(2R)-1,2,12,12aalpha-Tetrahydro-6abeta-methoxy-2alpha-isopropenyl-8,9-dimethoxy-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one

Details

• Internal ID: 4451b0d7-4eeb-4897-be7f-7666b0655936
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (1R,6R,13S)-13,16,17-trimethoxy-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=CC3=C2OC4COC5=CC(=C(C=C5C4(C3=O)OC)OC)OC
• SMILES (Isomeric): CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@]4(C3=O)OC)OC)OC
• InChI: InChI=1S/C24H24O7/c1-12(2)17-8-14-16(30-17)7-6-13-22(14)31-21-11-29-18-10-20(27-4)19(26-3)9-15(18)24(21,28-5)23(13)25/h6-7,9-10,17,21H,1,8,11H2,2-5H3/t17-,21-,24+/m1/s1
• InChI Key: KHDBBFYQRTYKSB-JKHABCDFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₄O₇
• Molecular Weight: 424.40 g/mol
• Exact Mass: 424.15220310 g/mol
• Topological Polar Surface Area (TPSA): 72.40 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.6052	60.52%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6771	67.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7782	77.82%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7356	73.56%
P-glycoprotein inhibitior	+	0.8522	85.22%
P-glycoprotein substrate	+	0.5731	57.31%
CYP3A4 substrate	+	0.6440	64.40%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	-	0.6978	69.78%
CYP3A4 inhibition	+	0.7826	78.26%
CYP2C9 inhibition	-	0.8090	80.90%
CYP2C19 inhibition	+	0.7784	77.84%
CYP2D6 inhibition	-	0.9115	91.15%
CYP1A2 inhibition	+	0.8288	82.88%
CYP2C8 inhibition	+	0.5150	51.50%
CYP inhibitory promiscuity	+	0.7106	71.06%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6466	64.66%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.5774	57.74%
Skin irritation	-	0.7561	75.61%
Skin corrosion	-	0.9433	94.33%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5515	55.15%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.6133	61.33%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.5662	56.62%
Acute Oral Toxicity (c)	II	0.5297	52.97%
Estrogen receptor binding	+	0.8831	88.31%
Androgen receptor binding	+	0.6091	60.91%
Thyroid receptor binding	+	0.8098	80.98%
Glucocorticoid receptor binding	+	0.8441	84.41%
Aromatase binding	+	0.5513	55.13%
PPAR gamma	+	0.8696	86.96%
Honey bee toxicity	+	0.6160	61.60%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.9837	98.37%

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	95.96%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.04%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.47%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.36%	94.80%
CHEMBL2581	P07339	Cathepsin D	93.03%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.19%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.48%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.96%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.44%	92.94%
CHEMBL1951	P21397	Monoamine oxidase A	89.08%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.46%	89.00%
CHEMBL2535	P11166	Glucose transporter	87.44%	98.75%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	86.71%	97.33%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.82%	82.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.77%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.16%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.10%	97.09%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.94%	96.86%
CHEMBL340	P08684	Cytochrome P450 3A4	84.29%	91.19%
CHEMBL4040	P28482	MAP kinase ERK2	84.27%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.89%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.06%	94.45%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.90%	89.50%
CHEMBL4208	P20618	Proteasome component C5	81.84%	90.00%

Plants that contains it

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

Cross-Links

• PubChem: 100970021
• NPASS: NPC98929