[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 9837abaf-7cab-487c-8b5d-9b2a493e716d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3-[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=O)OC1C(C(OC(C1OC(=O)C)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)COC(=O)C=CC5=CC=C(C=C5)O)OC(=O)C=CC6=CC=C(C=C6)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(=O)C)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)COC(=O)/C=C/C5=CC=C(C=C5)O)OC(=O)/C=C\C6=CC=C(C=C6)O
• InChI: InChI=1S/C43H36O17/c1-22(44)55-41-39(59-35(52)18-8-25-5-13-28(47)14-6-25)33(21-54-34(51)17-7-24-3-11-27(46)12-4-24)58-43(42(41)56-23(2)45)60-40-37(53)36-31(50)19-30(49)20-32(36)57-38(40)26-9-15-29(48)16-10-26/h3-20,33,39,41-43,46-50H,21H2,1-2H3/b17-7+,18-8-/t33-,39-,41+,42-,43+/m1/s1
• InChI Key: QFYWXPXFEBIELC-ASZZAFOJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₃₆O₁₇
• Molecular Weight: 824.70 g/mol
• Exact Mass: 824.19524968 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 4.84
• H-Bond Acceptor: 17
• H-Bond Donor: 5
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8485	84.85%
Caco-2	-	0.8687	86.87%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7223	72.23%
OATP2B1 inhibitior	-	0.5745	57.45%
OATP1B1 inhibitior	+	0.8326	83.26%
OATP1B3 inhibitior	-	0.3029	30.29%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9642	96.42%
P-glycoprotein inhibitior	+	0.8206	82.06%
P-glycoprotein substrate	-	0.5407	54.07%
CYP3A4 substrate	+	0.6953	69.53%
CYP2C9 substrate	-	0.6051	60.51%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.7175	71.75%
CYP2C9 inhibition	+	0.5170	51.70%
CYP2C19 inhibition	-	0.7954	79.54%
CYP2D6 inhibition	-	0.9265	92.65%
CYP1A2 inhibition	-	0.9390	93.90%
CYP2C8 inhibition	+	0.8899	88.99%
CYP inhibitory promiscuity	+	0.6264	62.64%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6631	66.31%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9003	90.03%
Skin irritation	-	0.8324	83.24%
Skin corrosion	-	0.9538	95.38%
Ames mutagenesis	-	0.5237	52.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4200	42.00%
Micronuclear	+	0.7592	75.92%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8443	84.43%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8930	89.30%
Acute Oral Toxicity (c)	III	0.6389	63.89%
Estrogen receptor binding	+	0.8160	81.60%
Androgen receptor binding	+	0.8513	85.13%
Thyroid receptor binding	+	0.5679	56.79%
Glucocorticoid receptor binding	+	0.7386	73.86%
Aromatase binding	-	0.5153	51.53%
PPAR gamma	+	0.7300	73.00%
Honey bee toxicity	-	0.7476	74.76%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9671	96.71%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3729	P22748	Carbonic anhydrase IV	62.2 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	26.6 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	399.7 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.13%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.42%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.26%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	96.66%	95.64%
CHEMBL1951	P21397	Monoamine oxidase A	95.91%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.80%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.69%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	93.27%	94.73%
CHEMBL3194	P02766	Transthyretin	92.79%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.45%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.45%	99.17%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.13%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.99%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.51%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.33%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.10%	95.56%
CHEMBL242	Q92731	Estrogen receptor beta	85.17%	98.35%
CHEMBL4208	P20618	Proteasome component C5	84.66%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.44%	99.15%
CHEMBL1929	P47989	Xanthine dehydrogenase	84.36%	96.12%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.56%	94.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.82%	95.78%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.75%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	80.66%	92.50%

Plants that contains it

• Aldama oblongifolia
• Allium neapolitanum
• Artemisia schimperi
• Cajanus trinervius
• Cycas armstrongii
• Cycas revoluta
• Elephantopus mollis
• Ephedra aphylla
• Euryops algoensis
• Gardenia jasminoides
• Gomortega keule
• Iris ensata
• Licaria armeniaca
• Litsea pungens
• Mammillaria magnimamma
• Munronia pinnata
• Nuphar lutea
• Petasites hybridus
• Phoenix loureiroi
• Picea mariana
• Plectocephalus chilensis
• Quercus laurifolia
• Quercus robur
• Quercus suber
• Salvia parryi
• Staphylea ternata
• Thalictrum longistylum
• Trichilia hirta
• Typha domingensis
• Viburnum urceolatum
• Xyris pterygoblephara

Cross-Links

• PubChem: 10418008
• NPASS: NPC114101
• LOTUS: LTS0006076
• wikiData: Q105219856