8-hydroxy-2-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxynaphthalene-1,4-dione

Details

• Internal ID: 726f4185-b1cc-4c3f-a977-2a124342e4e9
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 8-hydroxy-2-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxynaphthalene-1,4-dione
• SMILES (Canonical): CC1=CC(=O)C2=C(C=CC(=C2C1=O)O)OC3C(C(C(C(O3)COC4C(C(C(CO4)O)O)O)O)O)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C=CC(=C2C1=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H](CO4)O)O)O)O)O)O
• InChI: InChI=1S/C22H26O13/c1-7-4-9(24)13-11(3-2-8(23)14(13)15(7)26)34-22-20(31)18(29)17(28)12(35-22)6-33-21-19(30)16(27)10(25)5-32-21/h2-4,10,12,16-23,25,27-31H,5-6H2,1H3/t10-,12-,16+,17-,18+,19-,20-,21+,22-/m1/s1
• InChI Key: ZJUHWPBNDMEZKC-ZDFJRMNKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₁₃
• Molecular Weight: 498.40 g/mol
• Exact Mass: 498.13734088 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.64
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6605	66.05%
Caco-2	-	0.9233	92.33%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6286	62.86%
OATP2B1 inhibitior	-	0.8503	85.03%
OATP1B1 inhibitior	+	0.9148	91.48%
OATP1B3 inhibitior	+	0.9595	95.95%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6234	62.34%
P-glycoprotein inhibitior	-	0.7505	75.05%
P-glycoprotein substrate	-	0.7387	73.87%
CYP3A4 substrate	+	0.6221	62.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8731	87.31%
CYP3A4 inhibition	-	0.9302	93.02%
CYP2C9 inhibition	-	0.8230	82.30%
CYP2C19 inhibition	-	0.7639	76.39%
CYP2D6 inhibition	-	0.8535	85.35%
CYP1A2 inhibition	-	0.7678	76.78%
CYP2C8 inhibition	-	0.6884	68.84%
CYP inhibitory promiscuity	-	0.8611	86.11%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6826	68.26%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9254	92.54%
Skin irritation	-	0.8021	80.21%
Skin corrosion	-	0.9515	95.15%
Ames mutagenesis	+	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3945	39.45%
Micronuclear	-	0.5326	53.26%
Hepatotoxicity	-	0.6974	69.74%
skin sensitisation	-	0.7830	78.30%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7390	73.90%
Acute Oral Toxicity (c)	III	0.5236	52.36%
Estrogen receptor binding	+	0.8287	82.87%
Androgen receptor binding	+	0.5273	52.73%
Thyroid receptor binding	+	0.5203	52.03%
Glucocorticoid receptor binding	-	0.4790	47.90%
Aromatase binding	+	0.6431	64.31%
PPAR gamma	+	0.7575	75.75%
Honey bee toxicity	-	0.8448	84.48%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7550	75.50%
Fish aquatic toxicity	+	0.9452	94.52%

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	97.02%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.85%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.87%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.90%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	90.78%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.37%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.31%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	90.13%	91.49%
CHEMBL1937	Q92769	Histone deacetylase 2	89.64%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.19%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.71%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.68%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.70%	99.23%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.60%	89.62%
CHEMBL226	P30542	Adenosine A1 receptor	82.48%	95.93%
CHEMBL4208	P20618	Proteasome component C5	82.43%	90.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.85%	96.90%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.66%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.56%	99.15%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.89%	96.67%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.64%	100.00%

Plants that contains it

• Diospyros lycioides

Cross-Links

• PubChem: 10672935
• LOTUS: LTS0187927
• wikiData: Q105378168