NP-MRD: Showing NP-Card for methyl 4-O-feruloyl-5-O-caffeoylquinate (NP0028618)

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Record Information

Version

1.0

Created at

2021-06-19 20:27:28 UTC

Updated at

2021-06-29 23:55:31 UTC

NP-MRD ID

NP0028618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-O-feruloyl-5-O-caffeoylquinate

Provided By

JEOL Database JEOL Logo

Description

methyl 4-O-feruloyl-5-O-caffeoylquinate is found in Ponkan fruit. It was first documented in 2005 (Nogata, Y., et al.). Based on a literature review very few articles have been published on Methyl 4-feruloyl-5-caffeoylquinate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122273D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192122273D          

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M  END
> <DATABASE_ID>
NP0028618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@]2([H])C([H])([H])[C@](O[H])(C(=O)OC([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@@]2([H])OC(=O)C(\[H])=C(/[H])C2=C([H])C([H])=C(O[H])C(OC([H])([H])[H])=C2[H])C([H])=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O12/c1-36-21-12-16(4-8-18(21)29)6-10-24(33)39-25-20(31)13-27(35,26(34)37-2)14-22(25)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h3-12,20,22,25,28-31,35H,13-14H2,1-2H3/b9-5+,10-6+/t20-,22-,25-,27+/m1/s1

> <INCHI_KEY>
RTLCSWCXZWROFK-YODDMHFOSA-N

> <FORMULA>
C27H28O12

> <MOLECULAR_WEIGHT>
544.509

> <EXACT_MASS>
544.158076342

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
55.14169760466692

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
2.450018428666666

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.950856825029973

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.122152272650792

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2468836164082333

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
136.01559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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  8 46  1  6
  7 44  1  0
  7 45  1  0
 25 58  1  6
  1 40  1  0
  1 41  1  0
  1 42  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.389  -0.079   1.747  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.988   0.181   1.858  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.201  -0.766   1.256  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.626  -1.741   0.653  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.290  -0.385   1.433  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.469   0.189   2.743  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.189  -1.624   1.374  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.404  -2.162  -0.042  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.333  -3.246   0.052  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.891  -1.058  -1.007  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.183  -0.557  -0.594  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.256  -1.265  -1.018  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.217  -2.264  -1.722  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.525  -0.693  -0.527  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.604   0.331   0.337  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.877   0.869   0.836  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.967   1.097  -0.017  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.152   1.637   0.482  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.239   1.952   1.831  0.00  0.00           C+0
HETATM   20  O   UNK     0     -10.413   2.480   2.296  0.00  0.00           O+0
HETATM   21  C   UNK     0      -8.166   1.745   2.703  0.00  0.00           C+0
HETATM   22  O   UNK     0      -8.400   2.108   4.005  0.00  0.00           O+0
HETATM   23  C   UNK     0      -7.346   1.872   4.932  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.981   1.208   2.196  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.913   0.132  -1.006  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.381  -0.243  -1.513  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.489  -0.349  -2.860  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.394  -0.138  -3.671  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.869  -0.770  -3.171  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.244  -0.937  -4.448  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.594  -1.339  -4.871  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.052  -0.922  -6.134  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.320  -1.290  -6.601  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.128  -2.087  -5.803  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.375  -2.481  -6.199  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.677  -2.515  -4.558  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.476  -3.306  -3.781  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.420  -2.156  -4.089  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.709   0.683   0.411  0.00  0.00           C+0
HETATM   40  H   UNK     0       3.641  -1.030   2.227  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.695  -0.080   0.696  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.924   0.723   2.263  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.269   0.816   2.876  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.782  -2.422   2.010  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.164  -1.396   1.828  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.473  -2.590  -0.429  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.774  -3.358  -0.815  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.965  -1.474  -2.020  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.409  -1.197  -0.904  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.709   0.799   0.739  0.00  0.00           H+0
HETATM   51  H   UNK     0      -7.903   0.870  -1.079  0.00  0.00           H+0
HETATM   52  H   UNK     0      -9.999   1.814  -0.174  0.00  0.00           H+0
HETATM   53  H   UNK     0     -10.263   2.624   3.251  0.00  0.00           H+0
HETATM   54  H   UNK     0      -7.693   2.192   5.920  0.00  0.00           H+0
HETATM   55  H   UNK     0      -6.461   2.465   4.682  0.00  0.00           H+0
HETATM   56  H   UNK     0      -7.106   0.805   4.994  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.125   1.035   2.841  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.319   0.952  -1.614  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.537  -0.924  -2.332  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.530  -0.751  -5.250  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.424  -0.297  -6.766  0.00  0.00           H+0
HETATM   62  H   UNK     0       5.647  -0.948  -7.577  0.00  0.00           H+0
HETATM   63  H   UNK     0       7.540  -2.118  -7.086  0.00  0.00           H+0
HETATM   64  H   UNK     0       7.287  -3.434  -4.313  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.099  -2.532  -3.122  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.048   1.478   0.385  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.635   1.164   0.751  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    3    1                                                       
CONECT    3    4    2    5                                                  
CONECT    4    3                                                            
CONECT    5    7   39    6    3                                             
CONECT    6    5   43                                                       
CONECT    7    5    8   44   45                                             
CONECT    8    7   10    9   46                                             
CONECT    9    8   47                                                       
CONECT   10    8   25   11   48                                             
CONECT   11   12   10                                                       
CONECT   12   14   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15   12   49                                                  
CONECT   15   16   14   50                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   51                                                  
CONECT   18   19   17   52                                                  
CONECT   19   20   21   18                                                  
CONECT   20   19   53                                                       
CONECT   21   22   24   19                                                  
CONECT   22   21   23                                                       
CONECT   23   22   54   55   56                                             
CONECT   24   16   21   57                                                  
CONECT   25   10   39   26   58                                             
CONECT   26   27   25                                                       
CONECT   27   28   26   29                                                  
CONECT   28   27                                                            
CONECT   29   30   27   59                                                  
CONECT   30   31   29   60                                                  
CONECT   31   32   30   38                                                  
CONECT   32   31   33   61                                                  
CONECT   33   32   34   62                                                  
CONECT   34   35   33   36                                                  
CONECT   35   34   63                                                       
CONECT   36   38   37   34                                                  
CONECT   37   36   64                                                       
CONECT   38   36   31   65                                                  
CONECT   39   25    5   66   67                                             
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    6                                                            
CONECT   44    7                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   20                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   29                                                            
CONECT   60   30                                                            
CONECT   61   32                                                            
CONECT   62   33                                                            
CONECT   63   35                                                            
CONECT   64   37                                                            
CONECT   65   38                                                            
CONECT   66   39                                                            
CONECT   67   39                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  138    0
END

RDKit          3D

67 69  0  0  0  0  0  0  0  0999 V2000
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 25 58  1  6
  1 40  1  0
  1 41  1  0
  1 42  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl 4-feruloyl-5-caffeoylquinic acid	Generator

Chemical Formula

C₂₇H₂₈O₁₂

Average Mass

544.5090 Da

Monoisotopic Mass

544.15808 Da

IUPAC Name

methyl (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

Traditional Name

methyl (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@]2([H])C([H])([H])[C@](O[H])(C(=O)OC([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@@]2([H])OC(=O)C(\[H])=C(/[H])C2=C([H])C([H])=C(O[H])C(OC([H])([H])[H])=C2[H])C([H])=C1O[H]

InChI Identifier

InChI=1S/C27H28O12/c1-36-21-12-16(4-8-18(21)29)6-10-24(33)39-25-20(31)13-27(35,26(34)37-2)14-22(25)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h3-12,20,22,25,28-31,35H,13-14H2,1-2H3/b9-5+,10-6+/t20-,22-,25-,27+/m1/s1

InChI Key

RTLCSWCXZWROFK-YODDMHFOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ponkan fruit	JEOL database	Nogata, Y., et al, Phytochemistry 56, 729 (2005)

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
Methoxyphenol
Tricarboxylic acid or derivatives
Anisole
Catechol
Methoxybenzene
Phenol ether
Phenoxy compound
Styrene
Alkyl aryl ether
Cyclohexanol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Enoate ester
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Ether
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	2.35	ALOGPS
logP	2.45	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	136.02 m³·mol⁻¹	ChemAxon
Polarizability	55.14 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

552741

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

637085

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nogata, Y., et al. (2005). Nogata, Y., et al, Phytochemistry 56, 729 (2005). Phytochem..

Showing NP-Card for methyl 4-O-feruloyl-5-O-caffeoylquinate (NP0028618)

MOL for NP0028618 (methyl 4-O-feruloyl-5-O-caffeoylquinate)

3D MOL for NP0028618 (methyl 4-O-feruloyl-5-O-caffeoylquinate)

3D SDF for NP0028618 (methyl 4-O-feruloyl-5-O-caffeoylquinate)

3D-SDF for NP0028618 (methyl 4-O-feruloyl-5-O-caffeoylquinate)

PDB for NP0028618 (methyl 4-O-feruloyl-5-O-caffeoylquinate)

3D PDB for NP0028618 (methyl 4-O-feruloyl-5-O-caffeoylquinate)

SMILES for NP0028618 (methyl 4-O-feruloyl-5-O-caffeoylquinate)

INCHI for NP0028618 (methyl 4-O-feruloyl-5-O-caffeoylquinate)

Structure for NP0028618 (methyl 4-O-feruloyl-5-O-caffeoylquinate)

3D Structure for NP0028618 (methyl 4-O-feruloyl-5-O-caffeoylquinate)