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Record Information
Version2.0
Created at2022-03-17 20:56:08 UTC
Updated at2022-03-17 20:56:08 UTC
NP-MRD IDNP0048416
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhyscion
DescriptionPhyscion, also known as parienin or rheochrysidin, belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Physcion is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Physcion has been detected, but not quantified in, a few different foods, such as common sages, garden rhubarbs, and sorrels. This could make physcion a potential biomarker for the consumption of these foods. Physcion is found in Achyranthes bidentata, Alternaria porri, Alvaradoa jamaicensis, Annona montana, Aspergillus chevalieri, Aspergillus terreus , Berchemia discolor, Berchemia floribunda , Bletilla striata, Bourreria pulchra, Brassica rapa, Cortinarius rufo-olivaceus, Caloplaca saxicola, Cassia acutifolia , Cassia angustifolia , Cassia fistula, Senna sulfurea, Cassia nomae, Cassia occidentalis , Cassia roxburghii, Cassia tora , Cassia torosa L., Chamaecrista pumila, Cortinarius basirubescens, Dermocybe canaria, Cortinarius sanguineus, Cratoxylum arborescens, Cratoxylum formosum, Dendrobium loddigesii, Dendrobium thyrsiflorum, Derris oblonga, Entodon luridus, Ephedra sinica , Eupatorium cannabinum, Ageratina altissima, Fallopia multiflora, Fibraurea tinctoria, Flavocetraria cucullata, Frangula alnus, Fulgensia canariensis, Harrisonia perforata, Harungana madagascariensis, Leucosceptrum canum, Limonia acidissima, Maesopsis eminii, Mentha canadensis, Millettia leucantha, Morinda citrifolia, Morinda citrifolia L. , Morinda officinalis , Penicillium herquei, Cryptolepis nigrescens, Persicaria hydropiper, Polygonum cuspidatum , Polygonum multiflorum , Fallopia sachalinensis, Polyporus umbellatus, Polysiphonia urceolata, Pseudopenicillium megasporum, Psorospermum androsaemifolium, Ramalina hierrensis, Rhamnus cathartica, Rhamnus formosana, Rhamnus kurdica, Rhamnus nepalensis, Rhamnus prinoides , Rhamnus procumbens, Rhamnus virgata, Rhamnus wightii , Rheum emodi , Rheum kialense, Rheum maximowiczii, Rheum officinale , Rheum palmatum , Rheum rhaponticum, Rheum sublanceolatum, Rheum tanguticum , Rubia cordifolia, Rumex abyssinicus, Rumex acetosella , Rumex aquaticus , Rumex confertus , Rumex crispus , Rumex cristatus, Rumex dentata, Rumex dentatus , Rumex hydrolapathum, Rumex japonicus , Rumex nepalensis , Rumex obtusifolius , Rumex patientia , Rumex scutatus , Rumex vesicarius , Sanguisorba alpina, Sargentodoxa cuneata, Saururus chinensis, Saussurea laniceps, Senna alexandrina, Senna artemisioides, Senna corymbosa, Senna didymobotrya, Senna floribunda, Senna italica, Senna longiracemosa, Senna multiglandulosa, Cassia obtusifolia , Senna occidentalis, Senna petersiana, Senna polyphylla, Senna septemtrionalis, Senna siamea, Senna singueana, Senna sophera , Senna spectabilis, Senna tora, Senna villosa, Streptomyces piomogenus, Tribulus terrestris , Uncaria rhynchophylla, Ventilago denticulata, Ventilago madraspatana, Vismia cayennensis, Vismia guineensis, Vismia latifolia, Vismia laurentii and Xanthoria parietina. Physcion was first documented in 2006 (PMID: 17125234). A dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6 (PMID: 17397111).
Structure
Thumb
Synonyms
ValueSource
1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthracenedioneChEBI
1,8-Dihydroxy-3-methoxy-6-methylanthraquinoneChEBI
1,8-Dihydroxy-3-methyl-6-methoxyanthraquinoneChEBI
Emodin monomethyl etherChEBI
ParieninChEBI
ParietinChEBI
PhyscioneChEBI
RheochrysidinChEBI
Emodin 3-methyl etherMeSH
Chemical FormulaC16H12O5
Average Mass284.2635 Da
Monoisotopic Mass284.06847 Da
IUPAC Name1,8-dihydroxy-3-methoxy-6-methyl-9,10-dihydroanthracene-9,10-dione
Traditional Namephyscion
CAS Registry Number521-61-9
SMILES
COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(C)C=C1O)C2=O
InChI Identifier
InChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3
InChI KeyFFWOKTFYGVYKIR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achyranthes bidentataLOTUS Database
Alternaria porriLOTUS Database
Alvaradoa jamaicensisPlant
Annona montanaLOTUS Database
Aspergillus chevalieriLOTUS Database
Aspergillus terreusFungi
Berchemia discolorLOTUS Database
Berchemia floribundaPlant
Bletilla striataLOTUS Database
Bourreria pulchraLOTUS Database
Brassica rapaLOTUS Database
Calonarius rufo-olivaceusLOTUS Database
Caloplaca saxicolaLOTUS Database
Cassia acutifoliaPlant
Cassia angustifoliaPlant
Cassia fistulaLOTUS Database
Cassia glaucaLOTUS Database
Cassia nomaePlant
Cassia occidentalisPlant
Cassia roxburghiiLOTUS Database
Cassia toraPlant
Cassia torosa L.Plant
Chamaecrista pumilaLOTUS Database
Cortinarius basirubescensLOTUS Database
Cortinarius canariusLOTUS Database
Cortinarius sanguineusLOTUS Database
Cratoxylum arborescensLOTUS Database
Cratoxylum formosumLOTUS Database
Dendrobium loddigesiiLOTUS Database
Dendrobium thyrsiflorumLOTUS Database
Derris oblongaPlant
Entodon luridusLOTUS Database
Ephedra sinicaPlant
Eupatorium cannabinumLOTUS Database
Eupatorium rugosumLOTUS Database
Fallopia multifloraLOTUS Database
Fibraurea tinctoriaLOTUS Database
Flavocetraria cucullataLOTUS Database
Frangula alnusLOTUS Database
Fulgensia canariensisLOTUS Database
Harrisonia perforataLOTUS Database
Harungana madagascariensisLOTUS Database
Leucosceptrum canumLOTUS Database
Limonia acidissimaLOTUS Database
Maesopsis eminiiLOTUS Database
Mentha sachalinensisLOTUS Database
Millettia leucanthaLOTUS Database
Morinda citrifoliaLOTUS Database
Morinda citrifolia L.Plant
Morinda officinalisPlant
Penicillium herqueiLOTUS Database
Periploca nigrescensLOTUS Database
Persicaria hydropiperLOTUS Database
Polygonum cuspidatumPlant
Polygonum multiflorumPlant
Polygonum sachalinenseLOTUS Database
Polyporus umbellatusLOTUS Database
Polysiphonia urceolataLOTUS Database
Pseudopenicillium megasporumLOTUS Database
Psorospermum androsaemifoliumLOTUS Database
Ramalina hierrensisLOTUS Database
Rhamnus catharticaLOTUS Database
Rhamnus formosanaLOTUS Database
Rhamnus kurdicaLOTUS Database
Rhamnus nepalensisPlant
Rhamnus prinoidesPlant
Rhamnus procumbensLOTUS Database
Rhamnus virgataLOTUS Database
Rhamnus wightiiPlant
Rheum australePlant
Rheum kialenseLOTUS Database
Rheum maximowicziiPlant
Rheum officinalePlant
Rheum palmatumPlant
Rheum rhabarbarumFooDB
Rheum rhaponticumLOTUS Database
Rheum sublanceolatumLOTUS Database
Rheum tanguticumPlant
Rubia cordifoliaLOTUS Database
Rumex abyssinicusLOTUS Database
Rumex acetosaFooDB
Rumex acetosellaPlant
Rumex aquaticusPlant
Rumex confertusPlant
Rumex crispusPlant
Rumex cristatusLOTUS Database
Rumex dentataPlant
Rumex dentatusPlant
Rumex hydrolapathumPlant
Rumex japonicusPlant
Rumex nepalensisPlant
Rumex obtusifoliusPlant
Rumex patientiaPlant
Rumex scutatusPlant
Rumex vesicariusPlant
Salvia officinalisFooDB
Sanguisorba alpinaLOTUS Database
Sargentodoxa cuneataPlant
Saururus chinensisLOTUS Database
Saussurea lanicepsPlant
Senna alexandrinaLOTUS Database
Senna artemisioidesLOTUS Database
Senna corymbosaLOTUS Database
Senna didymobotryaLOTUS Database
Senna floribundaLOTUS Database
Senna italicaLOTUS Database
Senna longiracemosaLOTUS Database
Senna multiglandulosaLOTUS Database
Senna obtusifoliaPlant
Senna occidentalisLOTUS Database
Senna petersianaLOTUS Database
Senna polyphyllaLOTUS Database
Senna septemtrionalisLOTUS Database
Senna siameaLOTUS Database
Senna singueanaLOTUS Database
Senna sopheraPlant
Senna spectabilisLOTUS Database
Senna toraLOTUS Database
Senna villosaLOTUS Database
Streptomyces piomogenusLOTUS Database
Tribulus terrestrisPlant
Uncaria rhynchophyllaLOTUS Database
Ventilago denticulataLOTUS Database
Ventilago maderaspatanaLOTUS Database
Vismia cayennensisLOTUS Database
Vismia guineensisLOTUS Database
Vismia latifoliaLOTUS Database
Vismia laurentiiPlant
Xanthoria parietinaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentAnthraquinones
Alternative Parents
Substituents
  • Anthraquinone
  • 9,10-anthraquinone
  • Aryl ketone
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Vinylogous acid
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP2.95ALOGPS
logP3.97ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.89ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.62 m³·mol⁻¹ChemAxon
Polarizability28.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0180733
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014824
KNApSAcK IDC00019420
Chemspider IDNot Available
KEGG Compound IDC17045
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkParietin
METLIN IDNot Available
PubChem Compound10639
PDB IDNot Available
ChEBI ID38167
Good Scents IDNot Available
References
General References
  1. Wang S, Li XM, Teuscher F, Li DL, Diesel A, Ebel R, Proksch P, Wang BG: Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata. J Nat Prod. 2006 Nov;69(11):1622-5. doi: 10.1021/np060248n. [PubMed:17125234 ]
  2. Yang X, Yang L, Wang S, Yu D, Ni H: Synergistic interaction of physcion and chrysophanol on plant powdery mildew. Pest Manag Sci. 2007 May;63(5):511-5. doi: 10.1002/ps.1362. [PubMed:17397111 ]