[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-[(9R)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxyoxan-2-yl] benzoate

Details

• Internal ID: f06081a9-834d-4c24-8692-eb26269a51e8
• Taxonomy: Benzenoids > Anthracenes
• IUPAC Name: [(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-[(9R)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxyoxan-2-yl] benzoate
• SMILES (Canonical): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2(O)OC4C(C(C(C(O4)OC(=O)C5=CC=CC=C5)O)O)O)C=C(C=C3O)O
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O)C(=O)C3=C([C@]2(O)O[C@H]4[C@@H]([C@H]([C@H]([C@@H](O4)OC(=O)C5=CC=CC=C5)O)O)O)C=C(C=C3O)O
• InChI: InChI=1S/C27H24O12/c1-11-7-14-18(16(29)8-11)20(31)19-15(9-13(28)10-17(19)30)27(14,36)39-26-23(34)21(32)22(33)25(38-26)37-24(35)12-5-3-2-4-6-12/h2-10,21-23,25-26,28-30,32-34,36H,1H3/t21-,22+,23+,25+,26-,27+/m0/s1
• InChI Key: DEVGXIYJHCQNAZ-KGLQBNQBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₄O₁₂
• Molecular Weight: 540.50 g/mol
• Exact Mass: 540.12677620 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 0.49
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6257	62.57%
Caco-2	-	0.8578	85.78%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6301	63.01%
OATP2B1 inhibitior	+	0.5882	58.82%
OATP1B1 inhibitior	+	0.8839	88.39%
OATP1B3 inhibitior	+	0.9752	97.52%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.4701	47.01%
P-glycoprotein inhibitior	-	0.4824	48.24%
P-glycoprotein substrate	-	0.8311	83.11%
CYP3A4 substrate	+	0.6410	64.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	-	0.8378	83.78%
CYP2C9 inhibition	-	0.9392	93.92%
CYP2C19 inhibition	-	0.9195	91.95%
CYP2D6 inhibition	-	0.9700	97.00%
CYP1A2 inhibition	-	0.6237	62.37%
CYP2C8 inhibition	+	0.7723	77.23%
CYP inhibitory promiscuity	-	0.8761	87.61%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6520	65.20%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.8432	84.32%
Skin irritation	-	0.6286	62.86%
Skin corrosion	-	0.8973	89.73%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4048	40.48%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8863	88.63%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.5593	55.93%
Acute Oral Toxicity (c)	III	0.6364	63.64%
Estrogen receptor binding	+	0.7142	71.42%
Androgen receptor binding	+	0.5779	57.79%
Thyroid receptor binding	-	0.5144	51.44%
Glucocorticoid receptor binding	+	0.7651	76.51%
Aromatase binding	-	0.5061	50.61%
PPAR gamma	+	0.6606	66.06%
Honey bee toxicity	-	0.8466	84.66%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9613	96.13%

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	97.26%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.06%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.36%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.49%	99.23%
CHEMBL2581	P07339	Cathepsin D	94.48%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.40%	86.33%
CHEMBL240	Q12809	HERG	94.06%	89.76%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.44%	89.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.47%	83.00%
CHEMBL2535	P11166	Glucose transporter	90.63%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	90.27%	94.73%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.64%	94.62%
CHEMBL4208	P20618	Proteasome component C5	88.10%	90.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.63%	96.38%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.54%	85.31%
CHEMBL340	P08684	Cytochrome P450 3A4	86.46%	91.19%
CHEMBL3180	O00748	Carboxylesterase 2	84.45%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.14%	94.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	82.63%	97.53%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.31%	96.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.21%	96.09%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	81.07%	92.67%
CHEMBL4530	P00488	Coagulation factor XIII	81.01%	96.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.09%	95.64%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.08%	97.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.00%	93.04%

Plants that contains it

• Atalantia buxifolia
• Picramnia teapensis

Cross-Links

• PubChem: 162974126
• LOTUS: LTS0180318
• wikiData: Q105136359