Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:33:37 UTC
Update Date2022-03-07 02:55:16 UTC
HMDB IDHMDB0037322
Secondary Accession Numbers
  • HMDB37322
Metabolite Identification
Common NameDihydrooroxylin
DescriptionDihydrooroxylin belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, dihydrooroxylin is considered to be a flavonoid. Dihydrooroxylin has been detected, but not quantified in, fruits. This could make dihydrooroxylin a potential biomarker for the consumption of these foods. Dihydrooroxylin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Dihydrooroxylin.
Structure
Data?1563863010
Synonyms
ValueSource
5,7-Dihydroxy-6-methoxyflavanoneChEBI
Dihydrooroxylin aHMDB
DihydrooroxylinMeSH
Chemical FormulaC16H14O5
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
IUPAC Name5,7-dihydroxy-6-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namedihydrooroxylin A
CAS Registry Number18956-18-8
SMILES
COC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O
InChI Identifier
InChI=1S/C16H14O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-6,8,12,18-19H,7H2,1H3
InChI KeyQUAPPCXFYKSDSV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent6-O-methylated flavonoids
Alternative Parents
Substituents
  • 6-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Flavan
  • Chromone
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Organooxygen 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 Point177 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP3.01ALOGPS
logP2.98ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.44ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.77 m³·mol⁻¹ChemAxon
Polarizability29.33 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]+164.90431661259
DarkChem[M-H]-164.82431661259
DeepCCS[M+H]+162.38430932474
DeepCCS[M-H]-160.02630932474
DeepCCS[M-2H]-193.21730932474
DeepCCS[M+Na]+168.47730932474
AllCCS[M+H]+167.232859911
AllCCS[M+H-H2O]+163.532859911
AllCCS[M+NH4]+170.732859911
AllCCS[M+Na]+171.732859911
AllCCS[M-H]-168.432859911
AllCCS[M+Na-2H]-167.832859911
AllCCS[M+HCOO]-167.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydrooroxylinCOC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O3759.8Standard polar33892256
DihydrooroxylinCOC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O2546.2Standard non polar33892256
DihydrooroxylinCOC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O2515.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrooroxylin,1TMS,isomer #1COC1=C(O)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C2660.0Semi standard non polar33892256
Dihydrooroxylin,1TMS,isomer #2COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O2682.0Semi standard non polar33892256
Dihydrooroxylin,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C2676.4Semi standard non polar33892256
Dihydrooroxylin,1TBDMS,isomer #1COC1=C(O)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C(C)(C)C2891.4Semi standard non polar33892256
Dihydrooroxylin,1TBDMS,isomer #2COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O2919.0Semi standard non polar33892256
Dihydrooroxylin,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C(C)(C)C3079.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrooroxylin GC-MS (Non-derivatized) - 70eV, Positivesplash10-05g3-3490000000-9ae7565d0700b3592b112017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrooroxylin GC-MS (2 TMS) - 70eV, Positivesplash10-06dl-5719500000-560d4e9c3212dbf4b3a62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrooroxylin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrooroxylin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrooroxylin , positive-QTOFsplash10-00m0-0910000000-27c707ca1f3734432a8a2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 10V, Positive-QTOFsplash10-000i-0290000000-9124d61c9b4c9168b54f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 20V, Positive-QTOFsplash10-00li-0980000000-841336381aecd17caafb2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 40V, Positive-QTOFsplash10-0ldi-2900000000-3b1d097c03b13a1b692e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 10V, Negative-QTOFsplash10-000i-0090000000-512568fdac86ba822b172015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 20V, Negative-QTOFsplash10-000i-1390000000-7d54008aa89f5de591992015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 40V, Negative-QTOFsplash10-0g6r-5920000000-c8a34f8d8b40c7afaf4e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 10V, Positive-QTOFsplash10-000i-0090000000-b239d41c6032c85540b22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 20V, Positive-QTOFsplash10-001s-0940000000-7563f3723518f1ad8ed82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 40V, Positive-QTOFsplash10-001i-0900000000-2a0036a60b62e0e123822021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 10V, Negative-QTOFsplash10-000i-0090000000-72ed1dce05f1827799772021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 20V, Negative-QTOFsplash10-0019-0980000000-4752126b11a7fac030d82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrooroxylin 40V, Negative-QTOFsplash10-0udi-0900000000-0cf97750243d88d2ddc92021-09-25Wishart 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 IDFDB016342
KNApSAcK IDC00008148
Chemspider ID4475720
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5316733
PDB IDNot Available
ChEBI ID67376
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Dihydrooroxylin → 3,4,5-trihydroxy-6-[(5-hydroxy-6-methoxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]oxane-2-carboxylic aciddetails
Dihydrooroxylin → 3,4,5-trihydroxy-6-[(7-hydroxy-6-methoxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-5-yl)oxy]oxane-2-carboxylic aciddetails