ChemFOnt: Showing chemical card for Hypusine (CFc000006775)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:51 UTC

Chemfont ID

CFc000006775

Molecule Identification

Common Name

Hypusine

Definition

Hypusine 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N(6)-(4-amino-2-Hydroxybutyl)-L-lysine	HMDB, MeSH
(R)-N6-(4-Amino-2-hydroxybutyl)-L-lysine	MeSH
(+)-Hypusine	MeSH

Chemical Formula

C₁₀H₂₃N₃O₃

Average Molecular Weight

233.3079

Monoisotopic Molecular Weight

233.173941617

IUPAC Name

(2S)-2-amino-6-{[(2S)-4-amino-2-hydroxybutyl]amino}hexanoic acid

Traditional Name

hypusine

CAS Registry Number

34994-11-1

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 Key

BZUIJMCJNWUGKQ-IUCAKERBSA-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
1,3-aminoalcohol
1,2-aminoalcohol
Amino acid
Secondary alcohol
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Alcohol
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0011140)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	22.7 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-4.4	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	2.3	ChemAxon
pKa (Strongest Basic)	10.39	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	121.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	61.36 m³·mol⁻¹	ChemAxon
Polarizability	26.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0011140

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027916

KNApSAcK ID

Not Available

Chemspider ID

58862

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hypusine

METLIN ID

Not Available

PubChem Compound

65396

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Hypusine (CFc000006775)

MOL for CFc000006775 (Hypusine)

3D MOL for CFc000006775 (Hypusine)

3D SDF for CFc000006775 (Hypusine)

3D-SDF for CFc000006775 (Hypusine)

PDB for CFc000006775 (Hypusine)

3D PDB for CFc000006775 (Hypusine)

SMILES for CFc000006775 (Hypusine)

INCHI for CFc000006775 (Hypusine)

Structure for CFc000006775 (Hypusine)

3D Structure for CFc000006775 (Hypusine)