Absintholide (CHEM031555)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:44:27 UTC
Update Date2016-11-09 01:19:17 UTC
Accession NumberCHEM031555
Identification
Common NameAbsintholide
ClassSmall Molecule
DescriptionConstituent of Artemisia absinthium (wormwood). Absintholide is found in alcoholic beverages and herbs and spices.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC30H38O8
Average Molecular Mass526.618 g/mol
Monoisotopic Mass526.257 g/mol
CAS Registry Number91997-90-9
IUPAC Name(1S,2R,4S,7S,8S,11S,13S,14S,15R,17S,20S,21S,24S)-11,13,24-trihydroxy-2,7,11,15,20,24-hexamethyl-5,18-dioxaheptacyclo[13.10.1.0²,¹⁴.0³,¹².0⁴,⁸.0¹⁶,²⁵.0¹⁷,²¹]hexacosa-3(12),16(25)-diene-6,19,26-trione
Traditional Name(1S,2R,4S,7S,8S,11S,13S,14S,15R,17S,20S,21S,24S)-11,13,24-trihydroxy-2,7,11,15,20,24-hexamethyl-5,18-dioxaheptacyclo[13.10.1.0²,¹⁴.0³,¹².0⁴,⁸.0¹⁶,²⁵.0¹⁷,²¹]hexacosa-3(12),16(25)-diene-6,19,26-trione
SMILES[H][C@@]12C(=O)[C@@](C)(C3=C1[C@@](C)(O)CC[C@H]1[C@H](C)C(=O)O[C@H]31)[C@@]1([H])[C@H](O)C3=C([C@H]4OC(=O)[C@@H](C)[C@@H]4CC[C@]3(C)O)[C@@]21C
InChI IdentifierInChI=1S/C30H38O8/c1-11-13-7-9-27(3,35)15-17(21(13)37-25(11)33)30(6)23-20(31)16-18(29(23,5)19(15)24(30)32)22-14(8-10-28(16,4)36)12(2)26(34)38-22/h11-14,19-23,31,35-36H,7-10H2,1-6H3/t11-,12-,13-,14-,19-,20+,21-,22-,23-,27-,28-,29-,30-/m0/s1
InChI KeyANVQPXYQHSOZNE-UMDUJLOZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Prostaglandin skeleton
  • Eicosanoid
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Fatty acyl
  • Tertiary alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • 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 Solubility0.28 g/LALOGPS
logP2.12ALOGPS
logP0.94ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.26ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area130.36 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity135.65 m³·mol⁻¹ChemAxon
Polarizability55.41 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-1048950000-a4131d230bed43d41578Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-0001139000-45de5715331a7227886eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0000970000-1fff10de6af71714141bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-0000920000-e05bc31174207213b909Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0133900000-93a9155fb1764c62b86aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0000690000-d5bf18189ee1a12e5c60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-0000970000-be3c89e11933dcdb98d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-0001900000-9edde8842146afffb4efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000090000-b779f3c387e69eefba3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu3-0010950000-d4186b51d4ed467afa99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0193400000-a480cfbdbd768e08c983Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000190000-165cd87e93697615d835Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-0000790000-116ad23722c572e5c2b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056s-1010920000-b48723bf689996921892Spectrum
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 IDHMDB0038171
FooDB IDFDB017402
Phenol Explorer IDNot Available
KNApSAcK IDC00020967
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID101087895
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