[(2R,3S,4S,5S,6S)-6-[(2S,3S,4S,5S,6S)-4,5-dihydroxy-6-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxymethyl]-2-[7-hydroxy-5-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: e70af5a1-e297-476d-b765-6237f14ecdea
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: [(2R,3S,4S,5S,6S)-6-[(2S,3S,4S,5S,6S)-4,5-dihydroxy-6-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxymethyl]-2-[7-hydroxy-5-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3C(C(C(OC3OC4=C([O+]=C5C=C(C=C(C5=C4)OC6C(C(C(C(O6)CO)O)O)O)O)C7=CC(=C(C(=C7)O)O)O)COC(=O)C=CC8=CC(=C(C=C8)O)OC)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C=CC(=O)OC[C@@H]2[C@H]([C@@H]([C@@H]([C@@H](O2)O[C@H]3[C@H]([C@@H]([C@@H](O[C@H]3OC4=C([O+]=C5C=C(C=C(C5=C4)O[C@H]6[C@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)C7=CC(=C(C(=C7)O)O)O)COC(=O)C=CC8=CC(=C(C=C8)O)OC)O)O)O)O)O)O
• InChI: InChI=1S/C53H56O28/c1-71-32-11-21(3-7-26(32)56)5-9-38(60)73-19-36-42(64)45(67)48(70)52(79-36)81-50-46(68)43(65)37(20-74-39(61)10-6-22-4-8-27(57)33(12-22)72-2)80-53(50)77-34-17-25-30(75-49(34)23-13-28(58)40(62)29(59)14-23)15-24(55)16-31(25)76-51-47(69)44(66)41(63)35(18-54)78-51/h3-17,35-37,41-48,50-54,63-70H,18-20H2,1-2H3,(H5-,55,56,57,58,59,60,61,62)/p+1/t35-,36-,37+,41-,42-,43-,44+,45+,46+,47+,48+,50+,51-,52+,53-/m1/s1
• InChI Key: ODYACVLCHZXDNX-DUYDLLFCSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₅₇O₂₈+
• Molecular Weight: 1142.00 g/mol
• Exact Mass: 1141.30363616 g/mol
• Topological Polar Surface Area (TPSA): 431.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.66
• H-Bond Acceptor: 27
• H-Bond Donor: 15
• Rotatable Bonds: 18

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7706	77.06%
Caco-2	-	0.8633	86.33%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Nucleus	0.5031	50.31%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8533	85.33%
OATP1B3 inhibitior	+	0.9763	97.63%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7912	79.12%
P-glycoprotein inhibitior	+	0.7412	74.12%
P-glycoprotein substrate	+	0.5225	52.25%
CYP3A4 substrate	+	0.6895	68.95%
CYP2C9 substrate	-	0.8076	80.76%
CYP2D6 substrate	-	0.8569	85.69%
CYP3A4 inhibition	-	0.9288	92.88%
CYP2C9 inhibition	-	0.8757	87.57%
CYP2C19 inhibition	-	0.8746	87.46%
CYP2D6 inhibition	-	0.9353	93.53%
CYP1A2 inhibition	-	0.9179	91.79%
CYP2C8 inhibition	+	0.8646	86.46%
CYP inhibitory promiscuity	-	0.7977	79.77%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6681	66.81%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.8989	89.89%
Skin irritation	-	0.8353	83.53%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.5537	55.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7880	78.80%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.8216	82.16%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.9344	93.44%
Acute Oral Toxicity (c)	III	0.6160	61.60%
Estrogen receptor binding	+	0.7412	74.12%
Androgen receptor binding	+	0.7110	71.10%
Thyroid receptor binding	+	0.5876	58.76%
Glucocorticoid receptor binding	+	0.6214	62.14%
Aromatase binding	+	0.5709	57.09%
PPAR gamma	+	0.7582	75.82%
Honey bee toxicity	-	0.7165	71.65%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8991	89.91%

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	99.82%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.43%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.48%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.36%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.33%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.97%	96.09%
CHEMBL3194	P02766	Transthyretin	95.32%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.12%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.88%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.69%	97.36%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.23%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.96%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	88.68%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.27%	92.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.26%	99.15%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.55%	92.94%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.98%	94.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.25%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.44%	95.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.05%	97.28%
CHEMBL4208	P20618	Proteasome component C5	81.92%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.12%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.76%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	80.12%	92.50%

Plants that contains it

• Ajuga reptans

Cross-Links

• PubChem: 163188411
• LOTUS: LTS0029011
• wikiData: Q105190102