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Record Information
Version2.0
Created at2022-05-11 18:40:36 UTC
Updated at2022-05-11 18:40:36 UTC
NP-MRD IDNP0091531
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine
Description2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine, also known as 1-carboxy-3-(L-histidin-2-yl)-N-methylpropan-1-aminium, 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-(methylammonio)propyl)-L-histidine is a very strong basic compound (based on its pKa). An ammonium ion that is a derivative of L-histidine having a 3-carboxy-3-(methylammonio)propyl group at the 2-position on the imidazole ring. 2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
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 Mass271.2930 Da
Monoisotopic Mass271.14063 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0011654
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General ReferencesNot Available