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Showing NP-Card for Astragalin 2''-glucoside 6''-rhamnoside (NP0049532)

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Record Information
Version2.0
Created at2022-03-17 21:14:01 UTC
Updated at2022-03-17 21:14:01 UTC
NP-MRD IDNP0049532
Secondary Accession NumbersNone
Natural Product Identification
Common NameAstragalin 2''-glucoside 6''-rhamnoside
DescriptionKaempferol 3-(6''-rhamnosylsophoroside), also known as kaempferol 3-(2''-glucosylrutinoside) or astragalin 2''-glucoside 6''-rhamnoside, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-(6''-rhamnosylsophoroside) is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Kaempferol 3-(6''-rhamnosylsophoroside) has been detected, but not quantified in, several different foods, such as oil-seed camellia, potato, pulses, soy beans, and sweet cherries. Astragalin 2''-glucoside 6''-rhamnoside is found in Camellia sinensis, Hosta ventricosa, Hydrangea macrophylla, Morinda citrifolia, Styphnolobium japonicum and Thevetia peruviana. This could make kaempferol 3-(6''-rhamnosylsophoroside) a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049532 (Astragalin 2''-glucoside 6''-rhamnoside)


  Mrv0541 02241209112D          

 53 58  0  0  0  0            999 V2000
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   -2.1436   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 49 50  1  0  0  0  0
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 50 53  1  0  0  0  0
 51 52  1  0  0  0  0
M  END
Download

3D MOL for NP0049532 (Astragalin 2''-glucoside 6''-rhamnoside)

Download
3D SDF for NP0049532 (Astragalin 2''-glucoside 6''-rhamnoside)

  Mrv0541 02241209112D          

 53 58  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0049532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OCC2OC(OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC=C(O)C=C3)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H40O20/c1-10-19(38)23(42)26(45)31(48-10)47-9-17-21(40)25(44)30(53-32-27(46)24(43)20(39)16(8-34)50-32)33(51-17)52-29-22(41)18-14(37)6-13(36)7-15(18)49-28(29)11-2-4-12(35)5-3-11/h2-7,10,16-17,19-21,23-27,30-40,42-46H,8-9H2,1H3

> <INCHI_KEY>
VNLOLXSJMINBIS-UHFFFAOYSA-N

> <FORMULA>
C33H40O20

> <MOLECULAR_WEIGHT>
756.6587

> <EXACT_MASS>
756.21129372

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
72.65220301496385

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.58

> <JCHEM_LOGP>
-2.336031298999999

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.440141353760618

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.433888434192199

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6764969324490426

> <JCHEM_POLAR_SURFACE_AREA>
324.44

> <JCHEM_REFRACTIVITY>
170.57750000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0049532 (Astragalin 2''-glucoside 6''-rhamnoside)
Download
PDB for NP0049532 (Astragalin 2''-glucoside 6''-rhamnoside)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -2.667  -1.155   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667  -2.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -3.465   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -5.005   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667  -5.775   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -5.334  -1.155   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.334  -2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  -3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -5.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.334  -5.775   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.003  -5.775   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000  -7.315   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.335  -8.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -7.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -5.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.335  -5.005   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -5.775   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.332  -5.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.332  -3.465   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -2.695   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000  -1.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.335  -0.385   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -1.155   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.002  -0.385   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.002   1.155   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.336   1.925   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.336   3.465   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668   4.235   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.002  -8.085   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.332  -0.385   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.332   1.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667   1.925   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667   3.465   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.001   4.235   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -4.001   5.775   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -5.334   6.545   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.334   8.085   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.334   1.925   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -5.334   3.465   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -6.668   4.235   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.668   5.775   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -8.003   6.545   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -8.003   3.465   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       2.667   1.925   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       1.335   1.155   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.000   1.925   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       0.000   3.465   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       5.336  -2.695   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       5.336  -1.155   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.668  -0.385   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.668   1.155   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       8.003   1.925   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       8.003  -1.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4   18                                                       
CONECT    6    7                                                            
CONECT    7    3    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    4    9                                                       
CONECT   11    9                                                            
CONECT   12   13   17                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   18                                                  
CONECT   18    5   17   19                                                  
CONECT   19    2   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23   45                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   49                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   51                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   14                                                            
CONECT   30   21   31                                                       
CONECT   31   30   32   46                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36                                                            
CONECT   38   39                                                            
CONECT   39   34   38   40                                                  
CONECT   40   39   41   43                                                  
CONECT   41   36   40   42                                                  
CONECT   42   41                                                            
CONECT   43   40                                                            
CONECT   44   45                                                            
CONECT   45   22   44   46                                                  
CONECT   46   31   45   47                                                  
CONECT   47   46                                                            
CONECT   48   49                                                            
CONECT   49   24   48   50                                                  
CONECT   50   49   51   53                                                  
CONECT   51   26   50   52                                                  
CONECT   52   51                                                            
CONECT   53   50                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  116    0
END

Download
3D PDB for NP0049532 (Astragalin 2''-glucoside 6''-rhamnoside)
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SMILES for NP0049532 (Astragalin 2''-glucoside 6''-rhamnoside)
CC1OC(OCC2OC(OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC=C(O)C=C3)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C(O)C1O
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INCHI for NP0049532 (Astragalin 2''-glucoside 6''-rhamnoside)
InChI=1S/C33H40O20/c1-10-19(38)23(42)26(45)31(48-10)47-9-17-21(40)25(44)30(53-32-27(46)24(43)20(39)16(8-34)50-32)33(51-17)52-29-22(41)18-14(37)6-13(36)7-15(18)49-28(29)11-2-4-12(35)5-3-11/h2-7,10,16-17,19-21,23-27,30-40,42-46H,8-9H2,1H3
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View in JSmol
Synonyms
ValueSource
Astragalin 2''-glucoside 6''-rhamnosideHMDB
Kaempferol 3-(2''-glucosylrutinoside)HMDB
Kaempferol 3-(2g-glucosylrutinoside)HMDB
Kaempferol 3-(6'''-rhamnosyl-2'''-glucosyl-glucoside)HMDB
Kaempferol-gal-rha-gluMeSH
Camelliaside aMeSH
Chemical FormulaC33H40O20
Average Mass756.6587 Da
Monoisotopic Mass756.21129 Da
IUPAC Name3-[(4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Name3-[(4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
CAS Registry Number55696-58-7
SMILES
CC1OC(OCC2OC(OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC=C(O)C=C3)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C33H40O20/c1-10-19(38)23(42)26(45)31(48-10)47-9-17-21(40)25(44)30(53-32-27(46)24(43)20(39)16(8-34)50-32)33(51-17)52-29-22(41)18-14(37)6-13(36)7-15(18)49-28(29)11-2-4-12(35)5-3-11/h2-7,10,16-17,19-21,23-27,30-40,42-46H,8-9H2,1H3
InChI KeyVNLOLXSJMINBIS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Camellia oleiferaFooDB
Camellia sinensisLOTUS Database
Glycine maxFooDB
Hosta ventricosaLOTUS Database
Hydrangea macrophyllaLOTUS Database
Morinda citrifoliaLOTUS Database
Prunus aviumFooDB
Solanum tuberosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Styphnolobium japonicumLOTUS Database
Thevetia peruvianaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentFlavonoid-3-O-glycosides  
Alternative Parents
Substituents
  • Oligosaccharide
    • 

  • Flavonoid-3-o-glycoside
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Hydroxyflavonoid
    • 

  • Flavone
    • 

  • O-glycosyl compound
    • 

  • Chromone
    • 

  • Glycosyl compound
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Monocyclic benzene moiety
    • 

  • Oxane
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Secondary alcohol
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Polyol
    • 

  • Primary alcohol
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.58ALOGPS
logP-2.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area324.44 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity170.58 m³·mol⁻¹ChemAxon
Polarizability72.65 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0039951  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019613  
KNApSAcK IDC00005216  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14890565  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available