(1S)-1alpha,2beta,7aalpha-Trihydroxy-3,3-dimethyl-9,10-dimethoxy-2,3,13,13aalpha-tetrahydro-1H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one

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	c69e8709-121e-4060-8d08-b20726009c0f
Taxonomy	Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
IUPAC Name	(1R,5S,6R,14R)-5,6,14-trihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),10,15,17,19-hexaen-13-one
SMILES (Canonical)	CC1(C(C(C2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4(C3=O)O)OC)OC)O)O)C
SMILES (Isomeric)	CC1([C@@H]([C@H](C2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@]4(C3=O)O)OC)OC)O)O)C
InChI	InChI=1S/C23H24O9/c1-22(2)21(26)18(24)17-12(32-22)6-5-10-19(17)31-16-9-30-13-8-15(29-4)14(28-3)7-11(13)23(16,27)20(10)25/h5-8,16,18,21,24,26-27H,9H2,1-4H3/t16-,18+,21-,23-/m1/s1
InChI Key	XMGJLGOKKNELQY-QBXAIUQQSA-N
Popularity	1 reference in papers

Physical and Chemical Properties

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Molecular Formula	C₂₃H₂₄O₉
Molecular Weight	444.40 g/mol
Exact Mass	444.14203234 g/mol
Topological Polar Surface Area (TPSA)	124.00 Å²
XlogP	1.00
Atomic LogP (AlogP)	1.49
H-Bond Acceptor	9
H-Bond Donor	3
Rotatable Bonds	2

Synonyms

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(1S)-1alpha,2beta,7aalpha-Trihydroxy-3,3-dimethyl-9,10-dimethoxy-2,3,13,13aalpha-tetrahydro-1H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one

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	+	0.9406	94.06%
Caco-2	-	0.5491	54.91%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8132	81.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9059	90.59%
OATP1B3 inhibitior	+	0.9547	95.47%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7182	71.82%
P-glycoprotein inhibitior	+	0.6521	65.21%
P-glycoprotein substrate	+	0.5219	52.19%
CYP3A4 substrate	+	0.6500	65.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7464	74.64%
CYP3A4 inhibition	-	0.7818	78.18%
CYP2C9 inhibition	-	0.9182	91.82%
CYP2C19 inhibition	-	0.5497	54.97%
CYP2D6 inhibition	-	0.8036	80.36%
CYP1A2 inhibition	+	0.7393	73.93%
CYP2C8 inhibition	+	0.4725	47.25%
CYP inhibitory promiscuity	-	0.8860	88.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6193	61.93%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.8190	81.90%
Skin irritation	-	0.8275	82.75%
Skin corrosion	-	0.9541	95.41%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8726	87.26%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	-	0.7448	74.48%
skin sensitisation	-	0.8495	84.95%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4671	46.71%
Acute Oral Toxicity (c)	III	0.7455	74.55%
Estrogen receptor binding	+	0.8213	82.13%
Androgen receptor binding	+	0.6281	62.81%
Thyroid receptor binding	+	0.7487	74.87%
Glucocorticoid receptor binding	+	0.8086	80.86%
Aromatase binding	+	0.6198	61.98%
PPAR gamma	+	0.7923	79.23%
Honey bee toxicity	-	0.7338	73.38%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5851	58.51%
Fish aquatic toxicity	+	0.8156	81.56%

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	96.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.27%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.60%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	91.74%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.62%	86.33%
CHEMBL4208	P20618	Proteasome component C5	90.60%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.50%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.41%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.78%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.97%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	86.01%	91.19%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.83%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.41%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.15%	97.14%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.08%	90.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.93%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.68%	97.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.41%	89.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.06%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.28%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.84%	94.80%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.71%	82.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.57%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.49%	96.77%

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

Scopolia japonica