NP-MRD: Showing NP-Card for 2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid (NP0233054)

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Record Information

Version

2.0

Created at

2022-09-06 14:31:18 UTC

Updated at

2022-09-06 14:31:18 UTC

NP-MRD ID

NP0233054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid

Description

Caffeoyl-feruloyltartaric acid belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. 2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid is found in Echinodorus grandiflorus and Isodon rubescens. 2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid was first documented in 2011 (PMID: 21453943). Based on a literature review very few articles have been published on caffeoyl-feruloyltartaric acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062216312D          

 35 36  0  0  0  0            999 V2000
    5.5193    1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3058    0.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089    0.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2953   -0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985   -0.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2849   -1.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880   -1.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745   -2.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4776   -2.9302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412   -2.7166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880   -4.6803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4776   -3.6698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0246   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8111   -2.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8215   -3.5135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0246   -4.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8215   -4.2532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8111   -5.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944   -5.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1809   -6.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7643   -7.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5508   -8.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7539   -8.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5403   -9.0345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1705   -7.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3736   -7.8678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840   -6.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -0.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286    0.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255    0.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1390    1.4813    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
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  8  9  2  0  0  0  0
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 10 11  1  0  0  0  0
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 17 18  2  0  0  0  0
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  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 55 56  0  0  0  0  0  0  0  0999 V2000
    3.4907    4.0440    0.8955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    3.2141    1.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153    1.8675    0.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4247   -1.9694   -3.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -1.2641   -4.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317   -2.9026   -4.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2142   -2.5159   -1.4669 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7060   -2.5237   -0.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4319   -3.8881   -1.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710   -4.8491   -1.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241   -4.1421   -3.1819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3850   -1.6566   -1.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430   -1.7417   -2.6575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9162   -0.7315   -0.5971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4922   -0.4117    0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1047    0.5480    1.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553    0.7968    2.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0891    1.6937    3.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2316    2.3924    3.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6049   -0.7385    0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7021   -0.2106    0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086    1.1139    1.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8124    1.6750    1.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2326    3.9723   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7883    5.1004    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6613    2.0171   -0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418   -1.5968   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2092    1.1466   -0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528   -3.6648   -1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059   -3.4354   -5.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5536   -3.4602    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109   -4.5664   -3.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8423   -0.1805   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -0.8961    0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6617    0.2576    3.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6437    1.8792    4.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5970    3.7859    3.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3890    2.7217    0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7644    1.1398    0.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637   -1.7746   -0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5566   -0.8199    1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6093    1.0949    1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  2  0
  4  5  1  0
  5  6  1  0
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  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  6
 10 12  1  0
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 12 13  2  0
 10 15  1  0
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 34  3  1  0
 31 24  1  0
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 11 42  1  0
 14 43  1  0
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 28 50  1  0
 30 51  1  0
 31 52  1  0
 32 53  1  0
 33 54  1  0
 35 55  1  0
M  END


  Mrv1652309062216312D          

 35 36  0  0  0  0            999 V2000
    5.5193    1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3058    0.3146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5089    0.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2953   -0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985   -0.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2849   -1.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880   -1.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745   -2.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4776   -2.9302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412   -2.7166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880   -4.6803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9255    0.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  2  0  0  0  0
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  5  6  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0233054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)\C=C\C2=CC=C(O)C(O)=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O12/c1-35-17-11-13(3-7-15(17)25)5-9-19(28)23(34,21(31)32)22(33,20(29)30)18(27)8-4-12-2-6-14(24)16(26)10-12/h2-11,24-26,33-34H,1H3,(H,29,30)(H,31,32)/b8-4+,9-5+

> <INCHI_KEY>
DDCMPKZHPFYFQJ-KBXRYBNXSA-N

> <FORMULA>
C23H20O12

> <MOLECULAR_WEIGHT>
488.401

> <EXACT_MASS>
488.095476084

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.62369908356013

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid

> <JCHEM_LOGP>
2.197587224666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.1740487550382275

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7375193961216184

> <JCHEM_PKA_STRONGEST_BASIC>
-4.893919336376138

> <JCHEM_POLAR_SURFACE_AREA>
219.11999999999995

> <JCHEM_REFRACTIVITY>
118.9529

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      10.303   2.075   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.904   0.587   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.417   0.189   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.018  -1.299   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.530  -1.697   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.132  -3.185   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.644  -3.584   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.246  -5.071   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.758  -5.470   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.424  -5.071   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.246  -7.249   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.644  -8.736   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.758  -6.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.424  -7.249   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -8.338   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.513  -6.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.114  -4.672   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.000  -6.559   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.513  -8.338   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.000  -7.939   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.114  -9.825   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.203 -10.914   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.804 -12.402   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.893 -13.491   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.495 -14.978   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.007 -15.377   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.609 -16.864   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.918 -14.288   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.431 -14.687   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.317 -12.800   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.442  -0.608   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.840   0.879   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.328   1.278   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.726   2.765   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   15                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17   20                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24                                                       
CONECT   32    5   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
Caffeoyl-feruloyltartarate	Generator

Chemical Formula

C₂₃H₂₀O₁₂

Average Mass

488.4010 Da

Monoisotopic Mass

488.09548 Da

IUPAC Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid

Traditional Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)\C=C\C2=CC=C(O)C(O)=C2)=CC=C1O

InChI Identifier

InChI=1S/C23H20O12/c1-35-17-11-13(3-7-15(17)25)5-9-19(28)23(34,21(31)32)22(33,20(29)30)18(27)8-4-12-2-6-14(24)16(26)10-12/h2-11,24-26,33-34H,1H3,(H,29,30)(H,31,32)/b8-4+,9-5+

InChI Key

DDCMPKZHPFYFQJ-KBXRYBNXSA-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
Echinodorus grandiflorus	LOTUS Database	35616633
Isodon rubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Hydroxycinnamic acid or derivatives
Methoxyphenol
Medium-chain keto acid
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Gamma-keto acid
Catechol
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
B'-hydroxy-alpha,beta-unsaturated-ketone
Phenol
Hydroxy fatty acid
Branched fatty acid
Beta-keto acid
Alkyl aryl ether
Fatty acyl
Benzenoid
Unsaturated fatty acid
Monosaccharide
Keto acid
Hydroxy acid
Dicarboxylic acid or derivatives
Beta-hydroxy ketone
Monocyclic benzene moiety
Alpha-hydroxy acid
Acyloin
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Alpha-hydroxy ketone
Acryloyl-group
Ketone
1,2-diol
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.2	ChemAxon
pKa (Strongest Acidic)	2.74	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	219.12 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	118.95 m³·mol⁻¹	ChemAxon
Polarizability	45.62 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

67160527

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129724266

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jaiswal R, Kiprotich J, Kuhnert N: Determination of the hydroxycinnamate profile of 12 members of the Asteraceae family. Phytochemistry. 2011 Jun;72(8):781-90. doi: 10.1016/j.phytochem.2011.02.027. Epub 2011 Mar 30. [PubMed:21453943 ]
LOTUS database [Link]

Showing NP-Card for 2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid (NP0233054)

MOL for NP0233054 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid)

3D MOL for NP0233054 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid)

3D SDF for NP0233054 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid)

3D-SDF for NP0233054 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid)

PDB for NP0233054 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid)

3D PDB for NP0233054 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid)

SMILES for NP0233054 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid)

INCHI for NP0233054 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid)

Structure for NP0233054 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid)

3D Structure for NP0233054 (2-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxy-3-[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]butanedioic acid)