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

Details

• Internal ID: 6d5e1ff1-13c3-428d-a67e-50470a1afc31
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-5-O-glycosides
• IUPAC Name: (2S,3S,4R,5R,6S)-2-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C([O+]=C3C=C(C=C(C3=C2)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC(=C(C=C5)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)OC2=C([O+]=C3C=C(C=C(C3=C2)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC(=C(C=C5)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-9-19(32)21(34)23(36)26(38-9)41-17-7-12-15(39-25(17)10-2-3-13(30)14(31)4-10)5-11(29)6-16(12)40-27-24(37)22(35)20(33)18(8-28)42-27/h2-7,9,18-24,26-28,32-37H,8H2,1H3,(H2-,29,30,31)/p+1/t9-,18+,19-,20+,21+,22-,23-,24-,26-,27+/m0/s1
• InChI Key: MVXCPXSXBRABAU-PDZVGVTKSA-O
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₁O₁₅+
• Molecular Weight: 595.50 g/mol
• Exact Mass: 595.16629528 g/mol
• Topological Polar Surface Area (TPSA): 240.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.12
• 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	-	0.7958	79.58%
Caco-2	-	0.9093	90.93%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5182	51.82%
OATP2B1 inhibitior	-	0.5599	55.99%
OATP1B1 inhibitior	+	0.9174	91.74%
OATP1B3 inhibitior	+	0.9587	95.87%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5751	57.51%
P-glycoprotein inhibitior	-	0.5618	56.18%
P-glycoprotein substrate	-	0.7076	70.76%
CYP3A4 substrate	+	0.6005	60.05%
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	+	0.8011	80.11%
CYP inhibitory promiscuity	-	0.7346	73.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6426	64.26%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.8926	89.26%
Skin irritation	-	0.8200	82.00%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6910	69.10%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9229	92.29%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8247	82.47%
Acute Oral Toxicity (c)	III	0.5773	57.73%
Estrogen receptor binding	+	0.7330	73.30%
Androgen receptor binding	+	0.5512	55.12%
Thyroid receptor binding	+	0.5942	59.42%
Glucocorticoid receptor binding	+	0.5928	59.28%
Aromatase binding	+	0.5985	59.85%
PPAR gamma	+	0.6812	68.12%
Honey bee toxicity	-	0.7683	76.83%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5549	55.49%
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	99.28%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.98%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.69%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.13%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.57%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.50%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.08%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.11%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.17%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.70%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.41%	92.94%
CHEMBL3401	O75469	Pregnane X receptor	87.34%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.10%	95.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.33%	86.92%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	82.75%	97.31%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.48%	89.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.95%	96.00%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	80.42%	96.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.25%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163189007
• LOTUS: LTS0116698
• wikiData: Q105173412