[(2S,3S,4S,5R,6S)-4-acetyloxy-5-hydroxy-6-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: add1a303-4e40-426e-940e-ef8429d0ed4b
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2S,3S,4S,5R,6S)-4-acetyloxy-5-hydroxy-6-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-2-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O)OC(=O)C)OC(=O)C=CC6=CC=C(C=C6)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@H]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)OC(=O)C)OC(=O)/C=C/C6=CC=C(C=C6)O
• InChI: InChI=1S/C32H40O17/c1-13-25(46-19(37)8-5-15-3-6-16(36)7-4-15)27(44-14(2)35)24(41)31(43-13)47-26-17-9-10-42-29(20(17)32(12-34)28(26)49-32)48-30-23(40)22(39)21(38)18(11-33)45-30/h3-10,13,17-18,20-31,33-34,36,38-41H,11-12H2,1-2H3/b8-5+/t13-,17-,18+,20+,21+,22-,23+,24+,25-,26-,27-,28-,29-,30-,31-,32+/m0/s1
• InChI Key: HFGCHODICASFRK-HZDOHXSSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₀O₁₇
• Molecular Weight: 696.60 g/mol
• Exact Mass: 696.22654980 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.20
• H-Bond Acceptor: 17
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4897	48.97%
Caco-2	-	0.8849	88.49%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6439	64.39%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.7921	79.21%
OATP1B3 inhibitior	+	0.9547	95.47%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6380	63.80%
P-glycoprotein inhibitior	+	0.6384	63.84%
P-glycoprotein substrate	+	0.5759	57.59%
CYP3A4 substrate	+	0.7078	70.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.8978	89.78%
CYP2C9 inhibition	-	0.8882	88.82%
CYP2C19 inhibition	-	0.8528	85.28%
CYP2D6 inhibition	-	0.9305	93.05%
CYP1A2 inhibition	-	0.9008	90.08%
CYP2C8 inhibition	+	0.6964	69.64%
CYP inhibitory promiscuity	-	0.7892	78.92%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5864	58.64%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9147	91.47%
Skin irritation	-	0.7803	78.03%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3779	37.79%
Micronuclear	+	0.5233	52.33%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8014	80.14%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.5585	55.85%
Acute Oral Toxicity (c)	III	0.4601	46.01%
Estrogen receptor binding	+	0.7580	75.80%
Androgen receptor binding	+	0.5572	55.72%
Thyroid receptor binding	-	0.4912	49.12%
Glucocorticoid receptor binding	+	0.6360	63.60%
Aromatase binding	-	0.4857	48.57%
PPAR gamma	+	0.6994	69.94%
Honey bee toxicity	-	0.6672	66.72%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8514	85.14%

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	99.38%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.75%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.01%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.17%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.53%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.02%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.64%	96.00%
CHEMBL2581	P07339	Cathepsin D	91.31%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.17%	94.73%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.20%	89.67%
CHEMBL1951	P21397	Monoamine oxidase A	87.35%	91.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.47%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.79%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.63%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.21%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.51%	86.92%
CHEMBL1937	Q92769	Histone deacetylase 2	82.42%	94.75%
CHEMBL4208	P20618	Proteasome component C5	80.01%	90.00%

Plants that contains it

• Scrophularia nodosa

Cross-Links

• PubChem: 162909764
• LOTUS: LTS0218401
• wikiData: Q105027292