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

Details

• Internal ID: 391b02af-b299-456b-858e-0427a4cd8458
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanidin 3-O-p-coumaroyl glycosides > Anthocyanidin 3-O-6-p-coumaroyl glycosides
• IUPAC Name: 3-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxy-5-methoxyphenyl)-7-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl]oxychromenylium-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C2=C(C=C3C(=CC(=CC3=[O+]2)O)OC4C(C(C(C(O4)COC(=O)CC(=O)O)O)O)O)OC5C(C(C(C(O5)COC(=O)C=CC6=CC=C(C=C6)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)CC(=O)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C=CC6=CC=C(C=C6)O)O)O)O
• InChI: InChI=1S/C40H40O22/c1-55-24-9-17(8-21(43)31(24)48)38-25(60-40-37(54)35(52)32(49)26(62-40)14-56-29(46)7-4-16-2-5-18(41)6-3-16)12-20-22(58-38)10-19(42)11-23(20)59-39-36(53)34(51)33(50)27(61-39)15-57-30(47)13-28(44)45/h2-12,26-27,32-37,39-40,49-54H,13-15H2,1H3,(H4-,41,42,43,44,45,46,48)/p+1/t26-,27-,32-,33-,34+,35+,36-,37-,39-,40-/m1/s1
• InChI Key: ZCJAIHSCFUFLJV-KZGNYCDPSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₁O₂₂+
• Molecular Weight: 873.70 g/mol
• Exact Mass: 873.20894793 g/mol
• Topological Polar Surface Area (TPSA): 339.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.14
• H-Bond Acceptor: 20
• H-Bond Donor: 11
• Rotatable Bonds: 14

Synonyms

• 2-(3,4-Dihydroxy-5-methoxyphenyl)-3-[6-O-[(Z)-3-(4-hydroxyphenyl)propenoyl]-beta-D-glucopyranosyloxy]-5-[6-O-(2-carboxyacetyl)-beta-D-glucopyranosyloxy]-7-hydroxy-1-benzopyrylium
• 3',4',7-Trihydroxy-5'-methoxy-3-[6-O-[3-(4-hydroxyphenyl)propenoyl]-beta-D-glucopyranosyloxy]-5-[6-O-(1,3-dioxo-3-hydroxypropyl)-beta-D-glucopyranosyloxy]anthocyanidin

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6592	65.92%
Caco-2	-	0.8761	87.61%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.4645	46.45%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.8509	85.09%
OATP1B3 inhibitior	+	0.9685	96.85%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7716	77.16%
P-glycoprotein inhibitior	+	0.7249	72.49%
P-glycoprotein substrate	+	0.5856	58.56%
CYP3A4 substrate	+	0.6801	68.01%
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	+	0.8957	89.57%
CYP inhibitory promiscuity	-	0.8980	89.80%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5675	56.75%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9057	90.57%
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	+	0.8374	83.74%
Micronuclear	+	0.6859	68.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8850	88.50%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9271	92.71%
Acute Oral Toxicity (c)	III	0.6248	62.48%
Estrogen receptor binding	+	0.7659	76.59%
Androgen receptor binding	+	0.6491	64.91%
Thyroid receptor binding	+	0.5372	53.72%
Glucocorticoid receptor binding	+	0.6292	62.92%
Aromatase binding	+	0.5399	53.99%
PPAR gamma	+	0.7061	70.61%
Honey bee toxicity	-	0.7718	77.18%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
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	99.54%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.84%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.58%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.89%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.76%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.58%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.10%	85.14%
CHEMBL3194	P02766	Transthyretin	92.04%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.78%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.37%	89.62%
CHEMBL2581	P07339	Cathepsin D	87.86%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.50%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.75%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	85.34%	94.73%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.30%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.50%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.27%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.82%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.50%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.39%	92.62%

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: 100921412
• NPASS: NPC265184