(2R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-[4-hydroxy-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propanoic acid

Details

• Internal ID: db047337-6a50-4399-8d2a-48a428b82fb5
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-[4-hydroxy-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propanoic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C24H26O13/c25-10-18-20(30)21(31)22(32)24(37-18)36-16-8-12(2-5-14(16)27)9-17(23(33)34)35-19(29)6-3-11-1-4-13(26)15(28)7-11/h1-8,17-18,20-22,24-28,30-32H,9-10H2,(H,33,34)/b6-3+/t17-,18+,20+,21-,22+,24+/m1/s1
• InChI Key: UJQFXBKHYJKNFT-CPLHYMNVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₆O₁₃
• Molecular Weight: 522.50 g/mol
• Exact Mass: 522.13734088 g/mol
• Topological Polar Surface Area (TPSA): 224.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.77
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7181	71.81%
Caco-2	-	0.9377	93.77%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5598	55.98%
OATP2B1 inhibitior	-	0.7049	70.49%
OATP1B1 inhibitior	+	0.8999	89.99%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.4569	45.69%
P-glycoprotein inhibitior	-	0.6237	62.37%
P-glycoprotein substrate	-	0.8029	80.29%
CYP3A4 substrate	+	0.5889	58.89%
CYP2C9 substrate	-	0.6011	60.11%
CYP2D6 substrate	-	0.8646	86.46%
CYP3A4 inhibition	-	0.8010	80.10%
CYP2C9 inhibition	-	0.8339	83.39%
CYP2C19 inhibition	-	0.8920	89.20%
CYP2D6 inhibition	-	0.9306	93.06%
CYP1A2 inhibition	-	0.9384	93.84%
CYP2C8 inhibition	+	0.6948	69.48%
CYP inhibitory promiscuity	-	0.7888	78.88%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7548	75.48%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.9041	90.41%
Skin irritation	-	0.8418	84.18%
Skin corrosion	-	0.9592	95.92%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4814	48.14%
Micronuclear	+	0.5733	57.33%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8063	80.63%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9101	91.01%
Acute Oral Toxicity (c)	III	0.6655	66.55%
Estrogen receptor binding	+	0.7475	74.75%
Androgen receptor binding	+	0.5833	58.33%
Thyroid receptor binding	+	0.5215	52.15%
Glucocorticoid receptor binding	-	0.5322	53.22%
Aromatase binding	-	0.5750	57.50%
PPAR gamma	+	0.6931	69.31%
Honey bee toxicity	-	0.6855	68.55%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9334	93.34%

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	99.50%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.45%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.88%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.40%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.21%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.59%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.15%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.08%	86.33%
CHEMBL3194	P02766	Transthyretin	92.07%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.87%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.68%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	88.66%	83.82%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.26%	91.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.75%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.78%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.19%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	82.37%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.86%	86.92%

Plants that contains it

• Amentotaxus yunnanensis
• Artemisia siversiana
• Deguelia hatschbachii
• Delphinium cyphoplectrum
• Dioscorea communis
• Euphorbia retusa
• Hemionitis artax
• Salvia przewalskii
• Stauntonia obovatifoliola
• Uvaria klaineana
• Vicia sativa

Cross-Links

• PubChem: 25245849
• NPASS: NPC70867