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Showing NP-Card for Persicogenin 3'-glucoside (NP0049843)

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Record Information
Version2.0
Created at2022-03-17 21:19:01 UTC
Updated at2022-03-17 21:19:01 UTC
NP-MRD IDNP0049843
Secondary Accession NumbersNone
Natural Product Identification
Common NamePersicogenin 3'-glucoside
DescriptionPersicogenin 3'-glucoside belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Persicogenin 3'-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Persicogenin 3'-glucoside has been detected, but not quantified in, almonds and nuts. This could make persicogenin 3'-glucoside a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049843 (Persicogenin 3'-glucoside)


  Mrv0541 05061312392D          

 34 37  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
 10  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16  5  1  0  0  0  0
 16 14  2  0  0  0  0
 17  7  2  0  0  0  0
 18  9  1  0  0  0  0
 19 12  2  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24  9  1  0  0  0  0
 25 12  1  0  0  0  0
 26 13  2  0  0  0  0
 27 20  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  1  0  0  0  0
 30  1  1  0  0  0  0
 30 11  1  0  0  0  0
 31  2  1  0  0  0  0
 31 14  1  0  0  0  0
 32 15  1  0  0  0  0
 32 17  1  0  0  0  0
 33 16  1  0  0  0  0
 33 23  1  0  0  0  0
 34 18  1  0  0  0  0
 34 23  1  0  0  0  0
M  END
Download

3D MOL for NP0049843 (Persicogenin 3'-glucoside)

Download
3D SDF for NP0049843 (Persicogenin 3'-glucoside)

  Mrv0541 05061312392D          

 34 37  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
 10  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16  5  1  0  0  0  0
 16 14  2  0  0  0  0
 17  7  2  0  0  0  0
 18  9  1  0  0  0  0
 19 12  2  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24  9  1  0  0  0  0
 25 12  1  0  0  0  0
 26 13  2  0  0  0  0
 27 20  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  1  0  0  0  0
 30  1  1  0  0  0  0
 30 11  1  0  0  0  0
 31  2  1  0  0  0  0
 31 14  1  0  0  0  0
 32 15  1  0  0  0  0
 32 17  1  0  0  0  0
 33 16  1  0  0  0  0
 33 23  1  0  0  0  0
 34 18  1  0  0  0  0
 34 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049843

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC(OC2OC(CO)C(O)C(O)C2O)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O11/c1-30-11-6-12(25)19-13(26)8-15(32-17(19)7-11)10-3-4-14(31-2)16(5-10)33-23-22(29)21(28)20(27)18(9-24)34-23/h3-7,15,18,20-25,27-29H,8-9H2,1-2H3

> <INCHI_KEY>
VHGJMSVFUPCQGC-UHFFFAOYSA-N

> <FORMULA>
C23H26O11

> <MOLECULAR_WEIGHT>
478.4459

> <EXACT_MASS>
478.147511674

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
47.44978165829623

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-7-methoxy-2-(4-methoxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
0.26

> <JCHEM_LOGP>
0.5552627473333329

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.201147884118004

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.888383560937221

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549110475

> <JCHEM_POLAR_SURFACE_AREA>
164.36999999999998

> <JCHEM_REFRACTIVITY>
114.37969999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7-methoxy-2-(4-methoxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049843 (Persicogenin 3'-glucoside)
Download
PDB for NP0049843 (Persicogenin 3'-glucoside)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.671  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -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      14.671   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.004   6.160   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      14.671   2.310   0.000  0.00  0.00           O+0
CONECT    1   30                                                            
CONECT    2   31                                                            
CONECT    3    4   10                                                       
CONECT    4    3   14                                                       
CONECT    5   10   16                                                       
CONECT    6   11   12                                                       
CONECT    7   11   17                                                       
CONECT    8   13   15                                                       
CONECT    9   18   24                                                       
CONECT   10    3    5   15                                                  
CONECT   11    6    7   30                                                  
CONECT   12    6   19   25                                                  
CONECT   13    8   19   26                                                  
CONECT   14    4   16   31                                                  
CONECT   15    8   10   32                                                  
CONECT   16    5   14   33                                                  
CONECT   17    7   19   32                                                  
CONECT   18    9   20   34                                                  
CONECT   19   12   13   17                                                  
CONECT   20   18   21   27                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   33   34                                                  
CONECT   24    9                                                            
CONECT   25   12                                                            
CONECT   26   13                                                            
CONECT   27   20                                                            
CONECT   28   21                                                            
CONECT   29   22                                                            
CONECT   30    1   11                                                       
CONECT   31    2   14                                                       
CONECT   32   15   17                                                       
CONECT   33   16   23                                                       
CONECT   34   18   23                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

Download
3D PDB for NP0049843 (Persicogenin 3'-glucoside)
Download
SMILES for NP0049843 (Persicogenin 3'-glucoside)
COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC(OC2OC(CO)C(O)C(O)C2O)=C(OC)C=C1
Download
INCHI for NP0049843 (Persicogenin 3'-glucoside)
InChI=1S/C23H26O11/c1-30-11-6-12(25)19-13(26)8-15(32-17(19)7-11)10-3-4-14(31-2)16(5-10)33-23-22(29)21(28)20(27)18(9-24)34-23/h3-7,15,18,20-25,27-29H,8-9H2,1-2H3
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View in JSmol
Synonyms
ValueSource
5,3'-Dihydroxy-7,4'-dimethoxyflavanone 3'-glucosideHMDB
Chemical FormulaC23H26O11
Average Mass478.4459 Da
Monoisotopic Mass478.14751 Da
IUPAC Name5-hydroxy-7-methoxy-2-(4-methoxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5-hydroxy-7-methoxy-2-(4-methoxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC(OC2OC(CO)C(O)C(O)C2O)=C(OC)C=C1
InChI Identifier
InChI=1S/C23H26O11/c1-30-11-6-12(25)19-13(26)8-15(32-17(19)7-11)10-3-4-14(31-2)16(5-10)33-23-22(29)21(28)20(27)18(9-24)34-23/h3-7,15,18,20-25,27-29H,8-9H2,1-2H3
InChI KeyVHGJMSVFUPCQGC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Prunus dulcisFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentFlavonoid O-glycosides  
Alternative Parents
Substituents
  • Flavonoid-3p-o-glycoside
    • 

  • Flavonoid o-glycoside
    • 

  • 4p-methoxyflavonoid-skeleton
    • 

  • 7-methoxyflavonoid-skeleton
    • 

  • 5-hydroxyflavonoid
    • 

  • Flavanone
    • 

  • Hydroxyflavonoid
    • 

  • Flavan
    • 

  • Phenolic glycoside
    • 

  • Hexose monosaccharide
    • 

  • Chromone
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • 1-benzopyran
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • Anisole
    • 

  • Phenoxy compound
    • 

  • Phenol ether
    • 

  • Aryl ketone
    • 

  • Aryl alkyl ketone
    • 

  • Methoxybenzene
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Oxane
    • 

  • Benzenoid
    • 

  • Monosaccharide
    • 

  • Vinylogous acid
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Ether
    • 

  • Polyol
    • 

  • Organoheterocyclic compound
    • 

  • Primary alcohol
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organic oxide
    • 

  • 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
logP0.26ALOGPS
logP0.56ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)9.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area164.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity114.38 m³·mol⁻¹ChemAxon
Polarizability47.45 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0041398  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021337  
KNApSAcK IDC00014347  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74819423  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available