NP-MRD: Showing NP-Card for Syringetin 3-beta-O-glucoside (NP0043986)

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Record Information

Version

1.0

Created at

2021-06-22 17:44:07 UTC

Updated at

2021-06-22 17:44:07 UTC

NP-MRD ID

NP0043986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Syringetin 3-beta-O-glucoside

Description

SYRINGETIN-3-GLUCOSIDE 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. Syringetin 3-beta-O-glucoside is found in Anthyllis sericea, Cedrus spp., Chondropetalum tectolum, Elegia cuspidata, Heuchera cylindrica, Heuchera micrantha, Larix decidua , Larix laricina , Larix leptolepis, Lysimachia nummularia , Lysimachia vulgaris var. davurica , Philydrum lanuginosum, Pinus jeffreyi and Vitis vinifera. It was first documented in 2009 (PMID: 19061313). Based on a literature review very few articles have been published on SYRINGETIN-3-GLUCOSIDE (PMID: 34154041) (PMID: 34154040) (PMID: 23383696) (PMID: 21250736).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119442D          

 36 39  0  0  1  0            999 V2000
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   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  0  0  0  0
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 28 35  1  1  0  0  0
 27 36  1  6  0  0  0
M  END

NP0043986
     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
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   -3.3076    3.6404    1.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1860    4.9130    1.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070    5.6447    2.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293    5.4533    1.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051    4.7262    1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3959    5.3297    1.4591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869    3.4491    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0324    2.6477    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913    3.1075    0.4619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148    1.3469   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8936    0.6665   -0.4522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071   -0.1759    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4293   -1.3949   -0.6287 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306222119442D          

 36 39  0  0  1  0            999 V2000
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    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0043986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)C1=C(OC2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O13/c1-32-12-3-8(4-13(33-2)16(12)27)21-22(18(29)15-10(26)5-9(25)6-11(15)34-21)36-23-20(31)19(30)17(28)14(7-24)35-23/h3-6,14,17,19-20,23-28,30-31H,7H2,1-2H3/t14-,17-,19+,20-,23?/m1/s1

> <INCHI_KEY>
JMFWYRWPJVEZPV-BZMFKJDCSA-N

> <FORMULA>
C23H24O13

> <MOLECULAR_WEIGHT>
508.432

> <EXACT_MASS>
508.121690833

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.44457449928363

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
-0.15661250566666707

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.850277275448396

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.371618806373225

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98109237118166

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
120.22099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043986
     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
   -5.7460   -1.6415    0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9386   -2.4675   -0.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -2.0849   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1821   -0.8851   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784   -0.4800   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    0.8495   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318    1.6575    0.3812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2555    2.8637    0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3076    3.6404    1.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1860    4.9130    1.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070    5.6447    2.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293    5.4533    1.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051    4.7262    1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3959    5.3297    1.4591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869    3.4491    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0324    2.6477    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913    3.1075    0.4619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148    1.3469   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8936    0.6665   -0.4522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071   -0.1759    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340   -1.2990   -0.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4293   -1.3949   -0.6287 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7112   -2.6356   -1.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0765   -2.6368   -1.7655 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4054   -1.2378    0.5223 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5669   -0.5677    0.1727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7285   -0.5199    1.6752 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8931   -1.3581    2.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243    0.5573    1.0482 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5873    1.2351    0.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1078   -1.2698   -1.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6250   -2.4961   -1.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8947   -3.3314   -2.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4129   -3.1015   -2.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9101   -2.9100   -1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4175   -4.1166   -1.8363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2517   -1.4065    1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0561   -0.7182    0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6378   -2.2615    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8197   -0.2655    0.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3040    3.1978    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8291    6.2333    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    6.4578    2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2756    5.0493    1.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -0.4509    1.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6453   -0.5449   -1.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582   -3.5664   -1.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -2.5091   -2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -3.5460   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6661   -2.2512    0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3698   -0.9240    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0364    2.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9308   -2.3018    2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451    1.2136    1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2753    1.8023    0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1282   -0.9517   -1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438   -3.6768   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -3.5614   -4.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105   -2.0591   -3.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3495   -4.4006   -1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  5 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  2  0
 35 36  1  0
 35  3  1  0
 18  6  2  0
 29 20  1  0
 15  8  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  0
  9 41  1  0
 11 42  1  0
 12 43  1  0
 14 44  1  0
 20 45  1  0
 22 46  1  6
 23 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  1
 26 51  1  0
 27 52  1  1
 28 53  1  0
 29 54  1  1
 30 55  1  0
 31 56  1  0
 34 57  1  0
 34 58  1  0
 34 59  1  0
 36 60  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10                                                            
CONECT   12    5   13   22                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   12                                                       
CONECT   23   19                                                            
CONECT   24   17                                                            
CONECT   25   13   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   36                                                  
CONECT   28   27   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   29                                                            
CONECT   35   28                                                            
CONECT   36   27                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    NP0043986
HETATM    1  C1  UNL     1      -5.746  -1.641   0.543  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.939  -2.467  -0.265  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.672  -2.085  -0.621  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.182  -0.885  -0.188  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.878  -0.480  -0.548  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.475   0.849  -0.072  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.432   1.657   0.381  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.256   2.864   0.838  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.308   3.640   1.292  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.186   4.913   1.783  1.00  0.00           C  
HETATM   11  O3  UNL     1      -4.307   5.645   2.229  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.929   5.453   1.827  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.805   4.726   1.383  1.00  0.00           C  
HETATM   14  O4  UNL     1       0.396   5.330   1.459  1.00  0.00           O  
HETATM   15  C11 UNL     1      -0.987   3.449   0.898  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.032   2.648   0.440  1.00  0.00           C  
HETATM   17  O5  UNL     1       1.191   3.108   0.462  1.00  0.00           O  
HETATM   18  C13 UNL     1      -0.215   1.347  -0.042  1.00  0.00           C  
HETATM   19  O6  UNL     1       0.894   0.666  -0.452  1.00  0.00           O  
HETATM   20  C14 UNL     1       1.707  -0.176   0.361  1.00  0.00           C  
HETATM   21  O7  UNL     1       2.134  -1.299  -0.239  1.00  0.00           O  
HETATM   22  C15 UNL     1       3.429  -1.395  -0.629  1.00  0.00           C  
HETATM   23  C16 UNL     1       3.711  -2.636  -1.445  1.00  0.00           C  
HETATM   24  O8  UNL     1       5.076  -2.637  -1.765  1.00  0.00           O  
HETATM   25  C17 UNL     1       4.405  -1.238   0.522  1.00  0.00           C  
HETATM   26  O9  UNL     1       5.567  -0.568   0.173  1.00  0.00           O  
HETATM   27  C18 UNL     1       3.728  -0.520   1.675  1.00  0.00           C  
HETATM   28  O10 UNL     1       2.893  -1.358   2.408  1.00  0.00           O  
HETATM   29  C19 UNL     1       2.824   0.557   1.048  1.00  0.00           C  
HETATM   30  O11 UNL     1       3.587   1.235   0.109  1.00  0.00           O  
HETATM   31  C20 UNL     1      -1.108  -1.270  -1.321  1.00  0.00           C  
HETATM   32  C21 UNL     1      -1.625  -2.496  -1.756  1.00  0.00           C  
HETATM   33  O12 UNL     1      -0.895  -3.331  -2.533  1.00  0.00           O  
HETATM   34  C22 UNL     1       0.413  -3.101  -2.984  1.00  0.00           C  
HETATM   35  C23 UNL     1      -2.910  -2.910  -1.408  1.00  0.00           C  
HETATM   36  O13 UNL     1      -3.418  -4.117  -1.836  1.00  0.00           O  
HETATM   37  H1  UNL     1      -5.252  -1.406   1.528  1.00  0.00           H  
HETATM   38  H2  UNL     1      -6.056  -0.718   0.048  1.00  0.00           H  
HETATM   39  H3  UNL     1      -6.638  -2.262   0.820  1.00  0.00           H  
HETATM   40  H4  UNL     1      -3.820  -0.265   0.432  1.00  0.00           H  
HETATM   41  H5  UNL     1      -4.304   3.198   1.252  1.00  0.00           H  
HETATM   42  H6  UNL     1      -4.829   6.233   1.593  1.00  0.00           H  
HETATM   43  H7  UNL     1      -1.819   6.458   2.212  1.00  0.00           H  
HETATM   44  H8  UNL     1       1.276   5.049   1.227  1.00  0.00           H  
HETATM   45  H9  UNL     1       1.006  -0.451   1.220  1.00  0.00           H  
HETATM   46  H10 UNL     1       3.645  -0.545  -1.330  1.00  0.00           H  
HETATM   47  H11 UNL     1       3.358  -3.566  -1.010  1.00  0.00           H  
HETATM   48  H12 UNL     1       3.192  -2.509  -2.443  1.00  0.00           H  
HETATM   49  H13 UNL     1       5.414  -3.546  -1.573  1.00  0.00           H  
HETATM   50  H14 UNL     1       4.666  -2.251   0.868  1.00  0.00           H  
HETATM   51  H15 UNL     1       6.370  -0.924   0.629  1.00  0.00           H  
HETATM   52  H16 UNL     1       4.508  -0.036   2.293  1.00  0.00           H  
HETATM   53  H17 UNL     1       2.931  -2.302   2.073  1.00  0.00           H  
HETATM   54  H18 UNL     1       2.445   1.214   1.867  1.00  0.00           H  
HETATM   55  H19 UNL     1       4.275   1.802   0.541  1.00  0.00           H  
HETATM   56  H20 UNL     1      -0.128  -0.952  -1.620  1.00  0.00           H  
HETATM   57  H21 UNL     1       1.144  -3.677  -2.351  1.00  0.00           H  
HETATM   58  H22 UNL     1       0.537  -3.561  -4.015  1.00  0.00           H  
HETATM   59  H23 UNL     1       0.711  -2.059  -3.072  1.00  0.00           H  
HETATM   60  H24 UNL     1      -4.349  -4.401  -1.576  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3
CONECT    3    4    4   35
CONECT    4    5   40
CONECT    5    6   31   31
CONECT    6    7   18   18
CONECT    7    8
CONECT    8    9    9   15
CONECT    9   10   41
CONECT   10   11   12   12
CONECT   11   42
CONECT   12   13   43
CONECT   13   14   15   15
CONECT   14   44
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20
CONECT   20   21   29   45
CONECT   21   22
CONECT   22   23   25   46
CONECT   23   24   47   48
CONECT   24   49
CONECT   25   26   27   50
CONECT   26   51
CONECT   27   28   29   52
CONECT   28   53
CONECT   29   30   54
CONECT   30   55
CONECT   31   32   56
CONECT   32   33   35   35
CONECT   33   34
CONECT   34   57   58   59
CONECT   35   36
CONECT   36   60
END

NP0043986
     RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
   -5.7460   -1.6415    0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9386   -2.4675   -0.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724   -2.0849   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1821   -0.8851   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784   -0.4800   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    0.8495   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318    1.6575    0.3812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2555    2.8637    0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3076    3.6404    1.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1860    4.9130    1.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070    5.6447    2.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293    5.4533    1.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051    4.7262    1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3959    5.3297    1.4591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869    3.4491    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0324    2.6477    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1913    3.1075    0.4619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148    1.3469   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8936    0.6665   -0.4522 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071   -0.1759    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340   -1.2990   -0.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4293   -1.3949   -0.6287 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7112   -2.6356   -1.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0765   -2.6368   -1.7655 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4054   -1.2378    0.5223 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5669   -0.5677    0.1727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7285   -0.5199    1.6752 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8931   -1.3581    2.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243    0.5573    1.0482 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5873    1.2351    0.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1078   -1.2698   -1.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6250   -2.4961   -1.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8947   -3.3314   -2.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4129   -3.1015   -2.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9101   -2.9100   -1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4175   -4.1166   -1.8363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2517   -1.4065    1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0561   -0.7182    0.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6378   -2.2615    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8197   -0.2655    0.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3040    3.1978    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8291    6.2333    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    6.4578    2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2756    5.0493    1.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -0.4509    1.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6453   -0.5449   -1.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582   -3.5664   -1.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -2.5091   -2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -3.5460   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6661   -2.2512    0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3698   -0.9240    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0364    2.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9308   -2.3018    2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451    1.2136    1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2753    1.8023    0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1282   -0.9517   -1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438   -3.6768   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372   -3.5614   -4.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7105   -2.0591   -3.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3495   -4.4006   -1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
  5 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  2  0
 35 36  1  0
 35  3  1  0
 18  6  2  0
 29 20  1  0
 15  8  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  0
  9 41  1  0
 11 42  1  0
 12 43  1  0
 14 44  1  0
 20 45  1  0
 22 46  1  6
 23 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  1
 26 51  1  0
 27 52  1  1
 28 53  1  0
 29 54  1  1
 30 55  1  0
 31 56  1  0
 34 57  1  0
 34 58  1  0
 34 59  1  0
 36 60  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₄O₁₃

Average Mass

508.4320 Da

Monoisotopic Mass

508.12169 Da

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C1=C(OC2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C23H24O13/c1-32-12-3-8(4-13(33-2)16(12)27)21-22(18(29)15-10(26)5-9(25)6-11(15)34-21)36-23-20(31)19(30)17(28)14(7-24)35-23/h3-6,14,17,19-20,23-28,30-31H,7H2,1-2H3/t14-,17-,19+,20-,23?/m1/s1

InChI Key

JMFWYRWPJVEZPV-BZMFKJDCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anthyllis sericea	Plant	KNApSAcK
Cedrus spp.	Plant	KNApSAcK
Chondropetalum tectolum	Plant	KNApSAcK
Elegia cuspidata	Plant	KNApSAcK
Heuchera cylindrica	Plant	KNApSAcK
Heuchera micrantha	Plant	KNApSAcK
Larix decidua	Plant	KNApSAcK
Larix laricina	Plant	KNApSAcK
Larix leptolepis	Plant	KNApSAcK
Lysimachia nummularia	Plant	KNApSAcK
Lysimachia vulgaris var. davurica	Plant	KNApSAcK
Philydrum lanuginosum	Plant	KNApSAcK
Pinus jeffreyi	Plant	KNApSAcK
Vitis vinifera L.	Linigton's dataset	19061313

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Ether
Polyol
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.71	ALOGPS
logP	-0.16	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.22 m³·mol⁻¹	ChemAxon
Polarizability	48.44 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16740885

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20056942

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Castillo-Munoz N, Gomez-Alonso S, Garcia-Romero E, Gomez MV, Velders AH, Hermosin-Gutierrez I: Flavonol 3-O-glycosides series of Vitis vinifera Cv. Petit Verdot red wine grapes. J Agric Food Chem. 2009 Jan 14;57(1):209-19. doi: 10.1021/jf802863g. [PubMed:19061313 ]
Rustagi T, Badve S: Letter to the Editor: The Effect of Head Loading on Cervical Spine in Manual Laborers. Asian Spine J. 2021 Jun;15(3):412-413. doi: 10.31616/asj.2021.0149. Epub 2021 Jun 17. [PubMed:34154041 ]
Sethy SS, Ahuja K, Ifthekar S, Sarkar B, Kandwal P: Response to: Letter to the Editor, Is Anterior-Only Fixation Adequate for Three-Column Injuries of the Cervical Spine? Asian Spine J. 2021 Jun;15(3):410-411. doi: 10.31616/asj.2021.0108.r2. Epub 2021 Jun 17. [PubMed:34154040 ]
Yang LC, Li R, Tan J, Jiang ZT: Polyphenolics composition of the leaves of Zanthoxylum bungeanum Maxim. grown in Hebei, China, and their radical scavenging activities. J Agric Food Chem. 2013 Feb 27;61(8):1772-8. doi: 10.1021/jf3042825. Epub 2013 Feb 12. [PubMed:23383696 ]
Oliveira J, Petrov V, Parola AJ, Pina F, Azevedo J, Teixeira N, Bras NF, Fernandes PA, Mateus N, Ramos MJ, de Freitas V: Chemical behavior of methylpyranomalvidin-3-O-glucoside in aqueous solution studied by NMR and UV-visible spectroscopy. J Phys Chem B. 2011 Feb 17;115(6):1538-45. doi: 10.1021/jp110593c. Epub 2011 Jan 20. [PubMed:21250736 ]

Showing NP-Card for Syringetin 3-beta-O-glucoside (NP0043986)

MOL for NP0043986 (Syringetin 3-beta-O-glucoside)

3D MOL for NP0043986 (Syringetin 3-beta-O-glucoside)

3D SDF for NP0043986 (Syringetin 3-beta-O-glucoside)

3D-SDF for NP0043986 (Syringetin 3-beta-O-glucoside)

PDB for NP0043986 (Syringetin 3-beta-O-glucoside)

3D PDB for NP0043986 (Syringetin 3-beta-O-glucoside)

SMILES for NP0043986 (Syringetin 3-beta-O-glucoside)

INCHI for NP0043986 (Syringetin 3-beta-O-glucoside)

Structure for NP0043986 (Syringetin 3-beta-O-glucoside)

3D Structure for NP0043986 (Syringetin 3-beta-O-glucoside)