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Record Information
Version2.0
Created at2021-06-20 19:14:28 UTC
Updated at2021-08-20 00:00:32 UTC
NP-MRD IDNP0035932
Secondary Accession NumbersNone
Natural Product Identification
Common Nameeuxanthone
Provided ByJEOL DatabaseJEOL Logo
DescriptionEuxanthone, also known as purrenone, belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Euxanthone has been detected, but not quantified in, fruits and mammee apples (Mammea americana). This could make euxanthone a potential biomarker for the consumption of these foods. Euxanthone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. euxanthone is found in Bonnetia paniculata, Bonnettia spp., Calophyllum teysmannii, Cratoxylum arborescens, Cratoxylum cochinchinense, Cratoxylum formosum, Garcinia afzelii ENGL. , Garcinia bracteata, Garcinia subelliptica, Goniothalamus griffithii, Harungana madagascariensis, Hypericum androsaemum, Hypericum canariense, Hypericum erectum, Hypericum ericoides, Hypericum inodorum, Hypericum perforatum, Hypericum sampsonii, Mammea africana, Kayea assamica, Mesua ferrea, Pentadesma butyracea, Ploiarium alternifolium, Polygala tenuifolia, Senna obtusifolia, Syphonia globifera, Vismia latifolia and Weddellina squamulosa. euxanthone was first documented in 2000 (PMID: 10665986). Based on a literature review a small amount of articles have been published on Euxanthone (PMID: 11488451) (PMID: 12451499) (PMID: 16678494) (PMID: 17825492).
Structure
Thumb
Synonyms
ValueSource
1,7-DihydroxyxanthoneChEBI
EyxanthoneChEBI
PurrenoneChEBI
1,7-Dihydroxy-9H-xanthen-9-oneHMDB
1,7-Dihydroxy-9H-xanthen-9-one, 9ciHMDB
Chemical FormulaC13H8O4
Average Mass228.2002 Da
Monoisotopic Mass228.04226 Da
IUPAC Name1,7-dihydroxy-9H-xanthen-9-one
Traditional Nameeuxanthone
CAS Registry NumberNot Available
SMILES
[H]OC1=C([H])C2=C(OC3=C(C2=O)C(O[H])=C([H])C([H])=C3[H])C([H])=C1[H]
InChI Identifier
InChI=1S/C13H8O4/c14-7-4-5-10-8(6-7)13(16)12-9(15)2-1-3-11(12)17-10/h1-6,14-15H
InChI KeyKDXFPEKLLFWHMN-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bonnetia paniculataLOTUS Database
Bonnettia spp.-
Calophyllum bracteatumKNApSAcK Database
Calophyllum calabaKNApSAcK Database
Calophyllum cuneifoliumKNApSAcK Database
Calophyllum fragransKNApSAcK Database
Calophyllum inophyllumKNApSAcK Database
Calophyllum pulcherrimumKNApSAcK Database
Calophyllum ramiflorumKNApSAcK Database
Calophyllum sclerophyllumKNApSAcK Database
Calophyllum soulattriKNApSAcK Database
Calophyllum teysmanniiLOTUS Database
Calophyllum thwaitesiiKNApSAcK Database
Calophyllum tomentosumKNApSAcK Database
Calophyllum trapezifoliumKNApSAcK Database
Calophyllum walkeriKNApSAcK Database
Cratoxylum arborescensLOTUS Database
Cratoxylum cochinchinenseJEOL database
    • Ren, Y., et al, J. Nat. Prod. 74, 1117 (2011)
Cratoxylum formosanumKNApSAcK Database
Cratoxylum formosumLOTUS Database
Cratoxylum maingayiKNApSAcK Database
Garcinia afzeliiPlant
Garcinia afzelii ENGL.KNApSAcK Database
Garcinia bracteataKNApSAcK Database
Garcinia bracteata (nom. inval.)Plant
Garcinia cowaKNApSAcK Database
Garcinia dulcisKNApSAcK Database
Garcinia eugenifoliaKNApSAcK Database
Garcinia griffithiiKNApSAcK Database
Garcinia indicaKNApSAcK Database
Garcinia nobilisKNApSAcK Database
Garcinia oblongifoliaKNApSAcK Database
Garcinia schomburgkianaKNApSAcK Database
Garcinia spp.KNApSAcK Database
Garcinia subellipticaLOTUS Database
Garcinia xanthochymusKNApSAcK Database
Goniothalamus griffithiiLOTUS Database
Haploclathra spp.KNApSAcK Database
Harungana madagascariensisLOTUS Database
Hypericum androsaemumLOTUS Database
Hypericum ascyronKNApSAcK Database
Hypericum beaniiKNApSAcK Database
Hypericum canarienseLOTUS Database
Hypericum chinenseKNApSAcK Database
Hypericum erectumLOTUS Database
Hypericum ericoidesLOTUS Database
Hypericum geminiflorumKNApSAcK Database
Hypericum henryiKNApSAcK Database
Hypericum inodorumLOTUS Database
Hypericum perforatumLOTUS Database
Hypericum sampsoniiLOTUS Database
Hypericum scabrumKNApSAcK Database
Kayea assamicaKNApSAcK Database
Kielmeyera candidissimaKNApSAcK Database
Kielmeyera excelsaKNApSAcK Database
Lindera fruticosaKNApSAcK Database
Mammea africanaLOTUS Database
Mammea americanaKNApSAcK Database
Mammea siamensisKNApSAcK Database
Mangifera indicaKNApSAcK Database
Mesua assamicaPlant
Mesua ferreaLOTUS Database
Pentadesma butyraceaLOTUS Database
Platonia insignisKNApSAcK Database
Ploiarium alternifoliumLOTUS Database
Polygala caudataKNApSAcK Database
Polygala tenuifoliaLOTUS Database
Rheedia gardneriana Planch.et Triana.KNApSAcK Database
Securidaca inappendiculataKNApSAcK Database
Senna obtusifoliaLOTUS Database
Syphonia globifera-
Vismia latifoliaLOTUS Database
Vismia laurentiiKNApSAcK Database
Weddellina squamulosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthones
Alternative Parents
Substituents
  • Xanthone
  • Chromone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • 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 Solubility6.88 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.83ALOGPS
logP3ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)8.33ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.78 m³·mol⁻¹ChemAxon
Polarizability22.21 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0030724
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002648
KNApSAcK IDC00029364
Chemspider ID4444950
KEGG Compound IDC10061
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndian yellow
METLIN IDNot Available
PubChem Compound5281631
PDB IDNot Available
ChEBI ID4946
Good Scents IDrw1822271
References
General References
  1. Mak NK, Li WK, Zhang M, Wong RN, Tai LS, Yung KK, Leung HW: Effects of euxanthone on neuronal differentiation. Life Sci. 2000;66(4):347-54. doi: 10.1016/s0024-3205(99)00596-2. [PubMed:10665986 ]
  2. Mak NK, Lung HL, Wong RN, Leung HW, Tsang HY, Leung KN: Expression of protein kinase C isoforms in euxanthone-induced differentiation of neuroblastoma cells. Planta Med. 2001 Jul;67(5):400-5. doi: 10.1055/s-2001-15809. [PubMed:11488451 ]
  3. Saraiva L, Fresco P, Pinto E, Kijjoa A, Gonzalez MJ, Goncalves J: Differential activation of protein kinase C isoforms by euxanthone, revealed by an in vivo yeast phenotypic assay. Planta Med. 2002 Nov;68(11):1039-41. doi: 10.1055/s-2002-35655. [PubMed:12451499 ]
  4. Fang LH, Mu YM, Lin LL, Xiao PG, Du GH: Vasorelaxant effect of euxanthone in the rat thoracic aorta. Vascul Pharmacol. 2006 Aug;45(2):96-101. doi: 10.1016/j.vph.2006.03.011. Epub 2006 May 5. [PubMed:16678494 ]
  5. Naidu M, Kuan CY, Lo WL, Raza M, Tolkovsky A, Mak NK, Wong RN, Keynes R: Analysis of the action of euxanthone, a plant-derived compound that stimulates neurite outgrowth. Neuroscience. 2007 Sep 21;148(4):915-24. doi: 10.1016/j.neuroscience.2007.07.037. Epub 2007 Aug 1. [PubMed:17825492 ]
  6. Ren, Y., et al. (2011). Ren, Y., et al, J. Nat. Prod. 74, 1117 (2011). J. Nat. Prod..