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Showing NP-Card for 3,5-Di-O-caffeoylquinic acid (NP0338287)

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Record Information
Version2.0
Created at2024-09-11 14:44:49 UTC
Updated at2024-09-11 14:44:49 UTC
NP-MRD IDNP0338287
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,5-Di-O-caffeoylquinic acid
DescriptionDicaffeoylquinic acid, also known as 3,5-dicaffeoylquinate or 3,5-dcqa, 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. A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Dicaffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dicaffeoylquinic acid is found, on average, in the highest concentration within a few different foods, such as robusta coffee, coffee, and arabica coffee and in a lower concentration in carrots and quinces. Dicaffeoylquinic acid has also been detected, but not quantified in, several different foods, such as eggplants, fruits, potato, lettuces, and coffee and coffee products. 3,5-Di-O-caffeoylquinic acid was first documented in 2004 (PMID: 15022716). This could make dicaffeoylquinic acid a potential biomarker for the consumption of these foods (PMID: 18481014) (PMID: 21469692).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0338287 (3,5-Di-O-caffeoylquinic acid)


  Mrv0541 02241220232D          

 37 39  0  0  1  0            999 V2000
    3.1009   -4.8534    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1009   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -3.6159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6719   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719   -4.8534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9574   -5.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449   -5.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -6.6949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -5.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9301   -4.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551   -4.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9926   -5.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551   -5.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676   -6.6949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9301   -5.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -5.2659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3864   -2.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1009   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719   -3.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8153   -5.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2525   -5.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8652   -6.6940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0770   -5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3387   -6.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7759   -7.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6004   -7.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9877   -6.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8122   -6.5213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5505   -5.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7260   -5.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -6.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  1  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
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 11 18  1  0  0  0  0
  5 19  1  0  0  0  0
  1 19  1  0  0  0  0
  3 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  3 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
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 29 30  2  0  0  0  0
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 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
 19 37  1  6  0  0  0
M  END
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3D MOL for NP0338287 (3,5-Di-O-caffeoylquinic acid)

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3D SDF for NP0338287 (3,5-Di-O-caffeoylquinic acid)

  Mrv0541 02241220232D          

 37 39  0  0  1  0            999 V2000
    3.1009   -4.8534    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1009   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -3.6159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6719   -4.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719   -4.8534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9574   -5.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449   -5.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -6.6949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -5.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9301   -4.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551   -4.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9926   -5.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551   -5.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676   -6.6949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9301   -5.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -5.2659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3864   -2.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1009   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6719   -3.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8153   -5.2659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2525   -5.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8652   -6.6940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0770   -5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5142   -6.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3387   -6.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7759   -7.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6004   -7.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9877   -6.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8122   -6.5213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5505   -5.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9378   -5.1220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7260   -5.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -6.0909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  1  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 18  1  0  0  0  0
  5 19  1  0  0  0  0
  1 19  1  0  0  0  0
  3 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  3 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 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
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
 19 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0338287

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)C[C@@](O)(C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(=O)O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

> <INCHI_KEY>
KRZBCHWVBQOTNZ-PSEXTPKNSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.4509

> <EXACT_MASS>
516.126776232

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
49.460333255873635

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.158230316666666

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.907552884792997

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2760207075026906

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6040694695270155

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999997

> <JCHEM_REFRACTIVITY>
126.76419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0338287 (3,5-Di-O-caffeoylquinic acid)
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PDB for NP0338287 (3,5-Di-O-caffeoylquinic acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.788  -9.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.788  -7.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.455  -6.750   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.121  -7.520   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.121  -9.060   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.787  -9.830   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.017 -11.163   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.787 -12.497   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.523 -11.163   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.293  -9.830   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.833  -9.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.603  -8.496   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.143  -8.496   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.913  -9.830   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -7.453  -9.830   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.143 -11.163   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.913 -12.497   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.603 -11.163   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.455  -9.830   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.455  -5.210   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.121  -4.440   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.788  -4.440   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.121  -5.980   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.122  -9.830   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.938 -11.136   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.215 -12.495   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.477 -11.082   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.293 -12.388   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.832 -12.334   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.648 -13.640   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.187 -13.587   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.910 -12.227   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.449 -12.173   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.094 -10.921   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      14.817  -9.561   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      12.555 -10.975   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.455 -11.370   0.000  0.00  0.00           O+0
CONECT    1   24    2   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   20   23                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11                                                       
CONECT   19    5    1   37                                                  
CONECT   20    3   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    3                                                            
CONECT   24    1   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
CONECT   37   19                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

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3D PDB for NP0338287 (3,5-Di-O-caffeoylquinic acid)
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SMILES for NP0338287 (3,5-Di-O-caffeoylquinic acid)
O[C@H]1[C@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)C[C@@](O)(C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(=O)O
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INCHI for NP0338287 (3,5-Di-O-caffeoylquinic acid)
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
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Synonyms
ValueSource
(1S,3R,4S,5R)-1,3,4,5-Tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoateChEBI
3,5-DCQAChEBI
3,5-Dicaffeoylquinic acidChEBI
Isochlorogenic acid aChEBI
Quinic acid 3,5-di-O-caffeateChEBI
(1S,3R,4S,5R)-1,3,4,5-Tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoic acidGenerator
3,5-DicaffeoylquinateGenerator
Isochlorogenate aGenerator
Quinate 3,5-di-O-caffeateGenerator
Quinic acid 3,5-di-O-caffeic acidGenerator
DicaffeoylquinateGenerator
3,5-Di-O-caffeoyl quinateGenerator
3,5-Di-O-caffeoylquinateGenerator
Chemical FormulaC25H24O12
Average Mass516.4509 Da
Monoisotopic Mass516.12678 Da
IUPAC Name(1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid
Traditional Name(1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@H]1[C@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)C[C@@](O)(C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(=O)O
InChI Identifier
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
InChI KeyKRZBCHWVBQOTNZ-PSEXTPKNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentQuinic acids and derivatives  
Alternative Parents
Substituents
  • Quinic acid
    • 

  • Cinnamic acid or derivatives
    • 

  • Coumaric acid or derivatives
    • 

  • Hydroxycinnamic acid or derivatives
    • 

  • Cinnamic acid ester
    • 

  • Tricarboxylic acid or derivatives
    • 

  • Catechol
    • 

  • Styrene
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Cyclohexanol
    • 

  • Fatty acid ester
    • 

  • Phenol
    • 

  • Fatty acyl
    • 

  • Hydroxy acid
    • 

  • Monocyclic benzene moiety
    • 

  • Alpha-hydroxy acid
    • 

  • Benzenoid
    • 

  • Tertiary alcohol
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.05ALOGPS
logP2.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area211.28 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.76 m³·mol⁻¹ChemAxon
Polarizability49.46 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0029280  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002628  
KNApSAcK IDNot Available
Chemspider ID22912767  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCynarine  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID65751  
Good Scents IDNot Available
References
General References
  1. Choi SZ, Choi SU, Lee KR: Phytochemical constituents of the aerial parts from Solidago virga-aurea var. gigantea. Arch Pharm Res. 2004 Feb;27(2):164-8. doi: 10.1007/BF02980100. [PubMed:15022716  ] 
  2. An RB, Sohn DH, Jeong GS, Kim YC: In vitro hepatoprotective compounds from Suaeda glauca. Arch Pharm Res. 2008 May;31(5):594-7. doi: 10.1007/s12272-001-1198-1. Epub 2008  May 15. [PubMed:18481014  ] 
  3. Giner E, El Alami M, Manez S, Recio MC, Rios JL, Giner RM: Phenolic substances from Phagnalon rupestre protect against 2,4,6-trinitrochlorobenzene-induced contact hypersensitivity. J Nat Prod. 2011 May 27;74(5):1079-84. doi: 10.1021/np100934u. Epub 2011 Apr 6. [PubMed:21469692  ]