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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:45:33 UTC
Update Date2022-03-07 02:56:53 UTC
HMDB IDHMDB0041113
Secondary Accession Numbers
  • HMDB41113
Metabolite Identification
Common NameArtonin U
DescriptionArtonin U belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. Thus, artonin u is considered to be a flavonoid. Artonin U has been detected, but not quantified in, fruits and jackfruits (Artocarpus heterophyllus). This could make artonin u a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Artonin U.
Structure
Data?1563863624
Synonyms
ValueSource
4',5-Dihydroxy-7-methoxy-8-prenylflavoneHMDB
5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-oneHMDB
Chemical FormulaC21H20O5
Average Molecular Weight352.3805
Monoisotopic Molecular Weight352.13107375
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Traditional Nameartonin U
CAS Registry Number123549-17-7
SMILES
COC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C21H20O5/c1-12(2)4-9-15-19(25-3)11-17(24)20-16(23)10-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10-11,22,24H,9H2,1-3H3
InChI KeyBSZYNZDGUZYMDL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent8-prenylated flavones
Alternative Parents
Substituents
  • 8-prenylated flavone
  • 7-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Point238 - 239 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0065 g/LALOGPS
logP4.22ALOGPS
logP4.58ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)8.32ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.64 m³·mol⁻¹ChemAxon
Polarizability37.81 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+188.64830932474
DeepCCS[M-H]-186.2930932474
DeepCCS[M-2H]-220.07330932474
DeepCCS[M+Na]+195.37530932474
AllCCS[M+H]+185.132859911
AllCCS[M+H-H2O]+181.832859911
AllCCS[M+NH4]+188.132859911
AllCCS[M+Na]+189.032859911
AllCCS[M-H]-183.532859911
AllCCS[M+Na-2H]-183.032859911
AllCCS[M+HCOO]-182.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Artonin UCOC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C=C14730.4Standard polar33892256
Artonin UCOC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C=C13355.2Standard non polar33892256
Artonin UCOC1=C(CC=C(C)C)C2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C=C13444.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Artonin U,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1CC=C(C)C3378.3Semi standard non polar33892256
Artonin U,1TMS,isomer #2COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C=C3)OC2=C1CC=C(C)C3407.7Semi standard non polar33892256
Artonin U,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C=C3)OC2=C1CC=C(C)C3323.3Semi standard non polar33892256
Artonin U,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1CC=C(C)C3611.7Semi standard non polar33892256
Artonin U,1TBDMS,isomer #2COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)OC2=C1CC=C(C)C3642.9Semi standard non polar33892256
Artonin U,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)OC2=C1CC=C(C)C3830.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Artonin U GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1029000000-b607d86733c2cda7c9ec2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artonin U GC-MS (2 TMS) - 70eV, Positivesplash10-0089-2121900000-6ed8d1d528b6e419efcc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artonin U 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 U 10V, Positive-QTOFsplash10-0udi-0009000000-56ec9c33eac7a727877d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin U 20V, Positive-QTOFsplash10-0pvs-8059000000-a59be97e2f0440994d692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin U 40V, Positive-QTOFsplash10-0aor-9131000000-c0dc17985ccd9f82bbe72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin U 10V, Negative-QTOFsplash10-0udi-0009000000-b2af354bdc596b5bfa2b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin U 20V, Negative-QTOFsplash10-0udi-0019000000-4969f0137807ce811bf22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin U 40V, Negative-QTOFsplash10-06di-2936000000-0fe2bf3862b9f2567bc32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin U 10V, Negative-QTOFsplash10-0udi-0009000000-1d6850ea890a8c9b9a282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin U 20V, Negative-QTOFsplash10-0zg0-0009000000-abde728a1128c618231d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin U 10V, Positive-QTOFsplash10-0udi-0009000000-2df5fd0e444f819c89d02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin U 20V, Positive-QTOFsplash10-0udi-0009000000-427c924e6bdff42bdb4e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonin U 40V, Positive-QTOFsplash10-0ikl-0249000000-fc763badc112021fa5682021-09-23Wishart 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 IDFDB020995
KNApSAcK IDC00013410
Chemspider ID24843976
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44258358
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1889671
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.. .