(6S)-16,17-dimethoxy-6-propan-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),3(11),4(8),9,14,16,18-heptaen-12-one

Details

• Internal ID: 3c82f92d-9b56-4f49-8d63-598c46bcf880
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (6S)-16,17-dimethoxy-6-propan-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),3(11),4(8),9,14,16,18-heptaen-12-one
• SMILES (Canonical): CC(C)C1CC2=C(O1)C=CC3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4)OC)OC
• SMILES (Isomeric): CC(C)[C@@H]1CC2=C(O1)C=CC3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4)OC)OC
• InChI: InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,11,16H,8,10H2,1-4H3/t16-/m0/s1
• InChI Key: BHCBWJBSVOKHRJ-INIZCTEOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₆
• Molecular Weight: 394.40 g/mol
• Exact Mass: 394.14163842 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.33
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.7106	71.06%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7511	75.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9603	96.03%
OATP1B3 inhibitior	+	0.9713	97.13%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9125	91.25%
P-glycoprotein inhibitior	+	0.9293	92.93%
P-glycoprotein substrate	+	0.5714	57.14%
CYP3A4 substrate	+	0.6174	61.74%
CYP2C9 substrate	-	0.6145	61.45%
CYP2D6 substrate	-	0.7858	78.58%
CYP3A4 inhibition	-	0.6239	62.39%
CYP2C9 inhibition	-	0.6750	67.50%
CYP2C19 inhibition	+	0.8144	81.44%
CYP2D6 inhibition	-	0.6316	63.16%
CYP1A2 inhibition	+	0.8788	87.88%
CYP2C8 inhibition	-	0.6623	66.23%
CYP inhibitory promiscuity	+	0.5706	57.06%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5856	58.56%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.8753	87.53%
Skin irritation	-	0.8188	81.88%
Skin corrosion	-	0.9732	97.32%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5419	54.19%
Micronuclear	+	0.5159	51.59%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.7039	70.39%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.5551	55.51%
Acute Oral Toxicity (c)	III	0.8061	80.61%
Estrogen receptor binding	+	0.8635	86.35%
Androgen receptor binding	+	0.6775	67.75%
Thyroid receptor binding	+	0.6494	64.94%
Glucocorticoid receptor binding	+	0.8267	82.67%
Aromatase binding	+	0.6046	60.46%
PPAR gamma	+	0.7754	77.54%
Honey bee toxicity	-	0.6671	66.71%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9147	91.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.07%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.36%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.97%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.88%	94.45%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	93.82%	96.86%
CHEMBL2535	P11166	Glucose transporter	93.60%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.43%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.29%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.82%	94.80%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.78%	96.77%
CHEMBL5747	Q92793	CREB-binding protein	89.61%	95.12%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.35%	89.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.94%	97.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.24%	95.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.22%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.72%	92.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.56%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.15%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.35%	96.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	82.32%	95.53%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.28%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.84%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.34%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.79%	99.17%

Plants that contains it

• Tephrosia candida

Cross-Links

• PubChem: 40458929
• LOTUS: LTS0261340
• wikiData: Q104935863