methyl (1S,2S,3'R,4S,4'E,5S,6S,7S)-3'-hydroxy-4'-[(4-hydroxyphenyl)methylidene]-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'-oxolane]-10-carboxylate

Details

• Internal ID: b09da630-97c9-4844-a8f6-2c52eec68fb1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: methyl (1S,2S,3'R,4S,4'E,5S,6S,7S)-3'-hydroxy-4'-[(4-hydroxyphenyl)methylidene]-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'-oxolane]-10-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1C3C(C24C(C(=CC5=CC=C(C=C5)O)C(=O)O4)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@@]24[C@@H](/C(=C\C5=CC=C(C=C5)O)/C(=O)O4)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(39-25-18(31)17(30)16(29)13(7-27)37-25)15-14(12)19-21(38-19)26(15)20(32)11(23(34)40-26)6-9-2-4-10(28)5-3-9/h2-6,8,13-21,24-25,27-32H,7H2,1H3/b11-6+/t13-,14-,15-,16-,17+,18-,19+,20-,21+,24+,25+,26+/m1/s1
• InChI Key: PPNNIWJAKIMLID-HWPSEDJLSA-N
• Popularity: 2 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: -1.70
• Atomic LogP (AlogP): -2.32
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• AKOS040751198

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7750	77.50%
Caco-2	-	0.9061	90.61%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6756	67.56%
OATP2B1 inhibitior	-	0.8473	84.73%
OATP1B1 inhibitior	+	0.7419	74.19%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6407	64.07%
P-glycoprotein inhibitior	-	0.5328	53.28%
P-glycoprotein substrate	-	0.5311	53.11%
CYP3A4 substrate	+	0.6919	69.19%
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	+	0.7592	75.92%
CYP inhibitory promiscuity	-	0.6482	64.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5033	50.33%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.7540	75.40%
Skin corrosion	-	0.9365	93.65%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4094	40.94%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.6632	66.32%
skin sensitisation	-	0.7937	79.37%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.8188	81.88%
Acute Oral Toxicity (c)	III	0.4449	44.49%
Estrogen receptor binding	+	0.7354	73.54%
Androgen receptor binding	+	0.7127	71.27%
Thyroid receptor binding	+	0.5768	57.68%
Glucocorticoid receptor binding	+	0.5834	58.34%
Aromatase binding	-	0.4916	49.16%
PPAR gamma	+	0.7053	70.53%
Honey bee toxicity	-	0.7202	72.02%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.51%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	93.75%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	92.66%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.54%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.49%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.10%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.46%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.45%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.21%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.58%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.10%	97.09%
CHEMBL4208	P20618	Proteasome component C5	84.99%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.90%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.42%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.47%	94.45%

Plants that contains it

• Morinda citrifolia
• Morinda coreia

Cross-Links

• PubChem: 101415479
• NPASS: NPC86864
• LOTUS: LTS0042437
• wikiData: Q105212973