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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:59:28 UTC
Update Date2022-03-07 02:56:58 UTC
HMDB IDHMDB0041323
Secondary Accession Numbers
  • HMDB41323
Metabolite Identification
Common NameHeteroartonin A
DescriptionHeteroartonin A belongs to the class of organic compounds known as 3'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3'-position. Thus, heteroartonin a is considered to be a flavonoid. Heteroartonin A has been detected, but not quantified in, fruits and jackfruits (Artocarpus heterophyllus). This could make heteroartonin a a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Heteroartonin A.
Structure
Data?1563863650
Synonyms
ValueSource
2',5,5',7-Tetrahydroxy-4'-methoxy-3,3'-diprenylflavoneHMDB
2-[2,5-Dihydroxy-4-methoxy-3-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-3-(3-methyl-2-butenyl)-4H-1-benzopyran-4-oneHMDB
Chemical FormulaC26H28O7
Average Molecular Weight452.4963
Monoisotopic Molecular Weight452.18350325
IUPAC Name2-[2,5-dihydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Traditional Nameheteroartonin A
CAS Registry Number170894-23-2
SMILES
COC1=C(O)C=C(C(O)=C1CC=C(C)C)C1=C(CC=C(C)C)C(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C26H28O7/c1-13(2)6-8-16-23(30)18(12-20(29)26(16)32-5)25-17(9-7-14(3)4)24(31)22-19(28)10-15(27)11-21(22)33-25/h6-7,10-12,27-30H,8-9H2,1-5H3
InChI KeyONBLHZQNAGITBB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent3'-prenylated flavones
Alternative Parents
Substituents
  • 3-prenylated flavone
  • 3'-prenylated flavone
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Prenylbenzoquinol
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Anisole
  • Phenoxy compound
  • Hydroquinone
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • 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 Point206 - 208 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0071 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0052 g/LALOGPS
logP4.61ALOGPS
logP5.58ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)6.6ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.16 m³·mol⁻¹ChemAxon
Polarizability49 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+209.60430932474
DeepCCS[M-H]-207.24630932474
DeepCCS[M-2H]-240.38630932474
DeepCCS[M+Na]+215.69830932474
AllCCS[M+H]+209.032859911
AllCCS[M+H-H2O]+206.532859911
AllCCS[M+NH4]+211.232859911
AllCCS[M+Na]+211.932859911
AllCCS[M-H]-205.932859911
AllCCS[M+Na-2H]-206.032859911
AllCCS[M+HCOO]-206.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Heteroartonin ACOC1=C(O)C=C(C(O)=C1CC=C(C)C)C1=C(CC=C(C)C)C(=O)C2=C(O)C=C(O)C=C2O15956.2Standard polar33892256
Heteroartonin ACOC1=C(O)C=C(C(O)=C1CC=C(C)C)C1=C(CC=C(C)C)C(=O)C2=C(O)C=C(O)C=C2O13560.5Standard non polar33892256
Heteroartonin ACOC1=C(O)C=C(C(O)=C1CC=C(C)C)C1=C(CC=C(C)C)C(=O)C2=C(O)C=C(O)C=C2O13848.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Heteroartonin A,1TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C(O)=C1CC=C(C)C3719.6Semi standard non polar33892256
Heteroartonin A,1TMS,isomer #2COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C(O[Si](C)(C)C)=C1CC=C(C)C3688.8Semi standard non polar33892256
Heteroartonin A,1TMS,isomer #3COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C(O)=C1CC=C(C)C3673.5Semi standard non polar33892256
Heteroartonin A,1TMS,isomer #4COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C(O)=C1CC=C(C)C3712.5Semi standard non polar33892256
Heteroartonin A,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C(O)=C1CC=C(C)C3628.0Semi standard non polar33892256
Heteroartonin A,2TMS,isomer #2COC1=C(O[Si](C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C(O)=C1CC=C(C)C3604.2Semi standard non polar33892256
Heteroartonin A,2TMS,isomer #3COC1=C(O[Si](C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C(O[Si](C)(C)C)=C1CC=C(C)C3637.1Semi standard non polar33892256
Heteroartonin A,2TMS,isomer #4COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C(O[Si](C)(C)C)=C1CC=C(C)C3611.7Semi standard non polar33892256
Heteroartonin A,2TMS,isomer #5COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C(O[Si](C)(C)C)=C1CC=C(C)C3566.5Semi standard non polar33892256
Heteroartonin A,2TMS,isomer #6COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C(O)=C1CC=C(C)C3599.9Semi standard non polar33892256
Heteroartonin A,3TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C(O)=C1CC=C(C)C3567.6Semi standard non polar33892256
Heteroartonin A,3TMS,isomer #2COC1=C(O[Si](C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C(O[Si](C)(C)C)=C1CC=C(C)C3584.5Semi standard non polar33892256
Heteroartonin A,3TMS,isomer #3COC1=C(O[Si](C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C(O[Si](C)(C)C)=C1CC=C(C)C3553.5Semi standard non polar33892256
Heteroartonin A,3TMS,isomer #4COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C(O[Si](C)(C)C)=C1CC=C(C)C3593.6Semi standard non polar33892256
Heteroartonin A,4TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C(O[Si](C)(C)C)=C1CC=C(C)C3596.7Semi standard non polar33892256
Heteroartonin A,1TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C(O)=C1CC=C(C)C3971.0Semi standard non polar33892256
Heteroartonin A,1TBDMS,isomer #2COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C3932.5Semi standard non polar33892256
Heteroartonin A,1TBDMS,isomer #3COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C(O)=C1CC=C(C)C3920.4Semi standard non polar33892256
Heteroartonin A,1TBDMS,isomer #4COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O)=C1CC=C(C)C3955.9Semi standard non polar33892256
Heteroartonin A,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O)=C1CC=C(C)C4086.4Semi standard non polar33892256
Heteroartonin A,2TBDMS,isomer #2COC1=C(O[Si](C)(C)C(C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C(O)=C1CC=C(C)C4053.4Semi standard non polar33892256
Heteroartonin A,2TBDMS,isomer #3COC1=C(O[Si](C)(C)C(C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C4084.3Semi standard non polar33892256
Heteroartonin A,2TBDMS,isomer #4COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C4040.6Semi standard non polar33892256
Heteroartonin A,2TBDMS,isomer #5COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C3994.7Semi standard non polar33892256
Heteroartonin A,2TBDMS,isomer #6COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O)=C1CC=C(C)C4044.2Semi standard non polar33892256
Heteroartonin A,3TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O)=C1CC=C(C)C4161.5Semi standard non polar33892256
Heteroartonin A,3TBDMS,isomer #2COC1=C(O[Si](C)(C)C(C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C4168.0Semi standard non polar33892256
Heteroartonin A,3TBDMS,isomer #3COC1=C(O[Si](C)(C)C(C)(C)C)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C4120.8Semi standard non polar33892256
Heteroartonin A,3TBDMS,isomer #4COC1=C(O)C=C(C2=C(CC=C(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C4165.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Heteroartonin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2003900000-aaa9be9fa57cf02c00862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heteroartonin A GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1000029000-d29bdc98aef1c5367da02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heteroartonin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heteroartonin A 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 - Heteroartonin A 10V, Positive-QTOFsplash10-0udi-0001900000-e4c629d427282a6bc4c02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 20V, Positive-QTOFsplash10-052b-9026800000-9073673795a9ec7593482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 40V, Positive-QTOFsplash10-0673-9150100000-a6ee01c277e19d78d34c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 10V, Negative-QTOFsplash10-0udi-0000900000-41cbf302ce91fe71c2652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 20V, Negative-QTOFsplash10-0udi-0012900000-51c596efb771739bac202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 40V, Negative-QTOFsplash10-0670-1676900000-da9b6435e007cb02e9382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 10V, Negative-QTOFsplash10-0udi-0000900000-d9f68c1f6d8700c377462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 20V, Negative-QTOFsplash10-0udi-0000900000-d9f68c1f6d8700c377462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 40V, Negative-QTOFsplash10-0f6x-0609200000-7dd5c8b6cd8a79bdd3fa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 10V, Positive-QTOFsplash10-0udi-0000900000-ea7301fbaeabffa2e2e32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 20V, Positive-QTOFsplash10-0udi-0000900000-ea7301fbaeabffa2e2e32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroartonin A 40V, Positive-QTOFsplash10-0udi-0916600000-2ff27a660f5d49519e292021-09-25Wishart 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 IDFDB021243
KNApSAcK IDC00013421
Chemspider ID24843907
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15231526
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1891381
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.. .