[(2S,4aR,6R,7R,8S,8aR)-2-(3,4-dihydroxyphenyl)-6-(hydroxymethyl)-8-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-3,4a,6,7,8,8a-hexahydro-2H-pyrano[2,3-b][1,4]dioxin-7-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	4350ca89-ed71-4c35-9f29-6180b5b4081b
Taxonomy	Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
IUPAC Name	[(2S,4aR,6R,7R,8S)-2-(3,4-dihydroxyphenyl)-6-(hydroxymethyl)-8-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3,4a,6,7,8,8a-hexahydro-2H-pyrano[2,3-b][1,4]dioxin-7-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
SMILES (Canonical)	CC1C(C(C(C(O1)OC2C3C(OCC(O3)C4=CC(=C(C=C4)O)O)OC(C2OC(=O)C=CC5=CC(=C(C=C5)O)O)CO)O)O)O
SMILES (Isomeric)	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H](O[C@@H]3C2O[C@H](CO3)C4=CC(=C(C=C4)O)O)CO)OC(=O)/C=C/C5=CC(=C(C=C5)O)O)O)O)O
InChI	InChI=1S/C29H34O15/c1-12-22(36)23(37)24(38)28(40-12)44-26-25(43-21(35)7-3-13-2-5-15(31)17(33)8-13)19(10-30)42-29-27(26)41-20(11-39-29)14-4-6-16(32)18(34)9-14/h2-9,12,19-20,22-34,36-38H,10-11H2,1H3/b7-3+/t12-,19+,20+,22-,23+,24+,25+,26-,27?,28-,29+/m0/s1
InChI Key	FPOYEEKZOOLVJA-CROSMTIUSA-N
Popularity	7 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₉H₃₄O₁₅
Molecular Weight	622.60 g/mol
Exact Mass	622.18977037 g/mol
Topological Polar Surface Area (TPSA)	234.00 Å²
XlogP	-0.60
Atomic LogP (AlogP)	-0.48
H-Bond Acceptor	15
H-Bond Donor	8
Rotatable Bonds	7

Synonyms

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CHEMBL451273

C10481

[(2S,4aR,6R,7R,8S,8aR)-2-(3,4-dihydroxyphenyl)-6-(hydroxymethyl)-8-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-3,4a,6,7,8,8a-hexahydro-2H-pyrano[2,3-b][1,4]dioxin-7-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7655	76.55%
Caco-2	-	0.8949	89.49%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6549	65.49%
OATP2B1 inhibitior	-	0.8541	85.41%
OATP1B1 inhibitior	+	0.8747	87.47%
OATP1B3 inhibitior	+	0.9360	93.60%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8138	81.38%
P-glycoprotein inhibitior	-	0.5474	54.74%
P-glycoprotein substrate	-	0.5678	56.78%
CYP3A4 substrate	+	0.6559	65.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8720	87.20%
CYP3A4 inhibition	-	0.8874	88.74%
CYP2C9 inhibition	-	0.8716	87.16%
CYP2C19 inhibition	-	0.8600	86.00%
CYP2D6 inhibition	-	0.9398	93.98%
CYP1A2 inhibition	-	0.8779	87.79%
CYP2C8 inhibition	+	0.6649	66.49%
CYP inhibitory promiscuity	+	0.5722	57.22%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6598	65.98%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9200	92.00%
Skin irritation	-	0.8239	82.39%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6878	68.78%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8280	82.80%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.9589	95.89%
Acute Oral Toxicity (c)	III	0.6026	60.26%
Estrogen receptor binding	+	0.8229	82.29%
Androgen receptor binding	-	0.6258	62.58%
Thyroid receptor binding	+	0.6138	61.38%
Glucocorticoid receptor binding	+	0.6175	61.75%
Aromatase binding	+	0.5178	51.78%
PPAR gamma	+	0.7377	73.77%
Honey bee toxicity	-	0.6864	68.64%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5045	50.45%
Fish aquatic toxicity	+	0.8962	89.62%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	99.88%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.89%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.95%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.67%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.58%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.14%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.25%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	92.07%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.02%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.43%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.69%	97.36%
CHEMBL2581	P07339	Cathepsin D	89.39%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.71%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.18%	99.17%
CHEMBL3194	P02766	Transthyretin	84.88%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.81%	90.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.15%	91.71%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Globularia trichosantha