(2S,3R,4S,5S,6R)-2-[3-[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-7-hydroxychromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: e78d8e1a-bc75-4b6d-adbf-1bd470b69dcf
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-5-O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[3-[(2S,3R,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-7-hydroxychromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(C(C(O1)OC2C(C(C(OC2OC3=C([O+]=C4C=C(C=C(C4=C3)OC5C(C(C(C(O5)CO)O)O)O)O)C6=CC(=C(C=C6)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@@H]([C@@H]([C@H](O1)O[C@@H]2[C@H]([C@@H]([C@@H](O[C@H]2OC3=C([O+]=C4C=C(C=C(C4=C3)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)C6=CC(=C(C=C6)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C32H38O20/c33-7-19-22(40)24(42)27(45)31(50-19)48-17-5-11(35)4-16-12(17)6-18(28(47-16)10-1-2-13(36)14(37)3-10)49-32-29(25(43)23(41)20(8-34)51-32)52-30-26(44)21(39)15(38)9-46-30/h1-6,15,19-27,29-34,38-45H,7-9H2,(H2-,35,36,37)/p+1/t15-,19+,20-,21-,22+,23+,24-,25-,26-,27+,29+,30+,31+,32+/m0/s1
• InChI Key: OLBLWNPOURNBCY-QFEPKXLGSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₉O₂₀+
• Molecular Weight: 743.60 g/mol
• Exact Mass: 743.20346863 g/mol
• Topological Polar Surface Area (TPSA): 319.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -3.68
• H-Bond Acceptor: 19
• H-Bond Donor: 13
• Rotatable Bonds: 9

Synonyms

• Q23419061

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8094	80.94%
Caco-2	-	0.9145	91.45%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Nucleus	0.4922	49.22%
OATP2B1 inhibitior	-	0.7085	70.85%
OATP1B1 inhibitior	+	0.9162	91.62%
OATP1B3 inhibitior	+	0.9359	93.59%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.4642	46.42%
P-glycoprotein inhibitior	-	0.4689	46.89%
P-glycoprotein substrate	-	0.6244	62.44%
CYP3A4 substrate	+	0.6543	65.43%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8268	82.68%
CYP3A4 inhibition	-	0.9674	96.74%
CYP2C9 inhibition	-	0.9451	94.51%
CYP2C19 inhibition	-	0.8795	87.95%
CYP2D6 inhibition	-	0.8992	89.92%
CYP1A2 inhibition	-	0.9079	90.79%
CYP2C8 inhibition	+	0.7850	78.50%
CYP inhibitory promiscuity	-	0.8848	88.48%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6278	62.78%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8990	89.90%
Skin irritation	-	0.8130	81.30%
Skin corrosion	-	0.9616	96.16%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7799	77.99%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	-	0.8498	84.98%
skin sensitisation	-	0.9039	90.39%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9063	90.63%
Acute Oral Toxicity (c)	III	0.4867	48.67%
Estrogen receptor binding	+	0.7694	76.94%
Androgen receptor binding	+	0.5803	58.03%
Thyroid receptor binding	+	0.5364	53.64%
Glucocorticoid receptor binding	-	0.6559	65.59%
Aromatase binding	+	0.6107	61.07%
PPAR gamma	+	0.7222	72.22%
Honey bee toxicity	-	0.6835	68.35%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.6534	65.34%

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	99.68%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.08%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.77%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.59%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.27%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.03%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.89%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.51%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.42%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	89.29%	95.93%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.70%	95.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.78%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.24%	95.83%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.23%	89.62%
CHEMBL1937	Q92769	Histone deacetylase 2	85.29%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.27%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.66%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.20%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.01%	86.92%
CHEMBL4208	P20618	Proteasome component C5	81.62%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.03%	97.36%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.79%	83.00%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	80.68%	96.69%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.28%	97.28%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 139031039
• LOTUS: LTS0002231
• wikiData: Q23419061