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

Details

• Internal ID: 04db6f07-ed54-46d5-b59e-913fef376655
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6R)-5-acetyloxy-4-[(2S,3R,4R,5S,6S)-4-acetyloxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)CO)OC(=O)C=CC4=CC(=C(C=C4)O)O)O)OC(=O)C)O
• SMILES (Isomeric): C[C@H]1[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)OCCC3=CC(=C(C=C3)O)O)CO)OC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)OC(=O)C)O
• InChI: InChI=1S/C33H40O17/c1-15-26(42)29(46-16(2)35)27(43)32(45-15)50-30-28(49-25(41)9-6-18-4-7-20(37)22(39)12-18)24(14-34)48-33(31(30)47-17(3)36)44-11-10-19-5-8-21(38)23(40)13-19/h4-9,12-13,15,24,26-34,37-40,42-43H,10-11,14H2,1-3H3/b9-6+/t15-,24+,26-,27+,28+,29+,30-,31+,32-,33+/m0/s1
• InChI Key: QJBMDRGHYDWYHH-IGJRUOBASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₇
• Molecular Weight: 708.70 g/mol
• Exact Mass: 708.22654980 g/mol
• Topological Polar Surface Area (TPSA): 257.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 17
• H-Bond Donor: 7
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8307	83.07%
Caco-2	-	0.8792	87.92%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7562	75.62%
OATP2B1 inhibitior	-	0.7216	72.16%
OATP1B1 inhibitior	+	0.8650	86.50%
OATP1B3 inhibitior	+	0.9155	91.55%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9182	91.82%
P-glycoprotein inhibitior	+	0.6555	65.55%
P-glycoprotein substrate	-	0.5692	56.92%
CYP3A4 substrate	+	0.6638	66.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8730	87.30%
CYP3A4 inhibition	-	0.8089	80.89%
CYP2C9 inhibition	-	0.7386	73.86%
CYP2C19 inhibition	-	0.8886	88.86%
CYP2D6 inhibition	-	0.9220	92.20%
CYP1A2 inhibition	-	0.8632	86.32%
CYP2C8 inhibition	+	0.6921	69.21%
CYP inhibitory promiscuity	-	0.7886	78.86%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6859	68.59%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.8609	86.09%
Skin corrosion	-	0.9559	95.59%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7160	71.60%
Micronuclear	-	0.6667	66.67%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8584	85.84%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8884	88.84%
Acute Oral Toxicity (c)	III	0.7844	78.44%
Estrogen receptor binding	+	0.8128	81.28%
Androgen receptor binding	-	0.5566	55.66%
Thyroid receptor binding	+	0.5606	56.06%
Glucocorticoid receptor binding	+	0.6676	66.76%
Aromatase binding	-	0.4946	49.46%
PPAR gamma	+	0.7067	70.67%
Honey bee toxicity	-	0.6705	67.05%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8684	86.84%

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	99.76%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.51%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.08%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.55%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.30%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.51%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	94.33%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.29%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.25%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.23%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.72%	94.45%
CHEMBL3194	P02766	Transthyretin	89.37%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	87.17%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.66%	95.89%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.50%	80.78%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.32%	96.37%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.16%	95.56%

Plants that contains it

• Aeginetia indica

Cross-Links

• PubChem: 163186736
• LOTUS: LTS0259869
• wikiData: Q105222527