Compound: usnic acid
SMILES: O=C1C=C2Oc3c(c(O)c(c(c3C2(C)C(C1C(=O)C)=O)O)C)C(=O)C
InChIKey: CUCUKLJLRRAKFN-UHFFFAOYSA-N
Synonyms: usnic acid, 125-46-2, Usniacin, Usno, Usninic acid, 1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-, 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione, DTXSID0040123, 0W584PFJ77, NSC-8517, 1,3-(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-, RefChem:901508, DTXCID8020123, 204-740-7, 2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzofuran-1-one, CHEBI:38319, Usnein, UsnicAcid, Usninsaeure, usnic-acid, L-Usnic acid, NSC 8517, NSC5890, (+/-)-Usnic acid, 7-Hydroxy-(S)-usnate, 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bh)-dione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione, NSC5889, NSC8517, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-dibenzofuran-1,3-dione, Usninsaeure [German], (+-)-Uanic acid, Usinic acid, CCRIS 5518, HSDB 7170, EINECS 204-740-7, BRN 1299865, UNII-0W584PFJ77, AI3-50457, Uanic acid, 2,6-Diacetyl-1,2,3,9b-tetrahydro-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione, Spectrum_000177, Spectrum2_000744, Spectrum3_001195, Spectrum4_001811, Spectrum5_000541, USNIC ACID, (D), USNIC ACID, (L), (.+/-.)-Usnic acid, BSPBio_002869, KBioGR_002446, KBioSS_000657, DivK1c_001009, SCHEMBL177774, SPBio_000728, CHEBI:2264, orb1305098, CHEMBL1375951, SCHEMBL29406987, HMS503I19, KBio1_001009, KBio2_000657, KBio2_003225, KBio2_005793, KBio3_002369, NINDS_001009, HMS5084I03, HY-N0656, MSK10520, SAI_0021, BBL009902, CCG-40251, EBC-13246, s4953, STK801335, AKOS005613032, FU32857, SDCCGMLS-0066516.P001, IDI1_001009, NCGC00094823-01, NCGC00094823-02, NCGC00094823-03, NCGC00094823-04, AS-18744, DA-48608, NCI60_004436, NCI60_004437, CS-0009679, NS00004156, U0023, EN300-7388062, BRD-A85739295-001-03-6, Q27105599, WLN: T B656 CV EV HO FU BHT & JB1 DV1 KQ L1 MQ, 1,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-, Dibenzofuran-1,9bH)-dione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-, (+/-)-1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-, 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[b,d]furan-1,3(2H,9bh)-dione #, 2,6-Diacetyl-1,2,3,9b-tetrahydro-7,9-dihydroxy-8,9b-dimethyldiben- zofuran-1,3-dione/ Usno, 4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0,2,7]trideca-1(13),6,9,11-tetraene-3,5-dione, 4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),6,10,12-tetraene-3,5-dione
Theoretical properties:
molecular_formula: C18H16O7
molecular_weight: 344.3 g/mol
exact_mass: 344.08960285 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 2
heavy_atom_count: 25
topological_polar_surface_area: 118 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: ... yellowish /colored/ pigment.
color: ... yellowish /colored/ pigment.
melting_point: 204 °C
solubility: Solubility at 25 °C (g/100 ml): acetone, 0.77; ethyl acetate, 0.88; fural, 7.32; furfuryl alcohol, 1.21
Descriptions:
pubchem: 7-Hydroxy-(S)-usnate is a member of benzofurans.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Usnic acid is a naturally occurring dibenzofuran derivative found in several lichen species with the formula C18H16O7. It was first isolated by German scientist W. Knop in 1844 and first synthesized between 1933 and 1937 by Frank H. Curd and Alexander Robertson. Usnic acid was identified in many genera of lichens including Usnea, Cladonia, Hypotrachyna, Lecanora, Ramalina, Evernia, Parmelia and Alectoria. Although it is generally believed that usnic acid is exclusively restricted to lichens, in a few unconfirmed isolated cases the compound was found in kombucha tea and non-lichenized ascomycetes.
At normal conditions, usnic acid is a bitter, yellow, solid substance. It is known to occur in nature in both the d- and l-forms as well as a racemic mixture. Salts of usnic acid are called usnates (e.g. copper usnate).