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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:10 UTC
Update Date2022-03-07 02:52:38 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. Based on a literature review very few articles have been published on Artemidiol.
Structure
Data?1563862017
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
Description 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point131.5 - 133 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3308 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.05131661259
DarkChem[M-H]-150.96731661259
DeepCCS[M+H]+151.56530932474
DeepCCS[M-H]-149.20730932474
DeepCCS[M-2H]-182.71230932474
DeepCCS[M+Na]+158.15930932474
AllCCS[M+H]+154.232859911
AllCCS[M+H-H2O]+150.232859911
AllCCS[M+NH4]+157.932859911
AllCCS[M+Na]+159.032859911
AllCCS[M-H]-155.832859911
AllCCS[M+Na-2H]-155.832859911
AllCCS[M+HCOO]-156.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ArtemidiolCCC(O)C(O)C1=CC2=CC=CC=C2C(=O)O13179.7Standard polar33892256
ArtemidiolCCC(O)C(O)C1=CC2=CC=CC=C2C(=O)O12134.7Standard non polar33892256
ArtemidiolCCC(O)C(O)C1=CC2=CC=CC=C2C(=O)O12191.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Artemidiol,1TMS,isomer #1CCC(O[Si](C)(C)C)C(O)C1=CC2=CC=CC=C2C(=O)O12209.8Semi standard non polar33892256
Artemidiol,1TMS,isomer #2CCC(O)C(O[Si](C)(C)C)C1=CC2=CC=CC=C2C(=O)O12176.1Semi standard non polar33892256
Artemidiol,2TMS,isomer #1CCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CC2=CC=CC=C2C(=O)O12169.8Semi standard non polar33892256
Artemidiol,1TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)C(O)C1=CC2=CC=CC=C2C(=O)O12478.5Semi standard non polar33892256
Artemidiol,1TBDMS,isomer #2CCC(O)C(O[Si](C)(C)C(C)(C)C)C1=CC2=CC=CC=C2C(=O)O12424.0Semi standard non polar33892256
Artemidiol,2TBDMS,isomer #1CCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC2=CC=CC=C2C(=O)O12674.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Artemidiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4910000000-0d38dd131377ba61acbc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artemidiol GC-MS (2 TMS) - 70eV, Positivesplash10-0002-6394000000-d4ebd94f96c51258730a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artemidiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 10V, Negative-QTOFsplash10-001i-1590000000-9f4d0bf2c618bd622cd82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 20V, Negative-QTOFsplash10-0541-5950000000-7b4ebeaff92d6cc2dc772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 40V, Negative-QTOFsplash10-0670-9700000000-0d94a6b982fd4c0ddca32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 10V, Negative-QTOFsplash10-001i-1590000000-e6313ff31be1c234e3fb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 20V, Negative-QTOFsplash10-0a4j-9700000000-dd409af5c7b8b8edccd62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 40V, Negative-QTOFsplash10-0002-4900000000-2b5c44af45a522d46b792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 10V, Positive-QTOFsplash10-000i-1190000000-8c8cbec39773b0427cdf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 20V, Positive-QTOFsplash10-00p0-9670000000-d63e43d545d53bc9c06c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 40V, Positive-QTOFsplash10-0a4l-9400000000-76a289a89dec4efa14cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 10V, Positive-QTOFsplash10-000i-0390000000-84e7d6facca9c5381fe82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 20V, Positive-QTOFsplash10-00di-9510000000-f9f4dc966384d02899a12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artemidiol 40V, Positive-QTOFsplash10-0f6x-9600000000-6b27018e766c68604f402021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
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
FooDB IDFDB002554
KNApSAcK IDC00043285
Chemspider ID10352939
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23246261
PDB IDNot Available
ChEBI ID174201
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1821751
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