d-Usnic acid

Details

• Internal ID: f6e7efd8-ea43-46c6-8081-a4d5039e1d14
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Acetophenones
• IUPAC Name: (9bR)-2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzofuran-1-one
• SMILES (Canonical): CC1=C(C(=C2C(=C1O)C3(C(=CC(=C(C3=O)C(=O)C)O)O2)C)C(=O)C)O
• SMILES (Isomeric): CC1=C(C(=C2C(=C1O)[C@@]3(C(=CC(=C(C3=O)C(=O)C)O)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/h5,21-23H,1-4H3/t18-/m0/s1
• InChI Key: WEYVVCKOOFYHRW-SFHVURJKSA-N
• Popularity: 20 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): 121.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• (+)-Usnic acid
• (R)-Usnic acid
• Usnic acid, D-
• Usnic acid, (R)-
• d-Usnic acid
• 7562-61-0
• (-)-Usnic acid
• (R)-(+)-Usnic acid
• CHEBI:38320
• UNII-663456969I
• NSC-685596
• 663456969I
• NSC 5890
• EINECS 231-456-0
• ( )-Usnic acid
• (9bR)-2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-1(9bH)-one
• 1,3(2H,9bH)-dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-, (9bR)-
• CHEMBL242022
• 3(9bH)-dibenzofuranone, 2,6-diacetyl-8,9b-dimethyl-1,7,9-trihydroxy-, D-
• (9bR)-2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-(2H,9bH)-dibenzofuran-1,3-dione
• (R)-2,6-Diacetyl-3,7,9-trihydroxy-8,9b-dimethyl-9bH-dibenzofuran-1-one
• (+)-Usninic acid
• SCHEMBL177775
• USNIC ACID, (+)-
• 2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-1(9bH)-one
• CHEMBL4803064
• USNIC ACID D-FORM [MI]
• 3(9bH)-DIBENZOFURANONE, 2,6-DIACETYL-1,7,9-TRIHYDROXY-8,9b-DIMETHYL-, D-
• (+)-Usnic acid; (+)-Usniacin
• BDBM50202829
• AKOS032948335
• PD143629
• A838466
• EN300-18532942
• Q27888211
• Z3301414441
• (9bR)-2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyl-dibenzofuran-1-one
• (9bR)-2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyl-dibenzofuran-1-one;(+)-Usniacin
• 1(9BH)-DIBENZOFURANONE, 2,6-DIACETYL-3,7,9-TRIHYDROXY-8,9B-DIMETHYL-, (9BR)-
• 1(9BH)-DIBENZOFURANONE, 2,6-DIACETYL-3,7,9-TRIHYDROXY-8,9B-DIMETHYL-, (R)-
• (2S)-4,10-diacetyl-3,11,13-trihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0,2,7]trideca-1(13),3,6,9,11-pentaen-5-one
• (S)-1,1'-(1,7,9-trihydroxy-8,9b-dimethyl-3-oxo-3,9b-dihydrodibenzo[b,d]furan-2,6-diyl)diethanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9933	99.33%
Caco-2	+	0.6012	60.12%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7611	76.11%
OATP2B1 inhibitior	-	0.7099	70.99%
OATP1B1 inhibitior	-	0.7739	77.39%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7039	70.39%
P-glycoprotein inhibitior	-	0.8914	89.14%
P-glycoprotein substrate	-	0.7732	77.32%
CYP3A4 substrate	+	0.5751	57.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8643	86.43%
CYP3A4 inhibition	-	0.8281	82.81%
CYP2C9 inhibition	+	0.9194	91.94%
CYP2C19 inhibition	-	0.7857	78.57%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.7277	72.77%
CYP inhibitory promiscuity	+	0.8952	89.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Danger	0.5308	53.08%
Eye corrosion	-	0.9826	98.26%
Eye irritation	+	0.8294	82.94%
Skin irritation	-	0.5626	56.26%
Skin corrosion	-	0.9042	90.42%
Ames mutagenesis	-	0.6308	63.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.6566	65.66%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.7427	74.27%
skin sensitisation	-	0.6645	66.45%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.5893	58.93%
Acute Oral Toxicity (c)	III	0.4795	47.95%
Estrogen receptor binding	+	0.6587	65.87%
Androgen receptor binding	+	0.6110	61.10%
Thyroid receptor binding	-	0.6416	64.16%
Glucocorticoid receptor binding	-	0.5512	55.12%
Aromatase binding	-	0.6605	66.05%
PPAR gamma	+	0.5846	58.46%
Honey bee toxicity	-	0.9038	90.38%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9895	98.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	16400 nM	IC50	PMID: 18288807

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.52%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.44%	99.23%
CHEMBL2581	P07339	Cathepsin D	88.24%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.79%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.64%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	85.49%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.56%	93.65%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.47%	86.33%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.39%	85.30%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.80%	94.00%

Plants that contains it

• Allium cepa
• Euonymus alatus
• Helleborus niger

Cross-Links

• PubChem: 478125
• NPASS: NPC82920
• ChEMBL: CHEMBL367881
• LOTUS: LTS0119956
• wikiData: Q27888211