Keracyanin

Details

• Internal ID: ab401a99-0032-4e79-b7c5-5abc4a9dd379
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol chloride
• InChI: InChI=1S/C27H30O15.ClH/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10;/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31);1H/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+;/m0./s1
• InChI Key: ADZHXBNWNZIHIX-XYGAWYNKSA-N
• Popularity: 71 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₁ClO₁₅
• Molecular Weight: 631.00 g/mol
• Exact Mass: 630.1351480 g/mol
• Topological Polar Surface Area (TPSA): 240.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -3.76
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 18719-76-1
• KERACYANIN
• Antirrhinin
• Sambucin
• Prunicyanin
• Keracyanine
• Meralop
• cyanidin 3-O-rutinoside chloride
• Keracyaninum
• Meralops
• Cyanidin 3-rhamnoglucoside
• Anthocyanin a2
• keracianina
• V0N2VMB4FV
• CHEBI:16726
• DTXSID00927864
• (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol;chloride
• cyaninoside chloride
• (2R,3R,4R,5R,6S)-2-(((2R,3S,4S,5R,6S)-6-(2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl)oxy-3,4,5-trihydroxyoxan-2-yl)methoxy)-6-methyloxane-3,4,5-triol;chloride
• RefChem:40223
• DTXCID801356644
• cyanidin chloride 3-rhamnoglucoside
• 242-528-6
• 3-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyran osyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyrylium, chloride
• Cyanidin 3-rutinoside
• Cyaninoside
• Keracyanin (chloride)
• Cyanidin-3-O-rutinoside chloride
• Cyanidin-3-rhamnoglucoside chloride
• Cyanidin 3-rutinoside chloride
• Cyanidin 3-O-Rutinoside (75%)
• Keraciannai
• 1-Benzopyrylium, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-, chloride
• Rutinosyl-3-cyanidine
• Cyanidine 3-rutinoside
• Keracyanin [INN:DCF]
• Cyanidol 3-rhamnoglucoside
• Keracyanine [INN-French]
• Keracyaninum [INN-Latin]
• Keraciannai [INN-Spanish]
• Cyanidin 3-rhamnosylglucoside
• CCRIS 1960
• 3-O-Rutinosylcyanidin
• EINECS 242-528-6
• UNII-V0N2VMB4FV
• cyanidin-3-O-rutinoside
• 7,4'-Dihydroxyflavilium Chloride
• Meralop (TN)
• KERACYANIN [INN]
• Keracyanin chloride (INN)
• KERACYANIN [MART.]
• KERACYANIN [WHO-DD]
• 3-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-3',4',5,7-tetrahydroxyflavylium chloride
• SCHEMBL161440
• CHEMBL592218
• orb1297588
• SCHEMBL29620254
• SCHEMBL30533427
• Keracyanine chloride, HPLC Grade
• Cyanidin 3-rutinoside (chloride);Cyanidin 3-O-rutinoside (chloride);Sambucin (chloride)
• Keracyanin (chloride) (Standard)
• MSK40263
• AKOS030573634
• HY-105935R
• OC16172
• 3-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyran osyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1- benzopyrylium, chloride
• AS-76553
• HY-105935
• CS-0026976
• NS00100421
• C04491
• D08097
• E80656
• CYANIDIN CHLORIDE 3-RHAMNOGLUCOSIDE [MI]
• Q3814728
• Keracyanin chloride; Cyanidin-3-O-rhamnoglucoside chloride
• 1-Benzopyrylium,3-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-,chloride(1:1)
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenium-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside chloride
• 3-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-3',4',5,7-TETRAHYDROXYFLAVYLIUM CHLORIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5902	59.02%
Caco-2	-	0.9163	91.63%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4853	48.53%
OATP2B1 inhibitior	-	0.5634	56.34%
OATP1B1 inhibitior	+	0.9099	90.99%
OATP1B3 inhibitior	+	0.9244	92.44%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7324	73.24%
P-glycoprotein inhibitior	-	0.6474	64.74%
P-glycoprotein substrate	-	0.5541	55.41%
CYP3A4 substrate	+	0.6154	61.54%
CYP2C9 substrate	-	0.6124	61.24%
CYP2D6 substrate	-	0.8387	83.87%
CYP3A4 inhibition	-	0.9265	92.65%
CYP2C9 inhibition	-	0.8386	83.86%
CYP2C19 inhibition	-	0.7514	75.14%
CYP2D6 inhibition	-	0.8981	89.81%
CYP1A2 inhibition	-	0.8015	80.15%
CYP2C8 inhibition	+	0.8301	83.01%
CYP inhibitory promiscuity	-	0.6462	64.62%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5647	56.47%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9002	90.02%
Skin irritation	-	0.7897	78.97%
Skin corrosion	-	0.9301	93.01%
Ames mutagenesis	-	0.6207	62.07%
Human Ether-a-go-go-Related Gene inhibition	+	0.7029	70.29%
Micronuclear	+	0.6818	68.18%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8989	89.89%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.8891	88.91%
Acute Oral Toxicity (c)	III	0.5597	55.97%
Estrogen receptor binding	+	0.7711	77.11%
Androgen receptor binding	-	0.4810	48.10%
Thyroid receptor binding	+	0.5855	58.55%
Glucocorticoid receptor binding	+	0.5944	59.44%
Aromatase binding	+	0.6847	68.47%
PPAR gamma	+	0.7399	73.99%
Honey bee toxicity	-	0.7780	77.80%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5649	56.49%
Fish aquatic toxicity	+	0.9096	90.96%

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	99.47%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.26%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.29%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.10%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.69%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.68%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.11%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.62%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.14%	97.36%
CHEMBL226	P30542	Adenosine A1 receptor	90.07%	95.93%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.36%	89.62%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.95%	95.78%
CHEMBL3401	O75469	Pregnane X receptor	86.74%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.82%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.37%	95.83%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.02%	92.94%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	82.26%	96.69%
CHEMBL4208	P20618	Proteasome component C5	81.63%	90.00%
CHEMBL3194	P02766	Transthyretin	81.46%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.76%	86.92%

Plants that contains it

• Cichorium intybus
• Cichorium pumilum
• Morus alba
• Punica granatum
• Rubus chingii
• Rubus coreanus

Cross-Links

• PubChem: 29231
• NPASS: NPC15538