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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:14:48 UTC
Update Date2022-03-07 02:56:41 UTC
HMDB IDHMDB0040674
Secondary Accession Numbers
  • HMDB40674
Metabolite Identification
Common NameArtonin L
DescriptionArtonin L belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Thus, artonin L is considered to be a flavonoid. Artonin L has been detected, but not quantified in, fruits and jackfruits (Artocarpus heterophyllus). This could make artonin L a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Artonin L.
Structure
Data?1563863576
Synonyms
ValueSource
5a,6-dihydro-3,8-Dihydroxy-1,10-dimethoxy-5,5-dimethyl-5H,7H-benzofuro[3,4-BC]xanthen-7-oneHMDB
Chemical FormulaC22H20O7
Average Molecular Weight396.39
Monoisotopic Molecular Weight396.120902994
IUPAC Name8,17-dihydroxy-6,19-dimethoxy-14,14-dimethyl-3,15-dioxapentacyclo[11.6.1.0²,¹¹.0⁴,⁹.0¹⁶,²⁰]icosa-1(20),2(11),4(9),5,7,16,18-heptaen-10-one
Traditional Nameartonin L
CAS Registry Number148719-52-2
SMILES
COC1=CC2=C(C(O)=C1)C(=O)C1=C(O2)C2=C3C(C1)C(C)(C)OC3=C(O)C=C2OC
InChI Identifier
InChI=1S/C22H20O7/c1-22(2)11-7-10-19(25)17-12(23)5-9(26-3)6-15(17)28-20(10)18-14(27-4)8-13(24)21(29-22)16(11)18/h5-6,8,11,23-24H,7H2,1-4H3
InChI KeyLDQNIBPJKBVZEF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthones
Alternative Parents
Substituents
  • Naphthopyranone
  • Xanthone
  • Naphthopyran
  • Chromone
  • Naphthalene
  • Coumaran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point249 - 250 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.81 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP3.84ALOGPS
logP3.13ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)6.26ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity105.11 m³·mol⁻¹ChemAxon
Polarizability41.13 ųChemAxon
Number of Rings5ChemAxon
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]+189.8231661259
DarkChem[M-H]-191.22631661259
DeepCCS[M+H]+195.4830932474
DeepCCS[M-H]-193.08430932474
DeepCCS[M-2H]-226.01830932474
DeepCCS[M+Na]+201.39230932474
AllCCS[M+H]+191.932859911
AllCCS[M+H-H2O]+189.132859911
AllCCS[M+NH4]+194.532859911
AllCCS[M+Na]+195.232859911
AllCCS[M-H]-197.932859911
AllCCS[M+Na-2H]-197.532859911
AllCCS[M+HCOO]-197.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Artonin LCOC1=CC2=C(C(O)=C1)C(=O)C1=C(O2)C2=C3C(C1)C(C)(C)OC3=C(O)C=C2OC5127.7Standard polar33892256
Artonin LCOC1=CC2=C(C(O)=C1)C(=O)C1=C(O2)C2=C3C(C1)C(C)(C)OC3=C(O)C=C2OC3436.0Standard non polar33892256
Artonin LCOC1=CC2=C(C(O)=C1)C(=O)C1=C(O2)C2=C3C(C1)C(C)(C)OC3=C(O)C=C2OC3661.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Artonin L,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(OC)C=C(O)C2=C1C(C3)C(C)(C)O23424.9Semi standard non polar33892256
Artonin L,1TMS,isomer #2COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C(OC)C=C(O[Si](C)(C)C)C2=C1C(C3)C(C)(C)O23425.7Semi standard non polar33892256
Artonin L,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(OC)C=C(O[Si](C)(C)C)C2=C1C(C3)C(C)(C)O23345.1Semi standard non polar33892256
Artonin L,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(OC)C=C(O)C2=C1C(C3)C(C)(C)O23639.3Semi standard non polar33892256
Artonin L,1TBDMS,isomer #2COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C(OC)C=C(O[Si](C)(C)C(C)(C)C)C2=C1C(C3)C(C)(C)O23645.9Semi standard non polar33892256
Artonin L,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C(OC2=C1)C1=C(OC)C=C(O[Si](C)(C)C(C)(C)C)C2=C1C(C3)C(C)(C)O23798.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Artonin L GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gc1-0519000000-f572ec85456b80c015442017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artonin L GC-MS (2 TMS) - 70eV, Positivesplash10-00vi-3251890000-a96793fe0ccb430daacf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artonin L 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 - Artonin L 10V, Negative-QTOFsplash10-0002-0009000000-8bb90e754011fd1e7f0b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 20V, Negative-QTOFsplash10-0002-0009000000-523135af9e0212267dbe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 40V, Negative-QTOFsplash10-0002-1059000000-afc0bd40db8c18cd1d7f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 10V, Negative-QTOFsplash10-0002-0009000000-54596df843a8eea22e952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 20V, Negative-QTOFsplash10-0002-0009000000-54596df843a8eea22e952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 40V, Negative-QTOFsplash10-00di-0693000000-8f85486fac9976496c442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 10V, Positive-QTOFsplash10-0002-0009000000-f3e574f91e7ab9be88e42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 20V, Positive-QTOFsplash10-00mk-0109000000-1a873e75469f51ca11072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 40V, Positive-QTOFsplash10-000i-0429000000-1abe2eacb4ffd3d6350f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 10V, Positive-QTOFsplash10-0002-0009000000-bad59473d38f9f345cb42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 20V, Positive-QTOFsplash10-0002-0009000000-bad59473d38f9f345cb42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin L 40V, Positive-QTOFsplash10-014j-0729000000-b17925ac889f3a2cc9842021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB020471
KNApSAcK IDC00013479
Chemspider ID24844321
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44258662
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1885331
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.. .