12-[5-(7-hydroxy-3,4-dihydro-2H-chromen-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6H-chromeno[2,3-c]chromene-9,12a-diol

Details

• Internal ID: 4f0ff8ba-0bba-499b-9399-ce40fb3f7356
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids
• IUPAC Name: 12-[5-(7-hydroxy-3,4-dihydro-2H-chromen-3-yl)-2-methoxyphenyl]-3-methoxy-6a,12-dihydro-6H-chromeno[2,3-c]chromene-9,12a-diol
• SMILES (Canonical): COC1=CC2=C(C=C1)C3(C(CO2)OC4=C(C3C5=C(C=CC(=C5)C6CC7=C(C=C(C=C7)O)OC6)OC)C=CC(=C4)O)O
• SMILES (Isomeric): COC1=CC2=C(C=C1)C3(C(CO2)OC4=C(C3C5=C(C=CC(=C5)C6CC7=C(C=C(C=C7)O)OC6)OC)C=CC(=C4)O)O
• InChI: InChI=1S/C33H30O8/c1-37-23-7-9-26-30(15-23)40-17-31-33(26,36)32(24-8-6-22(35)14-29(24)41-31)25-12-18(4-10-27(25)38-2)20-11-19-3-5-21(34)13-28(19)39-16-20/h3-10,12-15,20,31-32,34-36H,11,16-17H2,1-2H3
• InChI Key: AAYNXSSLTTZFMB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₀O₈
• Molecular Weight: 554.60 g/mol
• Exact Mass: 554.19406791 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 5.01
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9509	95.09%
Caco-2	-	0.7058	70.58%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8206	82.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8859	88.59%
OATP1B3 inhibitior	+	0.9683	96.83%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9848	98.48%
P-glycoprotein inhibitior	+	0.8766	87.66%
P-glycoprotein substrate	+	0.6783	67.83%
CYP3A4 substrate	+	0.7045	70.45%
CYP2C9 substrate	-	0.5929	59.29%
CYP2D6 substrate	+	0.5126	51.26%
CYP3A4 inhibition	-	0.8898	88.98%
CYP2C9 inhibition	-	0.7237	72.37%
CYP2C19 inhibition	+	0.6648	66.48%
CYP2D6 inhibition	-	0.8909	89.09%
CYP1A2 inhibition	-	0.8119	81.19%
CYP2C8 inhibition	+	0.7330	73.30%
CYP inhibitory promiscuity	-	0.6694	66.94%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5964	59.64%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8866	88.66%
Skin irritation	-	0.8472	84.72%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8739	87.39%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8673	86.73%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6601	66.01%
Acute Oral Toxicity (c)	III	0.6478	64.78%
Estrogen receptor binding	+	0.8693	86.93%
Androgen receptor binding	+	0.7780	77.80%
Thyroid receptor binding	+	0.7442	74.42%
Glucocorticoid receptor binding	+	0.8458	84.58%
Aromatase binding	+	0.5318	53.18%
PPAR gamma	+	0.7015	70.15%
Honey bee toxicity	-	0.7762	77.62%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6151	61.51%
Fish aquatic toxicity	+	0.7513	75.13%

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	98.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.79%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.83%	97.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	94.38%	89.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.69%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.73%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.26%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.62%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.39%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.79%	93.99%
CHEMBL4208	P20618	Proteasome component C5	89.53%	90.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	89.39%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.53%	95.78%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	87.68%	95.55%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.61%	85.14%
CHEMBL3438	Q05513	Protein kinase C zeta	87.23%	88.48%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.05%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.67%	99.17%
CHEMBL236	P41143	Delta opioid receptor	86.32%	99.35%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.83%	97.14%
CHEMBL2535	P11166	Glucose transporter	85.73%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	85.32%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.30%	92.94%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.04%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.86%	94.00%
CHEMBL2581	P07339	Cathepsin D	83.09%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.20%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.19%	100.00%
CHEMBL3085	P43003	Excitatory amino acid transporter 1	81.89%	94.67%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.57%	93.40%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.83%	100.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	80.75%	91.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.08%	89.00%

Plants that contains it

• Gliricidia sepium

Cross-Links

• PubChem: 85183418
• LOTUS: LTS0155892
• wikiData: Q104908452