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Identification
YMDB IDYMDB00302
Name2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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). 2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
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-AdenosylmethionineS-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 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
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

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.