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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:25:37 UTC
Update Date2022-03-07 02:56:45 UTC
HMDB IDHMDB0040836
Secondary Accession Numbers
  • HMDB40836
Metabolite Identification
Common NameHeteroflavanone B
DescriptionHeteroflavanone B belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. Thus, heteroflavanone b is considered to be a flavonoid. Heteroflavanone B has been detected, but not quantified in, fruits and jackfruits (Artocarpus heterophyllus). This could make heteroflavanone b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Heteroflavanone B.
Structure
Data?1563863593
Synonyms
ValueSource
5-Hydroxy-2',4',6',7-tetramethoxy-8-prenylflavanoneHMDB
Chemical FormulaC24H28O7
Average Molecular Weight428.4749
Monoisotopic Molecular Weight428.18350325
IUPAC Name5-hydroxy-7-methoxy-8-(3-methylbut-2-en-1-yl)-2-(2,4,6-trimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Nameheteroflavanone B
CAS Registry Number151171-29-8
SMILES
COC1=CC(OC)=C(C2CC(=O)C3=C(O2)C(CC=C(C)C)=C(OC)C=C3O)C(OC)=C1
InChI Identifier
InChI=1S/C24H28O7/c1-13(2)7-8-15-18(28-4)11-16(25)22-17(26)12-21(31-24(15)22)23-19(29-5)9-14(27-3)10-20(23)30-6/h7,9-11,21,25H,8,12H2,1-6H3
InChI KeyCQHDMUSZBYPHBO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct Parent8-prenylated flavanones
Alternative Parents
Substituents
  • 8-prenylated flavanone
  • 2p-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Phenol ether
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Point145 - 147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.036 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0082 g/LALOGPS
logP2.75ALOGPS
logP4.54ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.86ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.45 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity117.42 m³·mol⁻¹ChemAxon
Polarizability45.85 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.16631661259
DarkChem[M-H]-200.96931661259
DeepCCS[M+H]+206.54730932474
DeepCCS[M-H]-204.18930932474
DeepCCS[M-2H]-237.50330932474
DeepCCS[M+Na]+212.73130932474
AllCCS[M+H]+204.632859911
AllCCS[M+H-H2O]+202.032859911
AllCCS[M+NH4]+207.132859911
AllCCS[M+Na]+207.832859911
AllCCS[M-H]-207.832859911
AllCCS[M+Na-2H]-208.332859911
AllCCS[M+HCOO]-209.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Heteroflavanone BCOC1=CC(OC)=C(C2CC(=O)C3=C(O2)C(CC=C(C)C)=C(OC)C=C3O)C(OC)=C14763.4Standard polar33892256
Heteroflavanone BCOC1=CC(OC)=C(C2CC(=O)C3=C(O2)C(CC=C(C)C)=C(OC)C=C3O)C(OC)=C13404.2Standard non polar33892256
Heteroflavanone BCOC1=CC(OC)=C(C2CC(=O)C3=C(O2)C(CC=C(C)C)=C(OC)C=C3O)C(OC)=C13405.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Heteroflavanone B,1TMS,isomer #1COC1=CC(OC)=C(C2CC(=O)C3=C(O[Si](C)(C)C)C=C(OC)C(CC=C(C)C)=C3O2)C(OC)=C13213.8Semi standard non polar33892256
Heteroflavanone B,1TBDMS,isomer #1COC1=CC(OC)=C(C2CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(OC)C(CC=C(C)C)=C3O2)C(OC)=C13433.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Heteroflavanone B GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-2119700000-0c4b767efcd9cb9030de2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heteroflavanone B GC-MS (1 TMS) - 70eV, Positivesplash10-0079-3110900000-46fbbb9e841e63cd99e02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heteroflavanone B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heteroflavanone B 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 - Heteroflavanone B 10V, Negative-QTOFsplash10-004i-0000900000-c491d78d8a0a2cb67a302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroflavanone B 20V, Negative-QTOFsplash10-02e9-0149700000-d2e3aecd82823e6e37b42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroflavanone B 40V, Negative-QTOFsplash10-001s-1918100000-d18abb61c23a4cb3200d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroflavanone B 10V, Positive-QTOFsplash10-004i-1234900000-ff63ee5cab88e7351dcb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroflavanone B 20V, Positive-QTOFsplash10-066r-8469400000-17d819cc5bd3a4d804f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroflavanone B 40V, Positive-QTOFsplash10-0cdi-8911100000-0a62f1d9f30600dbe6662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroflavanone B 10V, Positive-QTOFsplash10-004i-0030900000-8c88d95b03f4494d9d612021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroflavanone B 20V, Positive-QTOFsplash10-000i-0090000000-5a72c87eba9da5af60282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heteroflavanone B 40V, Positive-QTOFsplash10-000i-0090000000-989b7b0700365d34e2492021-09-24Wishart 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 IDFDB020658
KNApSAcK IDC00008505
Chemspider ID24846508
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound42608026
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1886891
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.. .