Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:23:48 UTC
Update Date2025-01-15 22:22:11 UTC
Metabolite IDMMDBc0032905
Metabolite Identification
Common Name2-(3-Carboxy-3-aminopropyl)-L-histidine
Description2-(3-Carboxy-3-aminopropyl)-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
2-(3-Carboxy-3-aminopropyl)-L-histidineChEBI
2-(3-amino-3-Carboxypropyl)-L-histidineHMDB
2-amino-4-[[4-(2-amino-2-Carboxy-ethyl)-1H-imidazol-2-yl]] butanoateHMDB
2-amino-4-[[4-(2-amino-2-Carboxy-ethyl)-1H-imidazol-2-yl]] butanoic acidHMDB
Molecular FormulaC10H16N4O4
Average Mass256.2584
Monoisotopic Mass256.11715502
IUPAC Name2-amino-4-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}butanoic acid
Traditional Name2-amino-4-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}butanoic acid
CAS Registry NumberNot Available
SMILES
NC(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O
InChI Identifier
InChI=1S/C10H16N4O4/c11-6(9(15)16)1-2-8-13-4-5(14-8)3-7(12)10(17)18/h4,6-7H,1-3,11-12H2,(H,13,14)(H,15,16)(H,17,18)/t6?,7-/m0/s1
InChI KeyCJCSNWWKPUXVRD-MLWJPKLSSA-N