[(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[[(1S,2S,4S,5S,6R,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-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 1eee37e1-20c7-43f8-bec4-e4e727a12ef3
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3R,4S,5R,6S)-4,5-dihydroxy-6-[[(1S,2S,4S,5S,6R,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-(3-hydroxy-4-methoxyphenyl)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)O)OC(=O)C=CC6=CC(=C(C=C6)OC)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)O)OC(=O)/C=C/C6=CC(=C(C=C6)OC)O
• InChI: InChI=1S/C31H40O17/c1-12-25(45-18(35)6-4-13-3-5-16(41-2)15(34)9-13)22(38)24(40)29(43-12)46-26-14-7-8-42-28(19(14)31(11-33)27(26)48-31)47-30-23(39)21(37)20(36)17(10-32)44-30/h3-9,12,14,17,19-30,32-34,36-40H,10-11H2,1-2H3/b6-4+/t12-,14+,17+,19+,20+,21-,22-,23+,24+,25-,26-,27-,28-,29-,30-,31+/m0/s1
• InChI Key: VEBQLXDMHALCLY-ZRIXAICDSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₀O₁₇
• Molecular Weight: 684.60 g/mol
• Exact Mass: 684.22654980 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.76
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6196	61.96%
Caco-2	-	0.8827	88.27%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5607	56.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8331	83.31%
OATP1B3 inhibitior	+	0.9623	96.23%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6033	60.33%
P-glycoprotein inhibitior	+	0.6015	60.15%
P-glycoprotein substrate	+	0.5940	59.40%
CYP3A4 substrate	+	0.6992	69.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8683	86.83%
CYP3A4 inhibition	-	0.8760	87.60%
CYP2C9 inhibition	-	0.8832	88.32%
CYP2C19 inhibition	-	0.7564	75.64%
CYP2D6 inhibition	-	0.8794	87.94%
CYP1A2 inhibition	-	0.8461	84.61%
CYP2C8 inhibition	+	0.7276	72.76%
CYP inhibitory promiscuity	-	0.7006	70.06%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6064	60.64%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9225	92.25%
Skin irritation	-	0.7865	78.65%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4099	40.99%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.7886	78.86%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8559	85.59%
Acute Oral Toxicity (c)	III	0.5416	54.16%
Estrogen receptor binding	+	0.7460	74.60%
Androgen receptor binding	-	0.5172	51.72%
Thyroid receptor binding	+	0.5142	51.42%
Glucocorticoid receptor binding	+	0.6462	64.62%
Aromatase binding	+	0.5638	56.38%
PPAR gamma	+	0.6865	68.65%
Honey bee toxicity	-	0.7006	70.06%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7344	73.44%

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	99.56%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.49%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.69%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.43%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.04%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.77%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.30%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	93.57%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.91%	92.94%
CHEMBL3194	P02766	Transthyretin	90.59%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.77%	99.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.78%	97.36%
CHEMBL4208	P20618	Proteasome component C5	87.74%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.25%	86.92%
CHEMBL2581	P07339	Cathepsin D	85.88%	98.95%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	82.68%	98.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.36%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	82.31%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.69%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.17%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.90%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.85%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.51%	94.00%

Plants that contains it

• Scrophularia nodosa
• Verbascum thapsus

Cross-Links

• PubChem: 10101114
• LOTUS: LTS0155764
• wikiData: Q105284503