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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:28:40 UTC
Update Date2022-03-07 02:53:50 UTC
HMDB IDHMDB0033720
Secondary Accession Numbers
  • HMDB33720
Metabolite Identification
Common Name6alpha-Hydroxymaackiain
Description6alpha-Hydroxymaackiain belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, 6alpha-hydroxymaackiain is considered to be a flavonoid. 6alpha-Hydroxymaackiain has been detected, but not quantified in, several different foods, such as herbal tea, common peas (Pisum sativum), teas (Camellia sinensis), red tea, and herbs and spices. This could make 6alpha-hydroxymaackiain a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6alpha-Hydroxymaackiain.
Structure
Data?1563862450
Synonyms
ValueSource
6a-HydroxymaackiainGenerator
6Α-hydroxymaackiainGenerator
3,6a-Dihydroxy-8,9-methylenedioxypterocarpanHMDB
6a-HydroxyinerminHMDB
Chemical FormulaC16H12O6
Average Molecular Weight300.2629
Monoisotopic Molecular Weight300.063388116
IUPAC Name5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaene-1,16-diol
Traditional Name6a-hydroxymaackiain
CAS Registry Number14602-93-8
SMILES
OC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO2
InChI Identifier
InChI=1S/C16H12O6/c17-8-1-2-9-11(3-8)19-6-16(18)10-4-13-14(21-7-20-13)5-12(10)22-15(9)16/h1-5,15,17-18H,6-7H2
InChI KeyGLMPLZUBQDAZEN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassFuranoisoflavonoids
Direct ParentPterocarpans
Alternative Parents
Substituents
  • Pterocarpan
  • Isoflavanol
  • Isoflavan
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Coumaran
  • Benzodioxole
  • Benzofuran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • 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 Point178 - 181 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.85 g/LALOGPS
logP2.03ALOGPS
logP1.63ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area77.38 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity73.45 m³·mol⁻¹ChemAxon
Polarizability29.44 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]+168.78731661259
DarkChem[M-H]-166.71631661259
DeepCCS[M+H]+172.33630932474
DeepCCS[M-H]-169.97830932474
DeepCCS[M-2H]-203.30230932474
DeepCCS[M+Na]+178.52930932474
AllCCS[M+H]+169.332859911
AllCCS[M+H-H2O]+165.732859911
AllCCS[M+NH4]+172.732859911
AllCCS[M+Na]+173.632859911
AllCCS[M-H]-172.432859911
AllCCS[M+Na-2H]-171.532859911
AllCCS[M+HCOO]-170.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6alpha-HydroxymaackiainOC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO24096.8Standard polar33892256
6alpha-HydroxymaackiainOC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO22630.1Standard non polar33892256
6alpha-HydroxymaackiainOC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1(O)CO22883.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6alpha-Hydroxymaackiain,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OCC1(O)C3=CC4=C(C=C3OC21)OCO42743.9Semi standard non polar33892256
6alpha-Hydroxymaackiain,1TMS,isomer #2C[Si](C)(C)OC12COC3=CC(O)=CC=C3C1OC1=CC3=C(C=C12)OCO32734.3Semi standard non polar33892256
6alpha-Hydroxymaackiain,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C)C3=CC4=C(C=C3OC21)OCO42771.3Semi standard non polar33892256
6alpha-Hydroxymaackiain,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OCC1(O)C3=CC4=C(C=C3OC21)OCO43033.5Semi standard non polar33892256
6alpha-Hydroxymaackiain,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC12COC3=CC(O)=CC=C3C1OC1=CC3=C(C=C12)OCO33027.6Semi standard non polar33892256
6alpha-Hydroxymaackiain,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C(C)(C)C)C3=CC4=C(C=C3OC21)OCO43323.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha-Hydroxymaackiain GC-MS (Non-derivatized) - 70eV, Positivesplash10-00e9-2491000000-26f6a52bb1441a699a1c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha-Hydroxymaackiain GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9306600000-9d9cfc38667e60ad550d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha-Hydroxymaackiain GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha-Hydroxymaackiain 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 - 6alpha-Hydroxymaackiain 10V, Positive-QTOFsplash10-0udi-0119000000-88a12010467f51a16e7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 20V, Positive-QTOFsplash10-0udi-0159000000-97ea99b0a2cc0e95db0f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 40V, Positive-QTOFsplash10-059i-4920000000-65e43ccd24522d03a1cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 10V, Negative-QTOFsplash10-0002-0090000000-77092a5451958d1ef64d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 20V, Negative-QTOFsplash10-0002-0090000000-30dabe2d04d67da1bc9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 40V, Negative-QTOFsplash10-01bi-2390000000-21099091b447e32b1fd22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 10V, Positive-QTOFsplash10-0udi-0009000000-545fc7c692e0abcd79662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 20V, Positive-QTOFsplash10-0udi-0019000000-62fb017d6994744e8a872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 40V, Positive-QTOFsplash10-03dr-1932000000-709479526669a409c2c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 10V, Negative-QTOFsplash10-0002-0090000000-fb4a565723d52a1e46242021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 20V, Negative-QTOFsplash10-0002-0090000000-57430cab9f56e0ef7f5b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxymaackiain 40V, Negative-QTOFsplash10-0002-0490000000-b932f2770060ce88c6b02021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB011839
KNApSAcK IDC00009677
Chemspider ID24785132
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257487
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .