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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:31 UTC
Update Date2022-03-07 02:55:00 UTC
HMDB IDHMDB0036629
Secondary Accession Numbers
  • HMDB36629
Metabolite Identification
Common 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. Outside of the human body, 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. A pentahydroxyflavone that is luteolin with an additional hydroxy group at position 6.
Structure
Data?1563862899
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-5,6,7-trihydroxy-4H-1-benzopyran-4-oneChEBI
3',4',5,6,7-PentahydroxyflavoneChEBI
5,6,7,3',4'-PentahydroxyflavoneChEBI
2-(3,4-Dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-oneHMDB
6-OH-LuteolinHMDB
3-Hydroxy-8,9-methylenedioxypterocarpaneChEBI
Inermin, (6ar-cis)-isomerMeSH, HMDB
Inermin, (6as-cis)-isomerMeSH, HMDB
6a,12a-dihydro-6H-(1,3)dioxolo(5,6)benzofuro(3,2-c)(1)Benzopyran-3-olMeSH, HMDB
InerminMeSH, HMDB
Chemical FormulaC16H12O5
Average Molecular Weight284.2635
Monoisotopic Molecular Weight284.068473494
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
Traditional 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
CAS Registry Number2035-15-6
SMILES
OC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1CO2
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point179 - 181 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.61Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.37731661259
DarkChem[M-H]-165.2431661259
DeepCCS[M+H]+168.66430932474
DeepCCS[M-H]-166.30630932474
DeepCCS[M-2H]-199.19230932474
DeepCCS[M+Na]+174.75730932474
AllCCS[M+H]+166.132859911
AllCCS[M+H-H2O]+162.332859911
AllCCS[M+NH4]+169.632859911
AllCCS[M+Na]+170.632859911
AllCCS[M-H]-170.232859911
AllCCS[M+Na-2H]-169.232859911
AllCCS[M+HCOO]-168.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-MaackiainOC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1CO23766.9Standard polar33892256
(-)-MaackiainOC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1CO22509.3Standard non polar33892256
(-)-MaackiainOC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1CO22774.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-Maackiain,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OCC1C3=CC4=C(C=C3OC21)OCO42699.8Semi standard non polar33892256
(-)-Maackiain,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OCC1C3=CC4=C(C=C3OC21)OCO42983.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Maackiain GC-MS (Non-derivatized) - 70eV, Positivesplash10-1159-1490000000-db9b5560f54efd8bc9162017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Maackiain GC-MS (1 TMS) - 70eV, Positivesplash10-00ec-6449000000-84980ba53447231be2972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Maackiain GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Maackiain GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Maackiain GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Maackiain , positive-QTOFsplash10-0uk9-0910000000-0944f6b9dd6a928f30a82017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 10V, Positive-QTOFsplash10-000i-0090000000-c7cbd6418a879e0416662015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 20V, Positive-QTOFsplash10-000i-0090000000-8348e7e4d29458b4ce4b2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 40V, Positive-QTOFsplash10-0hmt-9470000000-bf8ac90fedba7ff40fb82015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 10V, Negative-QTOFsplash10-001i-0090000000-95c433a225337b39a52d2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 20V, Negative-QTOFsplash10-001i-0090000000-b3b5bfae974a783c3f852015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 40V, Negative-QTOFsplash10-0wmr-2290000000-954882baaeaa154d058f2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 10V, Negative-QTOFsplash10-001i-0090000000-549f6b30f75977e8ff352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 20V, Negative-QTOFsplash10-001i-0090000000-09ee75f9980cbcca480e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 40V, Negative-QTOFsplash10-0fsr-0290000000-c4842c0eec92bc9f47f72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 10V, Positive-QTOFsplash10-000i-0090000000-edc9ea273e98ea6aa00a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 20V, Positive-QTOFsplash10-000i-0090000000-8e39ae184183711b863a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Maackiain 40V, Positive-QTOFsplash10-052r-0390000000-0c56add68e3a718eadd62021-09-22Wishart 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 ID278
FooDB IDFDB015551
KNApSAcK IDC00003884
Chemspider ID4444961
KEGG Compound IDC10072
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281642
PDB IDNot Available
ChEBI ID2197
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.. .