13-Hydroxy-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),5,9,14,16,18-heptaen-12-one

Details

• Internal ID: d6df9b3b-3b1d-4ca3-90db-ddddfd139966
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: 13-hydroxy-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),5,9,14,16,18-heptaen-12-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C3(C(CO2)OC4=C(C3=O)C=CC5=C4C=CO5)O)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C3(C(CO2)OC4=C(C3=O)C=CC5=C4C=CO5)O)OC
• InChI: InChI=1S/C20H16O7/c1-23-15-7-12-14(8-16(15)24-2)26-9-17-20(12,22)19(21)11-3-4-13-10(5-6-25-13)18(11)27-17/h3-8,17,22H,9H2,1-2H3
• InChI Key: KHAJUSVOOGYFIJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₆O₇
• Molecular Weight: 368.30 g/mol
• Exact Mass: 368.08960285 g/mol
• Topological Polar Surface Area (TPSA): 87.40 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	+	0.6708	67.08%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8275	82.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9305	93.05%
OATP1B3 inhibitior	+	0.9650	96.50%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7241	72.41%
P-glycoprotein inhibitior	+	0.7850	78.50%
P-glycoprotein substrate	+	0.5229	52.29%
CYP3A4 substrate	+	0.6233	62.33%
CYP2C9 substrate	-	0.8125	81.25%
CYP2D6 substrate	-	0.7578	75.78%
CYP3A4 inhibition	+	0.6344	63.44%
CYP2C9 inhibition	-	0.6748	67.48%
CYP2C19 inhibition	+	0.6992	69.92%
CYP2D6 inhibition	-	0.7253	72.53%
CYP1A2 inhibition	+	0.5085	50.85%
CYP2C8 inhibition	+	0.4489	44.89%
CYP inhibitory promiscuity	-	0.6539	65.39%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5044	50.44%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.6457	64.57%
Skin irritation	-	0.7984	79.84%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.5554	55.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5965	59.65%
Micronuclear	+	0.7459	74.59%
Hepatotoxicity	-	0.5426	54.26%
skin sensitisation	-	0.7420	74.20%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8110	81.10%
Acute Oral Toxicity (c)	III	0.6032	60.32%
Estrogen receptor binding	+	0.8958	89.58%
Androgen receptor binding	+	0.6449	64.49%
Thyroid receptor binding	+	0.7079	70.79%
Glucocorticoid receptor binding	+	0.8750	87.50%
Aromatase binding	-	0.5788	57.88%
PPAR gamma	+	0.8567	85.67%
Honey bee toxicity	-	0.7459	74.59%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7490	74.90%

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	97.34%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.89%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.45%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.14%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.73%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.82%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.57%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.55%	96.09%
CHEMBL2535	P11166	Glucose transporter	87.28%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.03%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.82%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.66%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.12%	94.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.71%	89.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.90%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.31%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.56%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.29%	97.09%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.96%	82.67%
CHEMBL4208	P20618	Proteasome component C5	81.65%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.38%	97.14%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.40%	89.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.23%	96.00%

Plants that contains it

• Derris trifoliata
• Millettia duchesnei
• Sarcolobus globosus

Cross-Links

• PubChem: 13846201
• LOTUS: LTS0240801
• wikiData: Q105141071