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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:28 UTC
Update Date2022-03-07 02:52:39 UTC
HMDB IDHMDB0030694
Secondary Accession Numbers
  • HMDB30694
Metabolite Identification
Common Name(S)-5,7-Dihydroxy-6,8-dimethylflavanone
Description(S)-5,7-Dihydroxy-6,8-dimethylflavanone, also known as demethoxymatteucinol, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, (S)-5,7-dihydroxy-6,8-dimethylflavanone is considered to be a flavonoid. Based on a literature review a significant number of articles have been published on (S)-5,7-Dihydroxy-6,8-dimethylflavanone.
Structure
Data?1563862023
Synonyms
ValueSource
(-)-DemethoxymatteucinolHMDB
DemethoxymatteucinolHMDB
Desmethoxy-matteucinolHMDB
DesmethoxymatteucinolHMDB
Chemical FormulaC17H16O4
Average Molecular Weight284.3065
Monoisotopic Molecular Weight284.104859
IUPAC Name5,7-dihydroxy-6,8-dimethyl-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namedesmethoxymatteucinol
CAS Registry Number56297-79-1
SMILES
CC1=C(O)C(C)=C2OC(CC(=O)C2=C1O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C17H16O4/c1-9-15(19)10(2)17-14(16(9)20)12(18)8-13(21-17)11-6-4-3-5-7-11/h3-7,13,19-20H,8H2,1-2H3
InChI KeyHAIHGFWQOPJMPV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanones
Alternative Parents
Substituents
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • 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
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point202 - 204 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP2.96ALOGPS
logP4.17ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.67ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.39 m³·mol⁻¹ChemAxon
Polarizability30.4 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]+165.78831661259
DarkChem[M-H]-164.57231661259
DeepCCS[M+H]+166.79230932474
DeepCCS[M-H]-164.43430932474
DeepCCS[M-2H]-197.78630932474
DeepCCS[M+Na]+173.01330932474
AllCCS[M+H]+166.832859911
AllCCS[M+H-H2O]+163.132859911
AllCCS[M+NH4]+170.232859911
AllCCS[M+Na]+171.232859911
AllCCS[M-H]-169.732859911
AllCCS[M+Na-2H]-169.132859911
AllCCS[M+HCOO]-168.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-5,7-Dihydroxy-6,8-dimethylflavanoneCC1=C(O)C(C)=C2OC(CC(=O)C2=C1O)C1=CC=CC=C13836.9Standard polar33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanoneCC1=C(O)C(C)=C2OC(CC(=O)C2=C1O)C1=CC=CC=C12622.3Standard non polar33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanoneCC1=C(O)C(C)=C2OC(CC(=O)C2=C1O)C1=CC=CC=C12548.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,1TMS,isomer #1CC1=C(O)C2=C(OC(C3=CC=CC=C3)CC2=O)C(C)=C1O[Si](C)(C)C2668.0Semi standard non polar33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,1TMS,isomer #2CC1=C(O)C(C)=C(O[Si](C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O2669.8Semi standard non polar33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O2691.3Semi standard non polar33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,1TBDMS,isomer #1CC1=C(O)C2=C(OC(C3=CC=CC=C3)CC2=O)C(C)=C1O[Si](C)(C)C(C)(C)C2891.1Semi standard non polar33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,1TBDMS,isomer #2CC1=C(O)C(C)=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O2888.0Semi standard non polar33892256
(S)-5,7-Dihydroxy-6,8-dimethylflavanone,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C1=CC=CC=C1)CC2=O3103.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-2590000000-785e0fbfff2f98942aa32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone GC-MS (2 TMS) - 70eV, Positivesplash10-0c2c-7928500000-689b4f38ea41c285fdf32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 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 - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 10V, Positive-QTOFsplash10-000i-0490000000-99936654c83854287bba2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 20V, Positive-QTOFsplash10-07wl-2940000000-9d545b0c06effa6d3ddd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 40V, Positive-QTOFsplash10-0bt9-2900000000-01951ed411e8fba53c372015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 10V, Negative-QTOFsplash10-001i-0190000000-aae499b09d9f06d8e1042015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 20V, Negative-QTOFsplash10-001i-1790000000-c3de3e95865363c9d3f52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 40V, Negative-QTOFsplash10-004r-6900000000-6aa05df22d78a14450fe2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 10V, Negative-QTOFsplash10-001i-0090000000-3ffcbf9f9605ea2feb0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 20V, Negative-QTOFsplash10-003r-0980000000-3dceb36665bdc42168cc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 40V, Negative-QTOFsplash10-0udi-0900000000-4e2d7aeec72c540f98132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 10V, Positive-QTOFsplash10-000i-0090000000-73f3d88b664986140f8c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 20V, Positive-QTOFsplash10-001s-0940000000-fe40b781b7c352a532bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6,8-dimethylflavanone 40V, Positive-QTOFsplash10-001i-0900000000-9c3186ac53707ab6c4e62021-09-22Wishart 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 IDFDB002615
KNApSAcK IDC00008168
Chemspider ID542961
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound625031
PDB IDNot Available
ChEBI IDNot Available
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. Resurreccion-Magno MH, Villasenor IM, Harada N, Monde K: Antihyperglycaemic flavonoids from Syzygium samarangense (Blume) Merr. and Perry. Phytother Res. 2005 Mar;19(3):246-51. [PubMed:15934025 ]
  2. (). 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
(S)-5,7-Dihydroxy-6,8-dimethylflavanone → 3,4,5-trihydroxy-6-[(7-hydroxy-6,8-dimethyl-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-5-yl)oxy]oxane-2-carboxylic aciddetails
(S)-5,7-Dihydroxy-6,8-dimethylflavanone → 3,4,5-trihydroxy-6-[(5-hydroxy-6,8-dimethyl-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]oxane-2-carboxylic aciddetails