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Showing Compound Eremanthin (FDB005879)

Record Information
Version1.0
Creation date2010-04-08 22:06:53 UTC
Update date2019-11-26 03:00:49 UTC
Primary IDFDB005879
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEremanthin
DescriptionEremanthin 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. Eremanthin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Eremanthin can be found in sweet bay, which makes eremanthin a potential biomarker for the consumption of this food product.
CAS Number37936-58-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP3.43ALOGPS
logP3.02ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity67.04 m³·mol⁻¹ChemAxon
Polarizability25.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H18O2
IUPAC name(3aS,6aR,9aR,9bS)-6-methyl-3,9-dimethylidene-2H,3H,3aH,4H,6aH,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one
InChI IdentifierInChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h4,11-14H,2-3,5-7H2,1H3/t11-,12-,13-,14-/m0/s1
InChI KeyBWRZDLYJNURUHS-XUXIUFHCSA-N
Isomeric SMILESCC1=CC[C@@H]2[C@H](OC(=O)C2=C)[C@@H]2[C@H]1CCC2=C
Average Molecular Weight230.3022
Monoisotopic Molecular Weight230.13067982
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
  • Guaiane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0390000000-52f39b3b546c3ae4bd082016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0930000000-db7c652dec6b8a113ce82016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9610000000-4ee207e1d9abd929f98c2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0290000000-ce52077fb1df2eb808322016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-0790000000-be4c79bac3c3284501932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1000-8900000000-85d7d83461abe2e9e2e02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-b8f7b2ad54b12c0158e32021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0390000000-13e3c3e2849e37ed95f62021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc0-1930000000-bfe3326d3296ee0735ed2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-fb2ff0c6ce4213f1f3762021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2590000000-e71ac4209ccc7a3787422021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1950000000-835bdb7f1dc6210778f02021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09406
Pubchem Compound ID100572
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 IDEREMANTHIN
BIGG IDNot Available
KNApSAcK IDC00003256
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
Sweet bayExpected but not quantifiedNot AvailableDUKE, KNAPSACK
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Biological Effects and Interactions
Health Effects / Bioactivities
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.