NP-MRD: Showing NP-Card for Neochlorogenic acid (NP0137488)

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Record Information

Version

2.0

Created at

2022-05-30 16:53:55 UTC

Updated at

2024-09-03 04:16:33 UTC

NP-MRD ID

NP0137488

Natural Product DOI

https://doi.org/10.57994/0708

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neochlorogenic acid

Description

5-Caffeoylquinic acid, also known as neochlorogenate or caffeoyl quinate, 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. 5-Caffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-Caffeoylquinic acid has been detected, but not quantified in, a few different foods, such as coffee and coffee products, fruits, and pears. This could make 5-caffeoylquinic acid a potential biomarker for the consumption of these foods. Neochlorogenic acid is found in Acer truncatum, Antonia ovata, Artemisia jacutica, Aster koraiensis, Astragalus robustus, Betula pendula, Betula pubescens, Brassica oleracea, Calligonum leucocladum, Camellia sinensis, Caragana spinosa, Carallia brachiata, Centaurea bracteata, Centaurea cyanus, Centaurea horrida, Centaurea jacea, Chrysanthemum morifolium, Cichorium intybus, Coffea canephora, Cussonia arborea, Cyclocarya paliurus, Cydonia oblonga, Cynara cardunculus, Dactylis glomerata, Eriobotrya japonica, Eupatorium perfoliatum, Euphorbia hirta, Euphorbia tirucalli, Ferula elaeochytris, Glycine max, Hedera helix, Helichrysum italicum, Helichrysum stoechas, Hydrangea macrophylla, Hydrastis canadensis, Hypericum androsaemum, Hypericum perforatum, Ilex paraguariensis, Ipomoea batatas, Lactuca indica, Laserpitium latifolium, Lonicera bournei, Lonicera japonica, Matricaria chamomilla, Molineria capitulata, Morus nigra, Ophiorrhiza pumila, Panzerina lanata, Peucedanum japonicum, Plantago lanceolata, Prunus avium, Prunus cerasus, Prunus domestica, Prunus dulcis, Prunus persica, Pyrus communis, Rhaponticum carthamoides, Rubus ulmifolius, Solanum lycocarpum, Solanum paniculatum, Solidago canadensis, Sorbus aucuparia, Sorbus torminalis, Spinacia oleracea, Spondias mombin, Stachys palustris, Symphyotrichum salignum, Vaccinium corymbosum, Viburnum dilatatum, Viburnum opulus, Vigna radiata, Werneria nubigena, Xanthium strumarium and Zanthoxylum piperitum. Neochlorogenic acid was first documented in 2013 (PMID: 24079179). A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 5-hydroxy group of quinic acid (PMID: 24619353) (PMID: 24842397).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310081920262D          

 30 31  0  0  1  0            999 V2000
    6.4302    1.2375    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1352   -4.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5225   -5.1406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3107   -4.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -3.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  4  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 16  6  1  0  0  0  0
 16  7  1  0  0  0  0
 16 15  1  6  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 11 19  1  6  0  0  0
 20 13  2  0  0  0  0
 14 21  1  6  0  0  0
 22 15  2  0  0  0  0
 23 15  1  0  0  0  0
 16 24  1  1  0  0  0
 12 25  1  1  0  0  0
 25 13  1  0  0  0  0
 26  2  1  0  0  0  0
 27  4  1  0  0  0  0
 11 28  1  1  0  0  0
 12 29  1  6  0  0  0
 14 30  1  6  0  0  0
M  END

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.2903    0.0924    2.7467 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801    0.1205    1.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510    0.0184    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.0506    0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7653   -0.0426    0.1240 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6451   -0.1741    1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0047   -0.2561    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4799   -0.2083   -0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8489   -0.3005   -0.6194 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -0.0740   -1.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0343   -0.0248   -2.7901 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297    0.0078   -1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727    0.2500    0.5089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8599    0.3573    0.4569 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4533   -0.8358   -0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9395   -0.9042   -0.0553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5089   -1.2852   -1.2876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2965   -1.9181    0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8975   -1.7844    2.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0727   -3.0190    0.6814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4381    0.4415    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7954    1.4944   -0.5210 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5229    2.6697   -0.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483    1.6663   -0.1179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5899    2.1302   -1.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3669   -0.0840    2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    0.1569   -0.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3080   -0.2142    2.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6678   -0.3609    1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2544   -0.2728   -1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9892   -0.0775   -3.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137    0.1137   -2.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375    0.3182    1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138   -0.8741   -1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9489   -1.7359    0.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3548   -1.7756   -1.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7893   -3.3450    1.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2482    0.6369    1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5406    0.4602    0.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109    1.1594   -1.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576    3.4652   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177    2.4100    0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6085    1.5475   -1.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  4  5  1  0
  5 12  2  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  3  2  1  0
  2  1  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 16 18  1  0
 18 20  1  0
 18 19  2  0
  6  5  1  0
 24 14  1  0
  3 26  1  0
  4 27  1  0
 12 32  1  0
 11 31  1  0
  9 30  1  0
  7 29  1  0
  6 28  1  0
 14 33  1  1
 15 34  1  0
 15 35  1  0
 17 36  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  6
 23 41  1  0
 24 42  1  1
 25 43  1  0
 20 37  1  0
M  END


  Mrv1652310081920262D          

 30 31  0  0  1  0            999 V2000
    6.4302    1.2375    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1352   -4.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5225   -5.1406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3107   -4.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -3.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  4  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 16  6  1  0  0  0  0
 16  7  1  0  0  0  0
 16 15  1  6  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 11 19  1  6  0  0  0
 20 13  2  0  0  0  0
 14 21  1  6  0  0  0
 22 15  2  0  0  0  0
 23 15  1  0  0  0  0
 16 24  1  1  0  0  0
 12 25  1  1  0  0  0
 25 13  1  0  0  0  0
 26  2  1  0  0  0  0
 27  4  1  0  0  0  0
 11 28  1  1  0  0  0
 12 29  1  6  0  0  0
 14 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0137488

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1

> <INCHI_KEY>
CWVRJTMFETXNAD-NXLLHMKUSA-N

> <FORMULA>
C16H18O9

> <MOLECULAR_WEIGHT>
354.3087

> <EXACT_MASS>
354.095082174

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.11854824161928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-0.26852975799999984

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.20854914523281

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3338531471838464

> <JCHEM_PKA_STRONGEST_BASIC>
-3.231823980915407

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
83.2347

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
neochlorogenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-19         0                                  
HETATM    1  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.852  -8.236   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.575  -9.596   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.313  -8.182   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.129  -6.984   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      12.003  -0.770   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       8.002   0.000   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      10.669  -6.160   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       9.336  -3.850   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       8.002  -6.160   0.000  0.00  0.00           H+0
CONECT    1    3    8                                                       
CONECT    2    4    8   26                                                  
CONECT    3    1    9                                                       
CONECT    4    2   13   27                                                  
CONECT    5    8   10                                                       
CONECT    6   11   16                                                       
CONECT    7   12   16                                                       
CONECT    8    1    2    5                                                  
CONECT    9    3   10   17                                                  
CONECT   10    5    9   18                                                  
CONECT   11    6   14   19   28                                             
CONECT   12    7   14   25   29                                             
CONECT   13    4   20   25                                                  
CONECT   14   11   12   21   30                                             
CONECT   15   16   22   23                                                  
CONECT   16    6    7   15   24                                             
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25   12   13                                                       
CONECT   26    2                                                            
CONECT   27    4                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   14                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
(1R,3R,4S,5R)-3-[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic acid	ChEBI
Caffeoyl quinic acid	ChEBI
Neochlorogenate	ChEBI
Neochlorogenic acid	ChEBI
trans-5-O-Caffeoyl-D-quinate	ChEBI
trans-Neochlorogenic acid	ChEBI
(1R,3R,4S,5R)-3-[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylate	Generator
Caffeoyl quinate	Generator
trans-5-O-Caffeoyl-D-quinic acid	Generator
trans-Neochlorogenate	Generator
5-Caffeoylquinate	Generator
5-O-Caffeoylquinic acid	MeSH
5'-O-Caffeoylquinic acid	MeSH

Chemical Formula

C₁₆H₁₈O₉

Average Mass

354.3087 Da

Monoisotopic Mass

354.09508 Da

IUPAC Name

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

Traditional Name

neochlorogenic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)O[C@]1([H])C[C@](O)(C[C@@]([H])(O)[C@]1([H])O)C(O)=O

InChI Identifier

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1

InChI Key

CWVRJTMFETXNAD-NXLLHMKUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD3OD, experimental)	jaewoo.choi@oregonstate.edu	Not Available	Not Available	2023-06-28	View Spectrum

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
Acer truncatum	LOTUS Database	35616633
Antonia ovata	LOTUS Database	35616633
Artemisia jacutica	LOTUS Database	35616633
Aster koraiensis	LOTUS Database	35616633
Astragalus robustus	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Betula pubescens	LOTUS Database	35616633
Brassica oleracea	LOTUS Database	35616633
Calligonum leucocladum	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Caragana spinosa	LOTUS Database	35616633
Carallia brachiata	LOTUS Database	35616633
Centaurea bracteata	LOTUS Database	35616633
Centaurea cyanus	LOTUS Database	35616633
Centaurea horrida	LOTUS Database	35616633
Centaurea jacea	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Cichorium intybus	LOTUS Database	35616633
Coffea canephora	LOTUS Database	35616633
Cussonia arborea	LOTUS Database	35616633
Cyclocarya paliurus	LOTUS Database	35616633
Cydonia oblonga	LOTUS Database	35616633
Cynara cardunculus	LOTUS Database	35616633
Dactylis glomerata	LOTUS Database	35616633
Eriobotrya japonica	LOTUS Database	35616633
Eupatorium perfoliatum	LOTUS Database	35616633
Euphorbia hirta	LOTUS Database	35616633
Euphorbia tirucalli	LOTUS Database	35616633
Ferula elaeochytris	LOTUS Database	35616633
Glycine max	LOTUS Database	35616633
Hedera helix	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Helichrysum stoechas	LOTUS Database	35616633
Hydrangea macrophylla	LOTUS Database	35616633
Hydrastis canadensis	LOTUS Database	35616633
Hypericum androsaemum	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Ilex paraguariensis	LOTUS Database	35616633
Ipomoea batatas	LOTUS Database	35616633
Lactuca indica	LOTUS Database	35616633
Laserpitium latifolium	LOTUS Database	35616633
Lonicera bournei Hemsl.	LOTUS Database	35616633
Lonicera japonica	LOTUS Database	35616633
Matricaria chamomilla	LOTUS Database	35616633
Molineria capitulata	LOTUS Database	35616633
Morus nigra	LOTUS Database	35616633
Ophiorrhiza pumila	LOTUS Database	35616633
Panzerina lanata	LOTUS Database	35616633
Peucedanum japonicum	LOTUS Database	35616633
Plantago lanceolata	LOTUS Database	35616633
Prunus avium	LOTUS Database	35616633
Prunus cerasus	LOTUS Database	35616633
Prunus domestica	LOTUS Database	35616633
Prunus dulcis	LOTUS Database	35616633
Prunus persica	LOTUS Database	35616633
Pyrus communis	LOTUS Database	35616633
Rhaponticum carthamoides	LOTUS Database	35616633
Rubus ulmifolius	LOTUS Database	35616633
Solanum lycocarpum	LOTUS Database	35616633
Solanum paniculatum	LOTUS Database	35616633
Solidago canadensis	LOTUS Database	35616633
Sorbus aucuparia	LOTUS Database	35616633
Sorbus torminalis	LOTUS Database	35616633
Spinacia oleracea	LOTUS Database	35616633
Spondias mombin	LOTUS Database	35616633
Stachys palustris	LOTUS Database	35616633
Symphyotrichum x salignum	LOTUS Database	35616633
Vaccinium corymbosum	LOTUS Database	35616633
Viburnum dilatatum	LOTUS Database	35616633
Viburnum opulus	LOTUS Database	35616633
Vigna radiata	LOTUS Database	35616633
Werneria nubigena	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633
Zanthoxylum piperitum	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 or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Fatty acyl
Hydroxy acid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha-hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cinnamate ester (CHEBI:16384 )
cyclitol carboxylic acid (CHEBI:16384 )
Caffeate derivatives (C17147 )

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	0.17	ALOGPS
logP	-0.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	33.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0240477

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020490

KNApSAcK ID

C00030807

Chemspider ID

Not Available

KEGG Compound ID

C17147

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Caffeoylquinic acid

METLIN ID

Not Available

PubChem Compound

5280633

PDB ID

Not Available

ChEBI ID

16384

Good Scents ID

Not Available

References

General References

Gaivelyte K, Jakstas V, Razukas A, Janulis V: Variation in the contents of neochlorogenic acid, chlorogenic acid and three quercetin glycosides in leaves and fruits of Rowan (Sorbus) species and varieties from collections in Lithuania. Nat Prod Commun. 2013 Aug;8(8):1105-10. [PubMed:24079179 ]
Venter A, Joubert E, de Beer D: Nutraceutical value of yellow- and red-fleshed South African plums (Prunus salicina Lindl.): evaluation of total antioxidant capacity and phenolic composition. Molecules. 2014 Mar 11;19(3):3084-109. doi: 10.3390/molecules19033084. [PubMed:24619353 ]
Wang Y, Wen J, Zheng W, Zhao L, Fu X, Wang Z, Xiong Z, Li F, Xiao W: Simultaneous determination of neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid and geniposide in rat plasma by UPLC-MS/MS and its application to a pharmacokinetic study after administration of Reduning injection. Biomed Chromatogr. 2015 Jan;29(1):68-74. doi: 10.1002/bmc.3241. Epub 2014 May 20. [PubMed:24842397 ]

Showing NP-Card for Neochlorogenic acid (NP0137488)

MOL for NP0137488 (Neochlorogenic acid)

3D MOL for NP0137488 (Neochlorogenic acid)

3D SDF for NP0137488 (Neochlorogenic acid)

3D-SDF for NP0137488 (Neochlorogenic acid)

PDB for NP0137488 (Neochlorogenic acid)

3D PDB for NP0137488 (Neochlorogenic acid)

SMILES for NP0137488 (Neochlorogenic acid)

INCHI for NP0137488 (Neochlorogenic acid)

Structure for NP0137488 (Neochlorogenic acid)

3D Structure for NP0137488 (Neochlorogenic acid)