[(2S,3R,4R,5S,6S)-3,5-dihydroxy-2-[[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-4-yl] (E)-3-(4-methoxyphenyl)prop-2-enoate

Details

• Internal ID: b26d6df6-0768-44ac-96a3-31eb4d690389
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: [(2S,3R,4R,5S,6S)-3,5-dihydroxy-2-[[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-4-yl] (E)-3-(4-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O)OC(=O)C=CC6=CC=C(C=C6)OC)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)OC(=O)/C=C/C6=CC=C(C=C6)OC)O
• InChI: InChI=1S/C31H40O16/c1-13-20(35)26(44-18(34)8-5-14-3-6-15(40-2)7-4-14)24(39)30(42-13)45-25-16-9-10-41-28(19(16)31(12-33)27(25)47-31)46-29-23(38)22(37)21(36)17(11-32)43-29/h3-10,13,16-17,19-30,32-33,35-39H,11-12H2,1-2H3/b8-5+/t13-,16+,17+,19+,20-,21+,22-,23+,24+,25-,26+,27-,28-,29-,30-,31+/m0/s1
• InChI Key: JTHGUCGELADHDS-QVPDUFJHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₀O₁₆
• Molecular Weight: 668.60 g/mol
• Exact Mass: 668.23163518 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.47
• H-Bond Acceptor: 16
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5615	56.15%
Caco-2	-	0.8766	87.66%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8208	82.08%
OATP1B3 inhibitior	+	0.9576	95.76%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7168	71.68%
P-glycoprotein inhibitior	+	0.5817	58.17%
P-glycoprotein substrate	+	0.5061	50.61%
CYP3A4 substrate	+	0.6962	69.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8707	87.07%
CYP3A4 inhibition	-	0.8864	88.64%
CYP2C9 inhibition	-	0.9052	90.52%
CYP2C19 inhibition	-	0.8105	81.05%
CYP2D6 inhibition	-	0.8901	89.01%
CYP1A2 inhibition	-	0.8831	88.31%
CYP2C8 inhibition	+	0.6100	61.00%
CYP inhibitory promiscuity	-	0.7308	73.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5721	57.21%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9256	92.56%
Skin irritation	-	0.7796	77.96%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8532	85.32%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.7907	79.07%
skin sensitisation	-	0.7980	79.80%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7534	75.34%
Acute Oral Toxicity (c)	III	0.5170	51.70%
Estrogen receptor binding	+	0.7453	74.53%
Androgen receptor binding	+	0.5380	53.80%
Thyroid receptor binding	+	0.5425	54.25%
Glucocorticoid receptor binding	+	0.6323	63.23%
Aromatase binding	+	0.5201	52.01%
PPAR gamma	+	0.6935	69.35%
Honey bee toxicity	-	0.7187	71.87%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.6722	67.22%

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	99.45%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.34%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.74%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.31%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.71%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.56%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.69%	97.36%
CHEMBL4208	P20618	Proteasome component C5	90.07%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.33%	86.92%
CHEMBL221	P23219	Cyclooxygenase-1	88.76%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.29%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.05%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.85%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	85.91%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	83.60%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.54%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.79%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	80.95%	95.93%
CHEMBL2581	P07339	Cathepsin D	80.85%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.38%	95.89%

Plants that contains it

• Buddleja japonica
• Verbascum thapsus

Cross-Links

• PubChem: 15736672
• LOTUS: LTS0159911
• wikiData: Q105134775