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

Details

• Internal ID: 61bf3270-7688-4fce-b070-cc1a8a2efe83
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3R,4R,5S,6S)-5-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4-dihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1C(C(C(O1)OC2C(C(C(OC2OCCC3=CC(=C(C=C3)O)O)COC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O)(CO)O
• SMILES (Isomeric): C1[C@]([C@@H]([C@H](O1)O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2OCCC3=CC(=C(C=C3)O)O)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O)(CO)O
• InChI: InChI=1S/C28H34O15/c29-12-28(38)13-41-27(25(28)37)43-24-23(36)22(35)20(11-40-21(34)6-3-14-1-4-16(30)18(32)9-14)42-26(24)39-8-7-15-2-5-17(31)19(33)10-15/h1-6,9-10,20,22-27,29-33,35-38H,7-8,11-13H2/b6-3+/t20-,22-,23+,24-,25+,26-,27+,28-/m0/s1
• InChI Key: NSDMGXRVIBQWAN-MIPKRDBNSA-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: -0.60
• Atomic LogP (AlogP): -1.40
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5697	56.97%
Caco-2	-	0.9088	90.88%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7602	76.02%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.8880	88.80%
OATP1B3 inhibitior	+	0.9496	94.96%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8964	89.64%
P-glycoprotein inhibitior	-	0.4439	44.39%
P-glycoprotein substrate	-	0.6410	64.10%
CYP3A4 substrate	+	0.6770	67.70%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8638	86.38%
CYP3A4 inhibition	-	0.8515	85.15%
CYP2C9 inhibition	-	0.8028	80.28%
CYP2C19 inhibition	-	0.8301	83.01%
CYP2D6 inhibition	-	0.8566	85.66%
CYP1A2 inhibition	-	0.8804	88.04%
CYP2C8 inhibition	+	0.7026	70.26%
CYP inhibitory promiscuity	-	0.7799	77.99%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5701	57.01%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9194	91.94%
Skin irritation	-	0.8065	80.65%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7284	72.84%
Micronuclear	-	0.6167	61.67%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8022	80.22%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9179	91.79%
Acute Oral Toxicity (c)	III	0.6656	66.56%
Estrogen receptor binding	+	0.7854	78.54%
Androgen receptor binding	+	0.5764	57.64%
Thyroid receptor binding	+	0.5478	54.78%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5754	57.54%
PPAR gamma	+	0.7152	71.52%
Honey bee toxicity	-	0.7000	70.00%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7714	77.14%

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	99.77%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	98.37%	95.93%
CHEMBL1951	P21397	Monoamine oxidase A	97.02%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.90%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.86%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.84%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.26%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.31%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.17%	97.09%
CHEMBL3194	P02766	Transthyretin	90.66%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.55%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.64%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.25%	94.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.84%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.44%	99.17%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.03%	95.17%
CHEMBL221	P23219	Cyclooxygenase-1	85.08%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.43%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	84.25%	94.73%
CHEMBL4208	P20618	Proteasome component C5	83.78%	90.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.63%	96.61%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.00%	94.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.97%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.90%	80.78%
CHEMBL2581	P07339	Cathepsin D	81.60%	98.95%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.11%	96.37%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.91%	94.00%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.10%	92.32%

Plants that contains it

• Lepisorus contortus

Cross-Links

• PubChem: 163188452
• LOTUS: LTS0050477
• wikiData: Q105184976