(2R,3S,4R,5R,6S)-2-[(2S,3S,4R,5R,6S)-2-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxychromenylium-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 663c2ead-d199-4551-a0fc-0e23e5e69d34
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: (2R,3S,4R,5R,6S)-2-[(2S,3S,4R,5R,6S)-2-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(1R,2R,3S,4R,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxychromenylium-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(C(C(C1OC2=CC(=CC3=[O+]C(=C(C=C23)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)C6=CC(=C(C=C6)O)O)O)O)O)O)CO
• SMILES (Isomeric): C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1OC2=CC(=CC3=[O+]C(=C(C=C23)O[C@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O[C@@H]5[C@H]([C@@H]([C@H]([C@@H](O5)CO)O)O)O)C6=CC(=C(C=C6)O)O)O)O)O)O)CO
• InChI: InChI=1S/C34H42O20/c35-8-12-4-19(24(42)27(45)23(12)41)49-17-5-13(38)6-18-14(17)7-20(31(50-18)11-1-2-15(39)16(40)3-11)51-34-32(29(47)26(44)22(10-37)53-34)54-33-30(48)28(46)25(43)21(9-36)52-33/h1-3,5-7,12,19,21-30,32-37,41-48H,4,8-10H2,(H2-,38,39,40)/p+1/t12-,19-,21+,22+,23-,24+,25+,26+,27+,28-,29-,30+,32+,33-,34-/m1/s1
• InChI Key: IUYMZNOSNRCAKE-IWLWTWLASA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₃O₂₀+
• Molecular Weight: 771.70 g/mol
• Exact Mass: 771.23476876 g/mol
• Topological Polar Surface Area (TPSA): 330.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -3.66
• H-Bond Acceptor: 19
• H-Bond Donor: 14
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8494	84.94%
Caco-2	-	0.9084	90.84%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Nucleus	0.4431	44.31%
OATP2B1 inhibitior	-	0.7108	71.08%
OATP1B1 inhibitior	+	0.9143	91.43%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5716	57.16%
P-glycoprotein inhibitior	-	0.4430	44.30%
P-glycoprotein substrate	-	0.5852	58.52%
CYP3A4 substrate	+	0.6624	66.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8024	80.24%
CYP3A4 inhibition	-	0.9662	96.62%
CYP2C9 inhibition	-	0.9043	90.43%
CYP2C19 inhibition	-	0.8149	81.49%
CYP2D6 inhibition	-	0.9110	91.10%
CYP1A2 inhibition	-	0.8934	89.34%
CYP2C8 inhibition	+	0.8041	80.41%
CYP inhibitory promiscuity	-	0.7658	76.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6229	62.29%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8984	89.84%
Skin irritation	-	0.8185	81.85%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7503	75.03%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	-	0.7748	77.48%
skin sensitisation	-	0.9093	90.93%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8080	80.80%
Acute Oral Toxicity (c)	IV	0.4162	41.62%
Estrogen receptor binding	+	0.7908	79.08%
Androgen receptor binding	+	0.6322	63.22%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.7053	70.53%
Aromatase binding	+	0.6099	60.99%
PPAR gamma	+	0.7071	70.71%
Honey bee toxicity	-	0.6423	64.23%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.7348	73.48%

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	99.76%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.02%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.59%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.68%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.59%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.67%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.87%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.58%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.01%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.74%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.25%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.74%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.25%	95.83%
CHEMBL213	P08588	Beta-1 adrenergic receptor	85.46%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.41%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.26%	86.92%
CHEMBL4208	P20618	Proteasome component C5	83.59%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.45%	99.17%
CHEMBL3194	P02766	Transthyretin	83.17%	90.71%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.76%	83.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	82.11%	97.31%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.82%	96.21%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.57%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	81.20%	95.93%
CHEMBL3891	P07384	Calpain 1	81.17%	93.04%

Plants that contains it

• Ajuga reptans
• Ipomoea batatas

Cross-Links

• PubChem: 5316224
• LOTUS: LTS0130511
• wikiData: Q105120921