6,9,11,12a-Tetrahydroxy-2,3-dimethoxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one

Details

• Internal ID: d96ecf89-9bbe-43b0-9ddb-3240d88b1f13
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: 6,9,11,12a-tetrahydroxy-2,3-dimethoxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one
• InChI: InChI=1S/C18H16O9/c1-24-11-5-8-10(6-12(11)25-2)27-17(22)16-18(8,23)15(21)14-9(20)3-7(19)4-13(14)26-16/h3-6,16-17,19-20,22-23H,1-2H3
• InChI Key: PYIMOMJIHXEJKY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₉
• Molecular Weight: 376.30 g/mol
• Exact Mass: 376.07943208 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.66
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8631	86.31%
Caco-2	-	0.5793	57.93%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6083	60.83%
OATP2B1 inhibitior	-	0.7121	71.21%
OATP1B1 inhibitior	+	0.9008	90.08%
OATP1B3 inhibitior	+	0.8933	89.33%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6600	66.00%
P-glycoprotein inhibitior	-	0.5367	53.67%
P-glycoprotein substrate	-	0.7458	74.58%
CYP3A4 substrate	+	0.5982	59.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8183	81.83%
CYP3A4 inhibition	-	0.5821	58.21%
CYP2C9 inhibition	-	0.9199	91.99%
CYP2C19 inhibition	-	0.7650	76.50%
CYP2D6 inhibition	-	0.8276	82.76%
CYP1A2 inhibition	-	0.7594	75.94%
CYP2C8 inhibition	+	0.4517	45.17%
CYP inhibitory promiscuity	-	0.6647	66.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5436	54.36%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.4887	48.87%
Skin irritation	-	0.6857	68.57%
Skin corrosion	-	0.9418	94.18%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8373	83.73%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8848	88.48%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.7689	76.89%
Acute Oral Toxicity (c)	III	0.6666	66.66%
Estrogen receptor binding	+	0.7806	78.06%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6519	65.19%
Glucocorticoid receptor binding	+	0.6891	68.91%
Aromatase binding	+	0.5348	53.48%
PPAR gamma	+	0.7196	71.96%
Honey bee toxicity	-	0.7132	71.32%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5049	50.49%
Fish aquatic toxicity	+	0.8751	87.51%

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	96.84%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.00%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.01%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.83%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.38%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.26%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.12%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.02%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.56%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.85%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.39%	91.07%
CHEMBL3194	P02766	Transthyretin	82.23%	90.71%
CHEMBL2535	P11166	Glucose transporter	81.86%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.77%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	81.38%	94.75%
CHEMBL4208	P20618	Proteasome component C5	80.49%	90.00%

Plants that contains it

• Clitoria fairchildiana

Cross-Links

• PubChem: 163003761
• LOTUS: LTS0170964
• wikiData: Q105216596