You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:34:37 UTC
Update Date2019-07-23 06:33:28 UTC
HMDB IDHMDB0040955
Secondary Accession Numbers
  • HMDB40955
Metabolite Identification
Common Name9alpha-(Angeloyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetate
Description9alpha-(Angeloyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetate is found in tea. 9alpha-(Angeloyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetate is a constituent of Tussilago farfara (coltsfoot).
Structure
Data?1563863608
Synonyms
ValueSource
9a-(Angeloyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetateGenerator
9a-(Angeloyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetic acidGenerator
9alpha-(Angeloyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetic acidGenerator
9Α-(angeloyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetateGenerator
9Α-(angeloyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetic acidGenerator
1-[1-(Acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2Z)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC22H32O5
Average Molecular Weight376.4865
Monoisotopic Molecular Weight376.224974134
IUPAC Name1-[1-(acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2Z)-2-methylbut-2-enoate
Traditional Name1-[1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1H-inden-5-yl (2Z)-2-methylbut-2-enoate
CAS Registry Number147742-08-3
SMILES
C\C=C(\C)C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)OC(C)=O)C1=C
InChI Identifier
InChI=1S/C22H32O5/c1-8-12(4)22(25)27-19-10-16(11(2)3)21-17(13(19)5)9-18(24)20(21)14(6)26-15(7)23/h8,11,14,16-17,19-21H,5,9-10H2,1-4,6-7H3/b12-8-
InChI KeyZYTJBCOGBFUTOP-WQLSENKSSA-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
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
logP3.3ALOGPS
logP4.1ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)19.17ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity103.43 m³·mol⁻¹ChemAxon
Polarizability41.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-8194000000-1326b8d03782d93f1154Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-3029000000-f6a19ca25e4dc932b97eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-9044000000-004517393cfc63770388Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0540-9010000000-dcc8b2484031ff68be2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1019000000-ee98daddc7fdfd4fe22bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-8039000000-33bd75697fc46eb64b96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5d-8091000000-b2ab7b675c4a3aec9d7aSpectrum
Biological Properties
Cellular Locations
  • 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 IDFDB020803
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752995
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.