Peonidin 3,5-diglucoside

Details

• Internal ID: bab17761-6e1d-4003-93e1-a6ea3f4b8d35
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-5-O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=C(C=C3C(=CC(=CC3=[O+]2)O)OC4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C28H32O16/c1-39-16-4-10(2-3-13(16)32)26-17(42-28-25(38)23(36)21(34)19(9-30)44-28)7-12-14(40-26)5-11(31)6-15(12)41-27-24(37)22(35)20(33)18(8-29)43-27/h2-7,18-25,27-30,33-38H,8-9H2,1H3,(H-,31,32)/p+1/t18-,19-,20-,21-,22+,23+,24-,25-,27-,28-/m1/s1
• InChI Key: IPVSUYLZIAYTOK-DPOJTEBASA-O
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₃O₁₆+
• Molecular Weight: 625.60 g/mol
• Exact Mass: 625.17685996 g/mol
• Topological Polar Surface Area (TPSA): 249.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.84
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• RefChem:860106
• (2S,3R,4S,5S,6R)-2-[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 47851-83-2
• Peonidin-3,5-O-di-beta-glucopyranoside
• AC1NUQWS
• L78DM2EW8J
• Peonidin 3,5-di-O-glucoside
• SCHEMBL29530365
• CHEBI:177075
• Q63408919
• 3,5-Bis(beta-D-glucopyranosyloxy)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-benzopyrylium
• 1-Benzopyrylium, 3,5-bis(beta-D-glucopyranosyloxy)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8414	84.14%
Caco-2	-	0.9011	90.11%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Nucleus	0.4423	44.23%
OATP2B1 inhibitior	-	0.7071	70.71%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.9763	97.63%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5765	57.65%
P-glycoprotein inhibitior	-	0.5189	51.89%
P-glycoprotein substrate	-	0.7668	76.68%
CYP3A4 substrate	+	0.5895	58.95%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.8108	81.08%
CYP3A4 inhibition	-	0.9668	96.68%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.8148	81.48%
CYP2D6 inhibition	-	0.9200	92.00%
CYP1A2 inhibition	-	0.8842	88.42%
CYP2C8 inhibition	+	0.8223	82.23%
CYP inhibitory promiscuity	-	0.7308	73.08%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6078	60.78%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9103	91.03%
Skin irritation	-	0.8259	82.59%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.5191	51.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.8065	80.65%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9235	92.35%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7335	73.35%
Acute Oral Toxicity (c)	III	0.6490	64.90%
Estrogen receptor binding	+	0.7743	77.43%
Androgen receptor binding	+	0.5618	56.18%
Thyroid receptor binding	+	0.5282	52.82%
Glucocorticoid receptor binding	+	0.5973	59.73%
Aromatase binding	+	0.6378	63.78%
PPAR gamma	+	0.6632	66.32%
Honey bee toxicity	-	0.8115	81.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5449	54.49%
Fish aquatic toxicity	-	0.4110	41.10%

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	98.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.15%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.40%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.31%	99.15%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.92%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.70%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.26%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.07%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.94%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.27%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.67%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.00%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.82%	85.14%
CHEMBL3438	Q05513	Protein kinase C zeta	83.82%	88.48%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.99%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.96%	92.62%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.04%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.00%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	81.47%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.36%	97.36%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5488811
• NPASS: NPC14447