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

Details

• Internal ID: 27314bc7-b796-49af-aeb6-2b8095994f4e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanidin 3-O-p-coumaroyl glycosides > Anthocyanidin 3-O-6-p-coumaroyl glycosides
• IUPAC Name: 3-oxo-3-[[(3S,4S,6S)-3,4,5-trihydroxy-6-[7-hydroxy-3-[(2S,5R)-3,4,5-trihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromenylium-5-yl]oxyoxan-2-yl]methoxy]propanoic acid
• SMILES (Canonical): C1=CC(=CC=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
• SMILES (Isomeric): C1=CC(=CC=C1C=CC(=O)OCC2[C@@H](C(C([C@@H](O2)OC3=C([O+]=C4C=C(C=C(C4=C3)O[C@H]5C([C@H]([C@@H](C(O5)COC(=O)CC(=O)O)O)O)O)O)C6=CC(=C(C(=C6)O)O)O)O)O)O)O
• InChI: InChI=1S/C39H38O22/c40-17-4-1-15(2-5-17)3-6-28(46)55-13-25-31(49)34(52)36(54)39(61-25)59-24-11-19-22(57-37(24)16-7-20(42)30(48)21(43)8-16)9-18(41)10-23(19)58-38-35(53)33(51)32(50)26(60-38)14-56-29(47)12-27(44)45/h1-11,25-26,31-36,38-39,49-54H,12-14H2,(H5-,40,41,42,43,44,45,46,48)/p+1/t25?,26?,31-,32+,33-,34?,35?,36?,38+,39+/m0/s1
• InChI Key: LXITVYYZHYMDFB-DCRFRZNTSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₃₉O₂₂+
• Molecular Weight: 859.70 g/mol
• Exact Mass: 859.19329787 g/mol
• Topological Polar Surface Area (TPSA): 350.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.44
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6906	69.06%
Caco-2	-	0.8793	87.93%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Nucleus	0.4731	47.31%
OATP2B1 inhibitior	-	0.7093	70.93%
OATP1B1 inhibitior	+	0.8602	86.02%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7917	79.17%
P-glycoprotein inhibitior	+	0.7206	72.06%
P-glycoprotein substrate	-	0.5348	53.48%
CYP3A4 substrate	+	0.6625	66.25%
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	+	0.8902	89.02%
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	-	0.9035	90.35%
Skin irritation	-	0.8197	81.97%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8010	80.10%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8681	86.81%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9303	93.03%
Acute Oral Toxicity (c)	III	0.4917	49.17%
Estrogen receptor binding	+	0.7444	74.44%
Androgen receptor binding	+	0.6834	68.34%
Thyroid receptor binding	+	0.5387	53.87%
Glucocorticoid receptor binding	+	0.5564	55.64%
Aromatase binding	+	0.5497	54.97%
PPAR gamma	+	0.6970	69.70%
Honey bee toxicity	-	0.7723	77.23%
Biodegradation	-	0.8000	80.00%
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	99.71%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.38%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.26%	96.00%
CHEMBL3194	P02766	Transthyretin	95.67%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.37%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.52%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	94.24%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.10%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.73%	99.15%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.62%	83.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.11%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.46%	89.62%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.27%	91.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.13%	95.64%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	85.46%	97.31%
CHEMBL3401	O75469	Pregnane X receptor	84.89%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.85%	95.83%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.78%	95.50%
CHEMBL2581	P07339	Cathepsin D	83.41%	98.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.44%	94.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.04%	97.09%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.00%	94.00%

Plants that contains it

• Apium graveolens
• Beta vulgaris
• Commelina communis
• Gynostemma pentaphyllum
• Hordeum vulgare
• Phaseolus coccineus

Cross-Links

• PubChem: 57003757
• NPASS: NPC93342