NP-MRD: Showing NP-Card for (3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid (NP0325294)

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Record Information

Version

2.0

Created at

2022-09-12 05:56:12 UTC

Updated at

2022-09-12 05:56:12 UTC

NP-MRD ID

NP0325294

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid

Description

(3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. (3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid is found in Citrus medica. Based on a literature review very few articles have been published on (3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207562D          

 45 48  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0329   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
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  6  5  1  6  0  0  0
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 33 39  1  0  0  0  0
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 40 41  1  0  0  0  0
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 41 43  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  2  0  0  0  0
  3 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END

     RDKit          3D

 77 80  0  0  0  0  0  0  0  0999 V2000
   -1.3148    2.6765   -4.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7353    3.0665   -2.7346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048    2.3201   -1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0194    1.5825   -0.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7261    1.4809   -0.5220 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1076    1.0973   -2.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6074    0.0991    1.0447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3856   -1.3011    0.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3071    0.9660   -0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3080   -0.4842    1.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.8617   -2.0439    2.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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M  END


  Mrv1652309122207562D          

 45 48  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   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
    1.4289    0.8250    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    4.2868    0.8250    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   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
    5.0013   -0.4125    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  1  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
  4 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 33 39  1  0  0  0  0
 32 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  2  0  0  0  0
  3 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O[C@@H]2O[C@H](COC(=O)C[C@@](C)(O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C(OC)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O16/c1-29(39,9-17(32)33)10-18(34)42-11-16-20(35)22(37)23(38)28(44-16)45-27-25(40-2)21(36)19-14(31)8-15(43-24(19)26(27)41-3)12-4-6-13(30)7-5-12/h4-8,16,20,22-23,28,30,35-39H,9-11H2,1-3H3,(H,32,33)/t16-,20-,22+,23-,28+,29+/m1/s1

> <INCHI_KEY>
KUBRQWGDWMRDKB-XMSKYJJOSA-N

> <FORMULA>
C29H32O16

> <MOLECULAR_WEIGHT>
636.559

> <EXACT_MASS>
636.16903495

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
61.390877492602684

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid

> <JCHEM_LOGP>
0.03950839266666639

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.246126616247306

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.75314919115492

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0083920901482806

> <JCHEM_POLAR_SURFACE_AREA>
248.19999999999993

> <JCHEM_REFRACTIVITY>
148.63020000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.795  -9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.875  -9.240   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.668 -13.090   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -8.002 -10.780   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   44                                                  
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    8   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    6   26                                                  
CONECT   26   25                                                            
CONECT   27    4   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   43                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   40                                                  
CONECT   33   32   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   33                                                       
CONECT   40   32   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   30   44                                                  
CONECT   44   43    3   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Value	Source
(3S)-3-Hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoate	Generator

Chemical Formula

C₂₉H₃₂O₁₆

Average Mass

636.5590 Da

Monoisotopic Mass

636.16903 Da

IUPAC Name

(3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid

Traditional Name

(3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(O[C@@H]2O[C@H](COC(=O)C[C@@](C)(O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C(OC)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C29H32O16/c1-29(39,9-17(32)33)10-18(34)42-11-16-20(35)22(37)23(38)28(44-16)45-27-25(40-2)21(36)19-14(31)8-15(43-24(19)26(27)41-3)12-4-6-13(30)7-5-12/h4-8,16,20,22-23,28,30,35-39H,9-11H2,1-3H3,(H,32,33)/t16-,20-,22+,23-,28+,29+/m1/s1

InChI Key

KUBRQWGDWMRDKB-XMSKYJJOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus medica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Saccharolipid
8-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
4'-hydroxyflavonoid
5-hydroxyflavonoid
Phenolic glycoside
Chromone
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Anisole
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Phenol
Fatty acyl
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Pyran
Monosaccharide
Oxane
Heteroaromatic compound
Tertiary alcohol
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Acetal
Ether
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
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	0.04	ChemAxon
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	248.2 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	148.63 m³·mol⁻¹	ChemAxon
Polarizability	61.39 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163045851

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid (NP0325294)

MOL for NP0325294 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid)

3D MOL for NP0325294 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid)

3D SDF for NP0325294 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid)

3D-SDF for NP0325294 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid)

PDB for NP0325294 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid)

3D PDB for NP0325294 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid)

SMILES for NP0325294 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid)

INCHI for NP0325294 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid)

Structure for NP0325294 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid)

3D Structure for NP0325294 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}pentanoic acid)