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Record Information
Version2.0
Created at2022-04-27 23:49:51 UTC
Updated at2022-04-27 23:49:51 UTC
NP-MRD IDNP0052980
Secondary Accession NumbersNone
Natural Product Identification
Common NameGossypetin
DescriptionGossypetin, also known as articulatidin or equisporol, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, gossypetin is considered to be a flavonoid lipid molecule. A hexahydroxyflavone having the hydroxy groups placed at the 3-, 3'-, 4'-, 5- 7- and 8-positions. Gossypetin is found in Abelmoschus manihot, Adina cordifolia Roxb. , Askidiosperma andreaeanum, Erica cinerea, Gossypium herbaceum , Hibiscus sabdariffa L. , Hibiscus sabdariffa, Lotus corniculatus, Millettia zechiana, Rhodiola rosea, Rhododendron intranervatum, Sedum album and Sinocrassula indica . Gossypetin was first documented in 1989 (PMID: 2676226). Gossypetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 19895818) (PMID: 22953867) (PMID: 8424824).
Structure
Thumb
Synonyms
ValueSource
3,3',4',5,7,8-HexahydroxyflavoneChEBI
ArticulatidinChEBI
EquisporolChEBI
2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4H-chromen-4-oneMeSH
Chemical FormulaC15H10O8
Average Mass318.2370 Da
Monoisotopic Mass318.03757 Da
IUPAC Name2-(3,4-dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4H-chromen-4-one
Traditional Namegossypetin
CAS Registry NumberNot Available
SMILES
OC1=CC(O)=C(O)C2=C1C(=O)C(O)=C(O2)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)14-13(22)12(21)10-8(18)4-9(19)11(20)15(10)23-14/h1-4,16-20,22H
InChI KeyYRRAGUMVDQQZIY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus manihotLOTUS Database
Adina cordifolia Roxb.Plant
Askidiosperma andreaeanumLOTUS Database
Erica cinereaPlant
Gossypium herbaceumPlant
Hibiscus sabbariffaPlant
Hibiscus sabdariffaLOTUS Database
Lotus corniculatusLOTUS Database
Millettia zechianaLOTUS Database
Rhodiola roseaLOTUS Database
Rhododendron intranervatumLOTUS Database
Sedum albumLOTUS Database
Sinocrassula indicaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 8-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.66ALOGPS
logP1.85ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.59ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area147.68 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity78.84 m³·mol⁻¹ChemAxon
Polarizability29.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0152473
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00004721
Chemspider IDNot Available
KEGG Compound IDC04109
BioCyc ID334578-HEXAHYDROXYFLAVONE
BiGG IDNot Available
Wikipedia LinkGossypetin
METLIN IDNot Available
PubChem Compound5280647
PDB IDNot Available
ChEBI ID16400
Good Scents IDNot Available
References
General References
  1. Yamaguchi Y, Masuda M, Sasakawa H, Nonaka T, Hanashima S, Hisanaga S, Kato K, Hasegawa M: Characterization of inhibitor-bound alpha-synuclein dimer: role of alpha-synuclein N-terminal region in dimerization and inhibitor binding. J Mol Biol. 2010 Jan 22;395(3):445-56. doi: 10.1016/j.jmb.2009.10.068. Epub 2009 Nov 3. [PubMed:19895818 ]
  2. Mammen D, Daniel M: A critical evaluation on the reliability of two aluminum chloride chelation methods for quantification of flavonoids. Food Chem. 2012 Dec 1;135(3):1365-8. doi: 10.1016/j.foodchem.2012.05.109. Epub 2012 Jun 7. [PubMed:22953867 ]
  3. Francis AR, Shetty TK, Bhattacharya RK: Modulating effect of plant flavonoids on the mutagenicity of N-methyl-N'-nitro-N-nitrosoguanidine. Carcinogenesis. 1989 Oct;10(10):1953-5. doi: 10.1093/carcin/10.10.1953. [PubMed:2676226 ]
  4. Rankin SM, de Whalley CV, Hoult JR, Jessup W, Wilkins GM, Collard J, Leake DS: The modification of low density lipoprotein by the flavonoids myricetin and gossypetin. Biochem Pharmacol. 1993 Jan 7;45(1):67-75. doi: 10.1016/0006-2952(93)90378-a. [PubMed:8424824 ]