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

Details

• Internal ID: 91210ffd-827b-4715-a4b7-6e4e8596c660
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCCC3=CC(=C(C=C3)O)O)COC(=O)C=CC4=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]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OCCC3=CC(=C(C=C3)O)O)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C29H36O15/c1-13-22(35)23(36)25(38)29(42-13)44-27-20(12-41-21(34)7-4-14-2-5-16(30)18(32)10-14)43-28(26(39)24(27)37)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29-/m0/s1
• InChI Key: PZUOYDXGZBHGLC-ZLSOWSIRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.60 g/mol
• Exact Mass: 624.20542044 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.02
• 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	-	0.7422	74.22%
Caco-2	-	0.9032	90.32%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8295	82.95%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.8887	88.87%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9258	92.58%
P-glycoprotein inhibitior	-	0.5666	56.66%
P-glycoprotein substrate	-	0.6697	66.97%
CYP3A4 substrate	+	0.6458	64.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.8916	89.16%
CYP2C9 inhibition	-	0.6602	66.02%
CYP2C19 inhibition	-	0.7703	77.03%
CYP2D6 inhibition	-	0.8769	87.69%
CYP1A2 inhibition	-	0.7757	77.57%
CYP2C8 inhibition	+	0.6864	68.64%
CYP inhibitory promiscuity	-	0.5420	54.20%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6274	62.74%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9204	92.04%
Skin irritation	-	0.8400	84.00%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6573	65.73%
Micronuclear	-	0.6267	62.67%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8042	80.42%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.9647	96.47%
Acute Oral Toxicity (c)	III	0.8082	80.82%
Estrogen receptor binding	+	0.7622	76.22%
Androgen receptor binding	-	0.5535	55.35%
Thyroid receptor binding	+	0.5288	52.88%
Glucocorticoid receptor binding	+	0.5591	55.91%
Aromatase binding	+	0.5437	54.37%
PPAR gamma	+	0.6867	68.67%
Honey bee toxicity	-	0.6707	67.07%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8693	86.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.68%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.45%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.99%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.71%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.40%	96.09%
CHEMBL3194	P02766	Transthyretin	93.84%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	93.52%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.01%	96.00%
CHEMBL2581	P07339	Cathepsin D	90.92%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.51%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	87.87%	80.78%
CHEMBL4208	P20618	Proteasome component C5	86.29%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.24%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.19%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.71%	97.36%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.96%	96.37%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.27%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.06%	96.61%

Plants that contains it

• Sesamum alatum

Cross-Links

• PubChem: 163190447
• LOTUS: LTS0245062
• wikiData: Q105217143