1-Hydroxy-16,17-dimethoxy-5,7,11,14-tetraoxapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-21-one

Details

• Internal ID: 5bf4d8f1-134f-45e0-a887-a99a59d38077
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: 1-hydroxy-16,17-dimethoxy-5,7,11,14-tetraoxapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-21-one
• SMILES (Canonical): COC1=C(C2=C(C=C1)C(=O)C3(C(O2)COC4=CC5=C(C=C43)OCO5)O)OC
• SMILES (Isomeric): COC1=C(C2=C(C=C1)C(=O)C3(C(O2)COC4=CC5=C(C=C43)OCO5)O)OC
• InChI: InChI=1S/C19H16O8/c1-22-11-4-3-9-16(17(11)23-2)27-15-7-24-12-6-14-13(25-8-26-14)5-10(12)19(15,21)18(9)20/h3-6,15,21H,7-8H2,1-2H3
• InChI Key: YCLLOJPGIQDROB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₆O₈
• Molecular Weight: 372.30 g/mol
• Exact Mass: 372.08451746 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.66
• H-Bond Acceptor: 8
• 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	+	0.9671	96.71%
Caco-2	+	0.7663	76.63%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7649	76.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9411	94.11%
OATP1B3 inhibitior	+	0.9602	96.02%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6298	62.98%
P-glycoprotein inhibitior	+	0.6826	68.26%
P-glycoprotein substrate	-	0.7491	74.91%
CYP3A4 substrate	+	0.6117	61.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7672	76.72%
CYP3A4 inhibition	+	0.7588	75.88%
CYP2C9 inhibition	-	0.5898	58.98%
CYP2C19 inhibition	+	0.7012	70.12%
CYP2D6 inhibition	-	0.7013	70.13%
CYP1A2 inhibition	-	0.8282	82.82%
CYP2C8 inhibition	-	0.6771	67.71%
CYP inhibitory promiscuity	-	0.5807	58.07%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4417	44.17%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.6423	64.23%
Skin irritation	-	0.8106	81.06%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.5854	58.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8222	82.22%
Micronuclear	+	0.8133	81.33%
Hepatotoxicity	+	0.5074	50.74%
skin sensitisation	-	0.7087	70.87%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4948	49.48%
Acute Oral Toxicity (c)	III	0.6041	60.41%
Estrogen receptor binding	+	0.9189	91.89%
Androgen receptor binding	+	0.5805	58.05%
Thyroid receptor binding	+	0.7613	76.13%
Glucocorticoid receptor binding	+	0.8252	82.52%
Aromatase binding	-	0.5405	54.05%
PPAR gamma	+	0.8216	82.16%
Honey bee toxicity	-	0.7999	79.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5251	52.51%
Fish aquatic toxicity	+	0.8153	81.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.35%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.09%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.44%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.38%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.31%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.71%	92.62%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.88%	94.80%
CHEMBL4208	P20618	Proteasome component C5	89.19%	90.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	87.97%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.85%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.68%	89.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.68%	82.67%
CHEMBL2581	P07339	Cathepsin D	87.43%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.98%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.95%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.02%	100.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	83.77%	96.86%
CHEMBL2535	P11166	Glucose transporter	83.72%	98.75%
CHEMBL4040	P28482	MAP kinase ERK2	83.34%	83.82%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.24%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	82.52%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.78%	95.89%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.66%	90.24%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.97%	96.00%

Plants that contains it

• Millettia usaramensis

Cross-Links

• PubChem: 162930624
• LOTUS: LTS0021479
• wikiData: Q105346350