NP-MRD: Showing NP-Card for (1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid (NP0308869)

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Record Information

Version

2.0

Created at

2022-09-11 02:59:39 UTC

Updated at

2022-09-11 02:59:39 UTC

NP-MRD ID

NP0308869

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid

Description

Isochlorogenic acid b, also known as isochlorogenate b or 3,4-dicqa, 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. (1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid is found in Artemisia capillaris, Aster spathulifolius, Baccharis dracunculifolia, Ericameria paniculata, Coffea arabica, Coffea canephora, Cuscuta reflexa, Cynara cardunculus, Isertia pittieri, Neurolaena lobata, Reichardia tingitana, Rhaponticum carthamoides, Selaginella delicatula, Sphagneticola calendulacea and Wedelia prostrata. (1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid was first documented in 2022 (PMID: 35850836). Based on a literature review a small amount of articles have been published on Isochlorogenic acid b (PMID: 35930833) (PMID: 35921697) (PMID: 35851123) (PMID: 35772236).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112204592D          

 37 39  0  0  1  0            999 V2000
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9033    3.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4336    4.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9639    4.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211    4.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1460    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
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  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 26  1  4  0  0  0
 28 29  2  0  0  0  0
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 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
M  END

     RDKit          3D

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    5.5247    4.2771    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4060    3.5669   -1.2232 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6126    2.0514   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9201   -1.6764    0.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3444   -2.9670    0.3860 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1824   -3.6821    1.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1335   -5.1336    1.4076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7689   -5.6084    2.5856 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9057   -5.6855    0.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0306   -5.3415    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893   -4.1346   -0.2181 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.1065    1.4058   -1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5059    4.1065    2.2360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3362    2.8031    0.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3684   -0.3559   -0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0671   -3.5410   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
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 13  2  1  0
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 11 43  1  0
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 37 61  1  0
 20 49  1  0
M  END


  Mrv1652309112204592D          

 37 39  0  0  1  0            999 V2000
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.8605    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
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  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
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 24 25  1  0  0  0  0
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 28 29  2  0  0  0  0
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 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
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 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C[C@](O)(CC(OC(=O)C=CC2=CC=C(O)C(O)=C2)C1OC(=O)C=CC1=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(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/t19?,20?,23?,25-/m0/s1

> <INCHI_KEY>
UFCLZKMFXSILNL-VCFKWBLOSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.455

> <EXACT_MASS>
516.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.28545653684387

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
2.158230316666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.907569606355128

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3113236711174387

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246879196378373

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999997

> <JCHEM_REFRACTIVITY>
126.76419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic 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       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.153   5.893   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.143   7.607   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.133   8.787   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.626   7.875   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.670   6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.670   3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.004   6.160   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.005   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.339   4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.673   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      22.673   2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      24.006   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      21.339   1.540   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      21.339   0.000   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   21                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   14   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   30                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
Isochlorogenate b	Generator
Methyl-3,5-di-O-caffeoylquinate	MeSH
3,4-DICQA	MeSH
3,4-Dicaffeoylquinic acid	MeSH
3,4-Di-O-caffeoylquinic acid	MeSH
Methyl 3,5-di-O-caffeoyl quinate	MeSH

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4550 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1C[C@](O)(CC(OC(=O)C=CC2=CC=C(O)C(O)=C2)C1OC(=O)C=CC1=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(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/t19?,20?,23?,25-/m0/s1

InChI Key

UFCLZKMFXSILNL-VCFKWBLOSA-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
Artemisia capillaris	LOTUS Database	35616633
Aster spathulifolius	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Chrysothamnus paniculatus	LOTUS Database	35616633
Coffea arabica	LOTUS Database	35616633
Coffea canephora	LOTUS Database	35616633
Cuscuta reflexa	LOTUS Database	35616633
Cynara cardunculus	LOTUS Database	35616633
Isertia pittieri	LOTUS Database	35616633
Neurolaena lobata	LOTUS Database	35616633
Reichardia tingitana (L.) Roth	LOTUS Database	35616633
Rhaponticum carthamoides	LOTUS Database	35616633
Selaginella delicatula	LOTUS Database	35616633
Sphagneticola calendulacea	LOTUS Database	35616633
Wedelia prostrata	LOTUS Database	35616633

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

Quinic acid
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Tricarboxylic acid or derivatives
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Cyclohexanol
Fatty acyl
Benzenoid
Hydroxy acid
Monocyclic benzene moiety
Alpha-hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxide
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	2.16	ChemAxon
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.76 m³·mol⁻¹	ChemAxon
Polarizability	49.29 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129316855

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Y, Luo J, Gu YZ, Luo Y, Tan T, Liao ZG, Yang M: [Comparative analysis of powder and piece decocting processes of Yinqiao Powder based on determination of multiple primary components]. Zhongguo Zhong Yao Za Zhi. 2022 Jul;47(14):3788-3797. doi: 10.19540/j.cnki.cjcmm.20210913.302. [PubMed:35850836 ]
Bian GL, Wang DM, Cheng XJ, Li DQ: Rapid screening of natural-origin tyrosinase regulators from Vernonia anthelmintica (L.) Willd. by offline two-dimensional liquid chromatography coupled with mass spectrometry. J Pharm Biomed Anal. 2022 Sep 20;219:114978. doi: 10.1016/j.jpba.2022.114978. Epub 2022 Aug 1. [PubMed:35930833 ]
Tian Z, Sun L, Chi B, Du Z, Zhang X, Liu Y, Zhou H: Affinity ultrafiltration and UPLC-HR-Orbitrap-MS based screening of neuraminidase inhibitors from Angelica pubescens. J Chromatogr B Analyt Technol Biomed Life Sci. 2022 Oct 1;1208:123398. doi: 10.1016/j.jchromb.2022.123398. Epub 2022 Jul 28. [PubMed:35921697 ]
Liu JS, Zhang XY, Li B, Wei XP, Qi YD, Liu HT, Zhang BG: [Anti-inflammatory active component in raw materials of Ligustici Rhizoma et Radix based on spectrum-effect relationship]. Zhongguo Zhong Yao Za Zhi. 2022 Jun;47(12):3295-3302. doi: 10.19540/j.cnki.cjcmm.20220215.202. [PubMed:35851123 ]
Chang Y, Li C, Wang R, Li X, Guo S, Zhang W, Liu B: The metabolic profile elucidation of Lonicera japonica flos water extract and the metabolic characteristics evaluation of bioactive compounds in human gastrointestinal tract in vitro. J Pharm Biomed Anal. 2022 Sep 20;219:114906. doi: 10.1016/j.jpba.2022.114906. Epub 2022 Jun 23. [PubMed:35772236 ]
LOTUS database [Link]

Showing NP-Card for (1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid (NP0308869)

MOL for NP0308869 ((1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid)

3D MOL for NP0308869 ((1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid)

3D SDF for NP0308869 ((1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid)

3D-SDF for NP0308869 ((1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid)

PDB for NP0308869 ((1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid)

3D PDB for NP0308869 ((1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid)

SMILES for NP0308869 ((1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid)

INCHI for NP0308869 ((1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid)

Structure for NP0308869 ((1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid)

3D Structure for NP0308869 ((1s)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid)