Usnic acid

Details

• Internal ID: 95a336f8-99b2-4950-84c2-9f7e46f07706
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Acetophenones
• IUPAC Name: 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione
• SMILES (Canonical): CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O
• SMILES (Isomeric): CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O
• InChI: InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3
• InChI Key: CUCUKLJLRRAKFN-UHFFFAOYSA-N
• Popularity: 535 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₇
• Molecular Weight: 344.30 g/mol
• Exact Mass: 344.08960285 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 1.40

Synonyms

• 125-46-2
• Usniacin
• Usno
• Usninic acid
• 1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-
• DTXSID0040123
• 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione
• 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
• CHEBI:2264
• NSC5889
• NSC8517
• 2,6-Diacetyl-1,2,3,9b-tetrahydro-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione
• 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-dibenzofuran-1,3-dione
• 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-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
• Usninsaeure [German]
• (+-)-Uanic acid
• CCRIS 5518
• HSDB 7170
• EINECS 204-740-7
• BRN 1299865
• UNII-0W584PFJ77
• Usinic acid
• AI3-50457
• Uanic acid
• 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
• orb1305098
• CHEMBL1375951
• SCHEMBL29406987
• CTK8B2970
• HMS503I19
• KBio1_001009
• KBio2_000657
• KBio2_003225
• KBio2_005793
• KBio3_002369
• NINDS_001009
• HMS5084I03
• HY-N0656
• MSK10520
• SAI_0021
• BBL009902
• CCG-40251
• 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
• I14-18000
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	19952.6 nM	Potency	via CMAUP
CHEMBL5990	P38398	Breast cancer type 1 susceptibility protein	31622.8 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	158.5 nM; 158.5 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.76%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.40%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.29%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.81%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	84.89%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.54%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.28%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.83%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	82.17%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.80%	94.00%

Plants that contains it

• Alysicarpus monilifer
• Euonymus alatus
• Myrtus communis

Cross-Links

• PubChem: 5646
• NPASS: NPC111201
• ChEMBL: CHEMBL1375951
• LOTUS: LTS0199944
• wikiData: Q27105599