12a-Hydroxy-2,3,9-trimethoxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one

Details

• Internal ID: a9299ea7-7576-4cae-8d87-b4c2be3e11ec
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: 12a-hydroxy-2,3,9-trimethoxy-11-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one
• SMILES (Canonical): COC1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C4(C(O2)COC5=CC(=C(C=C54)OC)OC)O
• SMILES (Isomeric): COC1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C4(C(O2)COC5=CC(=C(C=C54)OC)OC)O
• InChI: InChI=1S/C25H28O13/c1-32-10-4-15-19(16(5-10)37-24-22(29)21(28)20(27)17(8-26)38-24)23(30)25(31)11-6-13(33-2)14(34-3)7-12(11)35-9-18(25)36-15/h4-7,17-18,20-22,24,26-29,31H,8-9H2,1-3H3
• InChI Key: RUMXFCRBAPIWOY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₁₃
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.15299094 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.89
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6005	60.05%
Caco-2	-	0.8143	81.43%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5375	53.75%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9059	90.59%
OATP1B3 inhibitior	+	0.9625	96.25%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6031	60.31%
P-glycoprotein inhibitior	+	0.6089	60.89%
P-glycoprotein substrate	-	0.6640	66.40%
CYP3A4 substrate	+	0.6349	63.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8236	82.36%
CYP3A4 inhibition	-	0.9617	96.17%
CYP2C9 inhibition	-	0.9479	94.79%
CYP2C19 inhibition	-	0.8977	89.77%
CYP2D6 inhibition	-	0.9471	94.71%
CYP1A2 inhibition	-	0.8192	81.92%
CYP2C8 inhibition	-	0.6404	64.04%
CYP inhibitory promiscuity	-	0.8583	85.83%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6421	64.21%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.8415	84.15%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5608	56.08%
Micronuclear	+	0.5533	55.33%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.9065	90.65%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.4612	46.12%
Acute Oral Toxicity (c)	III	0.6807	68.07%
Estrogen receptor binding	+	0.8099	80.99%
Androgen receptor binding	+	0.5417	54.17%
Thyroid receptor binding	+	0.5337	53.37%
Glucocorticoid receptor binding	+	0.6218	62.18%
Aromatase binding	+	0.5505	55.05%
PPAR gamma	+	0.6874	68.74%
Honey bee toxicity	-	0.7154	71.54%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.6773	67.73%

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	98.50%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.71%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.57%	96.09%
CHEMBL4208	P20618	Proteasome component C5	92.12%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.02%	96.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.99%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.74%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	89.57%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.86%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.72%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.55%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.18%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.39%	95.89%
CHEMBL2581	P07339	Cathepsin D	87.33%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.21%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.86%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.85%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.29%	96.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.69%	91.07%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.79%	92.94%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.69%	94.80%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.13%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	80.92%	92.50%

Plants that contains it

• Clitoria fairchildiana

Cross-Links

• PubChem: 162974979
• LOTUS: LTS0168885
• wikiData: Q105245700