Petunidin 3-monoglucoside

Details

• Internal ID: fd7889f2-733b-4f78-b0f5-98783cc272a1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C2=[O+]C3=CC(=CC(=C3C=C2OC4C(C(C(C(O4)CO)O)O)O)O)O.[Cl-]
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)C2=[O+]C3=CC(=CC(=C3C=C2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O.[Cl-]
• InChI: InChI=1S/C22H22O12.ClH/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);1H/t16-,18-,19+,20-,22-;/m1./s1
• InChI Key: HBKZHMZCXXQMOX-YATQZQGFSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₃ClO₁₂
• Molecular Weight: 514.90 g/mol
• Exact Mass: 514.0878039 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -2.61
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

• Petunidin 3-monoglucoside
• Petunidin 3-glucoside
• Petunidin-3-glucoside
• Petunidin-3-glucoside chloride
• Petunidin-3-O-glucoside (chloride)
• Petunidin monoglucoside
• Petunidin-3-O-glucoside chloride
• UNII-AA9G36JBHT
• AA9G36JBHT
• petunidin 3-O-beta-D-glucoside
• Petunidin 3-O-beta-glucopyranoside chloride
• (2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
• Flavylium, 3-(beta-D-glucopyranosyloxy)-3',4',5,7-tetrahydroxy-5'-methoxy-, chloride
• 1-Benzopyrylium, 5,7-dihydroxy-2-(3,4-dihydroxy-5-methoxyphenyl)-3-(beta-D-glucopyranosyloxy)-, chloride
• Petunidin-3-O-glucoside
• C22H23O12.Cl
• C22-H23-O12.Cl
• EX-A4394
• HY-N7832
• Petunidin 3-O- beta -D-Glucoside
• Glucopyranoside, petunidin, beta-D-
• MFCD01762898
• PETUNIDIN 3-GLUCOSIDE CHLORIDE
• LS-40156
• MS-29565
• Petunidin 3-O-|A-glucopyranoside chloride
• CS-0138370
• Petunidin-3-glucoside chloride , HPLC Grade
• 1-BENZOPYRYLIUM, 2-(3,4-DIHYDROXY-5-METHOXYPHENYL)-3,5,7-TRIHYDROXY-, CHLORIDE (1:1), MONO-.BETA.-D-GLUCOPYRANOSIDE
• 1-BENZOPYRYLIUM, 2-(3,4-DIHYDROXY-5-METHOXYPHENYL)-3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-, CHLORIDE (1:1)
• 2-(3,4-dihydroxy-5-methoxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium Chloride

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6307	63.07%
Caco-2	-	0.8598	85.98%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Nucleus	0.4937	49.37%
OATP2B1 inhibitior	+	0.5836	58.36%
OATP1B1 inhibitior	+	0.8757	87.57%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5447	54.47%
P-glycoprotein inhibitior	-	0.5965	59.65%
P-glycoprotein substrate	-	0.6251	62.51%
CYP3A4 substrate	+	0.5974	59.74%
CYP2C9 substrate	-	0.6128	61.28%
CYP2D6 substrate	-	0.8319	83.19%
CYP3A4 inhibition	-	0.9149	91.49%
CYP2C9 inhibition	-	0.8455	84.55%
CYP2C19 inhibition	-	0.7540	75.40%
CYP2D6 inhibition	-	0.8933	89.33%
CYP1A2 inhibition	-	0.8376	83.76%
CYP2C8 inhibition	+	0.8121	81.21%
CYP inhibitory promiscuity	-	0.7025	70.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5900	59.00%
Eye corrosion	-	0.9832	98.32%
Eye irritation	-	0.8263	82.63%
Skin irritation	-	0.7939	79.39%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	-	0.6191	61.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.4509	45.09%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.7697	76.97%
skin sensitisation	-	0.9031	90.31%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.8638	86.38%
Acute Oral Toxicity (c)	III	0.6096	60.96%
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	-	0.8035	80.35%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6249	62.49%
Fish aquatic toxicity	+	0.7350	73.50%

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	99.39%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.88%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.29%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.34%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.07%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.10%	99.17%
CHEMBL2581	P07339	Cathepsin D	88.21%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.92%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.92%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.83%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.04%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.96%	89.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.66%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.09%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	83.51%	94.73%
CHEMBL4208	P20618	Proteasome component C5	81.58%	90.00%
CHEMBL3194	P02766	Transthyretin	81.48%	90.71%

Plants that contains it

• Crocus sativus
• Glycine max

Cross-Links

• PubChem: 176449
• NPASS: NPC232080