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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:58:54 UTC
Update Date2022-09-22 18:34:26 UTC
HMDB IDHMDB0035934
Secondary Accession Numbers
  • HMDB35934
Metabolite Identification
Common NameIsoalantolactone
DescriptionIsoalantolactone belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review a small amount of articles have been published on Isoalantolactone.
Structure
Data?1563862795
Synonyms
ValueSource
IsoheleninHMDB
Chemical FormulaC15H20O2
Average Molecular Weight232.3181
Monoisotopic Molecular Weight232.146329884
IUPAC Name8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one
Traditional Name8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one
CAS Registry Number470-17-7
SMILES
CC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C
InChI Identifier
InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3
InChI KeyCVUANYCQTOGILD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentEudesmanolides, secoeudesmanolides, and derivatives
Alternative Parents
Substituents
  • Eudesmanolide
  • Sesquiterpenoid
  • Naphthofuran
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point115 °CNot Available
Boiling Point364.00 to 365.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility35.49 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.42Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.063 g/LALOGPS
logP3.15ALOGPS
logP3.36ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.2 m³·mol⁻¹ChemAxon
Polarizability26.46 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.9531661259
DarkChem[M-H]-150.13831661259
DeepCCS[M-2H]-188.2930932474
DeepCCS[M+Na]+163.77430932474
AllCCS[M+H]+155.632859911
AllCCS[M+H-H2O]+151.832859911
AllCCS[M+NH4]+159.232859911
AllCCS[M+Na]+160.232859911
AllCCS[M-H]-161.332859911
AllCCS[M+Na-2H]-161.332859911
AllCCS[M+HCOO]-161.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsoalantolactoneCC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C2567.2Standard polar33892256
IsoalantolactoneCC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C1892.0Standard non polar33892256
IsoalantolactoneCC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C2007.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoalantolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1920000000-9b5d82ce2d414b53a21d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoalantolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoalantolactone 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 - Isoalantolactone 10V, Positive-QTOFsplash10-001i-0490000000-dfc1007aa212c5c01c722015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 20V, Positive-QTOFsplash10-053i-1930000000-599c13fb890140ea2cc42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 40V, Positive-QTOFsplash10-0gbc-9710000000-3bea9f3ad650c75df3de2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 10V, Positive-QTOFsplash10-001i-0490000000-dfc1007aa212c5c01c722015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 20V, Positive-QTOFsplash10-053i-1930000000-599c13fb890140ea2cc42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 40V, Positive-QTOFsplash10-0gbc-9710000000-3bea9f3ad650c75df3de2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 10V, Negative-QTOFsplash10-001i-0290000000-241b9389e5e00f1c05c62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 20V, Negative-QTOFsplash10-001r-0790000000-2c20c4eb68d8cb0a96992015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 40V, Negative-QTOFsplash10-0079-2900000000-edc4a447c8f51da83d4b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 10V, Negative-QTOFsplash10-001i-0290000000-241b9389e5e00f1c05c62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 20V, Negative-QTOFsplash10-001r-0790000000-2c20c4eb68d8cb0a96992015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 40V, Negative-QTOFsplash10-0079-2900000000-edc4a447c8f51da83d4b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 10V, Negative-QTOFsplash10-001i-0090000000-403b175a8d75af9b9dc42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 20V, Negative-QTOFsplash10-001i-0390000000-64e109a295e3ed5cb7692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 40V, Negative-QTOFsplash10-05di-1920000000-c4ee629fe827100b97512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 10V, Positive-QTOFsplash10-001i-0090000000-9ff721d02a369a8ce5282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 20V, Positive-QTOFsplash10-053r-0950000000-b6a83084d417e599f13d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoalantolactone 40V, Positive-QTOFsplash10-0aou-9700000000-44f32b7a10604426618a2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014737
KNApSAcK IDC00003306
Chemspider ID526129
KEGG Compound IDC09484
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHelenin
METLIN IDNot Available
PubChem Compound605266
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1065851
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.