3-[[(2R,3R,4S,5R,6S)-6-[3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-7-hydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid

Details

• Internal ID: c1ac9531-97b5-4f85-824c-9febc8288e49
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: 3-[[(2R,3R,4S,5R,6S)-6-[3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-7-hydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• 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)COC(=O)CC(=O)O)O)O)O)O)C7=CC(=C(C(=C7)O)O)O)COC(=O)C=CC8=CC=C(C=C8)O)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)COC(=O)CC(=O)O)O)O)O)O)C7=CC(=C(C(=C7)O)O)O)COC(=O)C=CC8=CC=C(C=C8)O)O)O)O)O)O)O
• InChI: InChI=1S/C55H56O30/c1-75-33-12-23(4-9-28(33)58)6-11-40(64)76-19-35-43(67)47(71)50(74)54(83-35)85-52-48(72)45(69)37(20-77-39(63)10-5-22-2-7-25(56)8-3-22)84-55(52)81-34-17-27-31(79-51(34)24-13-29(59)42(66)30(60)14-24)15-26(57)16-32(27)80-53-49(73)46(70)44(68)36(82-53)21-78-41(65)18-38(61)62/h2-17,35-37,43-50,52-55,67-74H,18-21H2,1H3,(H6-,56,57,58,59,60,61,62,63,64,66)/p+1/t35-,36-,37-,43+,44+,45+,46+,47+,48+,49-,50-,52-,53-,54+,55-/m1/s1
• InChI Key: GTFFIZJORYFPKL-OUUZTHKOSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₅₇O₃₀+
• Molecular Weight: 1198.00 g/mol
• Exact Mass: 1197.29346540 g/mol
• Topological Polar Surface Area (TPSA): 465.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.64
• H-Bond Acceptor: 28
• H-Bond Donor: 15
• Rotatable Bonds: 20

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6592	65.92%
Caco-2	-	0.8611	86.11%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.4645	46.45%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.8483	84.83%
OATP1B3 inhibitior	+	0.9685	96.85%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8802	88.02%
P-glycoprotein inhibitior	+	0.7412	74.12%
P-glycoprotein substrate	+	0.6454	64.54%
CYP3A4 substrate	+	0.7049	70.49%
CYP2C9 substrate	-	0.7971	79.71%
CYP2D6 substrate	-	0.8563	85.63%
CYP3A4 inhibition	-	0.9255	92.55%
CYP2C9 inhibition	-	0.8968	89.68%
CYP2C19 inhibition	-	0.8410	84.10%
CYP2D6 inhibition	-	0.9050	90.50%
CYP1A2 inhibition	-	0.8888	88.88%
CYP2C8 inhibition	+	0.8853	88.53%
CYP inhibitory promiscuity	-	0.8980	89.80%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5675	56.75%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.8979	89.79%
Skin irritation	-	0.8219	82.19%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8073	80.73%
Micronuclear	+	0.6859	68.59%
Hepatotoxicity	-	0.7466	74.66%
skin sensitisation	-	0.8850	88.50%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9496	94.96%
Acute Oral Toxicity (c)	III	0.6248	62.48%
Estrogen receptor binding	+	0.7264	72.64%
Androgen receptor binding	+	0.6978	69.78%
Thyroid receptor binding	+	0.5809	58.09%
Glucocorticoid receptor binding	+	0.6213	62.13%
Aromatase binding	+	0.5722	57.22%
PPAR gamma	+	0.7484	74.84%
Honey bee toxicity	-	0.7229	72.29%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9524	95.24%

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	99.84%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.91%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.20%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.80%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.79%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.72%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	94.91%	91.49%
CHEMBL3194	P02766	Transthyretin	94.32%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.62%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.84%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.20%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.15%	89.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.38%	94.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.92%	97.36%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.50%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	85.59%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.07%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.96%	95.89%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	83.52%	97.31%
CHEMBL5255	O00206	Toll-like receptor 4	83.44%	92.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.90%	83.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.21%	95.83%
CHEMBL2581	P07339	Cathepsin D	80.80%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.44%	95.64%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.13%	92.62%

Plants that contains it

• Ajuga reptans

Cross-Links

• PubChem: 163188122
• LOTUS: LTS0109336
• wikiData: Q105018582