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Human Metabolome Database Version 3.5

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Showing metabocard for Nookatone (HMDB13687)

Record Information
Version 3.5
Creation Date 2012-04-03 08:10:32 -0600
Update Date 2013-02-08 17:30:48 -0700
HMDB ID HMDB13687
Secondary Accession Numbers None
Metabolite Identification
Common Name Nookatone
Description Nootkatone is a natural organic compound and is the most important and expensive aromatic of grapefruit. It is a sesquiterpene and a ketone. Nootkatone was previously thought to be one of the main chemical components of the smell and flavour of grapefruits. In its solid form it is usually found as crystals. As a liquid, it is viscous and yellow. Nootkatone is typically extracted from grapefruit, but can also be manufactured with genetically modified organisms, or through the chemical or biochemical oxidation of valencene. It is also found in Alaska yellow cedar trees and vetiver grass.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one
  2. 4betaH,5alpha-Eremophila-1(10),11-dien-2-one
  3. 4betaH,5alpha-Eremorphila-1(10)11-dien-2-one
  4. Nootkatane
Chemical Formula C15H22O
Average Molecular Weight 218.3346
Monoisotopic Molecular Weight 218.167065326
IUPAC Name 4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one
Traditional IUPAC Name 4,4a-dimethyl-6-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one
CAS Registry Number 4674-50-4
SMILES CC1CC(=O)C=C2CCC(CC12C)C(C)=C
InChI Identifier InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3
InChI Key WTOYNNBCKUYIKC-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Homopolycyclic Compounds
Class Cycloalkenes
Sub Class N/A
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Cycloalkanes
  • Ketones
Substituents
  • N/A
Direct Parent Cycloalkenes
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 36 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.029 g/L ALOGPS
LogP 3.89 ALOGPS
LogP 3.7 ChemAxon
LogS -3.88 ALOGPS
pKa (strongest acidic) 18.91 ChemAxon
pKa (strongest basic) -4.8 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 17.07 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 68.07 ChemAxon
Polarizability 26.23 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 19575 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Nookatone Link_out
NuGOwiki Link HMDB13687 Link_out
Metagene Link HMDB13687 Link_out
METLIN ID Not Available
PubChem Compound 20797 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available