(6S,21S)-10,21-dihydroxy-16,17-dimethoxy-6-prop-1-en-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: d40034cf-cfb7-4606-a535-4ef27c43a5d4
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (6S,21S)-10,21-dihydroxy-16,17-dimethoxy-6-prop-1-en-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=C(C3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4O)OC)OC)O
• SMILES (Isomeric): CC(=C)[C@@H]1CC2=C(O1)C=C(C3=C2OC4=C(C3=O)C5=CC(=C(C=C5O[C@@H]4O)OC)OC)O
• InChI: InChI=1S/C23H20O8/c1-9(2)13-6-11-14(29-13)7-12(24)19-20(25)18-10-5-16(27-3)17(28-4)8-15(10)30-23(26)22(18)31-21(11)19/h5,7-8,13,23-24,26H,1,6H2,2-4H3/t13-,23-/m0/s1
• InChI Key: LMMACNCQNDTCON-NPMABZOXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₀O₈
• Molecular Weight: 424.40 g/mol
• Exact Mass: 424.11581759 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.45
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9848	98.48%
Caco-2	-	0.5536	55.36%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6353	63.53%
OATP2B1 inhibitior	-	0.7199	71.99%
OATP1B1 inhibitior	+	0.8800	88.00%
OATP1B3 inhibitior	+	0.8483	84.83%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6007	60.07%
P-glycoprotein inhibitior	+	0.7608	76.08%
P-glycoprotein substrate	-	0.5196	51.96%
CYP3A4 substrate	+	0.6531	65.31%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.8290	82.90%
CYP3A4 inhibition	-	0.5285	52.85%
CYP2C9 inhibition	-	0.8140	81.40%
CYP2C19 inhibition	+	0.7455	74.55%
CYP2D6 inhibition	-	0.8329	83.29%
CYP1A2 inhibition	+	0.5276	52.76%
CYP2C8 inhibition	+	0.5298	52.98%
CYP inhibitory promiscuity	+	0.6531	65.31%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.4523	45.23%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.7032	70.32%
Skin irritation	-	0.7303	73.03%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6978	69.78%
Micronuclear	+	0.6659	66.59%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.7169	71.69%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6486	64.86%
Acute Oral Toxicity (c)	II	0.5259	52.59%
Estrogen receptor binding	+	0.8457	84.57%
Androgen receptor binding	+	0.5554	55.54%
Thyroid receptor binding	+	0.6849	68.49%
Glucocorticoid receptor binding	+	0.8040	80.40%
Aromatase binding	+	0.7099	70.99%
PPAR gamma	+	0.8049	80.49%
Honey bee toxicity	-	0.5442	54.42%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9893	98.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.97%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.43%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.53%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.90%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.91%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.57%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.39%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.58%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.54%	92.94%
CHEMBL2535	P11166	Glucose transporter	89.20%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.73%	95.56%
CHEMBL217	P14416	Dopamine D2 receptor	87.15%	95.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.12%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.47%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.66%	99.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.07%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	83.88%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.56%	92.62%
CHEMBL1951	P21397	Monoamine oxidase A	83.32%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.20%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.67%	97.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.90%	96.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.78%	89.50%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.45%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.38%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.22%	90.71%

Plants that contains it

• Tephrosia villosa

Cross-Links

• PubChem: 163083440
• LOTUS: LTS0263551
• wikiData: Q105154048