[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methyl acetate

Details

• Internal ID: 3c11e715-d26e-4b16-8bb9-79736b517243
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2=CC3=C(C=C(C=C3[O+]=C2C4=CC(=C(C=C4)O)O)O)O)OC5C(C(C(CO5)O)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC3=C(C=C(C=C3[O+]=C2C4=CC(=C(C=C4)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O)O
• InChI: InChI=1S/C28H30O16/c1-10(29)39-9-20-22(36)23(37)26(44-27-24(38)21(35)17(34)8-40-27)28(43-20)42-19-7-13-15(32)5-12(30)6-18(13)41-25(19)11-2-3-14(31)16(33)4-11/h2-7,17,20-24,26-28,34-38H,8-9H2,1H3,(H3-,30,31,32,33)/p+1/t17-,20-,21+,22-,23+,24-,26-,27+,28-/m1/s1
• InChI Key: UCXVISAAKKHFGU-OSUYLXCRSA-O
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₁O₁₆+
• Molecular Weight: 623.50 g/mol
• Exact Mass: 623.16120990 g/mol
• Topological Polar Surface Area (TPSA): 246.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.58
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5732	57.32%
Caco-2	-	0.9191	91.91%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5165	51.65%
OATP2B1 inhibitior	-	0.7111	71.11%
OATP1B1 inhibitior	+	0.8923	89.23%
OATP1B3 inhibitior	+	0.9147	91.47%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8205	82.05%
P-glycoprotein inhibitior	-	0.5295	52.95%
P-glycoprotein substrate	-	0.5540	55.40%
CYP3A4 substrate	+	0.6835	68.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8627	86.27%
CYP3A4 inhibition	-	0.9703	97.03%
CYP2C9 inhibition	-	0.9522	95.22%
CYP2C19 inhibition	-	0.9209	92.09%
CYP2D6 inhibition	-	0.9274	92.74%
CYP1A2 inhibition	-	0.8742	87.42%
CYP2C8 inhibition	+	0.7465	74.65%
CYP inhibitory promiscuity	-	0.8887	88.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6583	65.83%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9169	91.69%
Skin irritation	-	0.8013	80.13%
Skin corrosion	-	0.9515	95.15%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6942	69.42%
Micronuclear	+	0.5533	55.33%
Hepatotoxicity	-	0.7412	74.12%
skin sensitisation	-	0.9156	91.56%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9128	91.28%
Acute Oral Toxicity (c)	III	0.6280	62.80%
Estrogen receptor binding	+	0.8809	88.09%
Androgen receptor binding	+	0.6153	61.53%
Thyroid receptor binding	+	0.5789	57.89%
Glucocorticoid receptor binding	+	0.6226	62.26%
Aromatase binding	+	0.6122	61.22%
PPAR gamma	+	0.7107	71.07%
Honey bee toxicity	-	0.7395	73.95%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	+	0.9073	90.73%

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	99.55%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.14%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.95%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.45%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.16%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.16%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.42%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.92%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.42%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.40%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	85.20%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	85.02%	94.75%
CHEMBL226	P30542	Adenosine A1 receptor	84.60%	95.93%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.16%	95.83%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.14%	97.09%
CHEMBL4208	P20618	Proteasome component C5	83.07%	90.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.80%	95.78%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.65%	94.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.80%	89.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.78%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.18%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.89%	97.28%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.46%	82.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.16%	91.19%

Plants that contains it

• Camellia reticulata

Cross-Links

• PubChem: 102033067
• LOTUS: LTS0257130
• wikiData: Q105270218