3',4',5',7-Tetrahydroxy-3-[[6-O-[3-(3,4-dihydroxyphenyl)acryloyl]-beta-D-glucopyranosyl]oxy]-5-[[6-O-(1,3-dioxo-3-hydroxypropyl)-beta-D-glucopyranosyl]oxy]flavylium

Details

• Internal ID: 31432ca6-597d-4a99-8dd9-f2ff8cc04e65
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: 3-[[(2R,3S,4S,5R,6S)-6-[3-[(2S,3R,4S,5S,6R)-6-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxymethyl]-3,4,5-trihydroxyoxan-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): C1=CC(=C(C=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=C([O+]=C4C=C(C=C(C4=C3)OC5C(C(C(C(O5)COC(=O)CC(=O)O)O)O)O)O)C6=CC(=C(C(=C6)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C=CC(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C([O+]=C4C=C(C=C(C4=C3)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)CC(=O)O)O)O)O)O)C6=CC(=C(C(=C6)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C39H38O23/c40-16-8-22-17(23(9-16)59-38-35(54)33(52)32(51)26(61-38)13-57-29(48)11-27(45)46)10-24(37(58-22)15-6-20(43)30(49)21(44)7-15)60-39-36(55)34(53)31(50)25(62-39)12-56-28(47)4-2-14-1-3-18(41)19(42)5-14/h1-10,25-26,31-36,38-39,50-55H,11-13H2,(H6-,40,41,42,43,44,45,46,47,49)/p+1/t25-,26-,31-,32-,33+,34+,35-,36-,38-,39-/m1/s1
• InChI Key: BRCDVDQOVIAQRF-AWJFVBHYSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₃₉O₂₃+
• Molecular Weight: 875.70 g/mol
• Exact Mass: 875.18821249 g/mol
• Topological Polar Surface Area (TPSA): 371.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.74
• H-Bond Acceptor: 21
• H-Bond Donor: 13
• Rotatable Bonds: 13

Synonyms

• 7-Hydroxy-3-[[6-O-[(E)-3,4-dihydroxycinnamoyl]-beta-D-glucopyranosyl]oxy]-5-[[6-O-(2-carboxy-1-oxoethyl)-beta-D-glucopyranosyl]oxy]-2-(3,4,5-trihydroxyphenyl)-1-benzopyrylium

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6906	69.06%
Caco-2	-	0.8768	87.68%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Nucleus	0.4731	47.31%
OATP2B1 inhibitior	-	0.7108	71.08%
OATP1B1 inhibitior	+	0.8766	87.66%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8088	80.88%
P-glycoprotein inhibitior	+	0.7253	72.53%
P-glycoprotein substrate	-	0.5587	55.87%
CYP3A4 substrate	+	0.6604	66.04%
CYP2C9 substrate	-	0.7946	79.46%
CYP2D6 substrate	-	0.8616	86.16%
CYP3A4 inhibition	-	0.9074	90.74%
CYP2C9 inhibition	-	0.9133	91.33%
CYP2C19 inhibition	-	0.8472	84.72%
CYP2D6 inhibition	-	0.9014	90.14%
CYP1A2 inhibition	-	0.9017	90.17%
CYP2C8 inhibition	+	0.8768	87.68%
CYP inhibitory promiscuity	-	0.9071	90.71%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6135	61.35%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9024	90.24%
Skin irritation	-	0.8197	81.97%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7811	78.11%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8681	86.81%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9402	94.02%
Acute Oral Toxicity (c)	III	0.4917	49.17%
Estrogen receptor binding	+	0.7335	73.35%
Androgen receptor binding	+	0.6738	67.38%
Thyroid receptor binding	+	0.5322	53.22%
Glucocorticoid receptor binding	+	0.5479	54.79%
Aromatase binding	+	0.5641	56.41%
PPAR gamma	+	0.7019	70.19%
Honey bee toxicity	-	0.7595	75.95%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9744	97.44%

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	99.88%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.15%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.51%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.13%	96.00%
CHEMBL3194	P02766	Transthyretin	95.37%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.22%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.99%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.52%	99.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	92.73%	83.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.42%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.42%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.94%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	85.53%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.30%	95.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.49%	95.83%
CHEMBL221	P23219	Cyclooxygenase-1	83.35%	90.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.08%	91.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.44%	94.33%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.26%	94.00%
CHEMBL2581	P07339	Cathepsin D	80.75%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.54%	97.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.13%	85.31%

Plants that contains it

• Aconitum fischeri
• Apocynum androsaemifolium
• Espeletia grandiflora
• Huperzia yunnanensis
• Hyacinthus orientalis
• Lagascea mollis
• Pulmonaria mollis
• Rosa rugosa
• Tetracera alnifolia

Cross-Links

• PubChem: 101633888
• NPASS: NPC226490