(2S)-3-(3,4-dihydroxyphenyl)-2-[(Z)-3-[2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl]prop-2-enoyl]oxypropanoic acid

Details

• Internal ID: 1794a763-c627-47ea-9a48-4e780cb223a6
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: (2S)-3-(3,4-dihydroxyphenyl)-2-[(Z)-3-[2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl]prop-2-enoyl]oxypropanoic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=C(C(=C(C=C2)O)O)C=CC3=CC(=C(C=C3)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@@H](C(=O)O)OC(=O)/C=C\C2=C(C(=C(C=C2)O)O)/C=C/C3=CC(=C(C=C3)O)O)O)O
• InChI: InChI=1S/C26H22O10/c27-18-7-2-14(11-21(18)30)1-6-17-16(4-9-20(29)25(17)33)5-10-24(32)36-23(26(34)35)13-15-3-8-19(28)22(31)12-15/h1-12,23,27-31,33H,13H2,(H,34,35)/b6-1+,10-5-/t23-/m0/s1
• InChI Key: YMGFTDKNIWPMGF-DXBMJSKRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₂O₁₀
• Molecular Weight: 494.40 g/mol
• Exact Mass: 494.12129689 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.34
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8756	87.56%
Caco-2	-	0.9365	93.65%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8306	83.06%
OATP2B1 inhibitior	-	0.5644	56.44%
OATP1B1 inhibitior	+	0.9038	90.38%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	+	0.5200	52.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8284	82.84%
P-glycoprotein inhibitior	+	0.6537	65.37%
P-glycoprotein substrate	-	0.8043	80.43%
CYP3A4 substrate	+	0.5201	52.01%
CYP2C9 substrate	-	0.5979	59.79%
CYP2D6 substrate	-	0.8612	86.12%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8754	87.54%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.6279	62.79%
CYP2C8 inhibition	+	0.6897	68.97%
CYP inhibitory promiscuity	-	0.8300	83.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8141	81.41%
Carcinogenicity (trinary)	Non-required	0.6152	61.52%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.7640	76.40%
Skin irritation	-	0.7211	72.11%
Skin corrosion	-	0.9416	94.16%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8161	81.61%
Micronuclear	+	0.7159	71.59%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	-	0.5655	56.55%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9408	94.08%
Acute Oral Toxicity (c)	III	0.7720	77.20%
Estrogen receptor binding	+	0.7305	73.05%
Androgen receptor binding	+	0.9404	94.04%
Thyroid receptor binding	+	0.5708	57.08%
Glucocorticoid receptor binding	+	0.6422	64.22%
Aromatase binding	-	0.7031	70.31%
PPAR gamma	+	0.6661	66.61%
Honey bee toxicity	-	0.7272	72.72%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9952	99.52%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3729	P22748	Carbonic anhydrase IV	66.6 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	71.4 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	39.8 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.21%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.08%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.89%	96.00%
CHEMBL3194	P02766	Transthyretin	95.74%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.50%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.14%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.94%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.45%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.53%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.50%	91.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.08%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.84%	99.15%
CHEMBL221	P23219	Cyclooxygenase-1	87.63%	90.17%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.59%	95.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.14%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	82.26%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.49%	95.50%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.34%	90.24%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.95%	86.92%

Plants that contains it

• Aconitum carmichaelii
• Annona reticulata
• Salvia miltiorrhiza
• Salvia przewalskii
• Theobroma cacao

Cross-Links

• PubChem: 9913656
• NPASS: NPC196512