(22S)-17,18,22-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),3(12),4(9),5,10,15,17,19-octaen-13-one

Details

• Internal ID: 1be56717-c974-4028-ba3f-9fee2c288961
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (22S)-17,18,22-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),3(12),4(9),5,10,15,17,19-octaen-13-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=CC3=C2OC4=C(C3=O)C5=CC(=C(C=C5OC4OC)OC)OC)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC3=C2OC4=C(C3=O)C5=CC(=C(C=C5O[C@@H]4OC)OC)OC)C
• InChI: InChI=1S/C24H22O7/c1-24(2)9-8-12-15(31-24)7-6-13-20(25)19-14-10-17(26-3)18(27-4)11-16(14)29-23(28-5)22(19)30-21(12)13/h6-11,23H,1-5H3/t23-/m0/s1
• InChI Key: VWSZNYHUCXFZPZ-QHCPKHFHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₂O₇
• Molecular Weight: 422.40 g/mol
• Exact Mass: 422.13655304 g/mol
• Topological Polar Surface Area (TPSA): 72.40 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.70
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9841	98.41%
Caco-2	+	0.6577	65.77%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6429	64.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.9809	98.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9469	94.69%
P-glycoprotein inhibitior	+	0.9623	96.23%
P-glycoprotein substrate	+	0.5871	58.71%
CYP3A4 substrate	+	0.6608	66.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8454	84.54%
CYP3A4 inhibition	+	0.7122	71.22%
CYP2C9 inhibition	-	0.9459	94.59%
CYP2C19 inhibition	+	0.6505	65.05%
CYP2D6 inhibition	-	0.7627	76.27%
CYP1A2 inhibition	+	0.6285	62.85%
CYP2C8 inhibition	+	0.5847	58.47%
CYP inhibitory promiscuity	+	0.5943	59.43%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.5475	54.75%
Eye corrosion	-	0.9806	98.06%
Eye irritation	-	0.7016	70.16%
Skin irritation	-	0.7798	77.98%
Skin corrosion	-	0.9722	97.22%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7516	75.16%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.5949	59.49%
skin sensitisation	-	0.8152	81.52%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.4615	46.15%
Acute Oral Toxicity (c)	III	0.4568	45.68%
Estrogen receptor binding	+	0.9501	95.01%
Androgen receptor binding	+	0.7387	73.87%
Thyroid receptor binding	+	0.7887	78.87%
Glucocorticoid receptor binding	+	0.8301	83.01%
Aromatase binding	+	0.5887	58.87%
PPAR gamma	+	0.8468	84.68%
Honey bee toxicity	-	0.6485	64.85%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9806	98.06%

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	97.22%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.46%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.16%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.72%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.68%	94.00%
CHEMBL2535	P11166	Glucose transporter	90.17%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.92%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.52%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.60%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.36%	92.62%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	86.84%	96.86%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.96%	86.33%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	84.39%	94.03%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.23%	95.71%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.62%	96.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.48%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.40%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.70%	94.80%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.24%	89.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.84%	97.28%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.06%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	80.06%	94.75%

Plants that contains it

• Millettia duchesnei

Cross-Links

• PubChem: 163004444
• LOTUS: LTS0240526
• wikiData: Q105298262