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Showing NP-Card for Myricetin 3-arabinoside (NP0049949)

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Record Information
Version2.0
Created at2022-03-17 21:20:43 UTC
Updated at2022-03-17 21:20:43 UTC
NP-MRD IDNP0049949
Secondary Accession NumbersNone
Natural Product Identification
Common NameMyricetin 3-arabinoside
DescriptionMyricetin 3-arabinoside 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. Myricetin 3-arabinoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Myricetin 3-arabinoside has been detected, but not quantified in, american cranberries. Myricetin 3-arabinoside is found in Cassiope spp., Cistus laurifolius, Diplusodon speciosus, Eucalyptus rostrata, Heuchera micrantha, Heuchera villosa, Lathyrus pratensis, Leptarrhena pyrolifolia, Limonium aureum, Limonium gmelinii, Myrsine africana, Norantea guianensis, Patersonia maxwellii and Woodfordia fruticosa . This could make myricetin 3-arabinoside a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049949 (Myricetin 3-arabinoside)


  Mrv0541 02241222502D          

 32 35  0  0  1  0            999 V2000
   -0.9041   -0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041    0.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6185    0.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3330    0.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3330   -0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6185   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6185   -1.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475   -1.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7620   -0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7620    0.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4764    0.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896    0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896    1.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249    2.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249    3.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393    1.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9538    2.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393    0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9538    0.5666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249    0.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041   -1.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041   -2.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -3.1459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5249   -2.7334    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5249   -1.9084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1896   -1.4959    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1896   -0.6709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393   -1.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394   -3.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -3.9709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 29  1  1  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
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  8  9  1  0  0  0  0
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 11 12  1  0  0  0  0
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 24 25  1  0  0  0  0
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 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 27 30  1  6  0  0  0
 26 31  1  1  0  0  0
 25 32  1  1  0  0  0
M  END
Download

3D MOL for NP0049949 (Myricetin 3-arabinoside)

Download
3D SDF for NP0049949 (Myricetin 3-arabinoside)

  Mrv0541 02241222502D          

 32 35  0  0  1  0            999 V2000
   -0.9041   -0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041    0.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6185    0.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3330    0.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3330   -0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6185   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6185   -1.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475   -1.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7620   -0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7620    0.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4764    0.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896    0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896    1.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249    2.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249    3.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393    1.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9538    2.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393    0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9538    0.5666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249    0.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041   -1.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041   -2.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -3.1459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5249   -2.7334    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5249   -1.9084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1896   -1.4959    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1896   -0.6709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393   -1.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2394   -3.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -3.9709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 29  1  1  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  4 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 14 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 27 30  1  6  0  0  0
 26 31  1  1  0  0  0
 25 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0049949

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CO[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O12/c21-7-3-8(22)13-12(4-7)31-18(6-1-9(23)14(26)10(24)2-6)19(16(13)28)32-20-17(29)15(27)11(25)5-30-20/h1-4,11,15,17,20-27,29H,5H2/t11-,15-,17+,20-/m0/s1

> <INCHI_KEY>
SBEOEJNITMVWLK-KJCLSZHRSA-N

> <FORMULA>
C20H18O12

> <MOLECULAR_WEIGHT>
450.3497

> <EXACT_MASS>
450.07982604

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
41.67425553842691

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
0.69

> <JCHEM_LOGP>
0.18193432433333304

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.077437159089559

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.42809370258755

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265985532894106

> <JCHEM_POLAR_SURFACE_AREA>
206.59999999999997

> <JCHEM_REFRACTIVITY>
105.29389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-3-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049949 (Myricetin 3-arabinoside)
Download
PDB for NP0049949 (Myricetin 3-arabinoside)
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  C   UNK     0      -1.688  -0.482   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.688   1.058   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.021   1.828   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.355   1.058   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.355  -0.482   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.021  -1.252   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.021  -2.792   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.689  -1.252   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.689  -2.792   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.022  -0.482   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.022   1.058   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -8.356   1.828   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.689   1.828   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.354   1.828   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.354   3.368   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.980   4.138   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.980   5.678   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.313   3.368   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.647   4.138   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.313   1.828   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.647   1.058   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.980   1.058   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.688  -3.562   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.688  -5.102   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.354  -5.872   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.980  -5.102   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.980  -3.562   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.354  -2.792   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.354  -1.252   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.313  -2.792   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.314  -5.872   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.354  -7.412   0.000  0.00  0.00           O+0
CONECT    1   29    2    6                                                  
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    4                                                       
CONECT   14    2   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14                                                       
CONECT   23   24   28                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   23   29                                                  
CONECT   29    1   28                                                       
CONECT   30   27                                                            
CONECT   31   26                                                            
CONECT   32   25                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

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3D PDB for NP0049949 (Myricetin 3-arabinoside)
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SMILES for NP0049949 (Myricetin 3-arabinoside)
O[C@H]1CO[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O
Download
INCHI for NP0049949 (Myricetin 3-arabinoside)
InChI=1S/C20H18O12/c21-7-3-8(22)13-12(4-7)31-18(6-1-9(23)14(26)10(24)2-6)19(16(13)28)32-20-17(29)15(27)11(25)5-30-20/h1-4,11,15,17,20-27,29H,5H2/t11-,15-,17+,20-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H18O12
Average Mass450.3497 Da
Monoisotopic Mass450.07983 Da
IUPAC Name5,7-dihydroxy-3-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
Traditional Name5,7-dihydroxy-3-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-4-one
CAS Registry Number132679-85-7
SMILES
O[C@H]1CO[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C20H18O12/c21-7-3-8(22)13-12(4-7)31-18(6-1-9(23)14(26)10(24)2-6)19(16(13)28)32-20-17(29)15(27)11(25)5-30-20/h1-4,11,15,17,20-27,29H,5H2/t11-,15-,17+,20-/m0/s1
InChI KeySBEOEJNITMVWLK-KJCLSZHRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cassiope spp.Plant
Cistus laurifoliusLOTUS Database
Diplusodon speciosusPlant
Eucalyptus rostrataPlant
Heuchera micranthaPlant
Heuchera villosaPlant
Lathyrus pratensisLOTUS Database
Leptarrhena pyrolifoliaPlant
Limonium aureumLOTUS Database
Limonium gmeliniiLOTUS Database
Myrsine africanaLOTUS Database
Norantea guianensisLOTUS Database
Patersonia maxwelliiPlant
Vaccinium macrocarponFooDB
Woodfordia fruticosaPlant
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
  • Flavonoid-3-o-glycoside
    • 

  • 3'-hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Flavone
    • 

  • Hydroxyflavonoid
    • 

  • Chromone
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Benzenetriol
    • 

  • Pyrogallol derivative
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Pyranone
    • 

  • Oxane
    • 

  • Pyran
    • 

  • Monocyclic benzene moiety
    • 

  • Monosaccharide
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Secondary alcohol
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Polyol
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP0.69ALOGPS
logP0.18ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.29 m³·mol⁻¹ChemAxon
Polarizability41.67 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041635  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021864  
KNApSAcK IDNot Available
Chemspider ID10283343  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21672568  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available