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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:37:19 UTC
Update Date2022-03-07 02:54:13 UTC
HMDB IDHMDB0034719
Secondary Accession Numbers
  • HMDB34719
Metabolite Identification
Common 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.
Structure
Data?1563862609
Synonyms
ValueSource
MaximolideHMDB
Chemical FormulaC15H20O4
Average Molecular Weight264.3169
Monoisotopic Molecular Weight264.136159128
IUPAC Name4-hydroxy-3,9-dimethyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione
Traditional Name4-hydroxy-3,9-dimethyl-6-methylidene-octahydro-3H-azuleno[4,5-b]furan-2,8-dione
CAS Registry Number30825-69-5
SMILES
CC1C2C3OC(=O)C(C)C3C(O)CC(=C)C2CC1=O
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point183 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.86531661259
DarkChem[M-H]-156.79131661259
DeepCCS[M+H]+162.70130932474
DeepCCS[M-H]-160.34330932474
DeepCCS[M-2H]-193.22930932474
DeepCCS[M+Na]+168.79430932474
AllCCS[M+H]+161.632859911
AllCCS[M+H-H2O]+158.032859911
AllCCS[M+NH4]+164.832859911
AllCCS[M+Na]+165.832859911
AllCCS[M-H]-165.632859911
AllCCS[M+Na-2H]-165.532859911
AllCCS[M+HCOO]-165.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsoamberboinCC1C2C3OC(=O)C(C)C3C(O)CC(=C)C2CC1=O3179.3Standard polar33892256
IsoamberboinCC1C2C3OC(=O)C(C)C3C(O)CC(=C)C2CC1=O2232.6Standard non polar33892256
IsoamberboinCC1C2C3OC(=O)C(C)C3C(O)CC(=C)C2CC1=O2326.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isoamberboin,1TMS,isomer #1C=C1CC(O[Si](C)(C)C)C2C(C)C(=O)OC2C2C(C)C(=O)CC122189.5Semi standard non polar33892256
Isoamberboin,1TMS,isomer #2C=C1CC(O)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C)CC122242.7Semi standard non polar33892256
Isoamberboin,1TMS,isomer #3C=C1CC(O)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C)=CC122175.8Semi standard non polar33892256
Isoamberboin,2TMS,isomer #1C=C1CC(O[Si](C)(C)C)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C)CC122307.1Semi standard non polar33892256
Isoamberboin,2TMS,isomer #1C=C1CC(O[Si](C)(C)C)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C)CC122194.2Standard non polar33892256
Isoamberboin,2TMS,isomer #2C=C1CC(O[Si](C)(C)C)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C)=CC122233.2Semi standard non polar33892256
Isoamberboin,2TMS,isomer #2C=C1CC(O[Si](C)(C)C)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C)=CC122166.8Standard non polar33892256
Isoamberboin,1TBDMS,isomer #1C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)OC2C2C(C)C(=O)CC122419.1Semi standard non polar33892256
Isoamberboin,1TBDMS,isomer #2C=C1CC(O)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC122473.4Semi standard non polar33892256
Isoamberboin,1TBDMS,isomer #3C=C1CC(O)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC122392.2Semi standard non polar33892256
Isoamberboin,2TBDMS,isomer #1C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC122749.2Semi standard non polar33892256
Isoamberboin,2TBDMS,isomer #1C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)OC2C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC122665.2Standard non polar33892256
Isoamberboin,2TBDMS,isomer #2C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC122682.2Semi standard non polar33892256
Isoamberboin,2TBDMS,isomer #2C=C1CC(O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)OC2C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC122546.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoamberboin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-4890000000-4bb6e591faf985f8ff522017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoamberboin GC-MS (1 TMS) - 70eV, Positivesplash10-00bl-6292000000-83863fb6e3cabe054ba52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoamberboin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoamberboin 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 - Isoamberboin 10V, Positive-QTOFsplash10-00kb-0190000000-6f9be36c3aa34356b55e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 20V, Positive-QTOFsplash10-00tb-0590000000-7bcb4c36e43bdcf3da352015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 40V, Positive-QTOFsplash10-0uxu-7920000000-6571f853883151dd24e32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 10V, Negative-QTOFsplash10-03di-0090000000-430712af8274b9f42ef72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 20V, Negative-QTOFsplash10-03xs-0190000000-3d05bced3f4b105a24f52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 40V, Negative-QTOFsplash10-0f6x-8910000000-919bc9093d0895c8f6082015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 10V, Negative-QTOFsplash10-03di-0090000000-16d43704d08f3756e03a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 20V, Negative-QTOFsplash10-03xu-0490000000-777fb4db99d8c24a3e2b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 40V, Negative-QTOFsplash10-006y-2970000000-b8efa1d1bb870369fe132021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 10V, Positive-QTOFsplash10-00mk-0090000000-7b21369ee9fade9011ff2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 20V, Positive-QTOFsplash10-004j-0390000000-8d2fa4bd23943ef0dae62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoamberboin 40V, Positive-QTOFsplash10-00kr-2970000000-b9332d5a4e19fcd171902021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB013256
KNApSAcK IDC00020538
Chemspider ID35013778
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14589063
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.