[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 98ab65c8-779f-4dde-818c-8c5115774b8a
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3(C(C(C(O3)CO)O)OC(=O)C=CC4=CC=C(C=C4)O)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O[C@]3([C@H]([C@@H]([C@H](O3)CO)O)OC(=O)/C=C/C4=CC=C(C=C4)O)CO)O)O)O)O
• InChI: InChI=1S/C30H34O15/c31-13-20-25(38)28(43-23(36)12-6-17-3-9-19(34)10-4-17)30(15-32,44-20)45-29-27(40)26(39)24(37)21(42-29)14-41-22(35)11-5-16-1-7-18(33)8-2-16/h1-12,20-21,24-29,31-34,37-40H,13-15H2/b11-5+,12-6+/t20-,21-,24-,25-,26+,27-,28+,29-,30+/m1/s1
• InChI Key: BWXRDCUDYDSUGH-JSCCKXNGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₄O₁₅
• Molecular Weight: 634.60 g/mol
• Exact Mass: 634.18977037 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.46
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8467	84.67%
Caco-2	-	0.9080	90.80%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7659	76.59%
OATP2B1 inhibitior	-	0.8523	85.23%
OATP1B1 inhibitior	+	0.8660	86.60%
OATP1B3 inhibitior	+	0.9538	95.38%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8517	85.17%
P-glycoprotein inhibitior	-	0.4791	47.91%
P-glycoprotein substrate	-	0.8104	81.04%
CYP3A4 substrate	+	0.6279	62.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8680	86.80%
CYP3A4 inhibition	-	0.8298	82.98%
CYP2C9 inhibition	-	0.8870	88.70%
CYP2C19 inhibition	-	0.8270	82.70%
CYP2D6 inhibition	-	0.9166	91.66%
CYP1A2 inhibition	-	0.9272	92.72%
CYP2C8 inhibition	+	0.7218	72.18%
CYP inhibitory promiscuity	-	0.7925	79.25%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6256	62.56%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9309	93.09%
Skin irritation	-	0.8510	85.10%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8199	81.99%
Micronuclear	-	0.5926	59.26%
Hepatotoxicity	-	0.8449	84.49%
skin sensitisation	-	0.8469	84.69%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7764	77.64%
Acute Oral Toxicity (c)	III	0.5918	59.18%
Estrogen receptor binding	+	0.8248	82.48%
Androgen receptor binding	+	0.6404	64.04%
Thyroid receptor binding	+	0.5156	51.56%
Glucocorticoid receptor binding	-	0.4657	46.57%
Aromatase binding	+	0.6079	60.79%
PPAR gamma	+	0.7299	72.99%
Honey bee toxicity	-	0.6832	68.32%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9452	94.52%

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	98.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.40%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.21%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.88%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.66%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	88.34%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.74%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.91%	94.45%
CHEMBL3194	P02766	Transthyretin	86.84%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.17%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.16%	89.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.08%	89.67%
CHEMBL226	P30542	Adenosine A1 receptor	82.38%	95.93%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.53%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.29%	86.92%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.89%	85.00%

Plants that contains it

• Lilium mackliniae

Cross-Links

• PubChem: 101608826
• LOTUS: LTS0067646
• wikiData: Q104947754