3,14-Dihydroxy-11,13-dihydrocostunolide (CHEM029547)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:14:20 UTC
Update Date2016-11-09 01:18:54 UTC
Accession NumberCHEM029547
Identification
Common Name3,14-Dihydroxy-11,13-dihydrocostunolide
ClassSmall Molecule
Description3,14-Dihydroxy-11,13-dihydrocostunolide is found in green vegetables. 3,14-Dihydroxy-11,13-dihydrocostunolide is a constituent of Lactuca sativa (lettuce)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC15H22O4
Average Molecular Mass266.333 g/mol
Monoisotopic Mass266.152 g/mol
CAS Registry Number102518-83-2
IUPAC Name9-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
Traditional Name9-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
SMILESCC1C2CC\C(CO)=C/CC(O)\C(C)=C/C2OC1=O
InChI IdentifierInChI=1S/C15H22O4/c1-9-7-14-12(10(2)15(18)19-14)5-3-11(8-16)4-6-13(9)17/h4,7,10,12-14,16-17H,3,5-6,8H2,1-2H3/b9-7-,11-4+
InChI KeyKUERQAIAYCRGOB-WHIYXEERSA-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
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
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 Solubility0.88 g/LALOGPS
logP1.37ALOGPS
logP1.16ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.55ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.43 m³·mol⁻¹ChemAxon
Polarizability29.13 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-004i-7590000000-93b37e18b1c36e444a81Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fi9-6019000000-ab6314e5e88586cc393cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0190000000-db681aceefc1df9eefd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-005a-0590000000-dd3924e3e2b8b5f49111Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-3920000000-de595b5d253be616f976Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-18f61c70e0241bfb4067Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0090000000-3551f27fe0d306cfeb32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frf-6940000000-fa79e93c581c31ee51abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-74fa67e73b13aa015226Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-0390000000-d61c59080ffd41d5a369Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-0290000000-73b549a6bc68856b5f10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-eb286f0cba09a2aafdb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0190000000-1681b5cd0138a6dd1ed7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fka-0890000000-0b64da2e29c864067049Spectrum
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 IDHMDB0035647
FooDB IDFDB014358
Phenol Explorer IDNot Available
KNApSAcK IDC00056356
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013970
ChEBI ID174498
PubChem Compound ID131751828
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