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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:31:15 UTC
Update Date2022-03-07 02:54:10 UTC
HMDB IDHMDB0034631
Secondary Accession Numbers
  • HMDB34631
Metabolite Identification
Common Name(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one
Description(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one.
Structure
Data?1563862594
Synonyms
ValueSource
(1Z)-1-Ethylidene-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2Z)-2-methylbut-2-enoic acidHMDB
Chemical FormulaC20H28O3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
IUPAC Name(1Z)-1-ethylidene-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2Z)-2-methylbut-2-enoate
Traditional Name(1Z)-1-ethylidene-7-isopropyl-4-methylidene-2-oxo-hexahydroinden-5-yl (2Z)-2-methylbut-2-enoate
CAS Registry Number237407-00-0
SMILES
C\C=C(\C)C(=O)OC1CC(C(C)C)C2C(CC(=O)\C2=C/C)C1=C
InChI Identifier
InChI=1S/C20H28O3/c1-7-12(5)20(22)23-18-10-15(11(3)4)19-14(8-2)17(21)9-16(19)13(18)6/h7-8,11,15-16,18-19H,6,9-10H2,1-5H3/b12-7-,14-8+
InChI KeyPGPPNCWYWQGYAU-FHGRNIPQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Oplopane sesquiterpenoid
  • Fatty acid ester
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility0.0071 g/LALOGPS
logP4.31ALOGPS
logP4.82ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.56 m³·mol⁻¹ChemAxon
Polarizability36.94 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+H]+182.65330932474
DeepCCS[M-H]-179.91630932474
DeepCCS[M-2H]-214.71230932474
DeepCCS[M+Na]+190.58830932474
AllCCS[M+H]+178.632859911
AllCCS[M+H-H2O]+175.732859911
AllCCS[M+NH4]+181.332859911
AllCCS[M+Na]+182.032859911
AllCCS[M-H]-183.532859911
AllCCS[M+Na-2H]-183.932859911
AllCCS[M+HCOO]-184.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-oneC\C=C(\C)C(=O)OC1CC(C(C)C)C2C(CC(=O)\C2=C/C)C1=C3064.6Standard polar33892256
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-oneC\C=C(\C)C(=O)OC1CC(C(C)C)C2C(CC(=O)\C2=C/C)C1=C2278.3Standard non polar33892256
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-oneC\C=C(\C)C(=O)OC1CC(C(C)C)C2C(CC(=O)\C2=C/C)C1=C2232.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one,1TMS,isomer #1C=C1C(OC(=O)/C(C)=C\C)CC(C(C)C)C2/C(=C/C)C(O[Si](C)(C)C)=CC122386.7Semi standard non polar33892256
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one,1TMS,isomer #1C=C1C(OC(=O)/C(C)=C\C)CC(C(C)C)C2/C(=C/C)C(O[Si](C)(C)C)=CC122294.5Standard non polar33892256
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one,1TBDMS,isomer #1C=C1C(OC(=O)/C(C)=C\C)CC(C(C)C)C2/C(=C/C)C(O[Si](C)(C)C(C)(C)C)=CC122585.8Semi standard non polar33892256
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one,1TBDMS,isomer #1C=C1C(OC(=O)/C(C)=C\C)CC(C(C)C)C2/C(=C/C)C(O[Si](C)(C)C(C)(C)C)=CC122477.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9450000000-54f00f86b994862fe3ae2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 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 - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 10V, Positive-QTOFsplash10-014i-5198000000-84101fb2b248fa1519042016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 20V, Positive-QTOFsplash10-067i-9251000000-0f632006241f27e8078f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 40V, Positive-QTOFsplash10-0kai-9100000000-73fc2c490c9e370affea2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 10V, Negative-QTOFsplash10-014i-1029000000-8b65b825ead3f15861502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 20V, Negative-QTOFsplash10-0159-8096000000-4429db6f947b1a88031d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 40V, Negative-QTOFsplash10-0kuu-9170000000-a541544a77ba6375a4902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 10V, Positive-QTOFsplash10-00or-0981000000-d48931654e4edefaa9942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 20V, Positive-QTOFsplash10-014r-0950000000-ff10e14aa37ecd22001e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 40V, Positive-QTOFsplash10-066r-9711000000-139616b086d8969b88db2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 10V, Negative-QTOFsplash10-014j-6029000000-98fbf5687e6b0abd87782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 20V, Negative-QTOFsplash10-0002-9010000000-1f90606de09292b5f3a52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 40V, Negative-QTOFsplash10-0pi0-9430000000-ffda12de702a2957574c2021-09-23Wishart 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 IDFDB013153
KNApSAcK IDNot Available
Chemspider ID35013752
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751596
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.