Record Information
Version1.0
Creation date2010-04-08 22:06:53 UTC
Update date2019-11-26 03:00:49 UTC
Primary IDFDB005870
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameArtecanin
DescriptionArtecanin belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Artecanin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Artecanin can be found in sweet bay, which makes artecanin a potential biomarker for the consumption of this food product.
CAS Number24959-84-0
Structure
Thumb
Synonyms
SynonymSource
Artecaninbiospider
Caninbiospider
Predicted Properties
PropertyValueSource
Water Solubility8.92 g/LALOGPS
logP0.73ALOGPS
logP0.77ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)13.77ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.59 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.24 m³·mol⁻¹ChemAxon
Polarizability27.95 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H18O5
IUPAC name(1R,2R,5S,9S,10S,11S,13R,14S)-2-hydroxy-2,11-dimethyl-6-methylidene-8,12,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0⁵,⁹.0¹¹,¹³]pentadecan-7-one
InChI IdentifierInChI=1S/C15H18O5/c1-6-7-4-5-13(2,17)15-9(8(7)18-12(6)16)14(3)10(19-14)11(15)20-15/h7-11,17H,1,4-5H2,2-3H3/t7-,8-,9-,10+,11-,13+,14-,15+/m0/s1
InChI KeyKXLUWEYBZBGJRZ-POEOZHCLSA-N
Isomeric SMILESC[C@@]12O[C@@H]1[C@@H]1O[C@]11[C@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC[C@@]1(C)O
Average Molecular Weight278.3004
Monoisotopic Molecular Weight278.115423686
Classification
Description Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative Parents
Substituents
  • Guaianolide-skeleton
  • Sesquiterpenoid
  • 1,4-dioxepane
  • Dioxepane
  • Gamma butyrolactone
  • Oxane
  • Cyclic alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-1d79f6cd69c7a2f47516Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvi-0390000000-eb302757a3b9f1476998Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9650000000-cec2da2a89a380eba96aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-d7defeb3436e8b8d075bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-0090000000-bbe4ad4c1b03567c1eccSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08i0-2920000000-aef09b7ae96016e51fb4Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09302
Pubchem Compound ID442175
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDARTECANIN
BIGG IDNot Available
KNApSAcK IDC00000239
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti aggregantDUKE
anti feedantDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti secretoryDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).