(1R,3S)-5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-3,4-dihydro-1H-benzo[g]isochromene-6,9-dione

Details

• Internal ID: 248bbffa-f80a-4d0b-88ec-d9480974f272
• Taxonomy: Phenylpropanoids and polyketides > Isochromanequinones
• IUPAC Name: (1R,3S)-5-(1,8-dihydroxy-6-methyl-9,10-dioxoanthracen-2-yl)-10-hydroxy-7-methoxy-1,3-dimethyl-3,4-dihydro-1H-benzo[g]isochromene-6,9-dione
• SMILES (Canonical): CC1CC2=C(C3=C(C(=O)C=C(C3=O)OC)C(=C2C(O1)C)O)C4=C(C5=C(C=C4)C(=O)C6=C(C5=O)C(=CC(=C6)C)O)O
• SMILES (Isomeric): C[C@H]1CC2=C(C3=C(C(=O)C=C(C3=O)OC)C(=C2[C@H](O1)C)O)C4=C(C5=C(C=C4)C(=O)C6=C(C5=O)C(=CC(=C6)C)O)O
• InChI: InChI=1S/C31H24O9/c1-11-7-17-23(18(32)8-11)31(38)24-15(27(17)34)6-5-14(28(24)35)22-16-9-12(2)40-13(3)21(16)30(37)25-19(33)10-20(39-4)29(36)26(22)25/h5-8,10,12-13,32,35,37H,9H2,1-4H3/t12-,13+/m0/s1
• InChI Key: JQICCSAZSNANIX-QWHCGFSZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₂₄O₉
• Molecular Weight: 540.50 g/mol
• Exact Mass: 540.14203234 g/mol
• Topological Polar Surface Area (TPSA): 147.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.49
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9567	95.67%
Caco-2	-	0.7315	73.15%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6778	67.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8844	88.44%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9394	93.94%
P-glycoprotein inhibitior	+	0.7499	74.99%
P-glycoprotein substrate	-	0.6038	60.38%
CYP3A4 substrate	+	0.6387	63.87%
CYP2C9 substrate	-	0.8110	81.10%
CYP2D6 substrate	-	0.8444	84.44%
CYP3A4 inhibition	-	0.7267	72.67%
CYP2C9 inhibition	+	0.5398	53.98%
CYP2C19 inhibition	+	0.5744	57.44%
CYP2D6 inhibition	-	0.7597	75.97%
CYP1A2 inhibition	+	0.6990	69.90%
CYP2C8 inhibition	+	0.5981	59.81%
CYP inhibitory promiscuity	+	0.6559	65.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5188	51.88%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8644	86.44%
Skin irritation	-	0.7830	78.30%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	+	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5166	51.66%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8672	86.72%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.4794	47.94%
Acute Oral Toxicity (c)	I	0.4609	46.09%
Estrogen receptor binding	+	0.7948	79.48%
Androgen receptor binding	+	0.6906	69.06%
Thyroid receptor binding	-	0.5261	52.61%
Glucocorticoid receptor binding	+	0.7964	79.64%
Aromatase binding	+	0.5941	59.41%
PPAR gamma	+	0.6988	69.88%
Honey bee toxicity	-	0.8372	83.72%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9776	97.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.56%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.71%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.11%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.69%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.78%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.62%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.96%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.38%	90.71%
CHEMBL4208	P20618	Proteasome component C5	89.16%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.57%	94.00%
CHEMBL2535	P11166	Glucose transporter	88.50%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.04%	85.14%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	87.47%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.05%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.30%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.71%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.09%	96.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.64%	96.67%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.45%	99.15%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.44%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.03%	96.38%

Plants that contains it

• Berchemia floribunda

Cross-Links

• PubChem: 25015595
• LOTUS: LTS0052601
• wikiData: Q105133490