Cyanidin chloride 3,5-diglucoside

Details

• Internal ID: deeee43f-eebb-4ad7-9489-58253a08e7ec
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-5-O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-7-hydroxy-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;chloride
• SMILES (Canonical): C1=CC(=C(C=C1C2=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)O.[Cl-]
• SMILES (Isomeric): C1=CC(=C(C=C1C2=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)O.[Cl-]
• InChI: InChI=1S/C27H30O16.ClH/c28-7-17-19(33)21(35)23(37)26(42-17)40-15-5-10(30)4-14-11(15)6-16(25(39-14)9-1-2-12(31)13(32)3-9)41-27-24(38)22(36)20(34)18(8-29)43-27;/h1-6,17-24,26-29,33-38H,7-8H2,(H2-,30,31,32);1H/t17-,18-,19-,20-,21+,22+,23-,24-,26-,27-;/m1./s1
• InChI Key: QDVZZZBBPRFPDG-DHJOXOLYSA-N
• Popularity: 579 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₁ClO₁₆
• Molecular Weight: 647.00 g/mol
• Exact Mass: 646.1300626 g/mol
• Topological Polar Surface Area (TPSA): 260.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -5.14
• H-Bond Acceptor: 15
• H-Bond Donor: 11
• Rotatable Bonds: 7

Synonyms

• 2611-67-8
• Cyanidin-3,5-di-O-glucoside
• SHISONIN A
• UTH12733J3
• NSC 81163
• UNII-UTH12733J3
• EINECS 220-034-1
• Cyanidin-3,5-O-diglucoside chloride
• Cyanidin 3,5-diglucoside (chloride)
• NSC-81163
• CYANIDIN CHLORIDE 3,5-DIGLUCOSIDE
• CYANIDOL 3,5-DIGLUCOSIDE CHLORIDE
• 2-(3,4-Dihydroxyphenyl)-3,5-bis(beta-D-glucopyranosyloxy)-7-hydroxy-1-benzopyrylium chloride
• 1-Benzopyrylium, 2-(3,4-dihydroxyphenyl)-3,5-bis(beta-D-glucopyranosyloxy)-7-hydroxy-, chloride (1:1)
• 3,5-BIS(GLUCOSYLOXY)-3',4',7-TRIHYDROXYFLAVYLIUM CHLORIDE
• Cyaninchlorid
• MFCD00135655
• Cyanin chloride, HPLC Grade
• C27H31O16.Cl
• CHEBI:38021
• DTXSID40949000
• Cyanidin 3,5-diglucoside chloride
• Cyanin chloride, >=90% (HPLC)
• AKOS030573537
• HY-129138
• CS-0103760
• CYANIDIN CHLORIDE 3,5-DIGLUCOSIDE [MI]
• W-202106
• 3,5-bis(beta-D-glucopyranosyloxy)-3',4',7-trihydroxyflavylium chloride
• 1-BENZOPYRYLIUM, 2-(3,4-DIHYDROXYPHENYL)-3,5-BIS(.BETA.-D-GLUCOPYRANOSYLOXY)-7-HYDROXY-, CHLORIDE
• 1-BENZOPYRYLIUM, 2-(3,4-DIHYDROXYPHENYL)-3,5-BIS(beta-D-GLUCOPYRANOSYLOXY)-7-HYDROXY-, CHLORIDE
• 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-7-hydroxychromenylium-5-yl beta-D-glucopyranoside chloride
• 2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-bis(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chromenylium chloride
• 2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-chromen-1-ylium chloride

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7039	70.39%
Caco-2	-	0.9184	91.84%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Nucleus	0.4805	48.05%
OATP2B1 inhibitior	-	0.5562	55.62%
OATP1B1 inhibitior	+	0.9359	93.59%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5172	51.72%
P-glycoprotein inhibitior	-	0.5337	53.37%
P-glycoprotein substrate	-	0.8274	82.74%
CYP3A4 substrate	+	0.5679	56.79%
CYP2C9 substrate	-	0.8017	80.17%
CYP2D6 substrate	-	0.8389	83.89%
CYP3A4 inhibition	-	0.9385	93.85%
CYP2C9 inhibition	-	0.8634	86.34%
CYP2C19 inhibition	-	0.7274	72.74%
CYP2D6 inhibition	-	0.8707	87.07%
CYP1A2 inhibition	-	0.8312	83.12%
CYP2C8 inhibition	+	0.8393	83.93%
CYP inhibitory promiscuity	-	0.7226	72.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5806	58.06%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.8783	87.83%
Skin irritation	-	0.7937	79.37%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7392	73.92%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	-	0.8571	85.71%
skin sensitisation	-	0.8894	88.94%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7527	75.27%
Acute Oral Toxicity (c)	III	0.4241	42.41%
Estrogen receptor binding	+	0.7187	71.87%
Androgen receptor binding	+	0.6079	60.79%
Thyroid receptor binding	+	0.5553	55.53%
Glucocorticoid receptor binding	-	0.5106	51.06%
Aromatase binding	+	0.6534	65.34%
PPAR gamma	+	0.6808	68.08%
Honey bee toxicity	-	0.7432	74.32%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	+	0.8155	81.55%

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%
CHEMBL1951	P21397	Monoamine oxidase A	96.00%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.65%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.32%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.23%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.39%	94.00%
CHEMBL2581	P07339	Cathepsin D	88.70%	98.95%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.88%	95.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.02%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.61%	92.94%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	85.24%	96.69%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.93%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.79%	89.62%
CHEMBL3194	P02766	Transthyretin	83.88%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	83.17%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	82.71%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.67%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.34%	95.83%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.62%	97.09%

Plants that contains it

• Punica granatum

Cross-Links

• PubChem: 164999
• NPASS: NPC139520