Anthecularin

Details

• Internal ID: 6796466b-d6ff-414e-8f66-759e53d75624
• Taxonomy: Organoheterocyclic compounds > Furofurans
• IUPAC Name: (1R,6R,10R,11S)-3,13-dimethyl-8,15-dioxatetracyclo[9.3.1.01,6.06,10]pentadeca-2,13-dien-7-one
• SMILES (Canonical): CC1=CC23C=C(CC(O2)C4C3(CC1)C(=O)OC4)C
• SMILES (Isomeric): CC1=C[C@]23C=C(C[C@H](O2)[C@@H]4[C@@]3(CC1)C(=O)OC4)C
• InChI: InChI=1S/C15H18O3/c1-9-3-4-15-11(8-17-13(15)16)12-5-10(2)7-14(15,6-9)18-12/h6-7,11-12H,3-5,8H2,1-2H3/t11-,12+,14-,15+/m1/s1
• InChI Key: YXZRMZMSHRWRLO-OSRDXIQISA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Auricularin
• SCHEMBL21319136
• (1R,6R,10R,11S)-3,13-dimethyl-8,15-dioxatetracyclo[9.3.1.01,6.06,10]pentadeca-2,13-dien-7-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	+	0.9312	93.12%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7300	73.00%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.9113	91.13%
OATP1B3 inhibitior	+	0.9694	96.94%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.9252	92.52%
P-glycoprotein inhibitior	-	0.9313	93.13%
P-glycoprotein substrate	-	0.8101	81.01%
CYP3A4 substrate	+	0.5422	54.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8082	80.82%
CYP3A4 inhibition	-	0.8856	88.56%
CYP2C9 inhibition	-	0.8871	88.71%
CYP2C19 inhibition	-	0.8288	82.88%
CYP2D6 inhibition	-	0.8705	87.05%
CYP1A2 inhibition	-	0.6696	66.96%
CYP2C8 inhibition	-	0.8538	85.38%
CYP inhibitory promiscuity	-	0.8431	84.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5903	59.03%
Eye corrosion	-	0.9730	97.30%
Eye irritation	+	0.5386	53.86%
Skin irritation	-	0.7292	72.92%
Skin corrosion	-	0.9481	94.81%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6266	62.66%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.7355	73.55%
skin sensitisation	-	0.7492	74.92%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5854	58.54%
Acute Oral Toxicity (c)	III	0.4619	46.19%
Estrogen receptor binding	+	0.5468	54.68%
Androgen receptor binding	+	0.6514	65.14%
Thyroid receptor binding	-	0.5720	57.20%
Glucocorticoid receptor binding	-	0.5946	59.46%
Aromatase binding	-	0.6802	68.02%
PPAR gamma	-	0.7657	76.57%
Honey bee toxicity	-	0.7271	72.71%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7700	77.00%
Fish aquatic toxicity	+	0.9698	96.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.12%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.55%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.84%	94.80%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.47%	93.40%
CHEMBL230	P35354	Cyclooxygenase-2	85.35%	89.63%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.26%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.17%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.57%	96.61%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.14%	86.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.84%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	81.82%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.59%	97.09%

Plants that contains it

• Anthemis auriculata

Cross-Links

• PubChem: 23651215
• LOTUS: LTS0042170
• wikiData: Q104399919