(3R)-4-[1,5-dihydroxy-6-[(2R,4R,5S,6R)-4-hydroxy-6-methyl-5-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxyoxan-2-yl]-9,10-dioxoanthracen-2-yl]-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxybutanoic acid

Details

• Internal ID: 74aa4945-22dc-4362-bf24-d80c4cf761a0
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: (3R)-4-[1,5-dihydroxy-6-[(2R,4R,5S,6R)-4-hydroxy-6-methyl-5-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxyoxan-2-yl]-9,10-dioxoanthracen-2-yl]-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxybutanoic acid
• SMILES (Canonical): CC1C(CCC(O1)OC2C(OC(CC2O)C3=C(C4=C(C=C3)C(=O)C5=C(C4=O)C=CC(=C5O)CC(C)(CC(=O)O)OC6CCC(C(O6)C)OC7C=CC(=O)C(O7)C)O)C)OC8C=CC(=O)C(O8)C
• SMILES (Isomeric): C[C@H]1[C@H](CC[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@H]2O)C3=C(C4=C(C=C3)C(=O)C5=C(C4=O)C=CC(=C5O)C[C@](C)(CC(=O)O)O[C@H]6CC[C@@H]([C@@H](O6)C)O[C@H]7C=CC(=O)[C@@H](O7)C)O)C)O[C@H]8C=CC(=O)[C@@H](O8)C
• InChI: InChI=1S/C49H58O18/c1-22-31(50)11-15-38(60-22)64-34-13-17-40(62-24(34)3)66-48-26(5)59-36(19-33(48)52)28-9-10-30-43(45(28)56)47(58)29-8-7-27(44(55)42(29)46(30)57)20-49(6,21-37(53)54)67-41-18-14-35(25(4)63-41)65-39-16-12-32(51)23(2)61-39/h7-12,15-16,22-26,33-36,38-41,48,52,55-56H,13-14,17-21H2,1-6H3,(H,53,54)/t22-,23-,24-,25-,26+,33+,34-,35-,36+,38-,39-,40-,41-,48+,49+/m0/s1
• InChI Key: NIXHEPPGVVKFMQ-SVDKGFTASA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₅₈O₁₈
• Molecular Weight: 935.00 g/mol
• Exact Mass: 934.36231500 g/mol
• Topological Polar Surface Area (TPSA): 249.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.82
• H-Bond Acceptor: 17
• H-Bond Donor: 4
• Rotatable Bonds: 13

Synonyms

• (3R)-4-[1,5-dihydroxy-6-[(2R,4R,5S,6R)-4-hydroxy-6-methyl-5-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxyoxan-2-yl]-9,10-dioxoanthracen-2-yl]-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxybutanoic acid
• OS-4742B2
• 2-Anthracenebutanoic acid, 6-(2,6-dideoxy-4-O-(5-((5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl)oxy)tetrahydro-6-methyl-2H-pyran-2-yl)-beta-arabino-hexopyranosyl)-beta-((5-((5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl)oxy)tetrahydro-6-methyl-2H-pyran-2-yl)oxy)-9,10-dihydro-1,5-dihyd roxy-beta-methyl-9,10-dioxo-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9419	94.19%
Caco-2	-	0.8632	86.32%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7557	75.57%
OATP2B1 inhibitior	-	0.7248	72.48%
OATP1B1 inhibitior	+	0.8269	82.69%
OATP1B3 inhibitior	-	0.4418	44.18%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7787	77.87%
BSEP inhibitior	+	0.9852	98.52%
P-glycoprotein inhibitior	+	0.7572	75.72%
P-glycoprotein substrate	+	0.7210	72.10%
CYP3A4 substrate	+	0.7163	71.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.8620	86.20%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.9336	93.36%
CYP2D6 inhibition	-	0.9611	96.11%
CYP1A2 inhibition	-	0.7818	78.18%
CYP2C8 inhibition	+	0.6289	62.89%
CYP inhibitory promiscuity	-	0.9046	90.46%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5995	59.95%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9052	90.52%
Skin irritation	-	0.7223	72.23%
Skin corrosion	-	0.9337	93.37%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7468	74.68%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.9048	90.48%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8319	83.19%
Acute Oral Toxicity (c)	I	0.5697	56.97%
Estrogen receptor binding	+	0.8702	87.02%
Androgen receptor binding	+	0.7442	74.42%
Thyroid receptor binding	+	0.5697	56.97%
Glucocorticoid receptor binding	+	0.7857	78.57%
Aromatase binding	+	0.7241	72.41%
PPAR gamma	+	0.8145	81.45%
Honey bee toxicity	-	0.7489	74.89%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9937	99.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.62%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.57%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.34%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.60%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.05%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.78%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.10%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.92%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.24%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.32%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.17%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	86.16%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.01%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.85%	99.15%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.53%	97.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.62%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.44%	100.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.43%	96.67%
CHEMBL4208	P20618	Proteasome component C5	82.24%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.07%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	80.91%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.55%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.14%	94.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 196552
• LOTUS: LTS0212604
• wikiData: Q105180029