Isoabsinthin (CHEM030136)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:40:47 UTC
Update Date2016-11-09 01:19:01 UTC
Accession NumberCHEM030136
Identification
Common NameIsoabsinthin
ClassSmall Molecule
DescriptionConstituent of Artemisia absinthium (wormwood). Isoabsinthin is found in alcoholic beverages and herbs and spices.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-AbsinthinHMDB
AbsynthinHMDB
Chemical FormulaC30H40O6
Average Molecular Mass496.635 g/mol
Monoisotopic Mass496.282 g/mol
CAS Registry Number11029-90-6
IUPAC Name(1R,2R,5R,8S,9S,12S,13R,14S,15S,16R,17S,20S,21S,24S)-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
Traditional Name(1R,2R,5R,8S,9S,12S,13R,14S,15S,16R,17S,20S,21S,24S)-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
SMILES[H][C@@]12CC[C@](C)(O)[C@@]3([H])C(=C(C)[C@@]4([H])[C@]3([H])[C@H]3C=C(C)[C@@]44[C@@]5([H])OC(=O)[C@@H](C)[C@]5([H])CC[C@](C)(O)[C@]34[H])[C@]1([H])OC(=O)[C@H]2C
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-NTGBWREQSA-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 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 Solubility0.014 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
Polarizability54.99 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-0fi0-0006900000-e8c767aaef1b6397d298Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004j-1002094000-21f7527ebee54735b593Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0000900000-2909fbf81fb602ac3040Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-d21c9a562619077b5674Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-0113900000-fbf7600ee6a63175538bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0000900000-2f932edb370d1947b262Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fba-0000900000-e3a2c3e35015199b3276Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-1005900000-f8c6020ac55c939ae28fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-3ce13dc0a54418d1eaa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000900000-675e4b5de9ee622e186eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-0000900000-7afc047653039e36577cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0000900000-4dfba645c32b3bfbcfd8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000900000-61a54a50ded657146305Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-0148900000-dabe332aee66d1b286d8Spectrum
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 IDHMDB0035742
FooDB IDFDB015295
Phenol Explorer IDNot Available
KNApSAcK IDC00020965
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAbsinthin
Chemspider ID308995
ChEBI ID2366
PubChem Compound ID131751859
Kegg Compound IDC09286
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Zhang W, Luo S, Fang F, Chen Q, Hu H, Jia X, Zhai H: Total synthesis of absinthin. J Am Chem Soc. 2005 Jan 12;127(1):18-9.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. 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.
4. 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.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
7. The lipid handbook with CD-ROM