2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine (YMDB00302)

Identification
YMDB IDYMDB00302
Name2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-(3-Carboxy-3-(methylammonio)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-(methylammonio)propyl)-L-histidine exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on 2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • [3-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]]-1-carboxy- propyl]-methyl-ammonium
  • 1-carboxy-3-(L-histidin-2-yl)-N-methylpropan-1-aminium
  • 2-[3-carboxy-3-(methylammonio)propyl]-His
  • 2-[3-carboxy-3-(methylammonio)propyl]-histidine
  • 2-[3-Carboxy-3-(methylammonio)propyl]-L-histidine
  • EF-2 2-[3-carboxy-3-(methylammonio)propyl]-L-histidine
  • Peptide 2-[3-carboxy-3-(methylammonio)propyl]-L-histidine
  • Elongation factor 2 2-[3-carboxy-3-(methylammonio)propyl]-L-histidine
CAS numberNot Available
WeightAverage: 271.293
Monoisotopic: 271.140630116
InChI KeyYBMOTEQVMANKGX-JAMMHHFISA-O
InChIInChI=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
IUPAC Name(3-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}-1-carboxypropyl)(methyl)azanium
Traditional IUPAC Name(3-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}-1-carboxypropyl)(methyl)azanium
Chemical FormulaC11H19N4O4
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C1=C([H])N=C(N1[H])C([H])([H])C([H])([H])C([H])(C(=O)O[H])[N+]([H])([H])C([H])([H])[H]
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
StateSolid
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
2-(3-Carboxy-3-aminopropyl)-L-histidine + S-Adenosylmethionine → S-Adenosylhomocysteine + hydron + 2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot 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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-0090000000-66a1fe26570d43a0aba7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0490000000-fae35f1d1ac38709f83fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002s-2900000000-0ca514fb76d9df5640ebJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Mattheakis, L. C., Shen, W. H., Collier, R. J. (1992). "DPH5, a methyltransferase gene required for diphthamide biosynthesis in Saccharomyces cerevisiae." Mol Cell Biol 12:4026-4037.1508200
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16475
HMDB IDHMDB11654
Pubchem Compound ID440444
Kegg IDC04692
ChemSpider ID389379
FOODB IDFDB028345
Wikipedia IDNot Available
BioCyc ID2-3-CARBOXY-3-METHYLAMMONIOPROPYL-L-

Enzymes

Protein Details
1. Diphthine synthase
General function:
Involved in methyltransferase activity
Specific function:
Required for the methylation step in diphthamide biosynthesis
Gene Name:
DPH5
Uniprot ID:
P32469
Molecular weight:
33847.0
Reactions
3 S-adenosyl-L-methionine + 2-(3-carboxy-3-aminopropyl)-L-histidine → 3 S-adenosyl-L-homocysteine + 2-(3-carboxy-3-(trimethylammonio)propyl)-L-histidine.