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Arlatin

Common Name

Arlatin Description

Arlatin is found in alcoholic beverages. Arlatin is a constituent of Artemisia absinthium (wormwood).Arlatin belongs to the family of Guaianolides and Derivatives. These are diterpene lactones whose strucuture is characterized by the presence of a gamm-lactone fused to a guiane, forming 3,6,9-trimethyl-azlieno[4,5-b]furan-2-one or a dderivative. Structure

MOLSDFPDBSMILESInChI

Structure for HMDB35740 (Arlatin)

Synonyms

Not Available Chemical Formlia

C15H22O4 Average Molecliar Weight

266.3328 Monoisotopic Molecliar Weight

266.151809192 IUPAC Name

6,6a-dihydroxy-3,6,9-trimethyl-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azlieno[4,5-b]furan-2-one Traditional Name

6,6a-dihydroxy-3,6,9-trimethyl-3H,3aH,4H,5H,7H,9aH,9bH-azlieno[4,5-b]furan-2-one CAS Registry Number

93552-69-3 SMILES

CC1C2CCC(C)(O)C3(O)CC=C(C)C3C2OC1=O

InChI Identifier

InChI=1S/C15H22O4/c1-8-4-7-15(18)11(8)12-10(5-6-14(15,3)17)9(2)13(16)19-12/h4,9-12,17-18H,5-7H2,1-3H3

InChI Key

VBQMPXNFLQSHMH-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azlieno[4,5-b]furan-2-one or a derivative. Kingdom

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Prenol lipids Direct Parent

Guaianolides and derivatives Alternative Parents

  • Guaianes
  • Gamma butyrolactones
  • Tetrahydrofurans
  • Tertiary alcohols
  • Cyclic alcohols and derivatives
  • Carboxylic acid esters
  • 1,2-diols
  • Oxacyclic compounds
  • Monocarboxylic acids and derivatives
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Guaianolide-skeleton
  • Guaiane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Tertiary alcohol
  • 1,2-diol
  • Carboxylic acid ester
  • Lactone
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • 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

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Not Available Experimental Properties

    Property Value Reference Melting Point203 – 205 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility4.73 mg/mLALOGPS logP1.07ALOGPS logP0.87ChemAxon logS-1.8ALOGPS pKa (Strongest Acidic)13.18ChemAxon pKa (Strongest Basic)-3.3ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area66.76 Å2ChemAxon Rotatable Bond Count0ChemAxon Refractivity70.5 m3·mol-1ChemAxon Polarizability28.54 Å3ChemAxon Number of Rings3ChemAxon 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

  • Cytoplasm
  • 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

    FDB014469 KNApSAcK ID

    C00020536 Chemspider ID

    Not Available KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB35740 Metagene Link

    HMDB35740 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    Not Available

    Product: TN2

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

    PMID: 11078331