1-Hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

Details

• Internal ID: f2e18722-a4e3-4b38-b3ec-3d13a83c5556
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: 1-hydroxy-6-(3-hydroxyprop-1-en-2-yl)-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
• InChI: InChI=1S/C23H22O8/c1-11(9-24)16-7-14-15(30-16)5-4-12-21(25)20-13-6-18(27-2)19(28-3)8-17(13)29-10-23(20,26)31-22(12)14/h4-6,8,16,20,24,26H,1,7,9-10H2,2-3H3
• InChI Key: LEBAJWSMKUWLHA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₈
• Molecular Weight: 426.40 g/mol
• Exact Mass: 426.13146766 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8633	86.33%
Caco-2	-	0.5409	54.09%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7214	72.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8047	80.47%
OATP1B3 inhibitior	+	0.9498	94.98%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4664	46.64%
P-glycoprotein inhibitior	+	0.7491	74.91%
P-glycoprotein substrate	+	0.5639	56.39%
CYP3A4 substrate	+	0.6560	65.60%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.7620	76.20%
CYP3A4 inhibition	+	0.6180	61.80%
CYP2C9 inhibition	-	0.8750	87.50%
CYP2C19 inhibition	-	0.5106	51.06%
CYP2D6 inhibition	-	0.8553	85.53%
CYP1A2 inhibition	-	0.8907	89.07%
CYP2C8 inhibition	+	0.5528	55.28%
CYP inhibitory promiscuity	+	0.5755	57.55%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5561	55.61%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.8347	83.47%
Skin irritation	-	0.7767	77.67%
Skin corrosion	-	0.9430	94.30%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5269	52.69%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	+	0.5854	58.54%
skin sensitisation	-	0.6983	69.83%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.6762	67.62%
Acute Oral Toxicity (c)	III	0.4485	44.85%
Estrogen receptor binding	+	0.8246	82.46%
Androgen receptor binding	+	0.7190	71.90%
Thyroid receptor binding	+	0.7199	71.99%
Glucocorticoid receptor binding	+	0.5998	59.98%
Aromatase binding	+	0.6423	64.23%
PPAR gamma	+	0.6843	68.43%
Honey bee toxicity	-	0.5705	57.05%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9688	96.88%

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	98.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.42%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.39%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.39%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.11%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.98%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.89%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.34%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.34%	89.00%
CHEMBL2535	P11166	Glucose transporter	88.08%	98.75%
CHEMBL4208	P20618	Proteasome component C5	87.70%	90.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.08%	94.80%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.42%	89.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.17%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.66%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.24%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.61%	96.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	84.22%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.48%	92.94%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.05%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.22%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.76%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.37%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	80.10%	83.82%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.01%	92.38%

Plants that contains it

• Amorpha fruticosa
• Brachylaena transvaalensis
• Heterocoma ekmaniana
• Proteopsis argentea

Cross-Links

• PubChem: 162853180
• LOTUS: LTS0180443
• wikiData: Q105113934