S-Furanopetasitin (CHEM029961)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:32:54 UTC
Update Date2016-11-09 01:18:59 UTC
Accession NumberCHEM029961
Identification
Common NameS-Furanopetasitin
ClassSmall Molecule
DescriptionS-Furanopetasitin is found in giant butterbur. S-Furanopetasitin is a constituent of Petasites japonicus (sweet coltsfoot)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(S)-FuranopetasitinHMDB
3,4a,5-Trimethyl-6-{[(2E)-3-(methylsulfanyl)prop-2-enoyl]oxy}-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoic acidGenerator
3,4a,5-Trimethyl-6-{[(2E)-3-(methylsulphanyl)prop-2-enoyl]oxy}-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoateGenerator
3,4a,5-Trimethyl-6-{[(2E)-3-(methylsulphanyl)prop-2-enoyl]oxy}-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC24H32O5S
Average Molecular Mass432.573 g/mol
Monoisotopic Mass432.197 g/mol
CAS Registry Number34335-97-2
IUPAC Name3,4a,5-trimethyl-6-{[(2E)-3-(methylsulfanyl)prop-2-enoyl]oxy}-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoate
Traditional Name3,4a,5-trimethyl-6-{[(2E)-3-(methylsulfanyl)prop-2-enoyl]oxy}-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoate
SMILESCS\C=C\C(=O)OC1CCC2CC3=C(C(OC(=O)C(\C)=C\C)C2(C)C1C)C(C)=CO3
InChI IdentifierInChI=1S/C24H32O5S/c1-7-14(2)23(26)29-22-21-15(3)13-27-19(21)12-17-8-9-18(16(4)24(17,22)5)28-20(25)10-11-30-6/h7,10-11,13,16-18,22H,8-9,12H2,1-6H3/b11-10+,14-7+
InChI KeyDZIJJEZRPMYRRP-QFPWAJRASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
Substituents
  • Furoeremophilane sesquiterpenoid
  • Naphthofuran
  • Benzofuran
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Vinylogous thioester
  • Heteroaromatic compound
  • Acrylic acid or derivatives
  • Furan
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Thioenolether
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Sulfenyl compound
  • Organosulfur compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.0059 g/LALOGPS
logP5.75ALOGPS
logP5.92ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area65.74 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity120.08 m³·mol⁻¹ChemAxon
Polarizability47.6 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, Positivesplash10-05ai-8192100000-2c544ae202a64b6e80d4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-5418900000-31007c83830492abbf1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-9555100000-bc359ea15dea8476604cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-9110000000-337e40e21b3556645596Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-9007600000-a3b1a9422ea2cf420a73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9002100000-6d13da3a506ae0734653Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9030000000-0c67c8ea05ad20bfffc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000100000-f48e459a18ba24ef3ac6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9003200000-3259136ff7fe382708e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-a13796696e9fac83da52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0035900000-28b336abc3ae71addbcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0091000000-ff9f85f04e4a3387d43dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ce9-9152000000-951a0293dc008abc6b70Spectrum
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 IDHMDB0036131
FooDB IDFDB014980
Phenol Explorer IDNot Available
KNApSAcK IDC00017353
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014101
ChEBI IDNot Available
PubChem Compound ID131751917
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