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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:08 UTC
Update Date2022-03-07 02:52:34 UTC
HMDB IDHMDB0030495
Secondary Accession Numbers
  • HMDB30495
Metabolite Identification
Common NameArtonol D
DescriptionArtonol D belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. Thus, artonol D is considered to be a flavonoid lipid molecule. Artonol D is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, artonol D has been detected, but not quantified in, breadfruits and fruits. This could make artonol D a potential biomarker for the consumption of these foods.
Structure
Data?1563861993
Synonyms
ValueSource
6-Hydroxy-3,3,12,12-tetramethyl-9-(1-methylethenyl)-3H,7H,8H-[1]benzopyrano[7,6-c]pyrano[3,2-H]xanthene-7,10,15(9H,12H)-trioneHMDB
Chemical FormulaC30H26O7
Average Molecular Weight498.5232
Monoisotopic Molecular Weight498.167853186
IUPAC Name17-hydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2(11),4(9),5,16(25),17,19(24),22-octaene-3,10,15-trione
Traditional Name17-hydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2(11),4(9),5,16(25),17,19(24),22-octaene-3,10,15-trione
CAS Registry Number186824-60-2
SMILES
CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(=O)C1=C(C=CC(C)(C)O1)C2=O
InChI Identifier
InChI=1S/C30H26O7/c1-13(2)16-11-17-24(33)21-18(31)12-19-14(7-9-29(3,4)36-19)26(21)35-27(17)22-20(16)25(34)28-15(23(22)32)8-10-30(5,6)37-28/h7-10,12,16,31H,1,11H2,2-6H3
InChI KeyBPBNMDXSLVPNFT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentPyranoxanthones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0029 g/LALOGPS
logP4.32ALOGPS
logP4.87ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)8.37ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area99.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity141.98 m³·mol⁻¹ChemAxon
Polarizability53.8 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+219.07230932474
DeepCCS[M-H]-216.70630932474
DeepCCS[M-2H]-249.94630932474
DeepCCS[M+Na]+224.98530932474
AllCCS[M+H]+220.032859911
AllCCS[M+H-H2O]+217.932859911
AllCCS[M+NH4]+222.032859911
AllCCS[M+Na]+222.632859911
AllCCS[M-H]-224.432859911
AllCCS[M+Na-2H]-225.532859911
AllCCS[M+HCOO]-226.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Artonol DCC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(=O)C1=C(C=CC(C)(C)O1)C2=O5233.0Standard polar33892256
Artonol DCC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(=O)C1=C(C=CC(C)(C)O1)C2=O3980.8Standard non polar33892256
Artonol DCC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(=O)C1=C(C=CC(C)(C)O1)C2=O4175.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Artonol D,1TMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C1C(=O)C1=C(C=CC(C)(C)O1)C2=O3949.3Semi standard non polar33892256
Artonol D,1TBDMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C1C(=O)C1=C(C=CC(C)(C)O1)C2=O4163.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Artonol D GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qd-4128900000-b672ccd77e0591b353da2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artonol D GC-MS (1 TMS) - 70eV, Positivesplash10-052f-5021790000-45c14d310e7dff4543f62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artonol D 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 - Artonol D 10V, Positive-QTOFsplash10-0002-0000900000-9265c8e2a3586fb0d9a02016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 20V, Positive-QTOFsplash10-0532-1000900000-db372d194b7fdfefc3822016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 40V, Positive-QTOFsplash10-014l-5001900000-a0868018459e7052c0b62016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 10V, Negative-QTOFsplash10-0002-0000900000-42d331ed5b623315b8592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 20V, Negative-QTOFsplash10-0002-0000900000-2e5b734c31cd218f389c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 40V, Negative-QTOFsplash10-01xt-1007900000-d4f6880feb496c3b87142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 10V, Positive-QTOFsplash10-0002-0000900000-49ba009c78e41d6913a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 20V, Positive-QTOFsplash10-0002-0000900000-2c1220ede40197c9ef502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 40V, Positive-QTOFsplash10-0a5c-1001900000-6a73c29a1a20c1e156242021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 10V, Negative-QTOFsplash10-0002-0000900000-81a00e8e9b17a468c82c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 20V, Negative-QTOFsplash10-052b-0000900000-b660e68c85ce0e71cab32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol D 40V, Negative-QTOFsplash10-0pb9-0000900000-1b98e0f6f8dd6597f9f42021-09-22Wishart 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 IDFDB002364
KNApSAcK IDC00013494
Chemspider ID8848293
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10672941
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .