(6aS,12aS)-12a-hydroxy-9-[(2E,5E)-7-hydroxy-3,7-dimethylocta-2,5-dienoxy]-2,3-dimethoxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one

Details

• Internal ID: acef9605-40eb-4a1a-bbef-46471d4ee0bd
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
• IUPAC Name: (6aS,12aS)-12a-hydroxy-9-[(2E,5E)-7-hydroxy-3,7-dimethylocta-2,5-dienoxy]-2,3-dimethoxy-6,6a-dihydrochromeno[3,4-b]chromen-12-one
• SMILES (Canonical): CC(=CCOC1=CC2=C(C=C1)C(=O)C3(C(O2)COC4=CC(=C(C=C43)OC)OC)O)CC=CC(C)(C)O
• SMILES (Isomeric): C/C(=C\COC1=CC2=C(C=C1)C(=O)[C@]3([C@@H](O2)COC4=CC(=C(C=C43)OC)OC)O)/C/C=C/C(C)(C)O
• InChI: InChI=1S/C28H32O8/c1-17(7-6-11-27(2,3)30)10-12-34-18-8-9-19-21(13-18)36-25-16-35-22-15-24(33-5)23(32-4)14-20(22)28(25,31)26(19)29/h6,8-11,13-15,25,30-31H,7,12,16H2,1-5H3/b11-6+,17-10+/t25-,28-/m0/s1
• InChI Key: VXBXQMZYISYYKS-GMZUZMGRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₈
• Molecular Weight: 496.50 g/mol
• Exact Mass: 496.20971797 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.97
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9689	96.89%
Caco-2	-	0.7004	70.04%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7504	75.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8772	87.72%
OATP1B3 inhibitior	+	0.9146	91.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9064	90.64%
BSEP inhibitior	+	0.9909	99.09%
P-glycoprotein inhibitior	+	0.8817	88.17%
P-glycoprotein substrate	+	0.5500	55.00%
CYP3A4 substrate	+	0.6887	68.87%
CYP2C9 substrate	-	0.8057	80.57%
CYP2D6 substrate	-	0.7383	73.83%
CYP3A4 inhibition	-	0.8164	81.64%
CYP2C9 inhibition	-	0.6116	61.16%
CYP2C19 inhibition	+	0.6280	62.80%
CYP2D6 inhibition	-	0.8133	81.33%
CYP1A2 inhibition	+	0.6249	62.49%
CYP2C8 inhibition	+	0.6119	61.19%
CYP inhibitory promiscuity	-	0.6321	63.21%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6450	64.50%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9211	92.11%
Skin irritation	-	0.8002	80.02%
Skin corrosion	-	0.9531	95.31%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4747	47.47%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5699	56.99%
skin sensitisation	-	0.7968	79.68%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6474	64.74%
Acute Oral Toxicity (c)	III	0.6084	60.84%
Estrogen receptor binding	+	0.8180	81.80%
Androgen receptor binding	+	0.5913	59.13%
Thyroid receptor binding	+	0.7087	70.87%
Glucocorticoid receptor binding	+	0.7830	78.30%
Aromatase binding	+	0.6383	63.83%
PPAR gamma	+	0.8093	80.93%
Honey bee toxicity	-	0.7439	74.39%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9899	98.99%

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	98.55%	91.11%
CHEMBL4208	P20618	Proteasome component C5	95.45%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.50%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.46%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.09%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.83%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.40%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.50%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.46%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.14%	94.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.01%	91.07%
CHEMBL1937	Q92769	Histone deacetylase 2	88.87%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.62%	95.56%
CHEMBL2535	P11166	Glucose transporter	87.94%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.56%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.41%	96.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	85.64%	96.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.81%	90.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.33%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.63%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.62%	94.80%
CHEMBL1907	P15144	Aminopeptidase N	82.30%	93.31%
CHEMBL1902	P62942	FK506-binding protein 1A	82.09%	97.05%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.53%	97.14%
CHEMBL3401	O75469	Pregnane X receptor	81.31%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.19%	85.14%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.71%	100.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.14%	91.03%

Plants that contains it

• Millettia griffoniana

Cross-Links

• PubChem: 162983581
• LOTUS: LTS0259083
• wikiData: Q105298410