1,3,6-trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6'-O-acetyl)-beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranoside

Details

• Internal ID: a69ca570-967b-4f94-a53c-bcda9a75738a
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methyl acetate
• InChI: InChI=1S/C28H30O15/c1-9-16(6-14-18(19(9)32)21(34)12-4-3-11(30)5-13(12)20(14)33)41-28-26(43-27-25(38)22(35)15(31)7-40-27)24(37)23(36)17(42-28)8-39-10(2)29/h3-6,15,17,22-28,30-32,35-38H,7-8H2,1-2H3/t15-,17-,22+,23-,24+,25-,26-,27+,28-/m1/s1
• InChI Key: JGCFTRKGKNECSV-ZIAPGWQOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₀O₁₅
• Molecular Weight: 606.50 g/mol
• Exact Mass: 606.15847025 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.61
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

• 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6'-O-acetyl)-beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranoside
• [(2R,3S,4S,5R,6S)-6-(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methyl acetate
• 9,10-Anthracenedione, 3-[(6-O-acetyl-2-O-beta-D-xylopyranosyl-beta-D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-
• orb1941297
• SCHEMBL23522443
• CHEBI:69538
• DTXSID001111274
• HY-N11894
• CS-0889227
• H50674
• Q27137878
• 3-[(6-O-Acetyl-2-O-I(2)-D-xylopyranosyl-I(2)-D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-9,10-anthracenedione
• 4,7-dihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl 6-O-acetyl-2-O-beta-D-xylopyranosyl-beta-D-glucopyranoside
• 9,10-Anthracenedione, 3-[(6-O-acetyl-2-O-|A-D-xylopyranosyl-|A-D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5097	50.97%
Caco-2	-	0.8951	89.51%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5254	52.54%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8341	83.41%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8815	88.15%
P-glycoprotein inhibitior	-	0.5402	54.02%
P-glycoprotein substrate	+	0.5153	51.53%
CYP3A4 substrate	+	0.6836	68.36%
CYP2C9 substrate	-	0.8204	82.04%
CYP2D6 substrate	-	0.8812	88.12%
CYP3A4 inhibition	-	0.9350	93.50%
CYP2C9 inhibition	-	0.9495	94.95%
CYP2C19 inhibition	-	0.9410	94.10%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.8705	87.05%
CYP2C8 inhibition	+	0.5313	53.13%
CYP inhibitory promiscuity	-	0.9454	94.54%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7112	71.12%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9301	93.01%
Skin irritation	-	0.8379	83.79%
Skin corrosion	-	0.9533	95.33%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3859	38.59%
Micronuclear	-	0.5067	50.67%
Hepatotoxicity	-	0.5380	53.80%
skin sensitisation	-	0.9060	90.60%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.9400	94.00%
Acute Oral Toxicity (c)	III	0.6793	67.93%
Estrogen receptor binding	+	0.8589	85.89%
Androgen receptor binding	+	0.5268	52.68%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6478	64.78%
Aromatase binding	+	0.6090	60.90%
PPAR gamma	+	0.6966	69.66%
Honey bee toxicity	-	0.7978	79.78%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.9312	93.12%

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	98.68%	91.49%
CHEMBL2581	P07339	Cathepsin D	98.52%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.36%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.79%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.93%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.21%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	92.99%	95.93%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.54%	97.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.50%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	89.49%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.13%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.60%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.24%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.17%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.51%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.04%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.85%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.68%	90.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.35%	96.90%
CHEMBL5255	O00206	Toll-like receptor 4	82.78%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.49%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.25%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.17%	96.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.96%	96.21%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.67%	89.62%
CHEMBL340	P08684	Cytochrome P450 3A4	80.54%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.35%	96.00%

Plants that contains it

• Rubia cordifolia

Cross-Links

• PubChem: 5319802
• NPASS: NPC28516