methyl 1-hydroxy-9,10-dioxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyanthracene-2-carboxylate

Details

• Internal ID: 1cc6133f-16d2-4530-aa93-5a9e81b79f22
• Taxonomy: Benzenoids > Anthracenes > Anthracenecarboxylic acids and derivatives > Anthracenecarboxylic acids
• IUPAC Name: methyl 1-hydroxy-9,10-dioxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyanthracene-2-carboxylate
• SMILES (Canonical): COC(=O)C1=C(C=C2C(=C1O)C(=O)C3=CC=CC=C3C2=O)OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O
• SMILES (Isomeric): COC(=O)C1=C(C=C2C(=C1O)C(=O)C3=CC=CC=C3C2=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O)O)O
• InChI: InChI=1S/C27H28O15/c1-38-25(37)16-13(6-11-15(21(16)33)18(30)10-5-3-2-4-9(10)17(11)29)41-27-24(36)22(34)20(32)14(42-27)8-40-26-23(35)19(31)12(28)7-39-26/h2-6,12,14,19-20,22-24,26-28,31-36H,7-8H2,1H3/t12-,14-,19+,20-,22+,23-,24-,26+,27-/m1/s1
• InChI Key: KOGRPONKHIUKLH-OETLEKFPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈O₁₅
• Molecular Weight: 592.50 g/mol
• Exact Mass: 592.14282018 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.40
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6135	61.35%
Caco-2	-	0.9040	90.40%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5273	52.73%
OATP2B1 inhibitior	-	0.8486	84.86%
OATP1B1 inhibitior	+	0.8368	83.68%
OATP1B3 inhibitior	+	0.9684	96.84%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5812	58.12%
P-glycoprotein inhibitior	-	0.6165	61.65%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6659	66.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8647	86.47%
CYP3A4 inhibition	-	0.9332	93.32%
CYP2C9 inhibition	-	0.9447	94.47%
CYP2C19 inhibition	-	0.9153	91.53%
CYP2D6 inhibition	-	0.9249	92.49%
CYP1A2 inhibition	-	0.8534	85.34%
CYP2C8 inhibition	+	0.5599	55.99%
CYP inhibitory promiscuity	-	0.9560	95.60%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6698	66.98%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9253	92.53%
Skin irritation	-	0.8482	84.82%
Skin corrosion	-	0.9580	95.80%
Ames mutagenesis	+	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7055	70.55%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	-	0.7148	71.48%
skin sensitisation	-	0.8986	89.86%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8153	81.53%
Acute Oral Toxicity (c)	III	0.6851	68.51%
Estrogen receptor binding	+	0.8135	81.35%
Androgen receptor binding	-	0.5312	53.12%
Thyroid receptor binding	-	0.5862	58.62%
Glucocorticoid receptor binding	-	0.5083	50.83%
Aromatase binding	-	0.4866	48.66%
PPAR gamma	+	0.7371	73.71%
Honey bee toxicity	-	0.8406	84.06%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.8338	83.38%

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	99.68%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.42%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	98.14%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.59%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.63%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.49%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.26%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	90.17%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	89.33%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.60%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.38%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.48%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.34%	94.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.03%	95.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.74%	99.17%
CHEMBL2535	P11166	Glucose transporter	84.17%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.41%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.32%	89.62%
CHEMBL5028	O14672	ADAM10	82.11%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.79%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.70%	90.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.53%	91.07%

Plants that contains it

• Saprosma scortechinii

Cross-Links

• PubChem: 11061003
• LOTUS: LTS0015193
• wikiData: Q105143813