(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(12H)-one, 1,2-dihydro-8,9-dimethoxy-2-(1-methylethenyl)-, (R)-

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	adb5b47e-4002-4d9a-90a3-9ce197687eb9
Taxonomy	Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
IUPAC Name	(6R)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),3(11),4(8),9,14,16,18-heptaen-12-one
SMILES (Canonical)	CC(=C)C1CC2=C(O1)C=CC3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4)OC)OC
SMILES (Isomeric)	CC(=C)[C@H]1CC2=C(O1)C=CC3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4)OC)OC
InChI	InChI=1S/C23H20O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16H,1,8,10H2,2-4H3/t16-/m1/s1
InChI Key	GFERNZCCTZEIET-MRXNPFEDSA-N
Popularity	7 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₃H₂₀O₆
Molecular Weight	392.40 g/mol
Exact Mass	392.12598835 g/mol
Topological Polar Surface Area (TPSA)	63.20 Å²
XlogP	4.00
Atomic LogP (AlogP)	4.25
H-Bond Acceptor	6
H-Bond Donor	0
Rotatable Bonds	3

Synonyms

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Rotenone, didehydro-

7,8-Didehydrorotenone

6a,12a-Dehydrorotenone

Rotenone, 7,8-didehydro-

NSC 194812

(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(12H)-one, 1,2-dihydro-8,9-dimethoxy-2-(1-methylethenyl)-, (2R)-

(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(12H)-one, 1,2-dihydro-8,9-dimethoxy-2-(1-methylethenyl)-, (R)-

3466-09-9

(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(12H)-one, 1,2-dihydro-2-alpha-isopropyl-8,9-dimethoxy-

NSC-194812

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.5633	56.33%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6885	68.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9599	95.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7922	79.22%
P-glycoprotein inhibitior	+	0.8834	88.34%
P-glycoprotein substrate	-	0.5360	53.60%
CYP3A4 substrate	+	0.6250	62.50%
CYP2C9 substrate	-	0.8101	81.01%
CYP2D6 substrate	-	0.7969	79.69%
CYP3A4 inhibition	+	0.7961	79.61%
CYP2C9 inhibition	-	0.7686	76.86%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.6671	66.71%
CYP inhibitory promiscuity	+	0.8226	82.26%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7166	71.66%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.5819	58.19%
Skin irritation	-	0.7739	77.39%
Skin corrosion	-	0.9622	96.22%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4178	41.78%
Micronuclear	+	0.5559	55.59%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.5678	56.78%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	+	0.4916	49.16%
Acute Oral Toxicity (c)	II	0.7236	72.36%
Estrogen receptor binding	+	0.8815	88.15%
Androgen receptor binding	+	0.6769	67.69%
Thyroid receptor binding	+	0.7715	77.15%
Glucocorticoid receptor binding	+	0.8397	83.97%
Aromatase binding	+	0.6420	64.20%
PPAR gamma	+	0.8521	85.21%
Honey bee toxicity	-	0.5801	58.01%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9833	98.33%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	98.43%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.78%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.58%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.51%	95.56%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	90.27%	96.86%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.15%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.25%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.16%	95.89%
CHEMBL2535	P11166	Glucose transporter	88.80%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.12%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.97%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.97%	86.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.24%	89.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.70%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.40%	94.00%
CHEMBL217	P14416	Dopamine D2 receptor	84.89%	95.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.11%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.10%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.07%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.01%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.67%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.65%	99.17%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.27%	92.38%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Pedicularis semitorta