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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:03 UTC
Update Date2022-03-07 02:52:37 UTC
HMDB IDHMDB0030628
Secondary Accession Numbers
  • HMDB30628
Metabolite Identification
Common NameRubraflavone A
DescriptionRubraflavone 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, rubraflavone a is considered to be a flavonoid. Based on a literature review very few articles have been published on Rubraflavone A.
Structure
Data?1563862014
Synonyms
ValueSource
2-(2,4-Dihydroxyphenyl)-3-(3,7-dimethyl-2,6-octadienyl)-7-hydroxy-4H-1-benzopyran-4-one, 9ciHMDB
3-Geranyl-2',4',7-trihydroxyflavoneHMDB
Chemical FormulaC25H26O5
Average Molecular Weight406.4709
Monoisotopic Molecular Weight406.178023942
IUPAC Name2-(2,4-dihydroxyphenyl)-3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-4H-chromen-4-one
Traditional Namerubraflavone A
CAS Registry Number54510-13-3
SMILES
CC(C)=CCC\C(C)=C\CC1=C(OC2=C(C=CC(O)=C2)C1=O)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C25H26O5/c1-15(2)5-4-6-16(3)7-10-21-24(29)20-12-9-18(27)14-23(20)30-25(21)19-11-8-17(26)13-22(19)28/h5,7-9,11-14,26-28H,4,6,10H2,1-3H3/b16-7+
InChI KeyVEQHJLTWOODSMA-FRKPEAEDSA-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
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Aromatic monoterpenoid
  • Benzopyran
  • Bicyclic monoterpenoid
  • 1-benzopyran
  • Monoterpenoid
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.019 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP5.32ALOGPS
logP5.33ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)6.47ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity120.28 m³·mol⁻¹ChemAxon
Polarizability44.99 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
DarkChem[M+H]+198.21231661259
DarkChem[M-H]-198.71531661259
DeepCCS[M+H]+203.81830932474
DeepCCS[M-H]-201.42230932474
DeepCCS[M-2H]-234.44430932474
DeepCCS[M+Na]+209.96230932474
AllCCS[M+H]+201.432859911
AllCCS[M+H-H2O]+198.732859911
AllCCS[M+NH4]+203.932859911
AllCCS[M+Na]+204.632859911
AllCCS[M-H]-195.332859911
AllCCS[M+Na-2H]-195.032859911
AllCCS[M+HCOO]-194.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Rubraflavone ACC(C)=CCC\C(C)=C\CC1=C(OC2=C(C=CC(O)=C2)C1=O)C1=C(O)C=C(O)C=C15222.6Standard polar33892256
Rubraflavone ACC(C)=CCC\C(C)=C\CC1=C(OC2=C(C=CC(O)=C2)C1=O)C1=C(O)C=C(O)C=C13429.5Standard non polar33892256
Rubraflavone ACC(C)=CCC\C(C)=C\CC1=C(OC2=C(C=CC(O)=C2)C1=O)C1=C(O)C=C(O)C=C13757.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Rubraflavone A,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O)C=C2O)OC2=CC(O[Si](C)(C)C)=CC=C2C1=O3574.2Semi standard non polar33892256
Rubraflavone A,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O)C=C2O[Si](C)(C)C)OC2=CC(O)=CC=C2C1=O3547.6Semi standard non polar33892256
Rubraflavone A,1TMS,isomer #3CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O[Si](C)(C)C)C=C2O)OC2=CC(O)=CC=C2C1=O3562.7Semi standard non polar33892256
Rubraflavone A,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O[Si](C)(C)C)C=C2O)OC2=CC(O[Si](C)(C)C)=CC=C2C1=O3475.6Semi standard non polar33892256
Rubraflavone A,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O)C=C2O[Si](C)(C)C)OC2=CC(O[Si](C)(C)C)=CC=C2C1=O3461.4Semi standard non polar33892256
Rubraflavone A,2TMS,isomer #3CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)OC2=CC(O)=CC=C2C1=O3465.5Semi standard non polar33892256
Rubraflavone A,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)OC2=CC(O[Si](C)(C)C)=CC=C2C1=O3464.9Semi standard non polar33892256
Rubraflavone A,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O)C=C2O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C1=O3839.1Semi standard non polar33892256
Rubraflavone A,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)OC2=CC(O)=CC=C2C1=O3802.8Semi standard non polar33892256
Rubraflavone A,1TBDMS,isomer #3CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)OC2=CC(O)=CC=C2C1=O3828.5Semi standard non polar33892256
Rubraflavone A,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C1=O3943.1Semi standard non polar33892256
Rubraflavone A,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C1=O3931.5Semi standard non polar33892256
Rubraflavone A,2TBDMS,isomer #3CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)OC2=CC(O)=CC=C2C1=O3927.7Semi standard non polar33892256
Rubraflavone A,3TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC1=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C1=O4087.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rubraflavone A GC-MS (Non-derivatized) - 70eV, Positivesplash10-060c-5329000000-7c99eac09f381e52c93c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rubraflavone A GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-4100069000-0b387eaa271fa60907b82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rubraflavone A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rubraflavone 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 - Rubraflavone A 10V, Positive-QTOFsplash10-0a4i-0235900000-80a4b73df17e322d92342016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 20V, Positive-QTOFsplash10-05v0-5976200000-651a5d9485faafdd0f1b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 40V, Positive-QTOFsplash10-0i00-9560000000-02dd22cd1fbe930ad3d42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 10V, Negative-QTOFsplash10-0a4i-0001900000-aafca611d6b04d4df61e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 20V, Negative-QTOFsplash10-0a4i-0024900000-a2afaabb8256d018f1ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 40V, Negative-QTOFsplash10-0aor-3968000000-efbe0ad67c16a376dfbc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 10V, Positive-QTOFsplash10-0a4i-0000900000-18eb98d75246f8994f012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 20V, Positive-QTOFsplash10-0a4i-0000900000-18eb98d75246f8994f012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 40V, Positive-QTOFsplash10-052r-0950600000-f320f25c83802faed8682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 10V, Negative-QTOFsplash10-0a4i-0000900000-4beb10611eb4ba1142872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 20V, Negative-QTOFsplash10-0a4i-0000900000-4beb10611eb4ba1142872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rubraflavone A 40V, Negative-QTOFsplash10-03dr-0409200000-4e301aa51cf6432f453d2021-09-22Wishart 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 IDFDB002529
KNApSAcK IDC00004018
Chemspider ID10306019
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21721909
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1821551
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.. .