(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide (CHEM025262)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:16:39 UTC
Update Date2016-11-09 01:18:02 UTC
Accession NumberCHEM025262
Identification
Common Name(6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide
ClassSmall Molecule
DescriptionIsolated from sage. (6beta,7alpha,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide is found in herbs and spices.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6b,7a,12b,13b)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olideGenerator
(6Β,7α,12β,13β)-7-hydroxy-11,16-dioxo-8,14-apianadien-22,6-olideGenerator
Chemical FormulaC23H28O5
Average Molecular Mass384.465 g/mol
Monoisotopic Mass384.194 g/mol
CAS Registry Number403613-16-1
IUPAC Name10-hydroxy-7,13,13-trimethyl-4-(propan-2-yl)-18-oxapentacyclo[9.5.2.0¹,¹².0²,⁹.0⁴,⁸]octadeca-2(9),6-diene-3,5,17-trione
Traditional Name10-hydroxy-4-isopropyl-7,13,13-trimethyl-18-oxapentacyclo[9.5.2.0¹,¹².0²,⁹.0⁴,⁸]octadeca-2(9),6-diene-3,5,17-trione
SMILESCC(C)C12C(C(C)=CC1=O)C1=C(C2=O)C23CCCC(C)(C)C2C(OC3=O)C1O
InChI IdentifierInChI=1S/C23H28O5/c1-10(2)23-12(24)9-11(3)14(23)13-15(19(23)26)22-8-6-7-21(4,5)18(22)17(16(13)25)28-20(22)27/h9-10,14,16-18,25H,6-8H2,1-5H3
InChI KeyIEPYKUBVROCHOQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.96ALOGPS
logP3.29ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)11.82ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity103.44 m³·mol⁻¹ChemAxon
Polarizability40.1 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-4935000000-e817af62ede7e6781fc4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-047u-9412300000-f5f3c91584e40bda4bf5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-437cd2eca9d88ad06c5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2129000000-37b6ff4a2e6a02b20514Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-9464000000-bd167c35d2dcaabcf8bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-11fc57598cf6c5282e05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-e7e67bc3b31bc597cb59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02g9-1923000000-d2e0ff755b2d0e5bc15eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-a1f14e47f80cf18311f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0009000000-e580a84f708d2c7ebd52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3719000000-44feec1ac79fbf693984Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-feedb729141e890033a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0009000000-25f6778205961372084eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-1319000000-49071520eda573e8c52cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031380
FooDB IDFDB003447
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID73880583
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM