Compound: Physcion
SMILES: O=C1c2c(O)cc(OC)cc2C(=O)c3c1c(O)cc(C)c3
InChIKey: FFWOKTFYGVYKIR-UHFFFAOYSA-N
Synonyms: Physcion, 521-61-9, Physcione, Rheochrysidin, Emodin 3-methyl ether, 1,8-dihydroxy-3-methoxy-6-methylanthracene-9,10-dione, 1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthracenedione, Parienin, Emodin monomethyl ether, H6PT94IV61, ANTHRAQUINONE, 1,8-DIHYDROXY-3-METHOXY-6-METHYL-, NSC-251670, CHEBI:38167, DTXSID20200101, RefChem:45131, DTXCID80122592, 208-315-7, Emodin-3-methyl ether, 1,8-Dihydroxy-3-methoxy-6-methylanthraquinone, NSC 251670, MFCD00017374, 1,8-Dihydroxy-3-methyl-6-methoxyanthraquinone, Rheochrysidin (Physcione), Parietin;Rheochrysidin, 1,8-Dihydroxy-3-methyl-6-methoxy-9,10-anthraquinone, NSC251670, CHEMBL42624, 1,8-Dihydroxy-3-methoxy-6-methyl-anthraquinone, 1,8-dihydroxy-3-methoxy-6-methyl-anthracene-9,10-dione, 9,10-Anthracenedione, 1,8-dihydroxy-3-methoxy-6-methyl-, Methoxyemodin, CCRIS 4399, 6-O-METHYLEMODIN, EINECS 208-315-7, BRN 1915778, fischione, physicion, UNII-H6PT94IV61, Physcion (Standard), emodin monomethylether, PHYSCIONE-, Spectrum_001782, SpecPlus_000471, Spectrum2_000503, Spectrum3_001829, Spectrum4_000909, Spectrum5_001742, 1,8-dihydroxy-6-methoxy-3-methylanthraquinone, BSPBio_003477, KBioGR_001378, KBioSS_002265, Physcion, analytical standard, DivK1c_006567, SCHEMBL486155, SPECTRUM1504070, SPBio_000425, MEGxm0_000018, orb1304617, orb3139667, SCHEMBL29404320, SCHEMBL30425832, HY-N0108R, KBio1_001511, KBio2_002264, KBio2_004832, KBio2_007400, KBio3_002981, HMS3656I15, HMS3874M13, Physcion, >=98.0% (TLC), EX-A6797, HY-N0108, MSK40046, QYB75127, EMODIN 3-METHYL ETHER [MI], BDBM50005886, CCG-38713, s2395, AKOS015905689, CHRYSOPHANIC ACID, 6-METHOXY-, AC-7979, FP27033, KS-5385, SDCCGMLS-0066772.P001, NCGC00096075-01, NCGC00096075-02, NCGC00096075-03, 9, 1,8-dihydroxy-3-methoxy-6-methyl-, AS-15488, DA-66695, NCI60_002011, SY028089, CS-0007795, NS00010362, SW219324-1, Anthraquinone,8-dihydroxy-3-methoxy-6-methyl-, C17045, AC-542/20316002, SR-05000002537, Q1668551, SR-05000002537-1, 8,9-dihydroxy-3-methyl-6-methoxy-1,10-anthraquinone, 8,9-dihydroxy-6-methyl-3-methoxy-1,10-anthraquinone, BRD-K67772619-001-03-6, BRD-K67772619-001-05-1, 1,8-Dihydroxy-3-methoxy-6-methylanthra-9,10-quinone #, 7-methoxy-2-methyl-4,5-dihydroxyanthracene-9,10-dione, 1,8-Dihydroxy-3-methoxy-6-methylanthraquinone, Emodin-3-methyl ether
Theoretical properties:
molecular_formula: C16H12O5
molecular_weight: 284.26 g/mol
exact_mass: 284.06847348 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 1
heavy_atom_count: 21
topological_polar_surface_area: 83.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Physcion is 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. It has been widely isolated and characterised from both terrestrial and marine sources. It has a role as a metabolite, an antibacterial agent, an antineoplastic agent, an antifungal agent, a hepatoprotective agent, an anti-inflammatory agent and an apoptosis inducer. It is functionally related to a 2-methylanthraquinone.
chebi: 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. It has been widely isolated and characterised from both terrestrial and marine sources.
chembl: PHYSCION is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Parietin, or physcion, is the predominant cortical pigment of lichens in the genus Caloplaca, a secondary product of the lichen Xanthoria parietina, and a pigment found in the roots of curled dock (Rumex crispus). It has an orange-yellow color and absorbs blue light.
Parietin has also been shown to protect lichens against UV-B light, at high altitudes in alpine regions. The UV-B light stimulates production of parietin, protecting the lichens from damage. Lichens in arctic regions such as Svalbard retain this capability though they do not encounter damaging levels of UV-B, a capability that could help protect the lichens in case of ozone layer thinning.
It has also shown antifungal activity against barley powdery mildew and cucumber powdery mildew, more efficiently in the latter case than treatments with fenarimol and polyoxin B.
It reacts with KOH to form a deep, reddish-magenta compound.