CHEBI:15949 - diphthamide

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ChEBI Name diphthamide
ChEBI ID CHEBI:15949
Definition A quaternary ammonium ion that is the derivative of L-histidine having a 4-amino-4-oxo-3-(trimethylammonio)butyl group at the 2-position of the imidazole ring.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:4643, CHEBI:14181, CHEBI:23840
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Formula C13H24N5O3
Net Charge +1
Average Mass 298.36080
Monoisotopic Mass 298.188
InChI InChI=1S/C13H23N5O3/c1-18(2,3)10(12(15)19)4-5-11-16-7-8(17-11)6-9(14)13(20)21/h7,9-10H,4-6,14H2,1-3H3,(H3-,15,16,17,19,20,21)/p+1/t9-,10-/m0/s1
InChIKey FOOBQHKMWYGHCE-UWVGGRQHSA-O
SMILES C[N+](C)(C)[C@@H](CCc1nc(C[C@H](N)C(O)=O)c[nH]1)C(N)=O
ChEBI Ontology
Outgoing diphthamide (CHEBI:15949) is a quaternary ammonium ion (CHEBI:35267)
diphthamide (CHEBI:15949) is tautomer of diphthamide zwitterion (CHEBI:57580)
Incoming diphthamide residue (CHEBI:16692) is substituent group from diphthamide (CHEBI:15949)
diphthamide zwitterion (CHEBI:57580) is tautomer of diphthamide (CHEBI:15949)
IUPAC Name
(2S)-1-amino-4-{4-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}-N,N,N-trimethyl-1-oxobutan-2-aminium
Synonyms Sources
2-(3-Carboxyamido-3-(trimethylammonio)propyl)histidine ChemIDplus
2-[(3R)-3-carbamoyl-3-(trimethylammonio)propyl]-L-histidine ChEBI
Diphthamide KEGG COMPOUND
Manual Xrefs Databases
C01803 KEGG COMPOUND
DB03223 DrugBank
Diphthamide Wikipedia
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Registry Number Type Source
75645-22-6 CAS Registry Number ChemIDplus
Last Modified
07 January 2015