[(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: 53e4a684-ef5c-4cf3-be64-26cc77ea94d9
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1CCOC2C(C(C(C(O2)CO)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1CCO[C@H]2[C@@H]([C@@H]([C@@H]([C@H](O2)CO)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O)O)O
• InChI: InChI=1S/C23H26O11/c24-11-18-22(34-19(29)6-3-12-1-4-14(25)16(27)9-12)20(30)21(31)23(33-18)32-8-7-13-2-5-15(26)17(28)10-13/h1-6,9-10,18,20-28,30-31H,7-8,11H2/b6-3+/t18-,20+,21-,22-,23-/m1/s1
• InChI Key: UHIGZYLCYRQESL-WMKRDXGESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₁₁
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.14751164 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 11
• 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	-	0.5000	50.00%
Caco-2	-	0.8911	89.11%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8426	84.26%
OATP2B1 inhibitior	-	0.5694	56.94%
OATP1B1 inhibitior	+	0.9065	90.65%
OATP1B3 inhibitior	+	0.9584	95.84%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7045	70.45%
P-glycoprotein inhibitior	-	0.6242	62.42%
P-glycoprotein substrate	-	0.8457	84.57%
CYP3A4 substrate	+	0.5958	59.58%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8603	86.03%
CYP3A4 inhibition	-	0.8849	88.49%
CYP2C9 inhibition	-	0.6055	60.55%
CYP2C19 inhibition	-	0.6646	66.46%
CYP2D6 inhibition	-	0.8604	86.04%
CYP1A2 inhibition	-	0.7733	77.33%
CYP2C8 inhibition	+	0.6429	64.29%
CYP inhibitory promiscuity	-	0.6047	60.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6719	67.19%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8639	86.39%
Skin irritation	-	0.8375	83.75%
Skin corrosion	-	0.9668	96.68%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4084	40.84%
Micronuclear	-	0.6167	61.67%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.7750	77.50%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.9167	91.67%
Acute Oral Toxicity (c)	III	0.7056	70.56%
Estrogen receptor binding	+	0.6141	61.41%
Androgen receptor binding	+	0.5622	56.22%
Thyroid receptor binding	+	0.5208	52.08%
Glucocorticoid receptor binding	-	0.4864	48.64%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5242	52.42%
Honey bee toxicity	-	0.6917	69.17%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8378	83.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL299	P17252	Protein kinase C alpha	600 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.62%	91.11%
CHEMBL3194	P02766	Transthyretin	95.83%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.51%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.13%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.00%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.56%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.53%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	91.20%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	90.15%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.52%	94.45%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	87.92%	96.37%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.78%	96.00%
CHEMBL2581	P07339	Cathepsin D	86.14%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.24%	94.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.21%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.65%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.27%	95.50%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.47%	80.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.82%	95.56%

Plants that contains it

• Hymenophyllum nephrophyllum

Cross-Links

• PubChem: 10457774
• LOTUS: LTS0266367
• wikiData: Q105272906