Anabsinthin (CHEM030138)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:40:50 UTC
Update Date2016-11-09 01:19:01 UTC
Accession NumberCHEM030138
Identification
Common NameAnabsinthin
ClassSmall Molecule
DescriptionIsolated from Artemisia absinthium (wormwood). Anabsinthin is found in alcoholic beverages and herbs and spices.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(1-Methylbutyl)-phenolHMDB
4-(1-Methylbutyl)phenolHMDB
4-Sec-amylphenolHMDB
4-Sec-pentyl-phenolHMDB
p-(1-Methylbutyl)-phenolHMDB
p-(1-METHYLBUTYL)phenolHMDB
p-(Sec-pentyl)-phenolHMDB
p-Sec-amyl phenolHMDB
p-Sec-amyl-phenolHMDB
p-Sec-amylphenolHMDB
Phenol, p-sec-amyl- (6ci)HMDB
Chemical FormulaC30H40O6
Average Molecular Mass496.635 g/mol
Monoisotopic Mass496.282 g/mol
CAS Registry Number6903-12-4
IUPAC Name(2R,5S,8S,9S,12S,13R,14S,15S,17R,19R,22S,23S,26S,27R)-12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione
Traditional Name(2R,5S,8S,9S,12S,13R,14S,15S,17R,19R,22S,23S,26S,27R)-12-hydroxy-3,8,12,17,19,23-hexamethyl-6,18,25-trioxaoctacyclo[13.11.1.0¹,¹⁷.0²,¹⁴.0⁴,¹³.0⁵,⁹.0¹⁹,²⁷.0²²,²⁶]heptacos-3-ene-7,24-dione
SMILES[H][C@]12C[C@@](C)(O)C[C@H]3[C@H](C)C(=O)O[C@@H]3C1=C(C)[C@@]1([H])[C@]2([H])[C@@]2([H])C[C@@]3(C)O[C@@]4(C)CC[C@H]5[C@H](C)C(=O)O[C@@H]5C13[C@@]24[H]
InChI IdentifierInChI=1S/C30H40O6/c1-12-15-7-8-28(5)23-18-11-29(6,36-28)30(23,24(15)35-26(12)32)21-14(3)19-17(20(18)21)10-27(4,33)9-16-13(2)25(31)34-22(16)19/h12-13,15-18,20-24,33H,7-11H2,1-6H3/t12-,13-,15-,16-,17-,18+,20-,21-,22-,23-,24-,27-,28-,29+,30?/m0/s1
InChI KeyOFWCLUGTFWQBDL-ICNZDFTESA-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
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • 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 Solubility0.0081 g/LALOGPS
logP3.43ALOGPS
logP2.71ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.7ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity131.23 m³·mol⁻¹ChemAxon
Polarizability59 ųChemAxon
Number of Rings8ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-0024900000-a8db7b07011c7aead87bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-1011490000-8f3e7ea7e9651e96f93bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Anabsinthin,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0000900000-ff81bea167a9802ed83dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pk9-0000900000-bfdb3b179b2c8fbcca88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3133900000-55f57278d5692f0aea3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0000900000-20cee9f16791d855b34eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f92-0000900000-eb8fc35c02d167519a32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k92-4005900000-85433c1ef9c956a575d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-3ce13dc0a54418d1eaa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000900000-203c0edb2677a68eb1fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-009e-1000900000-e4fabbd4941665f63ab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-afff19a91c925fa0c771Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0000900000-d9d8a6d496df885d1281Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05bk-1014900000-8dc2751b356fe9a34403Spectrum
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 IDHMDB0036415
FooDB IDFDB015297
Phenol Explorer IDNot Available
KNApSAcK IDC00020969
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
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