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(-)-Maackiain (FDB015548)

Record Information
Version1.0
Creation date2010-04-08 22:11:55 UTC
Update date2019-11-26 03:11:49 UTC
Primary IDFDB015548
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Maackiain
Description6-Hydroxyluteolin, also known as 6-OH-luteolin, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, 6-hydroxyluteolin is considered to be a flavonoid lipid molecule. 6-Hydroxyluteolin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 6-Hydroxyluteolin is found, on average, in the highest concentration within mexican oregano. 6-Hydroxyluteolin has also been detected, but not quantified in, a few different foods, such as common thymes, green vegetables, and lemon verbena. This could make 6-hydroxyluteolin a potential biomarker for the consumption of these foods.
CAS Number2035-15-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
logP2.19ALOGPS
logP2.29ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)9.42ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity72.36 m³·mol⁻¹ChemAxon
Polarizability28.64 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H12O5
IUPAC name5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-16-ol
InChI IdentifierInChI=1S/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2
InChI KeyHUKSJTUUSUGIDC-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1CO2
Average Molecular Weight284.2635
Monoisotopic Molecular Weight284.068473494
Classification
Description Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • 6-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.60%; H 4.25%; O 28.14%DFC
Melting PointMp 179-181°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.61ARNOLDI,A & MERLINI,L (1990)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -260 (c, 1.0 in Me2CO)DFC
Spectroscopic UV Data310 (e 8500) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(-)-Maackiain, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-1159-1490000000-db9b5560f54efd8bc916Spectrum
Predicted GC-MS(-)-Maackiain, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ec-6449000000-84980ba53447231be297Spectrum
Predicted GC-MS(-)-Maackiain, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Maackiain, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Maackiain, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , positivesplash10-0uk9-0910000000-0944f6b9dd6a928f30a82017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-c7cbd6418a879e0416662015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-8348e7e4d29458b4ce4b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hmt-9470000000-bf8ac90fedba7ff40fb82015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-95c433a225337b39a52d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-b3b5bfae974a783c3f852015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0wmr-2290000000-954882baaeaa154d058f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-549f6b30f75977e8ff352021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-09ee75f9980cbcca480e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsr-0290000000-c4842c0eec92bc9f47f72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-edc9ea273e98ea6aa00a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-8e39ae184183711b863a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0390000000-0c56add68e3a718eadd62021-09-22View Spectrum
NMRNot Available
ChemSpider ID323014
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID363863
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36629
CRC / DFC (Dictionary of Food Compounds) IDKDD61-G:KDD59-L
EAFUS IDNot Available
Dr. Duke ID(-)-MAACKIAIN
BIGG IDNot Available
KNApSAcK IDC00002546
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
quinone-reductase inducerDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.