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

Details

• Internal ID: be843564-d921-46af-874e-4d40db7d0a32
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C28H34O15/c29-11-20-25(42-21(35)6-3-13-1-4-15(30)17(32)9-13)26(43-27-23(37)22(36)19(34)12-40-27)24(38)28(41-20)39-8-7-14-2-5-16(31)18(33)10-14/h1-6,9-10,19-20,22-34,36-38H,7-8,11-12H2/b6-3+/t19-,20-,22+,23-,24-,25-,26-,27+,28-/m1/s1
• InChI Key: IIVINXPOHZUXQM-TYGLCWKWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₁₅
• Molecular Weight: 610.60 g/mol
• Exact Mass: 610.18977037 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.40
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7394	73.94%
Caco-2	-	0.9144	91.44%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6495	64.95%
OATP2B1 inhibitior	-	0.8486	84.86%
OATP1B1 inhibitior	+	0.8924	89.24%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6734	67.34%
P-glycoprotein inhibitior	-	0.5399	53.99%
P-glycoprotein substrate	-	0.6459	64.59%
CYP3A4 substrate	+	0.6570	65.70%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8603	86.03%
CYP3A4 inhibition	-	0.8998	89.98%
CYP2C9 inhibition	-	0.8496	84.96%
CYP2C19 inhibition	-	0.9033	90.33%
CYP2D6 inhibition	-	0.8819	88.19%
CYP1A2 inhibition	-	0.9171	91.71%
CYP2C8 inhibition	+	0.6565	65.65%
CYP inhibitory promiscuity	-	0.8789	87.89%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6947	69.47%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9023	90.23%
Skin irritation	-	0.8254	82.54%
Skin corrosion	-	0.9591	95.91%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6890	68.90%
Micronuclear	-	0.6367	63.67%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8049	80.49%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9664	96.64%
Acute Oral Toxicity (c)	III	0.7135	71.35%
Estrogen receptor binding	+	0.7811	78.11%
Androgen receptor binding	-	0.6679	66.79%
Thyroid receptor binding	+	0.5264	52.64%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5559	55.59%
PPAR gamma	+	0.6931	69.31%
Honey bee toxicity	-	0.6550	65.50%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.7100	71.00%

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	99.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.55%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.73%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.25%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.98%	89.00%
CHEMBL3194	P02766	Transthyretin	92.50%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.13%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	91.86%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.59%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.51%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.92%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.37%	98.95%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	87.83%	96.37%
CHEMBL3401	O75469	Pregnane X receptor	86.96%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	86.36%	95.93%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.50%	95.50%
CHEMBL4208	P20618	Proteasome component C5	81.45%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.91%	95.89%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.85%	80.78%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.57%	91.71%

Plants that contains it

• Gesneria pedicellaris
• Meehania urticifolia
• Polypremum procumbens
• Strobilanthes cusia

Cross-Links

• PubChem: 11192794
• LOTUS: LTS0253258
• wikiData: Q105352699