Record Information
Version1.0
Creation date2011-09-21 01:38:19 UTC
Update date2015-07-21 06:59:23 UTC
Primary IDFDB028345
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
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
[3-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]]-1-carboxy- propyl]-methyl-ammoniumhmdb
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
2-[3-Carboxy-3-(methylammonio)propyl]-L-histidineChEBI
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC11H19N4O4
IUPAC name(3-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}-1-carboxypropyl)(methyl)azanium
InChI IdentifierInChI=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
Isomeric SMILESC[NH2+]C(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O
Average Molecular Weight271.293
Monoisotopic Molecular Weight271.140630116
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00c3-5950000000-8d8531a8962d98bce733JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0uk9-6396000000-dad13bde2626e3b2434eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-1f393c0ea0a92d6031e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0090000000-0c7cb2be23e59d69e473JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02e9-9630000000-8921612205d259e1d741JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-8090000000-becfe845d15fd5c1b0e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9080000000-4b8c28900abb9566d066JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9010000000-e1ea27f3e9093efbaac5JSpectraViewer
ChemSpider ID389379
ChEMBL IDNot Available
KEGG Compound IDC04692
Pubchem Compound ID440443
Pubchem Substance IDNot Available
ChEBI ID16475
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11654
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference