(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol

Details

• Internal ID: 66ce8349-204d-4538-adc8-638879cf2ef5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC(=C(C=C5)O)O)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC(=C(C=C5)O)O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C26H28O15/c27-10-4-13(29)11-6-17(24(39-16(11)5-10)9-1-2-12(28)14(30)3-9)40-26-23(36)21(34)20(33)18(41-26)8-38-25-22(35)19(32)15(31)7-37-25/h1-6,15,18-23,25-26,31-36H,7-8H2,(H3-,27,28,29,30)/p+1/t15-,18-,19+,20-,21+,22-,23-,25+,26-/m1/s1
• InChI Key: PYHCIQHBARAJGO-UFAJABROSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₉O₁₅+
• Molecular Weight: 581.50 g/mol
• Exact Mass: 581.15064521 g/mol
• Topological Polar Surface Area (TPSA): 240.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.15
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7791	77.91%
Caco-2	-	0.9263	92.63%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4781	47.81%
OATP2B1 inhibitior	-	0.5592	55.92%
OATP1B1 inhibitior	+	0.9189	91.89%
OATP1B3 inhibitior	+	0.9120	91.20%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6179	61.79%
P-glycoprotein inhibitior	-	0.6188	61.88%
P-glycoprotein substrate	-	0.6407	64.07%
CYP3A4 substrate	+	0.6381	63.81%
CYP2C9 substrate	-	0.8065	80.65%
CYP2D6 substrate	-	0.8214	82.14%
CYP3A4 inhibition	-	0.9630	96.30%
CYP2C9 inhibition	-	0.9309	93.09%
CYP2C19 inhibition	-	0.8344	83.44%
CYP2D6 inhibition	-	0.8831	88.31%
CYP1A2 inhibition	-	0.9082	90.82%
CYP2C8 inhibition	+	0.7926	79.26%
CYP inhibitory promiscuity	-	0.8943	89.43%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6274	62.74%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8817	88.17%
Skin irritation	-	0.8157	81.57%
Skin corrosion	-	0.9621	96.21%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6627	66.27%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.8196	81.96%
skin sensitisation	-	0.9022	90.22%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.9269	92.69%
Acute Oral Toxicity (c)	III	0.5113	51.13%
Estrogen receptor binding	+	0.8057	80.57%
Androgen receptor binding	+	0.6058	60.58%
Thyroid receptor binding	+	0.6100	61.00%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.7111	71.11%
PPAR gamma	+	0.7929	79.29%
Honey bee toxicity	-	0.7499	74.99%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5849	58.49%
Fish aquatic toxicity	+	0.8580	85.80%

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	99.66%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.07%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.67%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.30%	99.15%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.99%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.46%	89.00%
CHEMBL2581	P07339	Cathepsin D	90.89%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	90.51%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.51%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.48%	94.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	90.10%	95.78%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.70%	92.94%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.62%	95.83%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.88%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.37%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	85.36%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.47%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.23%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.73%	99.17%
CHEMBL4208	P20618	Proteasome component C5	81.45%	90.00%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	80.75%	92.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.73%	92.62%
CHEMBL3194	P02766	Transthyretin	80.10%	90.71%

Plants that contains it

• Akebia quinata
• Alyxia reinwardtii
• Centaurea linifolia
• Cneoridium dumosum
• Leuzea centauroides
• Limonium gmelinii
• Machilus glaucescens
• Microtropis fokienensis
• Thymus vulgaris
• Vitellaria paradoxa

Cross-Links

• PubChem: 6325002
• NPASS: NPC175118