4-[[6-O-[3-(4-Hydroxyphenyl)-1-oxo-2-propenyl]-beta-D-glucopyranosyl]oxy]benzeneacrylic acid

Details

• Internal ID: a72372ec-a929-457f-b3a7-4d01010e8c95
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (E)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyphenyl]prop-2-enoic acid
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=CC=C(C=C3)C=CC(=O)O)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)OC3=CC=C(C=C3)/C=C/C(=O)O)O)O)O)O
• InChI: InChI=1S/C24H24O10/c25-16-7-1-14(2-8-16)6-12-20(28)32-13-18-21(29)22(30)23(31)24(34-18)33-17-9-3-15(4-10-17)5-11-19(26)27/h1-12,18,21-25,29-31H,13H2,(H,26,27)/b11-5+,12-6+/t18-,21-,22+,23-,24-/m1/s1
• InChI Key: KIUPQVRHLUTCHS-RMYWVIGVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₄O₁₀
• Molecular Weight: 472.40 g/mol
• Exact Mass: 472.13694696 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.93
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7317	73.17%
Caco-2	-	0.8679	86.79%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6707	67.07%
OATP2B1 inhibitior	-	0.8468	84.68%
OATP1B1 inhibitior	+	0.9092	90.92%
OATP1B3 inhibitior	+	0.9133	91.33%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.4627	46.27%
P-glycoprotein inhibitior	-	0.5865	58.65%
P-glycoprotein substrate	-	0.9316	93.16%
CYP3A4 substrate	+	0.5641	56.41%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	-	0.8727	87.27%
CYP3A4 inhibition	-	0.8624	86.24%
CYP2C9 inhibition	-	0.8523	85.23%
CYP2C19 inhibition	-	0.9071	90.71%
CYP2D6 inhibition	-	0.9352	93.52%
CYP1A2 inhibition	-	0.9455	94.55%
CYP2C8 inhibition	+	0.6998	69.98%
CYP inhibitory promiscuity	-	0.7900	79.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6675	66.75%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8956	89.56%
Skin irritation	-	0.8363	83.63%
Skin corrosion	-	0.9578	95.78%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6637	66.37%
Micronuclear	+	0.6166	61.66%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8432	84.32%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8264	82.64%
Acute Oral Toxicity (c)	III	0.7105	71.05%
Estrogen receptor binding	+	0.5586	55.86%
Androgen receptor binding	+	0.5250	52.50%
Thyroid receptor binding	-	0.5613	56.13%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6026	60.26%
PPAR gamma	+	0.6320	63.20%
Honey bee toxicity	-	0.8260	82.60%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9521	95.21%

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	97.71%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.93%	86.33%
CHEMBL206	P03372	Estrogen receptor alpha	93.98%	97.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.58%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.39%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.49%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.37%	97.09%
CHEMBL3194	P02766	Transthyretin	88.33%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.92%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.57%	89.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.11%	89.67%
CHEMBL221	P23219	Cyclooxygenase-1	85.95%	90.17%
CHEMBL226	P30542	Adenosine A1 receptor	85.25%	95.93%
CHEMBL1951	P21397	Monoamine oxidase A	84.28%	91.49%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.76%	91.71%
CHEMBL4208	P20618	Proteasome component C5	83.20%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.07%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	82.91%	94.73%

Plants that contains it

• Achillea nana
• Aconitum napellus
• Astragalus bisulcatus
• Baccharoides lasiopus
• Bidens pilosa
• Boenninghausenia albiflora
• Bothriocline ripensis
• Brachyglottis bidwillii
• Calea lantanoides
• Chromolaena odorata
• Cibotium barometz
• Coprosma lucida
• Coronilla cretica
• Drosera indica
• Drummondita hassellii
• Eleutherococcus sessiliflorus
• Ephedra distachya
• Flindersia xanthoxyla
• Fritillaria persica
• Galium mollugo
• Gardenia imperialis
• Gomesa radicans
• Grindelia scorzonerifolia
• Gymnosporia diversifolia
• Lepidium graminifolium
• Lonchocarpus atropurpureus
• Phalaenopsis cornu-cervi
• Pinus flexilis
• Psilotum nudum
• Rydingia limbata
• Senegalia mellifera
• Syagrus romanzoffiana
• Trinia scabra
• Typha latifolia
• Uncaria sterrophylla
• Vicia amoena

Cross-Links

• PubChem: 15071011
• NPASS: NPC291516
• LOTUS: LTS0145114
• wikiData: Q105141687