[(2S,3R,4R,5S,6S)-3-acetyloxy-5-hydroxy-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: 3808b955-0694-44a6-8651-0244443a94ce
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: [(2S,3R,4R,5S,6S)-3-acetyloxy-5-hydroxy-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)OC(=O)C)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)OC(=O)C)OC(=O)/C=C/C6=CC=C(C=C6)OC)O
• InChI: InChI=1S/C33H42O17/c1-14-22(38)27(47-20(37)9-6-16-4-7-17(42-3)8-5-16)28(45-15(2)36)32(44-14)48-26-18-10-11-43-30(21(18)33(13-35)29(26)50-33)49-31-25(41)24(40)23(39)19(12-34)46-31/h4-11,14,18-19,21-32,34-35,38-41H,12-13H2,1-3H3/b9-6+/t14-,18+,19+,21+,22-,23+,24-,25+,26-,27+,28+,29-,30-,31-,32-,33+/m0/s1
• InChI Key: ZRTBPOAMWLLGTO-FHCQAZNMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₂O₁₇
• Molecular Weight: 710.70 g/mol
• Exact Mass: 710.24219987 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.89
• H-Bond Acceptor: 17
• H-Bond Donor: 6
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4849	48.49%
Caco-2	-	0.8721	87.21%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5479	54.79%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8084	80.84%
OATP1B3 inhibitior	+	0.9477	94.77%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8055	80.55%
P-glycoprotein inhibitior	+	0.6629	66.29%
P-glycoprotein substrate	+	0.5526	55.26%
CYP3A4 substrate	+	0.7087	70.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8741	87.41%
CYP3A4 inhibition	-	0.8894	88.94%
CYP2C9 inhibition	-	0.8899	88.99%
CYP2C19 inhibition	-	0.8497	84.97%
CYP2D6 inhibition	-	0.9210	92.10%
CYP1A2 inhibition	-	0.8971	89.71%
CYP2C8 inhibition	+	0.6454	64.54%
CYP inhibitory promiscuity	-	0.8181	81.81%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5599	55.99%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9225	92.25%
Skin irritation	-	0.7856	78.56%
Skin corrosion	-	0.9411	94.11%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8066	80.66%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.7657	76.57%
skin sensitisation	-	0.8220	82.20%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6652	66.52%
Acute Oral Toxicity (c)	III	0.4818	48.18%
Estrogen receptor binding	+	0.7458	74.58%
Androgen receptor binding	+	0.5610	56.10%
Thyroid receptor binding	+	0.5576	55.76%
Glucocorticoid receptor binding	+	0.6457	64.57%
Aromatase binding	-	0.5204	52.04%
PPAR gamma	+	0.7163	71.63%
Honey bee toxicity	-	0.6834	68.34%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.7566	75.66%

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	97.51%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.49%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.24%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.87%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.47%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.77%	89.00%
CHEMBL4208	P20618	Proteasome component C5	90.50%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.91%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.31%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.85%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.37%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.16%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	85.91%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	85.82%	94.73%
CHEMBL2581	P07339	Cathepsin D	84.77%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.69%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.48%	91.07%
CHEMBL226	P30542	Adenosine A1 receptor	81.69%	95.93%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	81.30%	87.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.88%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.83%	94.08%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.52%	81.11%

Plants that contains it

• Buddleja japonica
• Scrophularia nodosa

Cross-Links

• PubChem: 75528863
• LOTUS: LTS0140775
• wikiData: Q105382240