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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-02-03 10:25:42 UTC
Update Date2020-02-26 21:35:34 UTC
HMDB IDHMDB0011654
Secondary Accession Numbers
  • HMDB11654
Metabolite Identification
Common Name2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine
Description2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine is an unusual amino acid that results from the post-translational modification of histidine in certain proteins. In particular, it is a post-translational derivative of histidine that exists in protein synthesis elongation factor 2 (EF2) at the site of diphtheria toxin-catalyzed ADP-ribosylation of elongation factor 2. It is a precursor for diphthamide. This compound is a substrate for the enzyme diphthine synthase (EC 2.1.1.98). This enzyme catalyzes the chemical reaction: S-adenosyl-L-methionine + 2-(3-carboxy-3-aminopropyl)-L-histidine = S-adenosyl-L-homocysteine + 2-[3-carboxy-3-(methylammonio)propyl]-L-histidine.
Structure
Data?1582752934
Synonyms
ValueSource
EF-2 2-[3-carboxy-3-(methylammonio)propyl]-L-histidineChEBI
Elongation factor 2 2-[3-carboxy-3-(methylammonio)propyl]-L-histidineChEBI
1-Carboxy-3-(L-histidin-2-yl)-N-methylpropan-1-aminiumHMDB
2-[3-Carboxy-3-(methylammonio)propyl]-hisHMDB
2-[3-Carboxy-3-(methylammonio)propyl]-histidineHMDB
[3-[[4-(2-Amino-2-carboxy-ethyl)-1H-imidazol-2-yl]]-1-carboxy- propyl]-methyl-ammoniumHMDB
Chemical FormulaC11H19N4O4
Average Molecular Weight271.293
Monoisotopic Molecular Weight271.140630116
IUPAC Name(3-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}-1-carboxypropyl)(methyl)azanium
Traditional Name(3-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}-1-carboxypropyl)(methyl)azanium
CAS Registry NumberNot Available
SMILES
C[NH2+]C(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O
InChI Identifier
InChI=1S/C11H18N4O4/c1-13-8(11(18)19)2-3-9-14-5-6(15-9)4-7(12)10(16)17/h5,7-8,13H,2-4,12H2,1H3,(H,14,15)(H,16,17)(H,18,19)/p+1/t7-,8?/m0/s1
InChI KeyYBMOTEQVMANKGX-JAMMHHFISA-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
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

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 Solubility1.2 g/LALOGPS
logP-1.3ALOGPS
logP-6.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.42ChemAxon
pKa (Strongest Basic)10.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity77.33 m³·mol⁻¹ChemAxon
Polarizability27.91 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, Positivesplash10-00c3-5950000000-8d8531a8962d98bce733Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0uk9-6396000000-dad13bde2626e3b2434eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-1f393c0ea0a92d6031e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0090000000-0c7cb2be23e59d69e473Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02e9-9630000000-8921612205d259e1d741Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-8090000000-becfe845d15fd5c1b0e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9080000000-4b8c28900abb9566d066Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9010000000-e1ea27f3e9093efbaac5Spectrum
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 IDFDB028345
KNApSAcK IDNot Available
Chemspider ID389379
KEGG Compound IDC04692
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440443
PDB IDNot Available
ChEBI ID16475
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