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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-29 14:42:24 UTC
Update Date2021-09-14 14:57:58 UTC
HMDB IDHMDB0011150
Secondary Accession Numbers
  • HMDB11150
Metabolite Identification
Common NameDeoxyhypusine
DescriptionDeoxyhypusine is an amino acid derivative of the unusual amino acid known as hypusine. It is a substrate of deoxyhypusine synthase which catalyzes the cleavage of the polyamine spermidine and transfer of its 4-aminobutyl moiety to the ε-amino group of one specific lysine residue of the eIF-5A precursor to form deoxyhypusine and 1,3-diaminopropane. By the addition of a hydroxyl group to the deoxyhypusine residue, deoxyhypusine hydroxylase mediates the formation of hypusine (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Amino-6-[(4-aminobutyl)amino]hexanoateGenerator
N(6)-(4-Aminobutyl)lysineChEBI
N(6)-(4-Aminobutyl)-L-lysineHMDB
DeoxyhypusineHMDB
N6-(4-Aminobutyl)-L-lysineHMDB
Chemical FormulaC10H23N3O2
Average Molecular Weight217.3085
Monoisotopic Molecular Weight217.179026995
IUPAC Name(2S)-2-amino-6-[(4-aminobutyl)amino]hexanoic acid
Traditional Namedeoxyhypusine
CAS Registry Number82543-85-9
SMILES
NCCCCNCCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C10H23N3O2/c11-6-2-4-8-13-7-3-1-5-9(12)10(14)15/h9,13H,1-8,11-12H2,(H,14,15)/t9-/m0/s1
InChI KeyPGPFBXMCOQNMJO-VIFPVBQESA-N
Chemical Taxonomy
Description 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
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Carbonyl group
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027925
KNApSAcK IDNot Available
Chemspider ID108888
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound122083
PDB IDNot Available
ChEBI ID50038
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in peptidyl-lysine modification to hypusine
Specific function:
Catalyzes the NAD-dependent oxidative cleavage of spermidine and the subsequent transfer of the butylamine moiety of spermidine to the epsilon-amino group of a specific lysine residue of the eIF-5A precursor protein to form the intermediate deoxyhypusine residue.
Gene Name:
DHPS
Uniprot ID:
P49366
Molecular weight:
40970.28
General function:
Involved in binding
Specific function:
Catalyzes the hydroxylation of the N(6)-(4-aminobutyl)-L-lysine intermediate to form hypusine, an essential post-translational modification only found in mature eIF-5A factor.
Gene Name:
DOHH
Uniprot ID:
Q9BU89
Molecular weight:
32903.885