Record Information
Version1.0
Creation date2010-04-08 22:10:37 UTC
Update date2019-11-26 03:08:12 UTC
Primary IDFDB013256
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoamberboin
DescriptionIsoamberboin belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review a small amount of articles have been published on Isoamberboin.
CAS Number30825-69-5
Structure
Thumb
Synonyms
SynonymSource
MaximolideHMDB
Isoamberboindb_source
Predicted Properties
PropertyValueSource
Water Solubility9.31 g/LALOGPS
logP0.07ALOGPS
logP1.01ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)14.77ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.63 m³·mol⁻¹ChemAxon
Polarizability27.75 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H20O4
IUPAC name4-hydroxy-3,9-dimethyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione
InChI IdentifierInChI=1S/C15H20O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7-9,11-14,17H,1,4-5H2,2-3H3
InChI KeyZAPNUFCAIXITRW-UHFFFAOYSA-N
Isomeric SMILESCC1C2C3OC(=O)C(C)C3C(O)CC(=C)C2CC1=O
Average Molecular Weight264.3169
Monoisotopic Molecular Weight264.136159128
Classification
Description Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative Parents
Substituents
  • Guaianolide-skeleton
  • Guaiane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Secondary alcohol
  • Cyclic ketone
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.16%; H 7.63%; O 24.21%DFC
Melting PointMp 183°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +138 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsoamberboin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-4890000000-4bb6e591faf985f8ff52Spectrum
Predicted GC-MSIsoamberboin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00bl-6292000000-83863fb6e3cabe054ba5Spectrum
Predicted GC-MSIsoamberboin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsoamberboin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0190000000-6f9be36c3aa34356b55eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00tb-0590000000-7bcb4c36e43bdcf3da35Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-7920000000-6571f853883151dd24e3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-430712af8274b9f42ef7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xs-0190000000-3d05bced3f4b105a24f5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-8910000000-919bc9093d0895c8f608Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-16d43704d08f3756e03aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xu-0490000000-777fb4db99d8c24a3e2bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006y-2970000000-b8efa1d1bb870369fe13Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00mk-0090000000-7b21369ee9fade9011ffSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0390000000-8d2fa4bd23943ef0dae6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-2970000000-b9332d5a4e19fcd17190Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID14589063
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34719
CRC / DFC (Dictionary of Food Compounds) IDJZL91-Q:HQG71-E
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00020538
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.