[(2S,3R,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl] (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate

Details

• Internal ID: 71b09e60-e1c2-4fd6-af39-457d6b0c6707
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3R,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-3-yl] (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C=CC(=O)OC2C(C(OC2(CO)OC3C(C(C(C(O3)CO)O)O)O)CO)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)O[C@@H]2[C@@H]([C@H](O[C@@]2(CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO)O
• InChI: InChI=1S/C24H34O15/c1-33-12-6-11(7-13(34-2)21(12)35-3)4-5-16(28)37-22-18(30)15(9-26)38-24(22,10-27)39-23-20(32)19(31)17(29)14(8-25)36-23/h4-7,14-15,17-20,22-23,25-27,29-32H,8-10H2,1-3H3/b5-4+/t14-,15-,17-,18-,19+,20-,22-,23-,24+/m1/s1
• InChI Key: PQHNJDATPYXLIX-GFBDJRIRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄O₁₅
• Molecular Weight: 562.50 g/mol
• Exact Mass: 562.18977037 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -3.11
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7375	73.75%
Caco-2	-	0.8686	86.86%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7360	73.60%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8811	88.11%
OATP1B3 inhibitior	+	0.9538	95.38%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6157	61.57%
P-glycoprotein inhibitior	-	0.5432	54.32%
P-glycoprotein substrate	-	0.7622	76.22%
CYP3A4 substrate	+	0.6204	62.04%
CYP2C9 substrate	-	0.8063	80.63%
CYP2D6 substrate	-	0.8609	86.09%
CYP3A4 inhibition	-	0.8005	80.05%
CYP2C9 inhibition	-	0.8516	85.16%
CYP2C19 inhibition	-	0.7967	79.67%
CYP2D6 inhibition	-	0.9145	91.45%
CYP1A2 inhibition	-	0.8859	88.59%
CYP2C8 inhibition	+	0.6778	67.78%
CYP inhibitory promiscuity	-	0.6013	60.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6444	64.44%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9367	93.67%
Skin irritation	-	0.8425	84.25%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4254	42.54%
Micronuclear	-	0.6126	61.26%
Hepatotoxicity	-	0.8393	83.93%
skin sensitisation	-	0.8219	82.19%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8575	85.75%
Acute Oral Toxicity (c)	III	0.6535	65.35%
Estrogen receptor binding	+	0.7978	79.78%
Androgen receptor binding	+	0.5299	52.99%
Thyroid receptor binding	+	0.5322	53.22%
Glucocorticoid receptor binding	+	0.5792	57.92%
Aromatase binding	+	0.6390	63.90%
PPAR gamma	+	0.6365	63.65%
Honey bee toxicity	-	0.6915	69.15%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8334	83.34%

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	97.95%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.64%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.57%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.66%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.20%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.49%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.60%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.57%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.21%	99.17%
CHEMBL4302	P08183	P-glycoprotein 1	85.51%	92.98%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.02%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.18%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.10%	95.83%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.98%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.52%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.12%	94.33%

Plants that contains it

• Polygala karensium
• Polygala sibirica

Cross-Links

• PubChem: 125181749
• LOTUS: LTS0257832
• wikiData: Q105213238