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Record Information
Version3.6
Creation Date2008-10-29 13:02:23 UTC
Update Date2016-02-11 01:20:15 UTC
HMDB IDHMDB11140
Secondary Accession NumbersNone
Metabolite Identification
Common NameHypusine
DescriptionHypusine is formed in eIF-5A by post-translational modification of one of the lysyl residues. There are two reactions and two enzymes involved:; Hypusine is an unusual amino acid found in all eukaryotes and in some archaea, but not in bacteria. The only known protein containing hypusine is eukaryotic translation initiation factor 5A (eIF-5A) and a similar protein found in archaebacteria. In human, two isoforms of eIF-5A have been described: eIF-5A-1 and eIF-5A-2. They are coded by two different genes. This protein is involved in protein biosynthesis and promotes the formation of the first peptide bond. The region surrounding the hypusine residue is highly conserved among the eukaryotes and is essential to the function of eIF-5A. Thus, hypusine and eIF-5A appear to be vital for the viability and proliferation of eukaryotic cells.
Structure
Thumb
Synonyms
ValueSource
N(6)-(4-amino-2-Hydroxybutyl)-L-lysineHMDB
Chemical FormulaC10H23N3O3
Average Molecular Weight233.3079
Monoisotopic Molecular Weight233.173941617
IUPAC Name(2S)-2-amino-6-{[(2S)-4-amino-2-hydroxybutyl]amino}hexanoic acid
Traditional Namehypusine
CAS Registry Number34994-11-1
SMILES
NCC[C@H](O)CNCCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C10H23N3O3/c11-5-4-8(14)7-13-6-2-1-3-9(12)10(15)16/h8-9,13-14H,1-7,11-12H2,(H,15,16)/t8-,9-/m0/s1
InChI KeyInChIKey=BZUIJMCJNWUGKQ-IUCAKERBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • 1,3-aminoalcohol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Protein biosynthesis
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 Solubility22.7 mg/mLALOGPS
logP-3.2ALOGPS
logP-4.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)2.3ChemAxon
pKa (Strongest Basic)10.39ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area121.6 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity61.36 m3·mol-1ChemAxon
Polarizability26.12 Å3ChemAxon
Number of Rings0ChemAxon
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 IDFDB027916
KNApSAcK IDNot Available
Chemspider ID58862
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11140
Metagene LinkHMDB11140
METLIN IDNot Available
PubChem Compound65396
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in RNA binding
Specific function:
mRNA-binding protein involved in translation elongation. Has an important function at the level of mRNA turnover, probably acting downstream of decapping. Involved in actin dynamics and cell cycle progression, mRNA decay and probably in a pathway involved in stress response and maintenance of cell wall integrity. With syntenin SDCBP, functions as a regulator of TP53/p53 and TP53/p53-dependent apoptosis. Regulates also TNF- alpha-mediated apoptosis. Mediates effects of polyamines on neuronal process extension and survival. May play an important role in brain development and function, and in skeletal muscle stem cell differentiation. Also described as a cellular cofactor of human T-cell leukemia virus type I (HTLV-1) Rex protein and of human immunodeficiency virus type 1 (HIV-1) Rev protein, essential for mRNA export of retroviral transcripts
Gene Name:
EIF5A
Uniprot ID:
P63241
Molecular weight:
16832.1
General function:
Involved in RNA binding
Specific function:
mRNA-binding protein involved in translation elongation. Has an important function at the level of mRNA turnover, probably acting downstream of decapping. Involved in actin dynamics and cell cycle progression, mRNA decay and probably in a pathway involved in stress response and maintenance of cell wall integrity. Functions as a regulator of apoptosis. Mediates effects of polyamines on neuronal process extension and survival. May play an important role in brain development and function, and in skeletal muscle stem cell differentiation
Gene Name:
EIF5A2
Uniprot ID:
Q9GZV4
Molecular weight:
16793.1
General function:
Involved in RNA binding
Specific function:
mRNA-binding protein involved in translation elongation. Has an important function at the level of mRNA turnover, probably acting downstream of decapping. Involved in actin dynamics and cell cycle progression, mRNA decay and probably in a pathway involved in stress response and maintenance of cell wall integrity. Functions as a regulator of apoptosis. Mediates effects of polyamines on neuronal process extension and survival. May play an important role in brain development and function, and in skeletal muscle stem cell differentiation
Gene Name:
EIF5AL1
Uniprot ID:
Q6IS14
Molecular weight:
16773.0