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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:54:17 UTC
Update Date2018-03-12 22:07:48 UTC
HMDB IDHMDB0037654
Secondary Accession Numbers
  • HMDB37654
Metabolite Identification
Common NameEphedrannin A
DescriptionEphedrannin a belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Ephedrannin a exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, ephedrannin a is primarily located in the membrane (predicted from logP). Outside of the human body, ephedrannin a can be found in fruits. This makes ephedrannin a a potential biomarker for the consumption of this food product.
Structure
Thumb
Synonyms
ValueSource
3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavoneHMDB
3,5,11,13,15-Pentahydroxy-2,8-bis(4-hydroxyphenyl)-8,14-methano-4H,14H-1-benzopyrano[7,8-D][1,3]benzodioxocin-4-one, 9ciHMDB
ent-Epiafzelechin(2a->o-7,4a->8)kaempferolHMDB
Chemical FormulaC30H20O11
Average Molecular Weight556.4732
Monoisotopic Molecular Weight556.100561482
IUPAC Name(1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one
Traditional Name(1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one
CAS Registry Number82001-39-6
SMILES
O[C@H]1[C@H]2C3=C(O[C@@]1(OC1=C2C2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)C=C(O)C=C3O
InChI Identifier
InChI=1S/C30H20O11/c31-14-5-1-12(2-6-14)27-26(37)25(36)22-18(35)11-20-23(28(22)39-27)24-21-17(34)9-16(33)10-19(21)40-30(41-20,29(24)38)13-3-7-15(32)8-4-13/h1-11,24,29,31-35,37-38H/t24-,29-,30+/m0/s1
InChI KeyGPBSBBVDERLESN-QZFRTWIZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative Parents
Substituents
  • Bi- and polyflavonoid skeleton
  • Pyranoflavonoid
  • 3-hydroxyflavone
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Flavone
  • Hydroxyflavonoid
  • Flavan
  • Pyranochromene
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Ketal
  • Phenol
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point360 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP3.31ALOGPS
logP4.56ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)7.97ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity143.1 m³·mol⁻¹ChemAxon
Polarizability54.48 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002r-0030290000-afbe0568fb9d4a9bd8b5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-009i-9000043000-5e9de233dd1d4d447257View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000090000-c9e2c206ef81ca356562View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0020090000-4da7fbd03d990273711fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9211010000-bb8a33f5767669710730View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0010190000-ec195d53109cff7da707View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0130290000-00196a1994a008185194View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00pi-1950010000-5e560630a0e079428932View in MoNA
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
FoodDB IDFDB016776
KNApSAcK IDC00009274
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21676348
PDB IDNot Available
ChEBI 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.. .