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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:32:49 UTC
Update Date2021-10-13 08:30:19 UTC
HMDB IDHMDB0040934
Secondary Accession Numbers
  • HMDB40934
Metabolite Identification
Common NameUralene
DescriptionUralene belongs to the class of organic compounds known as 2'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 2'-position. Thus, uralene is considered to be a flavonoid. Uralene has been detected, but not quantified in, herbs and spices. This could make uralene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Uralene.
Structure
Data?1563863605
Synonyms
ValueSource
2-[4,5-Dihydroxy-2-(3-methyl-2-butenyl)phenyl]-5,6-dihydroxy-3-methoxy-4H-1-benzopyran-4-oneHMDB
4',5,5',6-Tetrahydroxy-3-methoxy-2'-prenylflavoneHMDB
5,6,3',4'-Tetrahydroxy-3-methoxy-6'-isoprenylflavoneHMDB, MeSH
Chemical FormulaC21H20O7
Average Molecular Weight384.3793
Monoisotopic Molecular Weight384.120902994
IUPAC Name2-[4,5-dihydroxy-2-(3-methylbut-2-en-1-yl)phenyl]-5,6-dihydroxy-3-methoxy-4H-chromen-4-one
Traditional Nameuralene
CAS Registry Number150853-99-9
SMILES
COC1=C(OC2=C(C(O)=C(O)C=C2)C1=O)C1=CC(O)=C(O)C=C1CC=C(C)C
InChI Identifier
InChI=1S/C21H20O7/c1-10(2)4-5-11-8-14(23)15(24)9-12(11)20-21(27-3)19(26)17-16(28-20)7-6-13(22)18(17)25/h4,6-9,22-25H,5H2,1-3H3
InChI KeyQSIXTSXIETZHGN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 2'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent2'-prenylated flavones
Alternative Parents
Substituents
  • 2'-prenylated flavone
  • 3-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 6-hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point216 - 218 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.39 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP10(3.77) g/LALOGPS
logP10(4) g/LChemAxon
logS10(-4.4) g/LALOGPS
pKa (Strongest Acidic)8.21ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.86 m³·mol⁻¹ChemAxon
Polarizability39.28 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
DarkChem[M+H]+189.69131661259
DarkChem[M-H]-190.60431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
UraleneCOC1=C(OC2=C(C(O)=C(O)C=C2)C1=O)C1=CC(O)=C(O)C=C1CC=C(C)C5326.0Standard polar33892256
UraleneCOC1=C(OC2=C(C(O)=C(O)C=C2)C1=O)C1=CC(O)=C(O)C=C1CC=C(C)C3479.3Standard non polar33892256
UraleneCOC1=C(OC2=C(C(O)=C(O)C=C2)C1=O)C1=CC(O)=C(O)C=C1CC=C(C)C3456.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Uralene,1TMS,isomer #1COC1=C(C2=CC(O)=C(O)C=C2CC=C(C)C)OC2=CC=C(O)C(O[Si](C)(C)C)=C2C1=O3363.4Semi standard non polar33892256
Uralene,1TMS,isomer #2COC1=C(C2=CC(O)=C(O)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C)C(O)=C2C1=O3390.4Semi standard non polar33892256
Uralene,1TMS,isomer #3COC1=C(C2=CC(O[Si](C)(C)C)=C(O)C=C2CC=C(C)C)OC2=CC=C(O)C(O)=C2C1=O3363.2Semi standard non polar33892256
Uralene,1TMS,isomer #4COC1=C(C2=CC(O)=C(O[Si](C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O)C(O)=C2C1=O3399.9Semi standard non polar33892256
Uralene,2TMS,isomer #1COC1=C(C2=CC(O[Si](C)(C)C)=C(O)C=C2CC=C(C)C)OC2=CC=C(O)C(O[Si](C)(C)C)=C2C1=O3263.4Semi standard non polar33892256
Uralene,2TMS,isomer #2COC1=C(C2=CC(O)=C(O[Si](C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O)C(O[Si](C)(C)C)=C2C1=O3286.2Semi standard non polar33892256
Uralene,2TMS,isomer #3COC1=C(C2=CC(O)=C(O)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2C1=O3289.0Semi standard non polar33892256
Uralene,2TMS,isomer #4COC1=C(C2=CC(O[Si](C)(C)C)=C(O)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C)C(O)=C2C1=O3297.8Semi standard non polar33892256
Uralene,2TMS,isomer #5COC1=C(C2=CC(O)=C(O[Si](C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C)C(O)=C2C1=O3322.5Semi standard non polar33892256
Uralene,2TMS,isomer #6COC1=C(C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O)C(O)=C2C1=O3296.5Semi standard non polar33892256
Uralene,3TMS,isomer #1COC1=C(C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O)C(O[Si](C)(C)C)=C2C1=O3240.6Semi standard non polar33892256
Uralene,3TMS,isomer #2COC1=C(C2=CC(O[Si](C)(C)C)=C(O)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2C1=O3254.8Semi standard non polar33892256
Uralene,3TMS,isomer #3COC1=C(C2=CC(O)=C(O[Si](C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2C1=O3268.6Semi standard non polar33892256
Uralene,3TMS,isomer #4COC1=C(C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C)C(O)=C2C1=O3278.4Semi standard non polar33892256
Uralene,4TMS,isomer #1COC1=C(C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2C1=O3243.2Semi standard non polar33892256
Uralene,1TBDMS,isomer #1COC1=C(C2=CC(O)=C(O)C=C2CC=C(C)C)OC2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2C1=O3619.6Semi standard non polar33892256
Uralene,1TBDMS,isomer #2COC1=C(C2=CC(O)=C(O)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2C1=O3671.0Semi standard non polar33892256
Uralene,1TBDMS,isomer #3COC1=C(C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2CC=C(C)C)OC2=CC=C(O)C(O)=C2C1=O3632.3Semi standard non polar33892256
Uralene,1TBDMS,isomer #4COC1=C(C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O)C(O)=C2C1=O3673.6Semi standard non polar33892256
Uralene,2TBDMS,isomer #1COC1=C(C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2CC=C(C)C)OC2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2C1=O3748.1Semi standard non polar33892256
Uralene,2TBDMS,isomer #2COC1=C(C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2C1=O3772.2Semi standard non polar33892256
Uralene,2TBDMS,isomer #3COC1=C(C2=CC(O)=C(O)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C1=O3767.6Semi standard non polar33892256
Uralene,2TBDMS,isomer #4COC1=C(C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2C1=O3800.5Semi standard non polar33892256
Uralene,2TBDMS,isomer #5COC1=C(C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2C1=O3825.5Semi standard non polar33892256
Uralene,2TBDMS,isomer #6COC1=C(C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O)C(O)=C2C1=O3799.6Semi standard non polar33892256
Uralene,3TBDMS,isomer #1COC1=C(C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2C1=O3864.1Semi standard non polar33892256
Uralene,3TBDMS,isomer #2COC1=C(C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C1=O3879.2Semi standard non polar33892256
Uralene,3TBDMS,isomer #3COC1=C(C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C1=O3895.0Semi standard non polar33892256
Uralene,3TBDMS,isomer #4COC1=C(C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2C1=O3911.6Semi standard non polar33892256
Uralene,4TBDMS,isomer #1COC1=C(C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2CC=C(C)C)OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C1=O4005.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Uralene GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1309000000-e6e57f04b09da749d9f82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Uralene GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-1100019000-663f963ff6642e4e751f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Uralene 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 - Uralene 10V, Positive-QTOFsplash10-000i-0009000000-54a363ea4f9040de435f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 20V, Positive-QTOFsplash10-0a4i-4109000000-f9afb44153f25f0f92c12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 40V, Positive-QTOFsplash10-0ab9-6903000000-e11eaf9f0d4bf54b5d8c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 10V, Negative-QTOFsplash10-001i-0009000000-6f5e86940011b306c8b02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 20V, Negative-QTOFsplash10-001i-0109000000-ef21d07a2148d550a0c12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 40V, Negative-QTOFsplash10-0a4i-2902000000-02ceba989119befe57c62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 10V, Positive-QTOFsplash10-000i-0009000000-77d0b62f69f9bbae89032021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 20V, Positive-QTOFsplash10-000i-0009000000-b5cdc31410af73dd46ac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 40V, Positive-QTOFsplash10-0udr-1904000000-7ccbd9bff8b13bcb82252021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 10V, Negative-QTOFsplash10-001i-0009000000-14c49b5639821ac7aea52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 20V, Negative-QTOFsplash10-001i-0309000000-cc40537a638781be7ee12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Uralene 40V, Negative-QTOFsplash10-0f9i-1902000000-5efd011135ee5ca58b212021-09-24Wishart 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 IDFDB020775
KNApSAcK IDC00005030
Chemspider ID167059
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound192490
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1887871
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.. .