Pelargonidin 3-glucoside ion

Details

• Internal ID: 70321d80-f600-4fbc-8a35-10bf23774956
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C2=[O+]C3=CC(=CC(=C3C=C2OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=[O+]C3=CC(=CC(=C3C=C2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O10/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9/h1-7,16-19,21-22,26-28H,8H2,(H2-,23,24,25)/p+1/t16-,17-,18+,19-,21-/m1/s1
• InChI Key: ABVCUBUIXWJYSE-GQUPQBGVSA-O
• Popularity: 88 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₁O₁₀+
• Molecular Weight: 433.40 g/mol
• Exact Mass: 433.11347186 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.68
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• Pelargonidin 3-glucoside cation
• Pelargonidin 3-O-glucoside
• UNII-W623YHH61A
• W623YHH61A
• pelargonidin 3-O-beta-D-glucoside
• Pelargonidin 3-o-beta-glucopyranoside
• 47684-27-5
• Callistephin
• 1-Benzopyrylium, 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
• 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-4'-hydroxyflavylium
• 3-(beta-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride
• 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium chloride
• SCHEMBL347415
• CHEBI:31967
• DTXSID201336082
• 3-O-beta-D-Glucopyranosylpelargonidin
• PELARGONIDIN 3-O-.BETA.-GLUCOPYRANOSIDE
• Q23418996
• 1-BENZOPYRYLIUM, 3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8136	81.36%
Caco-2	-	0.8887	88.87%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Nucleus	0.4412	44.12%
OATP2B1 inhibitior	+	0.7126	71.26%
OATP1B1 inhibitior	+	0.9063	90.63%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.4920	49.20%
P-glycoprotein inhibitior	-	0.6463	64.63%
P-glycoprotein substrate	-	0.8748	87.48%
CYP3A4 substrate	+	0.5643	56.43%
CYP2C9 substrate	-	0.8053	80.53%
CYP2D6 substrate	-	0.8220	82.20%
CYP3A4 inhibition	-	0.9550	95.50%
CYP2C9 inhibition	-	0.9002	90.02%
CYP2C19 inhibition	-	0.8426	84.26%
CYP2D6 inhibition	-	0.9191	91.91%
CYP1A2 inhibition	-	0.8856	88.56%
CYP2C8 inhibition	+	0.8364	83.64%
CYP inhibitory promiscuity	-	0.7819	78.19%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6532	65.32%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.7478	74.78%
Skin irritation	-	0.8047	80.47%
Skin corrosion	-	0.9630	96.30%
Ames mutagenesis	-	0.5737	57.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5799	57.99%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.7946	79.46%
skin sensitisation	-	0.9067	90.67%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7908	79.08%
Acute Oral Toxicity (c)	III	0.4439	44.39%
Estrogen receptor binding	+	0.7780	77.80%
Androgen receptor binding	+	0.7343	73.43%
Thyroid receptor binding	+	0.6223	62.23%
Glucocorticoid receptor binding	+	0.7618	76.18%
Aromatase binding	+	0.7521	75.21%
PPAR gamma	+	0.7892	78.92%
Honey bee toxicity	-	0.7702	77.02%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5649	56.49%
Fish aquatic toxicity	+	0.7666	76.66%

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	98.93%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	92.26%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.04%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.04%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.80%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	91.53%	95.78%
CHEMBL2581	P07339	Cathepsin D	91.11%	98.95%
CHEMBL242	Q92731	Estrogen receptor beta	90.23%	98.35%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.12%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.34%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.26%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.40%	86.33%
CHEMBL3194	P02766	Transthyretin	84.56%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.33%	91.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.32%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.28%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.11%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.35%	95.83%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.21%	94.45%

Plants that contains it

• Aconitum violaceum
• Cichorium intybus
• Cichorium pumilum
• Codonopsis pilosula
• Delphinium shawurense
• Fagraea gracilipes
• Fragaria × ananassa
• Garcinia xipshuanbannaensis
• Glycine max
• Gutierrezia microcephala
• Helichrysum graveolens
• Ipomoea nil
• Iryanthera paraensis
• Lathyrus nissolia
• Leonurus persicus
• Lonicera caerulea
• Magnolia sieboldii
• Matthiola incana
• Passiflora edulis
• Peltogyne floribunda
• Petunia exserta
• Phaseolus vulgaris
• Punica granatum
• Ratibida mexicana
• Ribes nigrum
• Ribes rubrum
• Rubus chamaemorus
• Rubus idaeus

Cross-Links

• PubChem: 443648
• NPASS: NPC115216
• LOTUS: LTS0095399
• wikiData: Q23418996