(1S,6R,13R,21S)-10,13,21-trihydroxy-16,17-dimethoxy-6-prop-1-en-2-yl-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: 8a64a69a-7bc2-4c65-9779-41070cbf62d0
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (1S,6R,13R,21S)-10,13,21-trihydroxy-16,17-dimethoxy-6-prop-1-en-2-yl-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
• SMILES (Canonical): CC(=C)C1CC2=C(O1)C=C(C3=C2OC4C(OC5=CC(=C(C=C5C4(C3=O)O)OC)OC)O)O
• SMILES (Isomeric): CC(=C)[C@H]1CC2=C(O1)C=C(C3=C2O[C@@H]4[C@H](OC5=CC(=C(C=C5[C@@]4(C3=O)O)OC)OC)O)O
• InChI: InChI=1S/C23H22O9/c1-9(2)13-5-10-14(30-13)7-12(24)18-19(10)32-21-22(26)31-15-8-17(29-4)16(28-3)6-11(15)23(21,27)20(18)25/h6-8,13,21-22,24,26-27H,1,5H2,2-4H3/t13-,21-,22+,23+/m1/s1
• InChI Key: CDZUQIFWCXAIFB-GLDFNTMPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₉
• Molecular Weight: 442.40 g/mol
• Exact Mass: 442.12638228 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 1.83
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9725	97.25%
Caco-2	-	0.5969	59.69%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5606	56.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8399	83.99%
OATP1B3 inhibitior	+	0.8541	85.41%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6628	66.28%
P-glycoprotein inhibitior	+	0.6974	69.74%
P-glycoprotein substrate	-	0.5546	55.46%
CYP3A4 substrate	+	0.6553	65.53%
CYP2C9 substrate	-	0.8108	81.08%
CYP2D6 substrate	-	0.8182	81.82%
CYP3A4 inhibition	+	0.5504	55.04%
CYP2C9 inhibition	-	0.8228	82.28%
CYP2C19 inhibition	-	0.5131	51.31%
CYP2D6 inhibition	-	0.8597	85.97%
CYP1A2 inhibition	-	0.6623	66.23%
CYP2C8 inhibition	+	0.4673	46.73%
CYP inhibitory promiscuity	+	0.5994	59.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.4401	44.01%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.6805	68.05%
Skin irritation	-	0.7104	71.04%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7780	77.80%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.7189	71.89%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.7110	71.10%
Acute Oral Toxicity (c)	II	0.3628	36.28%
Estrogen receptor binding	+	0.7515	75.15%
Androgen receptor binding	+	0.5362	53.62%
Thyroid receptor binding	+	0.6452	64.52%
Glucocorticoid receptor binding	+	0.7136	71.36%
Aromatase binding	+	0.6103	61.03%
PPAR gamma	+	0.7854	78.54%
Honey bee toxicity	-	0.5271	52.71%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9864	98.64%

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	99.44%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.22%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	95.92%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.56%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.14%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.24%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.14%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.41%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.73%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.96%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.94%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.72%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.45%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	86.88%	91.19%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.86%	97.33%
CHEMBL2535	P11166	Glucose transporter	85.64%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.56%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	85.12%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.44%	100.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	83.26%	91.79%
CHEMBL217	P14416	Dopamine D2 receptor	81.90%	95.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.12%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.04%	91.07%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.45%	82.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.39%	97.14%

Plants that contains it

• Tephrosia villosa

Cross-Links

• PubChem: 98598071
• LOTUS: LTS0070652
• wikiData: Q104955366