NP-MRD: Showing NP-Card for 2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid (NP0316313)

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Record Information

Version

2.0

Created at

2022-09-11 15:25:35 UTC

Updated at

2022-09-11 15:25:35 UTC

NP-MRD ID

NP0316313

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid

Description

SCHEMBL961607 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. 2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid is found in Cichorium intybus, Echinodorus grandiflorus and Isodon rubescens. Based on a literature review very few articles have been published on SCHEMBL961607.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112217252D          

 34 35  0  0  0  0            999 V2000
    1.4776   -3.6698    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
    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   -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
    2.4880   -1.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9047   -1.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1182   -0.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5348    0.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    0.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453    1.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7588    1.8512    0.0000 O   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 O   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
    3.4412   -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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
M  END

     RDKit          3D

 52 53  0  0  0  0  0  0  0  0999 V2000
    0.7430   -1.6817    1.5478 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3226   -0.9094    2.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2794   -1.6051    3.5263 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967    0.5577    2.4485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3331    0.9526    3.6597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7359    1.0955    2.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9234    1.8119    3.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9448    1.0020    1.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893    0.3917    0.7648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4859    0.3779    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6155    0.9915    0.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7968    0.9052   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8580    0.2129   -1.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0483    0.1417   -2.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7084   -0.4095   -1.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7247   -1.1274   -3.0387 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5554   -0.3270   -1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073    1.2352    1.3583 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0903    0.9843    0.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3368    2.7301    1.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492    3.1822    2.6414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    3.5987    0.6003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8309    0.8031    1.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4140    0.9715    2.5639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5183    0.2001    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7764   -0.1765    0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5334   -0.7899   -0.5971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292   -1.0398   -1.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7985   -1.6302   -2.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1106   -1.9910   -2.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8747   -2.5843   -3.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6298   -1.7454   -1.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9284   -2.0773   -1.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8487   -1.1536   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757   -2.1321    4.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1711    0.4285    4.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    1.5233    2.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3847   -0.1362    0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6027    1.5460    1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6698    1.4236    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0635   -0.3782   -2.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9253   -1.5911   -3.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6848   -0.8424   -1.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0703    1.7400   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4298    4.3387    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9698    0.0742   -0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2361   -0.0016    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9920   -0.7602   -2.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3727   -1.8079   -3.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8267   -2.8582   -3.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5912   -2.5042   -1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2633   -0.9599    0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  4 18  1  0
 18 19  1  6
 18 20  1  0
 20 22  1  0
 20 21  2  0
 18 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  2  0
 17 10  1  0
 34 27  1  0
  3 35  1  0
  5 36  1  0
  8 37  1  0
  9 38  1  0
 11 39  1  0
 12 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 22 45  1  0
 25 46  1  0
 26 47  1  0
 28 48  1  0
 29 49  1  0
 31 50  1  0
 33 51  1  0
 34 52  1  0
M  END


  Mrv1652309112217252D          

 34 35  0  0  0  0            999 V2000
    1.4776   -3.6698    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
    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   -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
    2.4880   -1.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9047   -1.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1182   -0.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5348    0.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    0.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453    1.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7588    1.8512    0.0000 O   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 O   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
    3.4412   -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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(O)(C(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)(C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)21(33,19(29)30)22(34,20(31)32)18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,23-26,33-34H,(H,29,30)(H,31,32)/b7-3+,8-4+

> <INCHI_KEY>
IHFPHNHRXPJFAJ-FCXRPNKRSA-N

> <FORMULA>
C22H18O12

> <MOLECULAR_WEIGHT>
474.374

> <EXACT_MASS>
474.07982602

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.50589849988635

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-bis[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid

> <JCHEM_LOGP>
2.051693168666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.459826381380239

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4972050989645065

> <JCHEM_PKA_STRONGEST_BASIC>
-5.299110674408614

> <JCHEM_POLAR_SURFACE_AREA>
230.11999999999995

> <JCHEM_REFRACTIVITY>
114.47059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,3-bis[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0       2.758  -6.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.246  -7.249   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.644  -8.736   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.424  -5.071   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.246  -5.071   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.758  -5.470   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.644  -3.584   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.555  -2.495   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.954  -1.007   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.865   0.082   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.264   1.569   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.751   1.968   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.150   3.456   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.840   0.879   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.328   1.278   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.442  -0.608   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.424  -7.249   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -8.338   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.513  -6.160   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.114  -4.672   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.000  -6.559   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.513  -8.338   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.000  -7.939   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.114  -9.825   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.203 -10.914   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.804 -12.402   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.893 -13.491   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.495 -14.978   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.007 -15.377   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.609 -16.864   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.918 -14.288   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.431 -14.687   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.317 -12.800   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   18                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10                                                       
CONECT   18    4   19   20   23                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₁₈O₁₂

Average Mass

474.3740 Da

Monoisotopic Mass

474.07983 Da

IUPAC Name

2,3-bis[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid

Traditional Name

2,3-bis[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(O)(C(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)(C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)21(33,19(29)30)22(34,20(31)32)18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,23-26,33-34H,(H,29,30)(H,31,32)/b7-3+,8-4+

InChI Key

IHFPHNHRXPJFAJ-FCXRPNKRSA-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
Cichorium intybus	LOTUS Database	35616633
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
Medium-chain keto acid
Catechol
Gamma-keto acid
Styrene
Beta-keto acid
Branched fatty acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Hydroxy fatty acid
Phenol
Sugar acid
B'-hydroxy-alpha,beta-unsaturated-ketone
Beta-hydroxy ketone
Unsaturated fatty acid
Acyloin
Dicarboxylic acid or derivatives
Benzenoid
Hydroxy acid
Alpha-hydroxy acid
Fatty acyl
Monosaccharide
Monocyclic benzene moiety
Keto acid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Tertiary alcohol
Alpha-hydroxy ketone
Ketone
1,2-diol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
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	2.05	ChemAxon
pKa (Strongest Acidic)	2.5	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	230.12 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	114.47 m³·mol⁻¹	ChemAxon
Polarizability	43.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

16160174

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23131559

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid (NP0316313)

MOL for NP0316313 (2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid)

3D MOL for NP0316313 (2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid)

3D SDF for NP0316313 (2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid)

3D-SDF for NP0316313 (2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid)

PDB for NP0316313 (2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid)

3D PDB for NP0316313 (2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid)

SMILES for NP0316313 (2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid)

INCHI for NP0316313 (2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid)

Structure for NP0316313 (2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid)

3D Structure for NP0316313 (2,3-bis[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,3-dihydroxybutanedioic acid)