(1R,6S,13R)-10-hydroxy-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: 1454f667-c0d8-4daa-9975-c346bdda54c2
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (1R,6S,13R)-10-hydroxy-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=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC)O
• SMILES (Isomeric): CC(=C)[C@@H]1CC2=C(O1)C=C(C3=C2O[C@H]4COC5=CC(=C(C=C5[C@H]4C3=O)OC)OC)O
• InChI: InChI=1S/C23H22O7/c1-10(2)14-6-12-16(29-14)7-13(24)21-22(25)20-11-5-17(26-3)18(27-4)8-15(11)28-9-19(20)30-23(12)21/h5,7-8,14,19-20,24H,1,6,9H2,2-4H3/t14-,19-,20+/m0/s1
• InChI Key: ZPEHYKMRUBEPSQ-PNHOKKKMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₇
• Molecular Weight: 410.40 g/mol
• Exact Mass: 410.13655304 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9929	99.29%
Caco-2	+	0.5904	59.04%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7261	72.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3424	34.24%
OATP1B3 inhibitior	+	0.9471	94.71%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5306	53.06%
P-glycoprotein inhibitior	+	0.7078	70.78%
P-glycoprotein substrate	-	0.6224	62.24%
CYP3A4 substrate	+	0.6325	63.25%
CYP2C9 substrate	+	0.5973	59.73%
CYP2D6 substrate	-	0.7963	79.63%
CYP3A4 inhibition	+	0.7089	70.89%
CYP2C9 inhibition	-	0.7766	77.66%
CYP2C19 inhibition	+	0.8322	83.22%
CYP2D6 inhibition	-	0.9167	91.67%
CYP1A2 inhibition	+	0.8116	81.16%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.6453	64.53%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7189	71.89%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.7610	76.10%
Skin corrosion	-	0.9605	96.05%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7441	74.41%
Micronuclear	+	0.5859	58.59%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.6233	62.33%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	+	0.6192	61.92%
Acute Oral Toxicity (c)	II	0.6781	67.81%
Estrogen receptor binding	+	0.8218	82.18%
Androgen receptor binding	+	0.6225	62.25%
Thyroid receptor binding	+	0.7417	74.17%
Glucocorticoid receptor binding	+	0.7782	77.82%
Aromatase binding	-	0.5729	57.29%
PPAR gamma	+	0.8612	86.12%
Honey bee toxicity	+	0.8293	82.93%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9765	97.65%

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	98.96%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.47%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.71%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.61%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.29%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.73%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.18%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.38%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.03%	94.80%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.74%	93.40%
CHEMBL2581	P07339	Cathepsin D	85.93%	98.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.44%	97.33%
CHEMBL2535	P11166	Glucose transporter	85.29%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.99%	86.33%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.76%	82.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.53%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	84.32%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.71%	94.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	82.61%	80.96%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	82.51%	91.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.47%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.25%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.00%	99.17%

Plants that contains it

• Tephrosia villosa

Cross-Links

• PubChem: 145978778
• LOTUS: LTS0053809
• wikiData: Q105380864