Futoenone

Details

• Internal ID: 4e7e9a96-26e0-4c8b-98f3-fcbe030b8af8
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: (1S,8S,10S,11R)-10-(1,3-benzodioxol-5-yl)-3-methoxy-11-methyl-7-oxatricyclo[6.3.1.01,6]dodeca-2,5-dien-4-one
• SMILES (Canonical): CC1C(CC2CC13C=C(C(=O)C=C3O2)OC)C4=CC5=C(C=C4)OCO5
• SMILES (Isomeric): C[C@@H]1[C@H](C[C@H]2C[C@@]13C=C(C(=O)C=C3O2)OC)C4=CC5=C(C=C4)OCO5
• InChI: InChI=1S/C20H20O5/c1-11-14(12-3-4-16-17(5-12)24-10-23-16)6-13-8-20(11)9-18(22-2)15(21)7-19(20)25-13/h3-5,7,9,11,13-14H,6,8,10H2,1-2H3/t11-,13+,14+,20-/m1/s1
• InChI Key: SXHVHWXETMBKPP-KXXATPMCSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.13107373 g/mol
• Topological Polar Surface Area (TPSA): 54.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 19913-01-0
• (1S,8S,10S,11R)-10-(1,3-benzodioxol-5-yl)-3-methoxy-11-methyl-7-oxatricyclo[6.3.1.01,6]dodeca-2,5-dien-4-one
• (-)-Futoenone
• D09EUH
• CHEMBL295191
• SCHEMBL3468519
• CHEBI:132647
• SXHVHWXETMBKPP-KXXATPMCSA-N
• DTXSID201107665
• OAS 1136
• BDBM50213210
• AKOS032949051
• (2alpha,4alpha,5beta,5aalpha)-4-(1,3-Benzodioxol-5-yl)-2,3,4,5-tetrahydro-7-methoxy-5-methyl-8H-2,5a-methano-1-benzoxepin-8-one
• (2R,4R,5S,5aR)-rel-(-)-4-(1,3-benzodioxol-5-yl)-2,3,4,5- tetrahydro-7-methoxy-5-methyl-8H-2,5a-methano-benzoepin-8-one
• (2S,4S,5R,5aS)-4-(1,3-Benzodioxol-5-yl)-2,3,4,5-tetrahydro-7-methoxy-5-methyl-8H-2,5a-methano-1-benzoxepin-8-one
• (2S,4S,5R,5aS)-4-(2H-1,3-benzodioxol-5-yl)-7-methoxy-5-methyl-2,3,4,5-tetrahydro-8H-2,5a-methano-1-benzoxepin-8-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7583	75.83%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7721	77.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9320	93.20%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7694	76.94%
P-glycoprotein inhibitior	+	0.7211	72.11%
P-glycoprotein substrate	-	0.7710	77.10%
CYP3A4 substrate	+	0.6296	62.96%
CYP2C9 substrate	-	0.8049	80.49%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	+	0.8771	87.71%
CYP2C9 inhibition	-	0.5665	56.65%
CYP2C19 inhibition	+	0.6896	68.96%
CYP2D6 inhibition	-	0.7001	70.01%
CYP1A2 inhibition	-	0.7856	78.56%
CYP2C8 inhibition	-	0.6719	67.19%
CYP inhibitory promiscuity	+	0.7911	79.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4925	49.25%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.8457	84.57%
Skin irritation	-	0.7615	76.15%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6480	64.80%
Micronuclear	+	0.5674	56.74%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	-	0.6611	66.11%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.6517	65.17%
Acute Oral Toxicity (c)	III	0.4135	41.35%
Estrogen receptor binding	+	0.8488	84.88%
Androgen receptor binding	+	0.6908	69.08%
Thyroid receptor binding	+	0.6457	64.57%
Glucocorticoid receptor binding	+	0.8402	84.02%
Aromatase binding	+	0.6759	67.59%
PPAR gamma	-	0.4939	49.39%
Honey bee toxicity	-	0.7043	70.43%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9910	99.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL283	P08254	Matrix metalloproteinase 3	< 1000 nM	IC50	DOI: 10.1016/0960-894X(95)00282-X

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.47%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.12%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.72%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	96.83%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.95%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.79%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.01%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.94%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.47%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.55%	93.40%
CHEMBL2535	P11166	Glucose transporter	86.74%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.14%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.96%	97.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.48%	96.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.72%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.61%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.16%	95.89%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	83.14%	94.03%
CHEMBL2581	P07339	Cathepsin D	82.90%	98.95%
CHEMBL4444	P04070	Vitamin K-dependent protein C	82.77%	93.89%
CHEMBL4208	P20618	Proteasome component C5	82.35%	90.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.77%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.61%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.32%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.28%	99.23%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.98%	85.30%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	80.47%	95.55%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.30%	92.62%

Plants that contains it

• Magnolia biondii
• Magnolia denudata
• Magnolia kobus
• Magnolia salicifolia
• Magnolia sprengeri
• Piper hancei
• Piper kadsura

Cross-Links

• PubChem: 9819306
• NPASS: NPC178290
• ChEMBL: CHEMBL295191
• LOTUS: LTS0216104
• wikiData: Q105263128