Naematolone (CHEM029662)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:19:16 UTC
Update Date2016-11-09 01:18:55 UTC
Accession NumberCHEM029662
Identification
Common NameNaematolone
ClassSmall Molecule
DescriptionNaematolone is found in mushrooms. Naematolone is a metabolite of Hypholoma capnoides (conifer tuft
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
NaematolonMeSH
4-Acetyloxy-8-hydroxy-2-methylene-6,10,10-trimethyl-bicyclo(7.2.0)undec-5-ene-3,7-dioneMeSH
NematoloneHMDB
(5Z)-8-Hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxobicyclo[7.2.0]undec-5-en-4-yl acetic acidGenerator
Chemical FormulaC17H22O5
Average Molecular Mass306.354 g/mol
Monoisotopic Mass306.147 g/mol
CAS Registry Number92121-62-5
IUPAC Name(5Z)-8-hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxobicyclo[7.2.0]undec-5-en-4-yl acetate
Traditional Name(5Z)-8-hydroxy-6,10,10-trimethyl-2-methylidene-3,7-dioxobicyclo[7.2.0]undec-5-en-4-yl acetate
SMILESCC(=O)OC1\C=C(C)/C(=O)C(O)C2C(CC2(C)C)C(=C)C1=O
InChI IdentifierInChI=1S/C17H22O5/c1-8-6-12(22-10(3)18)15(20)9(2)11-7-17(4,5)13(11)16(21)14(8)19/h6,11-13,16,21H,2,7H2,1,3-5H3/b8-6-
InChI KeyBBRNVDBLOTVLMB-VURMDHGXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Caryophyllane sesquiterpenoid
  • Alpha-acyloxy ketone
  • Carboxylic acid ester
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.53 g/LALOGPS
logP1.57ALOGPS
logP2.12ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.02ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.74 m³·mol⁻¹ChemAxon
Polarizability31.86 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9030000000-fb729d71138b87948011Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9003000000-4ed8def703d257bc7eb3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0095000000-5ae5d6bac7b370c886bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mt-1291000000-0e30e9c406f132bf0d0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4920000000-ba29ab3532dffbc282c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3069000000-693edf59fca274bf2713Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-3092000000-34064a7173c26d74e651Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9310000000-52979b9a00c0ff89fb76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mk-0094000000-1e363cc03e41feec89f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-e4574dc329d6631f9a90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-0190000000-95c0a9f417d9bbcc3fbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-6009000000-c2d26eb0ded67c32e3dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-8090000000-da876a5b3f5dd36df6a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-7139f3a01c58a80ac336Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0035781
FooDB IDFDB014528
Phenol Explorer IDNot Available
KNApSAcK IDC00012495
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID20145021
ChEBI ID172533
PubChem Compound ID20839779
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM