Cyanidin-3-rutinoside

  • GreenMolBD CID : 379
  • Molecular Formula : C27H31O15
  • Molecular Weight : 595.53
  • Exact Molecular Mass : 595.166
  • 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
  • InChI : InChI=1S/C27H30O15/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)/p+1/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+/m0/s1
  • InChI Key : USNPULRDBDVJAO-FXCAAIILSA-O
  • Canonical SMILES : CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C([O+]=C4C=C(C=C(C4=C3)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
  • Isomeric SMILES : CC1C(C(C(C(O1)OCC2C(C(C(C(O2)Oc3cc4c(cc(cc4[o+]c3c5ccc(c(c5)O)O)O)O)O)O)O)O)O)O
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.

1.3. Alternative Parent

Flavonoid-3-O-glycosides; 3'-hydroxyflavonoids; 4'-hydroxyflavonoids; 5-hydroxyflavonoids; 7-hydroxyflavonoids; Anthocyanidins; Disaccharides; O-glycosyl compounds; 1-benzopyrans; Catechols; 1-hydroxy-2-unsubstituted benzenoids; 1-hydroxy-4-unsubstituted benzenoids; Benzene and substituted derivatives; Oxanes; Heteroaromatic compounds; Secondary alcohols; Acetals; Oxacyclic compounds; Polyols; Hydrocarbon derivatives; Organic cations;

1.4. Molecular Framework

Aromatic heteropolycyclic compounds

1.5. Substituents

Anthocyanidin-3-o-glycoside; Flavonoid-3-o-glycoside; Hydroxyflavonoid; 7-hydroxyflavonoid; 3'-hydroxyflavonoid; 4'-hydroxyflavonoid; 5-hydroxyflavonoid; Anthocyanidin; Disaccharide; Glycosyl compound; O-glycosyl compound; Benzopyran; 1-benzopyran; Catechol; Phenol; 1-hydroxy-2-unsubstituted benzenoid; 1-hydroxy-4-unsubstituted benzenoid; Monocyclic benzene moiety; Oxane; Benzenoid; Heteroaromatic compound; Secondary alcohol; Polyol; Acetal; Organoheterocyclic compound; Oxacycle; Organic oxygen compound; Hydrocarbon derivative; Alcohol; Organooxygen compound; Organic cation; Aromatic heteropolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
-0.7662 252.36 10 15 42 6 16 17 13.8333 698.27 515.413 0.852865

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-434.09549 16.93 -8.666 -11.64321 -5.68818 2.978

4. Compound Reactivity

DLP nRFG nLMR

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Non-Carcinogen Non-Mutagen Toxic 3.50509 22.5432 0.0848823 None None Mild Non-Degradable 1.00963 0.664064

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
No No Yes No Yes

7. Synonyms

Name
Cyanidin 3-O-rutinoside
KERACYANIN
Cyanidin 3-rutinoside
UNII-OR49FC491X
Cyaninoside
Prunicyanin
Sambucin
Cyanidin 3-O-rhamnosylglucoside
CHEBI:28064
Cyanidin 3-rhamnoglucoside
Antirrhinin
28338-59-2
Cyanidol 3-rhamnoglucoside
Cyanidin 3-rhamnosylglucoside
Meralop
3-O-Rutinosylcyanidin
Ceracyanin
Oleocyanin
Noctilux
Nyctalux
Sambucine
Keracyanin ion
Cyanidin 3-beta-D-O-rutinoside
Keracyanin, INN
AC1L9BG1
SCHEMBL410529
CHEMBL505251
OR49FC491X
ZINC4097715
Cyanidin 3-(6''-rhamnosylglucoside)
LS-194245
LS-194569
C08620
(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
1-Benzopyrylium, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenium-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
259813-55-3
Cyanidin-3-rutinoside
Cyanidin-3-O-rutinoside

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Cyanidin-3-rutinoside
Abutilon indicum (L.) Sw. Flower Petal 4 , 9
Ixora coccinea L.  Leaf 5
Litchi chinensis Fruit 3

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
104625813ABI ChemSource URLSource DetailAC1L9BG1Source Record URL
257140008ZINCSource URLSource DetailZINC4097715Source Record URL