(1S,6R,13S,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-3(11),4(8),9,14,16,18-hexaen-12-one

Details

• Internal ID: 1572be84-9524-4d78-85c7-fbafc73a14ac
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (1S,6R,13S,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-3(11),4(8),9,14,16,18-hexaen-12-one
• SMILES (Canonical): CC(=C)C1CC2=C(O1)C=C(C3=C2OC4C(C3=O)C5=CC(=C(C=C5OC4O)OC)OC)O
• SMILES (Isomeric): CC(=C)[C@H]1CC2=C(O1)C=C(C3=C2O[C@H]4[C@@H](C3=O)C5=CC(=C(C=C5O[C@@H]4O)OC)OC)O
• InChI: InChI=1S/C23H22O8/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/h5,7-8,13,18,22-24,26H,1,6H2,2-4H3/t13-,18-,22+,23+/m1/s1
• InChI Key: RMAYNNFCPNGTQW-SLYOZJLYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₈
• Molecular Weight: 426.40 g/mol
• Exact Mass: 426.13146766 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 2.73
• 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	-	0.5209	52.09%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6353	63.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7886	78.86%
OATP1B3 inhibitior	+	0.8483	84.83%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6476	64.76%
P-glycoprotein inhibitior	+	0.7096	70.96%
P-glycoprotein substrate	-	0.6586	65.86%
CYP3A4 substrate	+	0.6452	64.52%
CYP2C9 substrate	+	0.5979	59.79%
CYP2D6 substrate	-	0.8189	81.89%
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	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.6531	65.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.4523	45.23%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.6715	67.15%
Skin irritation	-	0.7303	73.03%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7209	72.09%
Micronuclear	+	0.6659	66.59%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.7169	71.69%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.7046	70.46%
Acute Oral Toxicity (c)	II	0.5259	52.59%
Estrogen receptor binding	+	0.7502	75.02%
Androgen receptor binding	+	0.5964	59.64%
Thyroid receptor binding	+	0.6871	68.71%
Glucocorticoid receptor binding	+	0.7220	72.20%
Aromatase binding	-	0.5562	55.62%
PPAR gamma	+	0.7271	72.71%
Honey bee toxicity	+	0.5510	55.10%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
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	99.11%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.18%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.97%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.81%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.71%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.26%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.01%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.65%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.24%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.76%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.50%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.92%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.66%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	83.55%	91.49%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.23%	82.67%
CHEMBL217	P14416	Dopamine D2 receptor	83.13%	95.62%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.04%	97.33%
CHEMBL2535	P11166	Glucose transporter	82.96%	98.75%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	82.74%	91.79%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.82%	93.40%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.89%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.68%	89.50%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	80.30%	96.86%

Plants that contains it

• Tephrosia villosa

Cross-Links

• PubChem: 51669404
• LOTUS: LTS0001122
• wikiData: Q105240671