11-Hydroxy-2,3,9-trimethoxy-6h-chromeno[3,4-b]chromen-12-one

Details

• Internal ID: b3670357-de05-4958-8521-5498161186f5
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: 11-hydroxy-2,3,9-trimethoxy-6H-chromeno[3,4-b]chromen-12-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC3=C(C2=O)C4=CC(=C(C=C4OC3)OC)OC)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC3=C(C2=O)C4=CC(=C(C=C4OC3)OC)OC)O
• InChI: InChI=1S/C19H16O7/c1-22-9-4-11(20)18-15(5-9)26-16-8-25-12-7-14(24-3)13(23-2)6-10(12)17(16)19(18)21/h4-7,20H,8H2,1-3H3
• InChI Key: AHASVNPHVWSIGH-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₆O₇
• Molecular Weight: 356.30 g/mol
• Exact Mass: 356.08960285 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.08
• 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	+	0.9720	97.20%
Caco-2	+	0.8786	87.86%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7740	77.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9174	91.74%
OATP1B3 inhibitior	+	0.9528	95.28%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.5144	51.44%
P-glycoprotein inhibitior	+	0.7348	73.48%
P-glycoprotein substrate	-	0.7775	77.75%
CYP3A4 substrate	+	0.5797	57.97%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.5900	59.00%
CYP2C9 inhibition	-	0.9372	93.72%
CYP2C19 inhibition	-	0.5329	53.29%
CYP2D6 inhibition	-	0.7890	78.90%
CYP1A2 inhibition	+	0.7230	72.30%
CYP2C8 inhibition	-	0.5915	59.15%
CYP inhibitory promiscuity	-	0.6929	69.29%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6540	65.40%
Eye corrosion	-	0.9821	98.21%
Eye irritation	-	0.5366	53.66%
Skin irritation	-	0.7972	79.72%
Skin corrosion	-	0.9836	98.36%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6826	68.26%
Micronuclear	+	0.7359	73.59%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8499	84.99%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.6455	64.55%
Acute Oral Toxicity (c)	III	0.5891	58.91%
Estrogen receptor binding	+	0.8752	87.52%
Androgen receptor binding	+	0.7175	71.75%
Thyroid receptor binding	+	0.6529	65.29%
Glucocorticoid receptor binding	+	0.7381	73.81%
Aromatase binding	+	0.5212	52.12%
PPAR gamma	+	0.8313	83.13%
Honey bee toxicity	-	0.8378	83.78%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5149	51.49%
Fish aquatic toxicity	+	0.6658	66.58%

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	97.65%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.03%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.44%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.24%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.52%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.72%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.04%	96.21%
CHEMBL2581	P07339	Cathepsin D	90.07%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.17%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.09%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.74%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.39%	94.45%
CHEMBL4208	P20618	Proteasome component C5	87.91%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.44%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.34%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.11%	92.94%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.57%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.07%	86.33%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.77%	82.67%
CHEMBL3194	P02766	Transthyretin	83.28%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.10%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	82.92%	91.19%
CHEMBL2535	P11166	Glucose transporter	82.14%	98.75%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.78%	95.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.25%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.69%	97.14%

Plants that contains it

• Millettia brandisiana

Cross-Links

• PubChem: 101368147
• LOTUS: LTS0138261
• wikiData: Q104912147