3b,6b-Diangeloyloxy-7(11)-eremophilen-12,8b-olide (CHEM034132)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:41:23 UTC
Update Date2016-11-09 01:21:04 UTC
Accession NumberCHEM034132
Identification
Common Name3b,6b-Diangeloyloxy-7(11)-eremophilen-12,8b-olide
ClassSmall Molecule
Description3b,6b-Diangeloyloxy-7(11)-eremophilen-12,8b-olide is a constituent of Petasites japonicus (sweet coltsfoot).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,4a,5-Trimethyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,4H,4ah,5H,6H,7H,8H,8ah,9H,9ah-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoic acidHMDB
Chemical FormulaC25H34O6
Average Molecular Mass430.534 g/mol
Monoisotopic Mass430.236 g/mol
CAS Registry Number149475-47-8
IUPAC Name3,4a,5-trimethyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate
Traditional Name3,4a,5-trimethyl-6-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-4H,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate
SMILESC\C=C(\C)C(=O)OC1CCC2CC3OC(=O)C(C)=C3C(OC(=O)C(\C)=C/C)C2(C)C1C
InChI IdentifierInChI=1S/C25H34O6/c1-8-13(3)22(26)29-18-11-10-17-12-19-20(15(5)24(28)30-19)21(25(17,7)16(18)6)31-23(27)14(4)9-2/h8-9,16-19,21H,10-12H2,1-7H3/b13-8-,14-9-
InChI KeyGNUFDZISEWLEOG-QKPPEBSVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Eremophilanolide or secoeremophilanolide
  • Sesquiterpenoid
  • Naphthofuran
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • 2-furanone
  • Fatty acyl
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility0.0052 g/LALOGPS
logP5.12ALOGPS
logP5.72ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)14.24ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity117.76 m³·mol⁻¹ChemAxon
Polarizability47.57 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-7098100000-4ab2fcf64a53a049fa54Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3019700000-1685dc1c5907efbcef7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06si-9067200000-ac88ba7af5b7dd4af440Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9012000000-1ebf48a571909756c94aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1007900000-f1692ef5bdeca47b2021Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-5019500000-f2183d33b0cb56551ce8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr5-4069000000-008b56e999c8f1a98b65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2000900000-982bd0baa9236af5387fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-7018900000-7310867d3b9771544ef7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pba-9000000000-46a5a5cc4ba91b880be0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0069300000-8edef645dead88fc97e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0093000000-533903210c63ed19d0a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9132000000-f859c6481018a9c74cddSpectrum
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 IDHMDB0040990
FooDB IDFDB020850
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35015066
ChEBI IDNot Available
PubChem Compound ID131753004
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