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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:18 UTC
Update Date2019-01-11 19:41:13 UTC
HMDB IDHMDB0030832
Secondary Accession Numbers
  • HMDB30832
Metabolite Identification
Common NameAmentoflavone
DescriptionAmentoflavone is found in fruits. Amentoflavone is obtained from Viburnum prunifolium (black haw
Structure
Data?1547235673
Synonyms
ValueSource
3',8''-BiapigeninChEBI
8-(5-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
Didemethyl-ginkgetinChEBI
3',8-Bi[4',5,7-trihydroxyflavone]HMDB
4',4''',5,5'',7,7''-hexahydroxy-3''',8-biflavone, 8ciHMDB
4',5,7-Trihydroxyflavone(3'->8)-4',5,7-trihydroxyflavoneHMDB
Chemical FormulaC30H18O10
Average Molecular Weight538.4579
Monoisotopic Molecular Weight538.089996796
IUPAC Name8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Nameamentoflavone
CAS Registry Number1617-53-4
SMILES
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C(=C2O1)C1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H
InChI KeyYUSWMAULDXZHPY-UHFFFAOYSA-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
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0072 g/LALOGPS
logP4.49ALOGPS
logP5.09ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)6.12ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area173.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity144.91 m³·mol⁻¹ChemAxon
Polarizability53.8 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c09-0200490000-63358733c6bb47bf6a40JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014r-1200009000-9c92f959ae5bf7dabc00JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0000090000-a2ad9524a4b5b2c3f42fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0000090000-e1b205013e032e02da57JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0000090000-3d45e3164b8d5d4877f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0002390000-dbb1987153fe31c83ecdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0003900000-2d367fc9a6536b2cb27cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0003900000-af93fe7c4b3d9b1dd498JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0003900000-023b65180070d0844e7bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0003900000-25032f63ef80927e4582JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000090000-595f2028bc04129bb51bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0000190000-0cf207dcedb3a61b05e6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ul0-4938860000-d61d32f383bfdc33f0fdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-631b14a2bc03068132c6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000190000-5964bc41496f1188a3b4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-5726940000-fa1d5c1697d66a7d066cJSpectraViewer | 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 IDFDB002788
KNApSAcK IDC00001015
Chemspider ID4444919
KEGG Compound IDC10018
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmentoflavone
METLIN IDNot Available
PubChem Compound5281600
PDB IDNot Available
ChEBI ID2631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tarallo V, Lepore L, Marcellini M, Dal Piaz F, Tudisco L, Ponticelli S, Lund FW, Roepstorff P, Orlandi A, Pisano C, De Tommasi N, De Falco S: The biflavonoid amentoflavone inhibits neovascularization preventing the activity of proangiogenic vascular endothelial growth factors. J Biol Chem. 2011 Jun 3;286(22):19641-51. doi: 10.1074/jbc.M110.186239. Epub 2011 Apr 6. [PubMed:21471210 ]
  2. Kim HK, Son KH, Chang HW, Kang SS, Kim HP: Amentoflavone, a plant biflavone: a new potential anti-inflammatory agent. Arch Pharm Res. 1998 Aug;21(4):406-10. [PubMed:9875467 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Amentoflavone → 6-[(2-{3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-4-hydroxyphenyl}-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Amentoflavone → 6-[(2-{3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-4-hydroxyphenyl}-7-hydroxy-4-oxo-4H-chromen-5-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Amentoflavone → 6-{2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Amentoflavone → 6-({8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Amentoflavone → 6-({8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Amentoflavone → 6-(4-{8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-4-oxo-4H-chromen-2-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails