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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:11:48 UTC
Update Date2022-09-22 18:35:10 UTC
HMDB IDHMDB0036131
Secondary Accession Numbers
  • HMDB36131
Metabolite Identification
Common NameS-Furanopetasitin
DescriptionS-Furanopetasitin 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. Based on a literature review a small amount of articles have been published on S-Furanopetasitin.
Structure
Data?1563862825
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 Weight432.573
Monoisotopic Molecular Weight432.197044824
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
CAS Registry Number34335-97-2
SMILES
CS\C=C\C(=O)OC1CCC2CC3=C(C(OC(=O)C(\C)=C\C)C2(C)C1C)C(C)=CO3
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point107 - 108 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0038 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.65831661259
DarkChem[M-H]-193.35831661259
DeepCCS[M+H]+204.82130932474
DeepCCS[M-H]-202.46330932474
DeepCCS[M-2H]-235.78230932474
DeepCCS[M+Na]+211.0130932474
AllCCS[M+H]+206.332859911
AllCCS[M+H-H2O]+204.232859911
AllCCS[M+NH4]+208.232859911
AllCCS[M+Na]+208.732859911
AllCCS[M-H]-202.932859911
AllCCS[M+Na-2H]-203.932859911
AllCCS[M+HCOO]-205.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
S-FuranopetasitinCS\C=C\C(=O)OC1CCC2CC3=C(C(OC(=O)C(\C)=C\C)C2(C)C1C)C(C)=CO34179.6Standard polar33892256
S-FuranopetasitinCS\C=C\C(=O)OC1CCC2CC3=C(C(OC(=O)C(\C)=C\C)C2(C)C1C)C(C)=CO33086.1Standard non polar33892256
S-FuranopetasitinCS\C=C\C(=O)OC1CCC2CC3=C(C(OC(=O)C(\C)=C\C)C2(C)C1C)C(C)=CO33153.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - S-Furanopetasitin GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ai-8192100000-2c544ae202a64b6e80d42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - S-Furanopetasitin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - S-Furanopetasitin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 10V, Positive-QTOFsplash10-001i-5418900000-31007c83830492abbf1c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 20V, Positive-QTOFsplash10-0f89-9555100000-bc359ea15dea8476604c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 40V, Positive-QTOFsplash10-0f89-9110000000-337e40e21b35566455962016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 10V, Negative-QTOFsplash10-001j-9007600000-a3b1a9422ea2cf420a732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 20V, Negative-QTOFsplash10-0002-9002100000-6d13da3a506ae07346532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 40V, Negative-QTOFsplash10-0002-9030000000-0c67c8ea05ad20bfffc92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 10V, Negative-QTOFsplash10-0002-9000100000-f48e459a18ba24ef3ac62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 20V, Negative-QTOFsplash10-0002-9003200000-3259136ff7fe382708e32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 40V, Negative-QTOFsplash10-0a4i-9000000000-a13796696e9fac83da522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 10V, Positive-QTOFsplash10-001i-0035900000-28b336abc3ae71addbcb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 20V, Positive-QTOFsplash10-014i-0091000000-ff9f85f04e4a3387d43d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - S-Furanopetasitin 40V, Positive-QTOFsplash10-0ce9-9152000000-951a0293dc008abc6b702021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014980
KNApSAcK IDC00017353
Chemspider ID35014101
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751917
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1853721
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.