[(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5R,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]-2-methyloxan-3-yl] (E)-3-(4-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 0bcf4d36-c085-4fae-a5f8-bdd3d89b74a1
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: [(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5R,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]-2-methyloxan-3-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)O)OC(=O)C=CC6=CC=C(C=C6)OC
• 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)O)OC(=O)/C=C/C6=CC=C(C=C6)OC
• InChI: InChI=1S/C31H40O16/c1-13-25(44-18(34)8-5-14-3-6-15(40-2)7-4-14)22(37)24(39)29(42-13)45-26-16-9-10-41-28(19(16)31(12-33)27(26)47-31)46-30-23(38)21(36)20(35)17(11-32)43-30/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: RTCISXKUWWQSRF-FYIXRQCESA-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	-	0.8749	87.49%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8227	82.27%
OATP1B3 inhibitior	+	0.9576	95.76%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5184	51.84%
P-glycoprotein inhibitior	+	0.6100	61.00%
P-glycoprotein substrate	-	0.5144	51.44%
CYP3A4 substrate	+	0.6977	69.77%
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	+	0.5986	59.86%
CYP inhibitory promiscuity	-	0.7308	73.08%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5721	57.21%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9231	92.31%
Skin irritation	-	0.7796	77.96%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7016	70.16%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.8157	81.57%
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	-	0.7520	75.20%
Acute Oral Toxicity (c)	III	0.5170	51.70%
Estrogen receptor binding	+	0.7532	75.32%
Androgen receptor binding	+	0.5297	52.97%
Thyroid receptor binding	+	0.5237	52.37%
Glucocorticoid receptor binding	+	0.6192	61.92%
Aromatase binding	+	0.5450	54.50%
PPAR gamma	+	0.6666	66.66%
Honey bee toxicity	-	0.7127	71.27%
Biodegradation	-	0.7750	77.50%
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	99.27%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.29%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.31%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.05%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.41%	96.09%
CHEMBL4208	P20618	Proteasome component C5	91.33%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.93%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.69%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.92%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	89.19%	90.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.06%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.85%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.75%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.80%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	81.83%	95.93%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.66%	91.07%
CHEMBL2581	P07339	Cathepsin D	80.96%	98.95%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.88%	87.67%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.62%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.38%	95.89%

Plants that contains it

• Gmelina arborea
• Scrophularia nodosa
• Verbascum georgicum

Cross-Links

• PubChem: 154497660
• LOTUS: LTS0239701
• wikiData: Q105245065