methyl (1S,2S,4S,5R,6S,7S)-4'-[(R)-hydroxy-(4-hydroxyphenyl)methyl]-5'-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,8-dioxatricyclo[4.4.0.02,4]dec-9-ene-5,2'-furan]-10-carboxylate

Details

• Internal ID: ca733b50-68a0-460e-bcad-e081fd478343
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: methyl (1S,2S,4S,5R,6S,7S)-4'-[(R)-hydroxy-(4-hydroxyphenyl)methyl]-5'-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,8-dioxatricyclo[4.4.0.02,4]dec-9-ene-5,2'-furan]-10-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1C3C(C24C=C(C(=O)O4)C(C5=CC=C(C=C5)O)O)O3)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1[C@H]3[C@@H]([C@@]24C=C(C(=O)O4)[C@@H](C5=CC=C(C=C5)O)O)O3)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C26H28O14/c1-35-22(33)12-8-36-24(39-25-19(32)18(31)17(30)13(7-27)37-25)15-14(12)20-21(38-20)26(15)6-11(23(34)40-26)16(29)9-2-4-10(28)5-3-9/h2-6,8,13-21,24-25,27-32H,7H2,1H3/t13-,14-,15-,16-,17-,18+,19-,20+,21+,24+,25+,26-/m1/s1
• InChI Key: JFWOLYYFIRMHLG-KMNNPNRKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₄
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.14790556 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.11
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7750	77.50%
Caco-2	-	0.9025	90.25%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6756	67.56%
OATP2B1 inhibitior	-	0.8493	84.93%
OATP1B1 inhibitior	+	0.7474	74.74%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6346	63.46%
P-glycoprotein inhibitior	-	0.5570	55.70%
P-glycoprotein substrate	+	0.5769	57.69%
CYP3A4 substrate	+	0.6969	69.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8613	86.13%
CYP3A4 inhibition	-	0.8261	82.61%
CYP2C9 inhibition	-	0.7712	77.12%
CYP2C19 inhibition	-	0.7561	75.61%
CYP2D6 inhibition	-	0.8935	89.35%
CYP1A2 inhibition	-	0.8509	85.09%
CYP2C8 inhibition	+	0.7193	71.93%
CYP inhibitory promiscuity	-	0.6482	64.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5033	50.33%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9054	90.54%
Skin irritation	-	0.7540	75.40%
Skin corrosion	-	0.9365	93.65%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3779	37.79%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.6457	64.57%
skin sensitisation	-	0.7937	79.37%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7692	76.92%
Acute Oral Toxicity (c)	III	0.4449	44.49%
Estrogen receptor binding	+	0.7769	77.69%
Androgen receptor binding	+	0.7311	73.11%
Thyroid receptor binding	+	0.5914	59.14%
Glucocorticoid receptor binding	+	0.6530	65.30%
Aromatase binding	+	0.5380	53.80%
PPAR gamma	+	0.6957	69.57%
Honey bee toxicity	-	0.7368	73.68%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.8355	83.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.47%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.28%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.80%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.88%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.17%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.84%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.93%	86.33%
CHEMBL4040	P28482	MAP kinase ERK2	88.34%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.16%	89.00%
CHEMBL4208	P20618	Proteasome component C5	87.91%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.63%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.82%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.57%	99.17%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.23%	89.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.33%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.73%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.28%	96.00%

Plants that contains it

• Gardneria nutans
• Morinda morindoides
• Pentas lanceolata

Cross-Links

• PubChem: 23643735
• LOTUS: LTS0009225
• wikiData: Q105329209