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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:27 UTC
Update Date2022-03-07 02:53:27 UTC
HMDB IDHMDB0032731
Secondary Accession Numbers
  • HMDB32731
Metabolite Identification
Common Name(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide
Description(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a small amount of articles have been published on (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide.
Structure
Data?1563862299
Synonyms
ValueSource
6-Hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-2H,3H,3ah,4H,5H,6H,9H,11ah-cyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoic acidHMDB
Chemical FormulaC20H24O7
Average Molecular Weight376.4004
Monoisotopic Molecular Weight376.152203122
IUPAC Name6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-2H,3H,3aH,4H,5H,6H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate
Traditional Name6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-3aH,4H,5H,11aH-cyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate
CAS Registry Number84588-88-5
SMILES
C\C=C(/C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C12
InChI Identifier
InChI=1S/C20H24O7/c1-5-11(2)18(23)27-16-9-20(4,25)7-6-14(22)13(10-21)8-15-17(16)12(3)19(24)26-15/h5-8,15-17,21,25H,3,9-10H2,1-2,4H3/b7-6-,11-5+,13-8-
InChI KeyNEJKUCWBWUMARI-IOZUUXKMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Germacrane sesquiterpenoid
  • Sesquiterpenoid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Cyclic ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Alcohol
  • Primary alcohol
  • 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
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 Solubility0.38 g/LALOGPS
logP0.83ALOGPS
logP1.83ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.2ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.62 m³·mol⁻¹ChemAxon
Polarizability37.21 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-225.1230932474
DeepCCS[M+Na]+200.34830932474
AllCCS[M+H]+189.932859911
AllCCS[M+H-H2O]+187.132859911
AllCCS[M+NH4]+192.432859911
AllCCS[M+Na]+193.132859911
AllCCS[M-H]-189.832859911
AllCCS[M+Na-2H]-190.232859911
AllCCS[M+HCOO]-190.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olideC\C=C(/C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C124402.1Standard polar33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olideC\C=C(/C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C122873.3Standard non polar33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olideC\C=C(/C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C122928.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,1TMS,isomer #1C=C1C(=O)OC2/C=C(/CO)C(=O)/C=C\C(C)(O[Si](C)(C)C)CC(OC(=O)/C(C)=C/C)C123075.0Semi standard non polar33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,1TMS,isomer #2C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C)C(=O)/C=C\C(C)(O)CC(OC(=O)/C(C)=C/C)C122941.5Semi standard non polar33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,2TMS,isomer #1C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C)C(=O)/C=C\C(C)(O[Si](C)(C)C)CC(OC(=O)/C(C)=C/C)C123011.0Semi standard non polar33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,1TBDMS,isomer #1C=C1C(=O)OC2/C=C(/CO)C(=O)/C=C\C(C)(O[Si](C)(C)C(C)(C)C)CC(OC(=O)/C(C)=C/C)C123297.7Semi standard non polar33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,1TBDMS,isomer #2C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C(C)(C)C)C(=O)/C=C\C(C)(O)CC(OC(=O)/C(C)=C/C)C123177.4Semi standard non polar33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,2TBDMS,isomer #1C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C(C)(C)C)C(=O)/C=C\C(C)(O[Si](C)(C)C(C)(C)C)CC(OC(=O)/C(C)=C/C)C123450.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9016000000-bef2adbc2c92f96a55612017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide GC-MS (2 TMS) - 70eV, Positivesplash10-053r-9000200000-f51b0b0c97c620e21b5f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 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 - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Positive-QTOFsplash10-0a6r-1029000000-c8039e5eac9db449ee782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Positive-QTOFsplash10-0a6r-7098000000-3a3561582a65f03839ca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Positive-QTOFsplash10-0kcr-9030000000-703e73dd13c0ae75111b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Negative-QTOFsplash10-004i-0019000000-bff603d61758396f465f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Negative-QTOFsplash10-056s-3029000000-9b5dfb1c37a88b9b47182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Negative-QTOFsplash10-052b-9531000000-88a0ee7cf89497b3968c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Negative-QTOFsplash10-004i-1091000000-4bc3070da694ddf765ee2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Negative-QTOFsplash10-004j-5090000000-b8a31a8898119e2691c12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Negative-QTOFsplash10-0bvj-2090000000-43dbba88bb426f1099b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Positive-QTOFsplash10-0a6r-0090000000-d4a1b38335caef243fae2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Positive-QTOFsplash10-0a4i-0090000000-a75aa32864f24d08a45d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Positive-QTOFsplash10-0aor-9040000000-1f5b5a179dee9f5c3ad62021-09-25Wishart 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 IDFDB010692
KNApSAcK IDNot Available
Chemspider ID35013476
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751292
PDB IDNot Available
ChEBI ID175829
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.