(2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Details

• Internal ID: 590ee045-c277-4aad-be1a-07f40986618b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC(=C(C(=C5)O)O)O)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[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)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-8-18(33)21(36)23(38)26(39-8)43-25-22(37)20(35)17(7-28)42-27(25)41-16-6-11-12(30)4-10(29)5-15(11)40-24(16)9-2-13(31)19(34)14(32)3-9/h2-6,8,17-18,20-23,25-28,33,35-38H,7H2,1H3,(H4-,29,30,31,32,34)/p+1/t8-,17+,18-,20+,21+,22-,23+,25+,26-,27+/m0/s1
• InChI Key: YVVWRBPFRASKOD-MOEMVUQXSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₁O₁₆+
• Molecular Weight: 611.50 g/mol
• Exact Mass: 611.16120990 g/mol
• Topological Polar Surface Area (TPSA): 260.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.06
• H-Bond Acceptor: 15
• H-Bond Donor: 11
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7958	79.58%
Caco-2	-	0.9117	91.17%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5182	51.82%
OATP2B1 inhibitior	-	0.5633	56.33%
OATP1B1 inhibitior	+	0.8727	87.27%
OATP1B3 inhibitior	+	0.9587	95.87%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5795	57.95%
P-glycoprotein inhibitior	-	0.5886	58.86%
P-glycoprotein substrate	-	0.5831	58.31%
CYP3A4 substrate	+	0.6348	63.48%
CYP2C9 substrate	-	0.8041	80.41%
CYP2D6 substrate	-	0.8317	83.17%
CYP3A4 inhibition	-	0.9608	96.08%
CYP2C9 inhibition	-	0.9020	90.20%
CYP2C19 inhibition	-	0.8633	86.33%
CYP2D6 inhibition	-	0.9390	93.90%
CYP1A2 inhibition	-	0.8603	86.03%
CYP2C8 inhibition	+	0.7423	74.23%
CYP inhibitory promiscuity	-	0.7346	73.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6426	64.26%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9050	90.50%
Skin irritation	-	0.8200	82.00%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.6191	61.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.7219	72.19%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9229	92.29%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9358	93.58%
Acute Oral Toxicity (c)	III	0.5773	57.73%
Estrogen receptor binding	+	0.8084	80.84%
Androgen receptor binding	+	0.5843	58.43%
Thyroid receptor binding	+	0.6419	64.19%
Glucocorticoid receptor binding	+	0.5937	59.37%
Aromatase binding	+	0.6860	68.60%
PPAR gamma	+	0.7748	77.48%
Honey bee toxicity	-	0.7434	74.34%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.7752	77.52%

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	99.64%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.00%	91.49%
CHEMBL3714130	P46095	G-protein coupled receptor 6	96.08%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.47%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.90%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.21%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.54%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.45%	83.57%
CHEMBL1937	Q92769	Histone deacetylase 2	89.69%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.49%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.31%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.17%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	87.85%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.33%	99.15%
CHEMBL3194	P02766	Transthyretin	86.23%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.64%	96.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	81.06%	97.31%
CHEMBL4208	P20618	Proteasome component C5	80.88%	90.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.25%	95.78%

Plants that contains it

• Clitoria ternatea
• Podocarpus nivalis

Cross-Links

• PubChem: 5493095
• LOTUS: LTS0022208
• wikiData: Q105366097