3-[[(2S,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3-oxopropanoic acid

Details

• Internal ID: 25dd2468-d511-4ba4-979d-9d8646db25ae
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: 3-[[(2S,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium-3-yl]oxy-3,4-dihydroxy-5-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• SMILES (Canonical): C1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC=C(C=C5)O)O)O)COC(=O)CC(=O)O)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=CC4=C(C=C(C=C4[O+]=C3C5=CC=C(C=C5)O)O)O)COC(=O)CC(=O)O)O)O)O)O)O
• InChI: InChI=1S/C29H30O17/c30-12-3-1-11(2-4-12)26-18(7-14-15(32)5-13(31)6-17(14)43-26)44-29-27(46-28-25(40)22(37)16(33)9-42-28)24(39)23(38)19(45-29)10-41-21(36)8-20(34)35/h1-7,16,19,22-25,27-29,33,37-40H,8-10H2,(H3-,30,31,32,34,35)/p+1/t16-,19-,22-,23-,24-,25-,27+,28-,29+/m0/s1
• InChI Key: OABKSQGALJKHFZ-KXGROZQPSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₁O₁₇+
• Molecular Weight: 651.50 g/mol
• Exact Mass: 651.15612452 g/mol
• Topological Polar Surface Area (TPSA): 263.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.83
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7822	78.22%
Caco-2	-	0.9162	91.62%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.4562	45.62%
OATP2B1 inhibitior	-	0.7075	70.75%
OATP1B1 inhibitior	+	0.8823	88.23%
OATP1B3 inhibitior	+	0.9352	93.52%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8616	86.16%
P-glycoprotein inhibitior	-	0.4655	46.55%
P-glycoprotein substrate	-	0.5350	53.50%
CYP3A4 substrate	+	0.6757	67.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.9248	92.48%
CYP2C9 inhibition	-	0.9282	92.82%
CYP2C19 inhibition	-	0.8755	87.55%
CYP2D6 inhibition	-	0.9262	92.62%
CYP1A2 inhibition	-	0.9003	90.03%
CYP2C8 inhibition	+	0.7961	79.61%
CYP inhibitory promiscuity	-	0.9414	94.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6336	63.36%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9079	90.79%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9538	95.38%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4125	41.25%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	-	0.6591	65.91%
skin sensitisation	-	0.9057	90.57%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.9654	96.54%
Acute Oral Toxicity (c)	III	0.4899	48.99%
Estrogen receptor binding	+	0.8743	87.43%
Androgen receptor binding	+	0.6358	63.58%
Thyroid receptor binding	+	0.5465	54.65%
Glucocorticoid receptor binding	+	0.5485	54.85%
Aromatase binding	+	0.6550	65.50%
PPAR gamma	+	0.7395	73.95%
Honey bee toxicity	-	0.7655	76.55%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9408	94.08%

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	99.52%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.92%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.48%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.64%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	93.44%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.82%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.55%	99.17%
CHEMBL205	P00918	Carbonic anhydrase II	90.19%	98.44%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	89.92%	95.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.01%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.70%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.23%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.45%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.14%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	83.24%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.95%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.30%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	82.03%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.41%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.22%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.11%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.33%	95.50%

Plants that contains it

• Anemone coronaria

Cross-Links

• PubChem: 163188468
• LOTUS: LTS0189080
• wikiData: Q105188576