NP-MRD: Showing NP-Card for methyl 4-O-galloychlorogenate (NP0026529)

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Record Information

Version

1.0

Created at

2021-06-19 18:22:48 UTC

Updated at

2021-06-29 23:52:07 UTC

NP-MRD ID

NP0026529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-O-galloychlorogenate

Provided By

JEOL Database JEOL Logo

Description

methyl 4-O-galloychlorogenate is found in Manilkara zapota and Manilkara zapota cv.Tikal . It was first documented in 2003 (PMID: 12880319). Based on a literature review very few articles have been published on methyl 4-O-galloylchlorogenate (PMID: 32405366).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120223D          

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     RDKit          3D

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M  END


  Mrv1652306192120223D          

 61 63  0  0  0  0            999 V2000
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   -1.2715   -3.7157    2.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2685   -7.7484    2.9850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -5.8609    1.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1722   -6.6797    0.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061   -4.5123    1.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3668    2.2188    0.4640 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0361    2.9376   -2.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1955    4.4469   -1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2322    4.4812    1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0772    3.8268   -1.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276    5.3581   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548    4.4446   -1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6680    4.9068    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074    2.0048   -1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4578    1.8338   -2.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7921    1.6219   -1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5305    2.3427    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    3.0640    3.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533    2.9260    1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710    2.4481    1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0141   -1.7564    0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648   -1.9270    3.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7167   -3.7110    4.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180   -6.1092    5.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380   -8.0735    2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059   -6.1533   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -4.0845    0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742    1.5976   -0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    1.8480    1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
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 28 29  1  0  0  0  0
 34 36  2  0  0  0  0
 36 29  1  0  0  0  0
 34 35  1  0  0  0  0
 32 33  1  0  0  0  0
 10  8  1  0  0  0  0
 25 26  2  0  0  0  0
 10 23  1  0  0  0  0
  3  4  2  0  0  0  0
 23 37  1  0  0  0  0
  3  2  1  0  0  0  0
 37  5  1  0  0  0  0
 15 16  2  0  0  0  0
 16 18  1  0  0  0  0
 18 20  2  0  0  0  0
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 29 30  2  0  0  0  0
 20 21  1  0  0  0  0
 24 25  1  0  0  0  0
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 14 12  1  0  0  0  0
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 31 32  2  0  0  0  0
  2  1  1  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  0  0  0  0
  5  6  1  1  0  0  0
  5  3  1  0  0  0  0
  8  9  1  0  0  0  0
 23 24  1  0  0  0  0
 27 53  1  0  0  0  0
 28 54  1  0  0  0  0
  6 41  1  0  0  0  0
  9 45  1  0  0  0  0
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 37 60  1  0  0  0  0
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  8 44  1  6  0  0  0
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 23 52  1  1  0  0  0
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 19 49  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@]2([H])C([H])([H])[C@](O[H])(C(=O)OC([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@@]2([H])OC(=O)C2=C([H])C(O[H])=C(O[H])C(O[H])=C2[H])C([H])=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O13/c1-35-23(33)24(34)9-17(29)21(37-22(32)12-7-15(27)20(31)16(28)8-12)18(10-24)36-19(30)5-3-11-2-4-13(25)14(26)6-11/h2-8,17-18,21,25-29,31,34H,9-10H2,1H3/b5-3+/t17-,18-,21-,24+/m1/s1

> <INCHI_KEY>
VMLJFBIJZLTOFL-IVBQVISXSA-N

> <FORMULA>
C24H24O13

> <MOLECULAR_WEIGHT>
520.443

> <EXACT_MASS>
520.121690833

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
50.53718415572047

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,6R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
1.4619681816666663

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.237333516261748

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.070466664612905

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246896819952239

> <JCHEM_POLAR_SURFACE_AREA>
220.50999999999996

> <JCHEM_REFRACTIVITY>
123.7685

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,6R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
   -6.8946    3.3964   -1.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3346    4.0757   -0.6328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9223    4.8711    0.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3746    2.4358   -0.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6732    2.0337   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9769    1.6099   -1.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5711    2.1166    0.8059 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2619    2.5557    1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6135    2.8065    2.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445    2.6433    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    1.9975    0.7396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6134    0.5731    0.7855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446   -0.0338    1.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995    0.4849    2.9797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582   -1.4528    1.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6414   -2.2932    2.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715   -3.7157    2.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171   -4.3048    4.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756   -5.6590    4.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6005   -6.4252    2.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685   -7.7484    2.9850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -5.8609    1.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1722   -6.6797    0.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061   -4.5123    1.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3668    2.2188    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0361    2.9376   -2.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1955    4.4469   -1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2322    4.4812    1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0772    3.8268   -1.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276    5.3581   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548    4.4446   -1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6680    4.9068    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074    2.0048   -1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4578    1.8338   -2.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7921    1.6219   -1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5305    2.3427    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    3.0640    3.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533    2.9260    1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710    2.4481    1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0141   -1.7564    0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648   -1.9270    3.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7167   -3.7110    4.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180   -6.1092    5.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380   -8.0735    2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059   -6.1533   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -4.0845    0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742    1.5976   -0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    1.8480    1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 34  1  0
 28 29  1  0
 34 36  2  0
 36 29  1  0
 34 35  1  0
 32 33  1  0
 10  8  1  0
 25 26  2  0
 10 23  1  0
  3  4  2  0
 23 37  1  0
  3  2  1  0
 37  5  1  0
 15 16  2  0
 16 18  1  0
 18 20  2  0
 10 11  1  0
 20 22  1  0
 22 14  2  0
 14 15  1  0
 25 27  1  0
 16 17  1  0
 29 30  2  0
 20 21  1  0
 24 25  1  0
 18 19  1  0
 30 31  1  0
 14 12  1  0
 27 28  2  0
 12 13  2  0
 12 11  1  0
 31 32  2  0
  2  1  1  0
  5  7  1  0
  8  7  1  0
  5  6  1  1
  5  3  1  0
  8  9  1  0
 23 24  1  0
 27 53  1  0
 28 54  1  0
  6 41  1  0
  9 45  1  0
 10 46  1  6
 37 60  1  0
 37 61  1  0
  8 44  1  6
  7 42  1  0
  7 43  1  0
 23 52  1  1
 30 55  1  0
 31 56  1  0
 36 59  1  0
 35 58  1  0
 33 57  1  0
 15 47  1  0
 22 51  1  0
 17 48  1  0
 21 50  1  0
 19 49  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -6.895   3.396  -1.660  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.511   3.291  -1.317  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.194   3.842  -0.116  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.987   4.372   0.654  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.698   3.691   0.209  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.394   4.420   1.414  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.827   4.282  -0.909  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.335   4.076  -0.633  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.922   4.871   0.487  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.014   2.587  -0.391  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.375   2.436  -0.019  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.260   2.457  -1.043  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.979   2.509  -2.229  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.648   2.375  -0.518  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.673   2.034  -1.413  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.979   1.949  -0.951  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.977   1.610  -1.817  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.273   2.207   0.382  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.571   2.117   0.806  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.262   2.556   1.270  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.614   2.807   2.567  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.945   2.643   0.832  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.874   1.998   0.740  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.613   0.573   0.786  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.845  -0.034   1.975  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.300   0.485   2.980  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.458  -1.453   1.842  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.641  -2.293   2.872  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.272  -3.716   2.852  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.817  -4.305   4.045  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.476  -5.659   4.090  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.601  -6.425   2.943  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.269  -7.748   2.985  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.064  -5.861   1.758  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.172  -6.680   0.667  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.406  -4.512   1.704  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.367   2.219   0.464  0.00  0.00           C+0
HETATM   38  H   UNK     0      -7.036   2.938  -2.642  0.00  0.00           H+0
HETATM   39  H   UNK     0      -7.196   4.447  -1.721  0.00  0.00           H+0
HETATM   40  H   UNK     0      -7.510   2.857  -0.933  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.232   4.481   1.922  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.077   3.827  -1.875  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.028   5.358  -0.989  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.755   4.445  -1.485  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.668   4.907   1.125  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.207   2.005  -1.303  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.458   1.834  -2.460  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.792   1.622  -1.276  0.00  0.00           H+0
HETATM   49  H   UNK     0       6.531   2.343   1.758  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.814   3.064   3.059  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.153   2.926   1.520  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.571   2.448   1.694  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.014  -1.756   0.903  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.065  -1.927   3.807  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.717  -3.711   4.951  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.118  -6.109   5.011  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.438  -8.073   2.079  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.506  -6.153  -0.080  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.786  -4.085   0.782  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.674   1.598  -0.388  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.947   1.848   1.319  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    3    1                                                       
CONECT    3    4    2    5                                                  
CONECT    4    3                                                            
CONECT    5   37    7    6    3                                             
CONECT    6    5   41                                                       
CONECT    7    5    8   42   43                                             
CONECT    8   10    7    9   44                                             
CONECT    9    8   45                                                       
CONECT   10    8   23   11   46                                             
CONECT   11   10   12                                                       
CONECT   12   14   13   11                                                  
CONECT   13   12                                                            
CONECT   14   22   15   12                                                  
CONECT   15   16   14   47                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16   48                                                       
CONECT   18   16   20   19                                                  
CONECT   19   18   49                                                       
CONECT   20   18   22   21                                                  
CONECT   21   20   50                                                       
CONECT   22   20   14   51                                                  
CONECT   23   10   37   24   52                                             
CONECT   24   25   23                                                       
CONECT   25   26   27   24                                                  
CONECT   26   25                                                            
CONECT   27   25   28   53                                                  
CONECT   28   29   27   54                                                  
CONECT   29   28   36   30                                                  
CONECT   30   29   31   55                                                  
CONECT   31   30   32   56                                                  
CONECT   32   34   33   31                                                  
CONECT   33   32   57                                                       
CONECT   34   32   36   35                                                  
CONECT   35   34   58                                                       
CONECT   36   34   29   59                                                  
CONECT   37   23    5   60   61                                             
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    6                                                            
CONECT   42    7                                                            
CONECT   43    7                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   15                                                            
CONECT   48   17                                                            
CONECT   49   19                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   23                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
CONECT   55   30                                                            
CONECT   56   31                                                            
CONECT   57   33                                                            
CONECT   58   35                                                            
CONECT   59   36                                                            
CONECT   60   37                                                            
CONECT   61   37                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  126    0
END

RDKit          3D

61 63  0  0  0  0  0  0  0  0999 V2000
   -6.8946    3.3964   -1.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5111    3.2911   -1.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1941    3.8417   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9875    4.3722    0.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6982    3.6910    0.2094 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3937    4.4196    1.4140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268    4.2819   -0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3346    4.0757   -0.6328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9223    4.8711    0.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0139    2.5873   -0.3910 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3746    2.4358   -0.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2605    2.4566   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792    2.5091   -2.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6475    2.3748   -0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6732    2.0337   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792    1.9491   -0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769    1.6099   -1.8172 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2733    2.2069    0.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5711    2.1166    0.8059 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2619    2.5557    1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6135    2.8065    2.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445    2.6433    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8740    1.9975    0.7396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6134    0.5731    0.7855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446   -0.0338    1.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995    0.4849    2.9797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582   -1.4528    1.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6414   -2.2932    2.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715   -3.7157    2.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171   -4.3048    4.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756   -5.6590    4.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6005   -6.4252    2.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685   -7.7484    2.9850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -5.8609    1.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1722   -6.6797    0.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061   -4.5123    1.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3668    2.2188    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0361    2.9376   -2.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1955    4.4469   -1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5101    2.8572   -0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2322    4.4812    1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0772    3.8268   -1.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276    5.3581   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548    4.4446   -1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6680    4.9068    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2074    2.0048   -1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4578    1.8338   -2.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7921    1.6219   -1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5305    2.3427    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    3.0640    3.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533    2.9260    1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710    2.4481    1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0141   -1.7564    0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648   -1.9270    3.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7167   -3.7110    4.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180   -6.1092    5.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380   -8.0735    2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5059   -6.1533   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -4.0845    0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742    1.5976   -0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    1.8480    1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 34  1  0
 28 29  1  0
 34 36  2  0
 36 29  1  0
 34 35  1  0
 32 33  1  0
 10  8  1  0
 25 26  2  0
 10 23  1  0
  3  4  2  0
 23 37  1  0
  3  2  1  0
 37  5  1  0
 15 16  2  0
 16 18  1  0
 18 20  2  0
 10 11  1  0
 20 22  1  0
 22 14  2  0
 14 15  1  0
 25 27  1  0
 16 17  1  0
 29 30  2  0
 20 21  1  0
 24 25  1  0
 18 19  1  0
 30 31  1  0
 14 12  1  0
 27 28  2  0
 12 13  2  0
 12 11  1  0
 31 32  2  0
  2  1  1  0
  5  7  1  0
  8  7  1  0
  5  6  1  1
  5  3  1  0
  8  9  1  0
 23 24  1  0
 27 53  1  0
 28 54  1  0
  6 41  1  0
  9 45  1  0
 10 46  1  6
 37 60  1  0
 37 61  1  0
  8 44  1  6
  7 42  1  0
  7 43  1  0
 23 52  1  1
 30 55  1  0
 31 56  1  0
 36 59  1  0
 35 58  1  0
 33 57  1  0
 15 47  1  0
 22 51  1  0
 17 48  1  0
 21 50  1  0
 19 49  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl 4-O-galloylchlorogenic acid	Generator

Chemical Formula

C₂₄H₂₄O₁₃

Average Mass

520.4430 Da

Monoisotopic Mass

520.12169 Da

IUPAC Name

(1R,2R,4S,6R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate

Traditional Name

(1R,2R,4S,6R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,6-dihydroxy-4-(methoxycarbonyl)cyclohexyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@]2([H])C([H])([H])[C@](O[H])(C(=O)OC([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@@]2([H])OC(=O)C2=C([H])C(O[H])=C(O[H])C(O[H])=C2[H])C([H])=C1O[H]

InChI Identifier

InChI=1S/C24H24O13/c1-35-23(33)24(34)9-17(29)21(37-22(32)12-7-15(27)20(31)16(28)8-12)18(10-24)36-19(30)5-3-11-2-4-13(25)14(26)6-11/h2-8,17-18,21,25-29,31,34H,9-10H2,1H3/b5-3+/t17-,18-,21-,24+/m1/s1

InChI Key

VMLJFBIJZLTOFL-IVBQVISXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Manilkara zapota	JEOL database	Ma, J., et al, J. Nat. Prod. 66, 983 (2003)
Manilkara zapota cv.Tikal	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Galloyl ester
Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Gallic acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Tricarboxylic acid or derivatives
Benzoyl
Catechol
Styrene
Phenol
Fatty acid ester
Cyclohexanol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.54	ALOGPS
logP	1.46	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.07	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	220.51 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	123.77 m³·mol⁻¹	ChemAxon
Polarizability	50.54 Å³	ChemAxon
Number of Rings	3	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

9126661

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10951440

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Riaz MB, Khan AU, Qazi NG: Pharmacological and computational evaluation of Sapodilla and its constituents for therapeutic potential in hyperactive gastrointestinal disorders. Iran J Basic Med Sci. 2020 Feb;23(2):224-235. doi: 10.22038/IJBMS.2019.35595.8488. [PubMed:32405366 ]
Ma J, Luo XD, Protiva P, Yang H, Ma C, Basile MJ, Weinstein IB, Kennelly EJ: Bioactive novel polyphenols from the fruit of Manilkara zapota (Sapodilla). J Nat Prod. 2003 Jul;66(7):983-6. doi: 10.1021/np020576x. [PubMed:12880319 ]
Ma, J., et al. (2003). Ma, J., et al, J. Nat. Prod. 66, 983 (2003). J. Nat. Prod..

Showing NP-Card for methyl 4-O-galloychlorogenate (NP0026529)

MOL for NP0026529 (methyl 4-O-galloychlorogenate)

3D MOL for NP0026529 (methyl 4-O-galloychlorogenate)

3D SDF for NP0026529 (methyl 4-O-galloychlorogenate)

3D-SDF for NP0026529 (methyl 4-O-galloychlorogenate)

PDB for NP0026529 (methyl 4-O-galloychlorogenate)

3D PDB for NP0026529 (methyl 4-O-galloychlorogenate)

SMILES for NP0026529 (methyl 4-O-galloychlorogenate)

INCHI for NP0026529 (methyl 4-O-galloychlorogenate)

Structure for NP0026529 (methyl 4-O-galloychlorogenate)

3D Structure for NP0026529 (methyl 4-O-galloychlorogenate)