(2R,3S,4S,5S,6R)-2-[2-[(1S,6R,12R,13R)-12-hydroxy-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-6-yl]prop-2-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: b6d3ce2b-098f-421f-8f01-0454422223a7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Rotenoid O-glycosides
• IUPAC Name: (2R,3S,4S,5S,6R)-2-[2-[(1S,6R,12R,13R)-12-hydroxy-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-6-yl]prop-2-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=C2C(=C1)C3C(CO2)OC4=C(C3O)C=CC5=C4CC(O5)C(=C)COC6C(C(C(C(O6)CO)O)O)O)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)[C@H]3[C@@H](CO2)OC4=C([C@@H]3O)C=CC5=C4C[C@@H](O5)C(=C)CO[C@H]6[C@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)OC
• InChI: InChI=1S/C29H34O12/c1-12(10-38-29-27(34)26(33)25(32)21(9-30)41-29)17-7-15-16(39-17)5-4-13-24(31)23-14-6-19(35-2)20(36-3)8-18(14)37-11-22(23)40-28(13)15/h4-6,8,17,21-27,29-34H,1,7,9-11H2,2-3H3/t17-,21-,22-,23+,24+,25-,26+,27+,29-/m1/s1
• InChI Key: YRUIPRJNLCHFCW-JUEHTJRRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₂
• Molecular Weight: 574.60 g/mol
• Exact Mass: 574.20502652 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6200	62.00%
Caco-2	-	0.8397	83.97%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6110	61.10%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.7978	79.78%
OATP1B3 inhibitior	+	0.9696	96.96%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7267	72.67%
P-glycoprotein inhibitior	+	0.6202	62.02%
P-glycoprotein substrate	+	0.5551	55.51%
CYP3A4 substrate	+	0.6534	65.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7526	75.26%
CYP3A4 inhibition	-	0.6939	69.39%
CYP2C9 inhibition	-	0.8757	87.57%
CYP2C19 inhibition	-	0.5955	59.55%
CYP2D6 inhibition	-	0.8626	86.26%
CYP1A2 inhibition	-	0.8475	84.75%
CYP2C8 inhibition	+	0.7072	70.72%
CYP inhibitory promiscuity	+	0.5929	59.29%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6146	61.46%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9293	92.93%
Skin irritation	-	0.8001	80.01%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8391	83.91%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	-	0.7374	73.74%
skin sensitisation	-	0.7719	77.19%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.4577	45.77%
Acute Oral Toxicity (c)	III	0.5743	57.43%
Estrogen receptor binding	+	0.7815	78.15%
Androgen receptor binding	+	0.6363	63.63%
Thyroid receptor binding	+	0.6558	65.58%
Glucocorticoid receptor binding	+	0.6383	63.83%
Aromatase binding	+	0.5789	57.89%
PPAR gamma	+	0.6336	63.36%
Honey bee toxicity	-	0.5508	55.08%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9690	96.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.65%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.54%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	95.10%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	94.24%	83.82%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.64%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.90%	94.80%
CHEMBL2581	P07339	Cathepsin D	88.42%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	87.94%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.53%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.37%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.14%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.87%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.74%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.24%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.03%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.43%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.99%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.69%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	82.99%	94.73%

Plants that contains it

• Dalbergia cochinchinensis

Cross-Links

• PubChem: 162974736
• LOTUS: LTS0258751
• wikiData: Q105353085