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

Details

• Internal ID: 7f7c311b-9b24-4d3b-a49b-db0b9f8d2a8e
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5S)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-4-hydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2COC(C(C2O)OC(=O)C=CC3=CC(=C(C=C3)O)O)OCCC4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CO[C@H]([C@@H]([C@H]2O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)OCCC4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C28H34O14/c1-13-22(34)24(36)25(37)27(40-13)41-20-12-39-28(38-9-8-15-3-6-17(30)19(32)11-15)26(23(20)35)42-21(33)7-4-14-2-5-16(29)18(31)10-14/h2-7,10-11,13,20,22-32,34-37H,8-9,12H2,1H3/b7-4+/t13-,20-,22-,23-,24+,25+,26+,27-,28+/m0/s1
• InChI Key: OKYGZQQZUUMFNQ-FHAPXRCOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₁₄
• Molecular Weight: 594.60 g/mol
• Exact Mass: 594.19485575 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.38
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7044	70.44%
Caco-2	-	0.8940	89.40%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8557	85.57%
OATP2B1 inhibitior	-	0.8542	85.42%
OATP1B1 inhibitior	+	0.8887	88.87%
OATP1B3 inhibitior	+	0.9433	94.33%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8624	86.24%
P-glycoprotein inhibitior	-	0.5582	55.82%
P-glycoprotein substrate	-	0.5323	53.23%
CYP3A4 substrate	+	0.6606	66.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9292	92.92%
CYP2C9 inhibition	-	0.7823	78.23%
CYP2C19 inhibition	-	0.7941	79.41%
CYP2D6 inhibition	-	0.8977	89.77%
CYP1A2 inhibition	-	0.7730	77.30%
CYP2C8 inhibition	+	0.7051	70.51%
CYP inhibitory promiscuity	-	0.7592	75.92%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6843	68.43%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9290	92.90%
Skin irritation	-	0.8493	84.93%
Skin corrosion	-	0.9601	96.01%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7018	70.18%
Micronuclear	-	0.7126	71.26%
Hepatotoxicity	-	0.7572	75.72%
skin sensitisation	-	0.8313	83.13%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.9806	98.06%
Acute Oral Toxicity (c)	III	0.7399	73.99%
Estrogen receptor binding	+	0.7567	75.67%
Androgen receptor binding	-	0.7311	73.11%
Thyroid receptor binding	+	0.5259	52.59%
Glucocorticoid receptor binding	+	0.5765	57.65%
Aromatase binding	+	0.5345	53.45%
PPAR gamma	+	0.7582	75.82%
Honey bee toxicity	-	0.7013	70.13%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9317	93.17%

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	99.71%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.54%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.68%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.25%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.00%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.51%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.95%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.76%	96.00%
CHEMBL4208	P20618	Proteasome component C5	91.50%	90.00%
CHEMBL3194	P02766	Transthyretin	88.43%	90.71%
CHEMBL221	P23219	Cyclooxygenase-1	88.19%	90.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.30%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.92%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	86.70%	94.73%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.07%	90.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.40%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.13%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.02%	96.95%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.84%	80.78%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.59%	97.33%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.92%	96.37%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.11%	91.71%

Plants that contains it

• Forsythia koreana

Cross-Links

• PubChem: 163188287
• LOTUS: LTS0219888
• wikiData: Q105193821