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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:10 UTC
Update Date2018-03-12 21:57:14 UTC
HMDB IDHMDB0030648
Secondary Accession Numbers
  • HMDB30648
Metabolite Identification
Common NameArtemidiol
DescriptionArtemidiol belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Artemidiol exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Within the cell, artemidiol is primarily located in the cytoplasm. Outside of the human body, artemidiol can be found in herbs and spices. This makes artemidiol a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
3-(1,2-Dihydroxybutyl)-1H-2-benzopyran-1-oneHMDB
Chemical FormulaC13H14O4
Average Molecular Weight234.2479
Monoisotopic Molecular Weight234.089208936
IUPAC Name3-(1,2-dihydroxybutyl)-1H-isochromen-1-one
Traditional Name3-(1,2-dihydroxybutyl)isochromen-1-one
CAS Registry Number54963-30-3
SMILES
CCC(O)C(O)C1=CC2=CC=CC=C2C(=O)O1
InChI Identifier
InChI=1S/C13H14O4/c1-2-10(14)12(15)11-7-8-5-3-4-6-9(8)13(16)17-11/h3-7,10,12,14-15H,2H2,1H3
InChI KeyCRXSSRPVDGICML-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsocoumarins and derivatives
Sub ClassNot Available
Direct ParentIsocoumarins and derivatives
Alternative Parents
Substituents
  • Isocoumarin
  • Benzopyran
  • 2-benzopyran
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • 1,2-diol
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Aromatic alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point131.5 - 133 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.66 g/LALOGPS
logP1.14ALOGPS
logP1.52ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.86ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity63.75 m³·mol⁻¹ChemAxon
Polarizability24.09 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4910000000-0d38dd131377ba61acbcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-6394000000-d4ebd94f96c51258730aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1190000000-8c8cbec39773b0427cdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00p0-9670000000-d63e43d545d53bc9c06cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9400000000-76a289a89dec4efa14ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1590000000-9f4d0bf2c618bd622cd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0541-5950000000-7b4ebeaff92d6cc2dc77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0670-9700000000-0d94a6b982fd4c0ddca3View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002554
KNApSAcK IDNot Available
Chemspider ID10352939
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23246261
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot 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.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Artemidiol → [2-hydroxy-1-(1-oxo-1H-isochromen-3-yl)butoxy]sulfonic aciddetails
Artemidiol → {[1-hydroxy-1-(1-oxo-1H-isochromen-3-yl)butan-2-yl]oxy}sulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Artemidiol → 3,4,5-trihydroxy-6-[2-hydroxy-1-(1-oxo-1H-isochromen-3-yl)butoxy]oxane-2-carboxylic aciddetails
Artemidiol → 3,4,5-trihydroxy-6-{[1-hydroxy-1-(1-oxo-1H-isochromen-3-yl)butan-2-yl]oxy}oxane-2-carboxylic aciddetails