(3S)-3,8,9-trihydroxy-6-methoxy-3-methyl-10-[(2S)-2,5,10-trihydroxy-7-methoxy-2-methyl-4-oxo-1,3-dihydroanthracen-9-yl]-2,4-dihydroanthracen-1-one

Details

• Internal ID: 8ef2732d-cd2e-473f-8b4d-de5d6b0103b8
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: (3S)-3,8,9-trihydroxy-6-methoxy-3-methyl-10-[(2S)-2,5,10-trihydroxy-7-methoxy-2-methyl-4-oxo-1,3-dihydroanthracen-9-yl]-2,4-dihydroanthracen-1-one
• SMILES (Canonical): CC1(CC2=C(C3=C(C(=CC(=C3)OC)O)C(=C2C(=O)C1)O)C4=C5CC(CC(=O)C5=C(C6=C4C=C(C=C6O)OC)O)(C)O)O
• SMILES (Isomeric): C[C@@]1(CC2=C(C3=C(C(=CC(=C3)OC)O)C(=C2C(=O)C1)O)C4=C5C[C@](CC(=O)C5=C(C6=C4C=C(C=C6O)OC)O)(C)O)O
• InChI: InChI=1S/C32H30O10/c1-31(39)9-17-23(15-5-13(41-3)7-19(33)25(15)29(37)27(17)21(35)11-31)24-16-6-14(42-4)8-20(34)26(16)30(38)28-18(24)10-32(2,40)12-22(28)36/h5-8,33-34,37-40H,9-12H2,1-4H3/t31-,32-/m0/s1
• InChI Key: NYURKVQAEBXAOF-ACHIHNKUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₀O₁₀
• Molecular Weight: 574.60 g/mol
• Exact Mass: 574.18389715 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.26
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9850	98.50%
Caco-2	-	0.6415	64.15%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7824	78.24%
OATP2B1 inhibitior	-	0.7142	71.42%
OATP1B1 inhibitior	+	0.8836	88.36%
OATP1B3 inhibitior	+	0.9247	92.47%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9113	91.13%
P-glycoprotein inhibitior	+	0.7062	70.62%
P-glycoprotein substrate	-	0.7588	75.88%
CYP3A4 substrate	+	0.5818	58.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7969	79.69%
CYP3A4 inhibition	-	0.6102	61.02%
CYP2C9 inhibition	-	0.7770	77.70%
CYP2C19 inhibition	-	0.7446	74.46%
CYP2D6 inhibition	-	0.7968	79.68%
CYP1A2 inhibition	+	0.5503	55.03%
CYP2C8 inhibition	-	0.7302	73.02%
CYP inhibitory promiscuity	-	0.8309	83.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8532	85.32%
Carcinogenicity (trinary)	Non-required	0.5819	58.19%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.7545	75.45%
Skin irritation	-	0.7827	78.27%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8176	81.76%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.5319	53.19%
skin sensitisation	-	0.9247	92.47%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5566	55.66%
Acute Oral Toxicity (c)	III	0.5596	55.96%
Estrogen receptor binding	+	0.7666	76.66%
Androgen receptor binding	+	0.6265	62.65%
Thyroid receptor binding	+	0.5774	57.74%
Glucocorticoid receptor binding	+	0.7645	76.45%
Aromatase binding	+	0.7098	70.98%
PPAR gamma	+	0.7049	70.49%
Honey bee toxicity	-	0.8594	85.94%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9762	97.62%

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	99.76%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.90%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.43%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.53%	95.56%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	93.33%	92.68%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.60%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.06%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.09%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.16%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.84%	93.99%
CHEMBL4208	P20618	Proteasome component C5	87.53%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.80%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.56%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.34%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.95%	96.77%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	84.71%	91.79%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.92%	91.07%
CHEMBL1937	Q92769	Histone deacetylase 2	82.71%	94.75%
CHEMBL2535	P11166	Glucose transporter	82.50%	98.75%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.68%	96.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.39%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.17%	95.89%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.06%	80.00%

Plants that contains it

• Senna occidentalis

Cross-Links

• PubChem: 21769374
• LOTUS: LTS0007214
• wikiData: Q105187701