1,3,6-Tmaqag

Details

• Internal ID: 511c182c-0cad-4766-830e-51c8d7eb26bc
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1=C(C=C2C(=C1O)C(=O)C3=C(C2=O)C=C(C=C3)O)OC4C(C(C(C(O4)COC(=O)C)O)O)O
• SMILES (Isomeric): CC1=C(C=C2C(=C1O)C(=O)C3=C(C2=O)C=C(C=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)C)O)O)O
• InChI: InChI=1S/C23H22O11/c1-8-14(33-23-22(31)21(30)20(29)15(34-23)7-32-9(2)24)6-13-16(17(8)26)19(28)11-4-3-10(25)5-12(11)18(13)27/h3-6,15,20-23,25-26,29-31H,7H2,1-2H3/t15-,20-,21+,22-,23-/m1/s1
• InChI Key: NZFWKPNBKZRWCW-NOGCDZMRSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₁₁
• Molecular Weight: 474.40 g/mol
• Exact Mass: 474.11621151 g/mol
• Topological Polar Surface Area (TPSA): 180.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.07
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 132367-98-7
• 1,3,6-Trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6'-acetylglucoside)
• 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6'-O-acetyl)-beta-D-glucopyranoside
• SCHEMBL23522396
• CHEBI:69536
• DTXSID20927644
• [(2R,3S,4S,5R,6S)-6-(4,7-dihydroxy-3-methyl-9,10-dioxoanthracen-2-yl)oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• Q27137876
• 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone-3-O-(6/'-acetylglucoside)
• 4,7-Dihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl 6-O-acetylhexopyranoside
• 4,7-dihydroxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl 6-O-acetyl-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5582	55.82%
Caco-2	-	0.8300	83.00%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6270	62.70%
OATP2B1 inhibitior	-	0.8365	83.65%
OATP1B1 inhibitior	+	0.8247	82.47%
OATP1B3 inhibitior	+	0.9202	92.02%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8038	80.38%
P-glycoprotein inhibitior	-	0.5684	56.84%
P-glycoprotein substrate	-	0.7343	73.43%
CYP3A4 substrate	+	0.6240	62.40%
CYP2C9 substrate	-	0.8204	82.04%
CYP2D6 substrate	-	0.8812	88.12%
CYP3A4 inhibition	-	0.8944	89.44%
CYP2C9 inhibition	-	0.8712	87.12%
CYP2C19 inhibition	-	0.8965	89.65%
CYP2D6 inhibition	-	0.9261	92.61%
CYP1A2 inhibition	-	0.6402	64.02%
CYP2C8 inhibition	+	0.5174	51.74%
CYP inhibitory promiscuity	-	0.8478	84.78%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7485	74.85%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9024	90.24%
Skin irritation	-	0.8241	82.41%
Skin corrosion	-	0.9527	95.27%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4178	41.78%
Micronuclear	+	0.5492	54.92%
Hepatotoxicity	-	0.5841	58.41%
skin sensitisation	-	0.9191	91.91%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7949	79.49%
Acute Oral Toxicity (c)	III	0.6437	64.37%
Estrogen receptor binding	+	0.7978	79.78%
Androgen receptor binding	+	0.5346	53.46%
Thyroid receptor binding	-	0.5473	54.73%
Glucocorticoid receptor binding	+	0.6548	65.48%
Aromatase binding	-	0.4880	48.80%
PPAR gamma	+	0.5832	58.32%
Honey bee toxicity	-	0.8609	86.09%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6750	67.50%
Fish aquatic toxicity	+	0.9681	96.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.31%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.13%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.12%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.02%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.36%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.31%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.83%	94.73%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.66%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.61%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.50%	94.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.20%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.70%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.56%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.29%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.40%	99.23%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.51%	96.21%
CHEMBL226	P30542	Adenosine A1 receptor	82.33%	95.93%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.26%	96.90%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.96%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.56%	90.71%
CHEMBL220	P22303	Acetylcholinesterase	81.20%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.62%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.57%	96.00%

Plants that contains it

• Rubia yunnanensis

Cross-Links

• PubChem: 195713
• NPASS: NPC42682
• LOTUS: LTS0185675
• wikiData: Q27137876