Record Information
Version1.0
Creation date2010-04-08 22:11:17 UTC
Update date2019-11-26 03:10:07 UTC
Primary IDFDB014471
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAbsinthin
DescriptionConstituent of Artemisia absinthium (wormwood) (+)-Absinthin is a naturally produced molecule from the plant Artemisia absinthium (Wormwood). It constitutes one of the most bitter chemical agents responsible for Absinthe's distinct taste. The compound shows biological activity and has shown promise as an anti-inflammatory agent, and should not to be confused with thujone, the psychoactive toxin found in Absinthe.
CAS Number1362-42-1
Structure
Thumb
Synonyms
SynonymSource
(+)-Absinthinbiospider
Absinthin (VAN) (8CI)biospider
Absynthinbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.38ALOGPS
logP2.38ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.42ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity133.98 m³·mol⁻¹ChemAxon
Polarizability54.72 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H40O6
IUPAC name(1R,5S,8S,12S,13R,15S,17S,20S,21S)-12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.0¹,¹⁶.0²,¹⁴.0⁴,¹³.0⁵,⁹.0²⁰,²⁴]hexacosa-3,25-diene-7,22-dione
InChI IdentifierInChI=1S/C30H40O6/c1-12-11-18-20-21(30(12)24(18)29(6,34)10-8-17-14(3)27(32)36-25(17)30)15(4)19-22(20)28(5,33)9-7-16-13(2)26(31)35-23(16)19/h11,13-14,16-18,20-25,33-34H,7-10H2,1-6H3/t13-,14-,16?,17-,18+,20?,21?,22-,23-,24?,25?,28-,29-,30+/m0/s1
InChI KeyPZHWYURJZAPXAN-BPLZWQIUSA-N
Isomeric SMILES[H][C@@]12C3[C@H]4C=C(C)[C@@]5(C6OC(=O)[C@@H](C)[C@@H]6CC[C@](C)(O)C45)C3C(C)=C1[C@H]1OC(=O)[C@@H](C)C1CC[C@]2(C)O
Average Molecular Weight496.635
Monoisotopic Molecular Weight496.282489012
Classification
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
  • Gamma butyrolactone
  • Dicarboxylic acid or derivatives
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 72.55%; H 8.12%; O 19.33%DFC
Melting PointMp 182-183° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +180DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0000900000-2909fbf81fb602ac3040JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-d21c9a562619077b5674JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-0113900000-fbf7600ee6a63175538bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0000900000-2f932edb370d1947b262JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fba-0000900000-e3a2c3e35015199b3276JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-1005900000-f8c6020ac55c939ae28fJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09286
Pubchem Compound ID442138
Pubchem Substance IDNot Available
ChEBI ID2366
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJRB32-X:JRB32-X
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000172
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAbsinthin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference