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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:12:36 UTC
Update Date2022-03-07 02:54:48 UTC
HMDB IDHMDB0036146
Secondary Accession Numbers
  • HMDB36146
Metabolite Identification
Common Name6-Angeloylfuranofukinol
Description6-Angeloylfuranofukinol 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 6-Angeloylfuranofukinol.
Structure
Data?1563862828
Synonyms
ValueSource
6-Hydroxy-3,4a,5-trimethyl-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoic acidHMDB
Chemical FormulaC20H28O4
Average Molecular Weight332.4339
Monoisotopic Molecular Weight332.198759384
IUPAC Name6-hydroxy-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoate
Traditional Name6-hydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
C\C=C(/C)C(=O)OC1C2=C(CC3CCC(O)C(C)C13C)OC=C2C
InChI Identifier
InChI=1S/C20H28O4/c1-6-11(2)19(22)24-18-17-12(3)10-23-16(17)9-14-7-8-15(21)13(4)20(14,18)5/h6,10,13-15,18,21H,7-9H2,1-5H3/b11-6+
InChI KeyQSXNOUPYXMWUKT-IZZDOVSWSA-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
  • Fatty acyl
  • Cyclic alcohol
  • Heteroaromatic compound
  • Furan
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP4.39ALOGPS
logP4.26ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)14.94ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity93.43 m³·mol⁻¹ChemAxon
Polarizability37.21 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.72431661259
DarkChem[M-H]-175.85731661259
DeepCCS[M-2H]-212.51230932474
DeepCCS[M+Na]+187.73830932474
AllCCS[M+H]+180.832859911
AllCCS[M+H-H2O]+177.932859911
AllCCS[M+NH4]+183.532859911
AllCCS[M+Na]+184.232859911
AllCCS[M-H]-187.032859911
AllCCS[M+Na-2H]-187.232859911
AllCCS[M+HCOO]-187.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-AngeloylfuranofukinolC\C=C(/C)C(=O)OC1C2=C(CC3CCC(O)C(C)C13C)OC=C2C3470.5Standard polar33892256
6-AngeloylfuranofukinolC\C=C(/C)C(=O)OC1C2=C(CC3CCC(O)C(C)C13C)OC=C2C2356.2Standard non polar33892256
6-AngeloylfuranofukinolC\C=C(/C)C(=O)OC1C2=C(CC3CCC(O)C(C)C13C)OC=C2C2497.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Angeloylfuranofukinol,1TMS,isomer #1C/C=C(\C)C(=O)OC1C2=C(CC3CCC(O[Si](C)(C)C)C(C)C31C)OC=C2C2553.6Semi standard non polar33892256
6-Angeloylfuranofukinol,1TBDMS,isomer #1C/C=C(\C)C(=O)OC1C2=C(CC3CCC(O[Si](C)(C)C(C)(C)C)C(C)C31C)OC=C2C2785.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-Angeloylfuranofukinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05o0-9053000000-be01ea31423dfe8058032017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Angeloylfuranofukinol GC-MS (1 TMS) - 70eV, Positivesplash10-0569-9225000000-910ac19c39e5979dbf9a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Angeloylfuranofukinol 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 - 6-Angeloylfuranofukinol 10V, Positive-QTOFsplash10-00lr-2039000000-2b969d352b2c0472963b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 20V, Positive-QTOFsplash10-001i-9562000000-5eebc899456b45e0d6582016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 40V, Positive-QTOFsplash10-0kai-9210000000-0e69aad016e0a7b82b552016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 10V, Negative-QTOFsplash10-001i-1019000000-609104691c0fca84352a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 20V, Negative-QTOFsplash10-001i-7059000000-4e04a0087e62ad93ddd62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 40V, Negative-QTOFsplash10-05nb-7290000000-86b5266725199b58e7952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 10V, Negative-QTOFsplash10-001j-7039000000-f71ac89f2443e259a1a02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 20V, Negative-QTOFsplash10-001j-9056000000-9a79012566eb092663562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 40V, Negative-QTOFsplash10-0pb9-9000000000-aa5880a0b8fe9ddffe662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 10V, Positive-QTOFsplash10-00lr-0094000000-626cad1dbd0e012997c22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 20V, Positive-QTOFsplash10-0159-0194000000-2b6fa55833db6793f0aa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Angeloylfuranofukinol 40V, Positive-QTOFsplash10-0a4i-8491000000-ae31a375e4155bf3f6e62021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014997
KNApSAcK IDNot Available
Chemspider ID4900481
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6374435
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.