(C(O)=O)[N+](C)(C)C)N1)C(O)=O
InChI Identifier
InChI=1S/C13H22N4O4/c1-17(2,3)10(13(20)21)4-5-11-15-7-8(16-11)6-9(14)12(18)19/h7,9-10H,4-6,14H2,1-3H3,(H2-,15,16,18,19,20,21)/p+1/t9-,10?/m0/s1
InChI KeyCBQVLMCHMFGPMX-RGURZIINSA-O
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
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Azole
  • Imidazole
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Heteroaromatic compound
  • Amino acid
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic salt
  • Carbonyl group
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP-1.2ALOGPS
logP-7.8ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)1.4ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity87.13 m³·mol⁻¹ChemAxon
Polarizability31.5 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, Positivesplash10-0a4i-3490000000-16039970f611e258eaebSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a70-9175100000-74eec40c8d4fd59623f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-0090000000-d7a1654f66c6769cf4d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zg0-0090000000-a62f20efe42486ea47dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-2930000000-fd91e8e07b5574f46708Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71464657
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
S-adenosyl-L-methionine-dependent methyltransferase that catalyzes the trimethylation of the amino group of the modified target histidine residue in translation elongation factor 2 (EF-2), to form an intermediate called diphthine. The three successive methylation reactions represent the second step of diphthamide biosynthesis (By similarity).
Gene Name:
DPH5
Uniprot ID:
Q9H2P9
Molecular weight:
31651.17
Reactions
S-Adenosylmethionine + 2-(3-Carboxy-3-aminopropyl)-L-histidine → S-Adenosylhomocysteine + 2-(3-carboxy-3-(trimethylammonio)propyl)-L-histidinedetails