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Absinthin

Common Name

Absinthin Description

Isoabsinthin is found in alcoholic beverages. Isoabsinthin is a constituent of Artemisia absinthium (wormwood). Structure

MOLSDFPDBSMILESInChI

Structure for HMDB35742 (Absinthin)

Synonyms

Value Source (+)-AbsinthinHMDB AbsynthinHMDB

Chemical Formlia

C30H40O6 Average Molecliar Weight

496.635 Monoisotopic Molecliar Weight

496.282489012 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 CAS Registry Number

1362-42-1 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 Identifier

InChI=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 Key

PZHWYURJZAPXAN-NTGBWREQSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. Kingdom

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Prenol lipids Direct Parent

Sesterterpenoids Alternative Parents

  • Gamma butyrolactones
  • Dicarboxylic acids and derivatives
  • Tetrahydrofurans
  • Tertiary alcohols
  • Cyclic alcohols and derivatives
  • Carboxylic acid esters
  • Oxacyclic compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Sesterterpenoid
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound

    • Molecliar Framework

    Aliphatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

  • Food

    • Biofunction

  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient

    • Application

  • Nutrient
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Extracellliar
  • Membrane

    • Physical Properties State

    Not Available Experimental Properties

    Property Value Reference Melting Point182 – 183 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.014 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count0ChemAxon Refractivity133.98 m3·mol-1ChemAxon Polarizability54.99 Å3ChemAxon Number of Rings7ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane

    • Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB015295 KNApSAcK ID

    C00020965 Chemspider ID

    308995 KEGG Compound ID

    C09286 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Absinthin NuGOwiki Link

    HMDB35742 Metagene Link

    HMDB35742 METLIN ID

    Not Available PubChem Compound

    348165 PDB ID

    Not Available ChEBI ID

    2366

    Product: 9-Nitrotryptanthrin

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not 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. [PubMed:15631427 ]
    2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

    PMID: 16221685