1-[1-hydroxy-3,5-dimethyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxynaphthalen-2-yl]ethanone

Details

• Internal ID: 56c0dc55-f076-4703-a287-b5e2bdd2ffb0
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 1-[1-hydroxy-3,5-dimethyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxynaphthalen-2-yl]ethanone
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C4C(=C(C=C3)C)C=C(C(=C4O)C(=O)C)C)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C4C(=C(C=C3)C)C=C(C(=C4O)C(=O)C)C)O)O)O)O)O)O
• InChI: InChI=1S/C26H34O12/c1-9-5-6-14(17-13(9)7-10(2)16(11(3)27)20(17)30)37-26-24(34)22(32)19(29)15(38-26)8-35-25-23(33)21(31)18(28)12(4)36-25/h5-7,12,15,18-19,21-26,28-34H,8H2,1-4H3/t12-,15+,18-,19+,21+,22-,23+,24+,25+,26+/m0/s1
• InChI Key: XEOCDMLNLYKZOM-BLHDARAHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₂
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.20502652 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.60
• H-Bond Acceptor: 12
• 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	-	0.5469	54.69%
Caco-2	-	0.8521	85.21%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6659	66.59%
OATP2B1 inhibitior	-	0.8519	85.19%
OATP1B1 inhibitior	+	0.8607	86.07%
OATP1B3 inhibitior	+	0.8898	88.98%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8459	84.59%
P-glycoprotein inhibitior	-	0.6498	64.98%
P-glycoprotein substrate	-	0.5874	58.74%
CYP3A4 substrate	+	0.6178	61.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8649	86.49%
CYP3A4 inhibition	-	0.9366	93.66%
CYP2C9 inhibition	-	0.9445	94.45%
CYP2C19 inhibition	-	0.9242	92.42%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	-	0.7743	77.43%
CYP2C8 inhibition	+	0.6499	64.99%
CYP inhibitory promiscuity	-	0.7873	78.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6904	69.04%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9249	92.49%
Skin irritation	-	0.8333	83.33%
Skin corrosion	-	0.9666	96.66%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3739	37.39%
Micronuclear	+	0.6392	63.92%
Hepatotoxicity	-	0.6444	64.44%
skin sensitisation	-	0.9193	91.93%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9073	90.73%
Acute Oral Toxicity (c)	III	0.6765	67.65%
Estrogen receptor binding	+	0.7609	76.09%
Androgen receptor binding	-	0.6442	64.42%
Thyroid receptor binding	+	0.5663	56.63%
Glucocorticoid receptor binding	-	0.5234	52.34%
Aromatase binding	+	0.6116	61.16%
PPAR gamma	+	0.6658	66.58%
Honey bee toxicity	-	0.8309	83.09%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9001	90.01%

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	98.91%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.58%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	95.54%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.08%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.66%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.59%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.40%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	88.82%	91.49%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	87.41%	93.65%
CHEMBL2581	P07339	Cathepsin D	86.87%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.67%	89.62%
CHEMBL220	P22303	Acetylcholinesterase	85.22%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.88%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.68%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.09%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.62%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.03%	95.89%

Plants that contains it

• Hemerocallis fulva

Cross-Links

• PubChem: 101203816
• LOTUS: LTS0093160
• wikiData: Q105326494