(2S,5R)-2-[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: ea087a13-6d03-4e9d-9942-398596a0db8c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: (2S,5R)-2-[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C2=[O+]C3=CC(=CC(=C3C=C2OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)C2=[O+]C3=CC(=CC(=C3C=C2O[C@H]4C(C([C@H](C(O4)CO)O)O)O)O)O
• InChI: InChI=1S/C22H22O12/c1-31-14-3-8(2-12(26)17(14)27)21-15(6-10-11(25)4-9(24)5-13(10)32-21)33-22-20(30)19(29)18(28)16(7-23)34-22/h2-6,16,18-20,22-23,28-30H,7H2,1H3,(H3-,24,25,26,27)/p+1/t16?,18-,19?,20?,22+/m0/s1
• InChI Key: CCQDWIRWKWIUKK-AABNTQHHSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₃O₁₂+
• Molecular Weight: 479.40 g/mol
• Exact Mass: 479.11895116 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.39
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

• LMPK12010348

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8059	80.59%
Caco-2	-	0.8598	85.98%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Nucleus	0.4385	43.85%
OATP2B1 inhibitior	+	0.5836	58.36%
OATP1B1 inhibitior	+	0.8722	87.22%
OATP1B3 inhibitior	+	0.9726	97.26%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5447	54.47%
P-glycoprotein inhibitior	-	0.5965	59.65%
P-glycoprotein substrate	-	0.6698	66.98%
CYP3A4 substrate	+	0.5980	59.80%
CYP2C9 substrate	-	0.8057	80.57%
CYP2D6 substrate	-	0.8169	81.69%
CYP3A4 inhibition	-	0.9475	94.75%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.8383	83.83%
CYP2D6 inhibition	-	0.9199	91.99%
CYP1A2 inhibition	-	0.8757	87.57%
CYP2C8 inhibition	+	0.7929	79.29%
CYP inhibitory promiscuity	-	0.7426	74.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6325	63.25%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8263	82.63%
Skin irritation	-	0.8156	81.56%
Skin corrosion	-	0.9529	95.29%
Ames mutagenesis	-	0.6091	60.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.4509	45.09%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9266	92.66%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.8387	83.87%
Acute Oral Toxicity (c)	III	0.6492	64.92%
Estrogen receptor binding	+	0.7962	79.62%
Androgen receptor binding	+	0.5979	59.79%
Thyroid receptor binding	+	0.5541	55.41%
Glucocorticoid receptor binding	+	0.8004	80.04%
Aromatase binding	+	0.6872	68.72%
PPAR gamma	+	0.7077	70.77%
Honey bee toxicity	-	0.8058	80.58%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6149	61.49%
Fish aquatic toxicity	-	0.3662	36.62%

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	99.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.30%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.29%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.56%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.16%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.87%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.65%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.45%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.30%	97.36%
CHEMBL2581	P07339	Cathepsin D	86.84%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.47%	96.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.83%	89.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.56%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.96%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	83.32%	94.73%
CHEMBL3194	P02766	Transthyretin	82.74%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.94%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	80.95%	94.75%

Plants that contains it

• Vaccinium angustifolium
• Vaccinium corymbosum
• Vaccinium myrtillus
• Vaccinium uliginosum

Cross-Links

• PubChem: 44256953
• LOTUS: LTS0098960
• wikiData: Q104389037