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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:58:58 UTC
Update Date2022-03-07 02:54:42 UTC
HMDB IDHMDB0035935
Secondary Accession Numbers
  • HMDB35935
Metabolite Identification
Common NameDihydroisoalantolactone
DescriptionDihydroisoalantolactone 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 Dihydroisoalantolactone.
Structure
Data?1563862795
Synonyms
ValueSource
4(15)-Eudesmen-12,8b-olideHMDB
Chemical FormulaC15H22O2
Average Molecular Weight234.334
Monoisotopic Molecular Weight234.161979948
IUPAC Name3,8a-dimethyl-5-methylidene-dodecahydronaphtho[2,3-b]furan-2-one
Traditional Name3,8a-dimethyl-5-methylidene-octahydro-3H-naphtho[2,3-b]furan-2-one
CAS Registry NumberNot Available
SMILES
CC1C2CC3C(=C)CCCC3(C)CC2OC1=O
InChI Identifier
InChI=1S/C15H22O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h10-13H,1,4-8H2,2-3H3
InChI KeyYYJRTJYCOMIDIC-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
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • 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 Point172 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP3.45ALOGPS
logP3.22ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.39 m³·mol⁻¹ChemAxon
Polarizability27.16 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]+156.05631661259
DarkChem[M-H]-152.5431661259
DeepCCS[M+H]+151.36430932474
DeepCCS[M-H]-148.29730932474
DeepCCS[M-2H]-184.73430932474
DeepCCS[M+Na]+160.27230932474
AllCCS[M+H]+156.432859911
AllCCS[M+H-H2O]+152.632859911
AllCCS[M+NH4]+159.932859911
AllCCS[M+Na]+160.932859911
AllCCS[M-H]-163.032859911
AllCCS[M+Na-2H]-163.132859911
AllCCS[M+HCOO]-163.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydroisoalantolactoneCC1C2CC3C(=C)CCCC3(C)CC2OC1=O2575.9Standard polar33892256
DihydroisoalantolactoneCC1C2CC3C(=C)CCCC3(C)CC2OC1=O1945.9Standard non polar33892256
DihydroisoalantolactoneCC1C2CC3C(=C)CCCC3(C)CC2OC1=O1997.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroisoalantolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-1920000000-4a428ecac726eec138ca2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydroisoalantolactone 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 - Dihydroisoalantolactone 10V, Positive-QTOFsplash10-000i-0490000000-918af1857b0ee7a0b2882015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 20V, Positive-QTOFsplash10-000l-2930000000-ee105d5d6bc2e86c68252015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 40V, Positive-QTOFsplash10-0gbc-9510000000-24fbfe06bf8d8db0c8622015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 10V, Negative-QTOFsplash10-001i-0390000000-88142d5b3c1724a365ea2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 20V, Negative-QTOFsplash10-001r-1790000000-306a84470ba7dddb2bf72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 40V, Negative-QTOFsplash10-0079-2900000000-3927d5f43bb3f7b85f862015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 10V, Negative-QTOFsplash10-001i-0090000000-9087f47ed0ae51229a172021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 20V, Negative-QTOFsplash10-000i-0900000000-8e3065cda4a27c948e142021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 40V, Negative-QTOFsplash10-0a4r-3930000000-9c2619c69ff9c8beb25a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 10V, Positive-QTOFsplash10-000i-0190000000-fa50a39e29274a23a7042021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 20V, Positive-QTOFsplash10-000i-0950000000-79c1c02723d98b246a242021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydroisoalantolactone 40V, Positive-QTOFsplash10-0a4i-3900000000-df6ed91897ee591df2ca2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB014738
KNApSAcK IDC00022678
Chemspider ID4280210
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5104810
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.