(-)-Maackiain (CHEM030291)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:47:46 UTC
Update Date2016-11-09 01:19:02 UTC
Accession NumberCHEM030291
Identification
Common Name(-)-Maackiain
ClassSmall Molecule
DescriptionA pentahydroxyflavone that is luteolin with an additional hydroxy group at position 6.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass284.264 g/mol
Monoisotopic Mass284.068 g/mol
CAS Registry Number2035-15-6
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
SMILESOC1=CC2=C(C=C1)C1OC3=CC4=C(OCO4)C=C3C1CO2
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-1159-1490000000-db9b5560f54efd8bc916Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ec-6449000000-84980ba53447231be297Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uk9-0910000000-0944f6b9dd6a928f30a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-c7cbd6418a879e041666Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-8348e7e4d29458b4ce4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hmt-9470000000-bf8ac90fedba7ff40fb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-95c433a225337b39a52dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-b3b5bfae974a783c3f85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0wmr-2290000000-954882baaeaa154d058fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-549f6b30f75977e8ff35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-09ee75f9980cbcca480eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsr-0290000000-c4842c0eec92bc9f47f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-edc9ea273e98ea6aa00aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-8e39ae184183711b863aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0390000000-0c56add68e3a718eadd6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0036632
FooDB IDFDB015551
Phenol Explorer ID278
KNApSAcK IDC00003884
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444961
ChEBI ID2197
PubChem Compound ID5281642
Kegg Compound IDC10072
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10048707
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12693635
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19666078
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21236437
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.