Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:28:58 UTC
Update Date2025-01-15 22:18:27 UTC
Metabolite IDMMDBc0032960
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
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
Molecular FormulaC11H19N4O4
Average Mass271.293
Monoisotopic Mass271.140630116
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