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Record Information
Version3.6
Creation Date2009-02-03 10:33:25 UTC
Update Date2016-02-11 01:21:54 UTC
HMDB IDHMDB11655
Secondary Accession NumbersNone
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
Thumb
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
Chemical FormulaC10H16N4O4
Average Molecular Weight256.2584
Monoisotopic Molecular Weight256.11715502
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 KeyInChIKey=CJCSNWWKPUXVRD-MLWJPKLSSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Amino fatty acid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.71 mg/mLALOGPS
logP-4.1ALOGPS
logP-6.5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.63ChemAxon
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.32 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity61.14 m3·mol-1ChemAxon
Polarizability25.54 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028346
KNApSAcK IDNot Available
Chemspider ID389308
KEGG Compound IDC04441
BioCyc ID2-3-CARBOXY-3-AMINOPROPYL-L-HISTIDINE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11655
Metagene LinkHMDB11655
METLIN IDNot Available
PubChem Compound440342
PDB IDNot Available
ChEBI ID17144
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
S-adenosyl-L-methionine-dependent methyltransferase that catalyzes the trimethylation of the amino group of the modified target histidine residue in translation elongation factor 2 (EF-2), to form an intermediate called diphthine. The three successive methylation reactions represent the second step of diphthamide biosynthesis (By similarity).
Gene Name:
DPH5
Uniprot ID:
Q9H2P9
Molecular weight:
31651.17
Reactions
S-Adenosylmethionine + 2-(3-Carboxy-3-aminopropyl)-L-histidine → S-Adenosylhomocysteine + 2-(3-carboxy-3-(trimethylammonio)propyl)-L-histidinedetails