1-[1,5-dihydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxynaphthalen-2-yl]ethanone

Details

• Internal ID: 41b4de1b-6735-4da6-b688-f2b509a75c19
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 1-[1,5-dihydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxynaphthalen-2-yl]ethanone
• SMILES (Canonical): CC1=CC2=C(C=CC(=C2C(=C1C(=O)C)O)OC3C(C(C(C(O3)COC4C(C(C(CO4)O)O)O)O)O)O)O
• SMILES (Isomeric): CC1=CC2=C(C=CC(=C2C(=C1C(=O)C)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)O
• InChI: InChI=1S/C24H30O13/c1-8-5-10-11(26)3-4-13(16(10)19(30)15(8)9(2)25)36-24-22(33)20(31)18(29)14(37-24)7-35-23-21(32)17(28)12(27)6-34-23/h3-5,12,14,17-18,20-24,26-33H,6-7H2,1-2H3/t12-,14-,17-,18-,20+,21-,22-,23-,24-/m1/s1
• InChI Key: PXPMKWLZBSCHGL-XLUJFQMNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₁₃
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.16864101 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.60
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5076	50.76%
Caco-2	-	0.8962	89.62%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6516	65.16%
OATP2B1 inhibitior	-	0.8507	85.07%
OATP1B1 inhibitior	+	0.8908	89.08%
OATP1B3 inhibitior	+	0.9312	93.12%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8129	81.29%
P-glycoprotein inhibitior	-	0.6854	68.54%
P-glycoprotein substrate	-	0.5394	53.94%
CYP3A4 substrate	+	0.6439	64.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8649	86.49%
CYP3A4 inhibition	-	0.9126	91.26%
CYP2C9 inhibition	-	0.9614	96.14%
CYP2C19 inhibition	-	0.9259	92.59%
CYP2D6 inhibition	-	0.9113	91.13%
CYP1A2 inhibition	-	0.8354	83.54%
CYP2C8 inhibition	+	0.5702	57.02%
CYP inhibitory promiscuity	-	0.9094	90.94%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7096	70.96%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9336	93.36%
Skin irritation	-	0.8433	84.33%
Skin corrosion	-	0.9653	96.53%
Ames mutagenesis	+	0.6146	61.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.6582	65.82%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8943	89.43%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9466	94.66%
Acute Oral Toxicity (c)	III	0.6565	65.65%
Estrogen receptor binding	+	0.7817	78.17%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5392	53.92%
Glucocorticoid receptor binding	-	0.5620	56.20%
Aromatase binding	+	0.6469	64.69%
PPAR gamma	+	0.7210	72.10%
Honey bee toxicity	-	0.8420	84.20%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8974	89.74%

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	99.60%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	98.65%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	95.06%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.99%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.78%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	93.47%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.94%	94.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.73%	89.62%
CHEMBL2581	P07339	Cathepsin D	87.49%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.90%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.89%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.61%	97.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.26%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.19%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.33%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.71%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.81%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.56%	96.90%

Plants that contains it

• Dianella nigra

Cross-Links

• PubChem: 154497519
• LOTUS: LTS0196545
• wikiData: Q105216320