(6Ar,12aR)-9,12a-dihydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6,6a-dihydrochromeno[3,4-b]chromen-12-one

Details

• Internal ID: 7cf4bb24-3259-4c61-bd58-d172909f3b98
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (6aR,12aR)-9,12a-dihydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6,6a-dihydrochromeno[3,4-b]chromen-12-one
• SMILES (Canonical): CC(=CCC1=C(C=CC2=C1OC3COC4=CC(=C(C=C4C3(C2=O)O)OC)OC)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC2=C1O[C@@H]3COC4=CC(=C(C=C4[C@@]3(C2=O)O)OC)OC)O)C
• InChI: InChI=1S/C23H24O7/c1-12(2)5-6-13-16(24)8-7-14-21(13)30-20-11-29-17-10-19(28-4)18(27-3)9-15(17)23(20,26)22(14)25/h5,7-10,20,24,26H,6,11H2,1-4H3/t20-,23-/m1/s1
• InChI Key: GHBZHAWROFXWAR-NFBKMPQASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₇
• Molecular Weight: 412.40 g/mol
• Exact Mass: 412.15220310 g/mol
• Topological Polar Surface Area (TPSA): 94.50 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 12a-Hydroxyrotenonic acid
• AKOS040734291
• (6Ar,12aR)-9,12a-dihydroxy-2,3-dimethoxy-8-(3-methylbut-2-enyl)-6,6a-dihydrochromeno[3,4-b]chromen-12-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9882	98.82%
Caco-2	+	0.6561	65.61%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7534	75.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9299	92.99%
OATP1B3 inhibitior	+	0.8793	87.93%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8539	85.39%
P-glycoprotein inhibitior	+	0.7668	76.68%
P-glycoprotein substrate	+	0.5232	52.32%
CYP3A4 substrate	+	0.6315	63.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7253	72.53%
CYP3A4 inhibition	-	0.8381	83.81%
CYP2C9 inhibition	-	0.5257	52.57%
CYP2C19 inhibition	+	0.8160	81.60%
CYP2D6 inhibition	-	0.6737	67.37%
CYP1A2 inhibition	+	0.7456	74.56%
CYP2C8 inhibition	-	0.5813	58.13%
CYP inhibitory promiscuity	+	0.5685	56.85%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7228	72.28%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.7114	71.14%
Skin irritation	-	0.7992	79.92%
Skin corrosion	-	0.9516	95.16%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8497	84.97%
Micronuclear	-	0.5541	55.41%
Hepatotoxicity	-	0.5321	53.21%
skin sensitisation	-	0.7385	73.85%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6334	63.34%
Acute Oral Toxicity (c)	III	0.6702	67.02%
Estrogen receptor binding	+	0.9094	90.94%
Androgen receptor binding	+	0.6115	61.15%
Thyroid receptor binding	+	0.6894	68.94%
Glucocorticoid receptor binding	+	0.8404	84.04%
Aromatase binding	+	0.6473	64.73%
PPAR gamma	+	0.8659	86.59%
Honey bee toxicity	-	0.7180	71.80%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9610	96.10%

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	99.33%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.26%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.11%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.71%	93.40%
CHEMBL1951	P21397	Monoamine oxidase A	91.64%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.16%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.36%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.01%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.04%	96.09%
CHEMBL4208	P20618	Proteasome component C5	88.15%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.78%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.34%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.47%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.32%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.07%	92.62%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.97%	90.24%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.44%	89.50%
CHEMBL1937	Q92769	Histone deacetylase 2	84.01%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.84%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.68%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	82.38%	91.19%
CHEMBL2535	P11166	Glucose transporter	81.75%	98.75%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.69%	97.28%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.05%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.42%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.05%	94.00%

Plants that contains it

• Achillea cretica
• Ageratina riparia
• Cordia americana
• Glycosmis lanceolata
• Millettia pachycarpa
• Pedicularis semitorta
• Scopolia japonica

Cross-Links

• PubChem: 51136534
• NPASS: NPC274810
• LOTUS: LTS0257710
• wikiData: Q105008426