NP-MRD: Showing NP-Card for 4,5-Dicaffeoylquinic acid (NP0044042)

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Record Information

Version

1.0

Created at

2021-11-12 23:46:56 UTC

Updated at

2021-11-26 17:44:46 UTC

NP-MRD ID

NP0044042

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-Dicaffeoylquinic acid

Description

4,5-Di-O-caffeoylquinic acid, also known as 4,5-dcqa or isochlorogenic acid c, 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. 4,5-Di-O-caffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4,5-Di-O-caffeoylquinic 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. 4,5-Di-O-caffeoylquinic acid has also been detected, but not quantified in, several different foods, such as coffee and coffee products, eggplants, lettuces, pears, and yali pears. 4,5-Dicaffeoylquinic acid is found in Antonia ovata, Arnica montana, Artemisia annua , Artemisia capillaris , Artemisia montana, Artemisia princeps, Artemisia spp. , Aster koraiensis, Aster scaber, Athyrium filix-femina, Baccharis dracunculifolia, Bidens pilosa, Centaurea bracteata, Centaurea bracteata Scop., Centella asiatica, Chrysothamnus paniculatus, Coffea arabica , Coffea robusta, Cuscuta chinensis, Cussonia arborea, Echinacea pallida, Gardenia jasminoides, Helichrysum italicum, Ilex dumosa, Ipomoea batatas, Isertia pittieri, Lactuca indica, Neurolaena lobata, Nicotiana tabacum , Phagnalon rupestre, Pluchea sagittalis , Psydrax schimperiana, Pterocaulon virgatum , Rhaponticum carthamoides, Selaginella delicatula, Simira rubescens, Solidago canadensis, Sphagneticola calendulacea, Stevia rebaudiana, Streptocaulon juventas, Strychnos axillaris, Tessaria integrifolia and Withania somnifera. It was first documented in 2002 (PMID: 12494749). This could make 4,5-di-O-caffeoylquinic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100462D          

 37 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652311132100462D          

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 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
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 32 35  1  0  0  0  0
 31 36  1  0  0  0  0
  2 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044042

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H]1OC(=O)\C=C\C1=CC(O)=C(O)C=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)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

> <INCHI_KEY>
UFCLZKMFXSILNL-RVXRWRFUSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.4509

> <EXACT_MASS>
516.126776232

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.95837333059022

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.158230316666666

> <ALOGPS_LOGS>
-3.62

> <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>
126.76419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.278  -5.570   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.094  -4.264   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.739  -5.517   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.724  -5.570   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.668 -20.790   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.336 -19.250   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   37                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7   10                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11    4   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
CONECT   23   18                                                            
CONECT   24    3   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   32                                                            
CONECT   36   31                                                            
CONECT   37    2                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
4,5-Di-O-caffeoylquinate	Generator
4,5-Bis(3,4-dihydroxycinnamoyl)quinic acid	HMDB
4,5-DCQA	HMDB
4,5-Dicaffeoylquinic acid	HMDB
Isochlorogenic acid c	HMDB
(1R,3R,4S,5R)-3,4-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylate	Generator
3,4-Dicaffeoylquinic acid	MeSH
Isochlorogenic acid b	MeSH
Methyl-3,5-di-O-caffeoylquinate	MeSH
3,4-DICQA	MeSH
Methyl 3,5-di-O-caffeoyl quinate	MeSH
3,4-Di-O-caffeoylquinic acid	MeSH

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4509 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H]1OC(=O)\C=C\C1=CC(O)=C(O)C=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)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

InChI Key

UFCLZKMFXSILNL-RVXRWRFUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Deuterium oxide, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Deuterium oxide, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Deuterium oxide, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Deuterium oxide, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Deuterium oxide, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Deuterium oxide, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Deuterium oxide, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Deuterium oxide, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Deuterium oxide, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Deuterium oxide, 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
Antonia ovata	LOTUS Database	35616633
Arnica montana	LOTUS Database	35616633
Artemisia annua	Plant	KNApSAcK
Artemisia capillaris	Plant	KNApSAcK
Artemisia montana	LOTUS Database	35616633
Artemisia princeps	LOTUS Database	35616633
Artemisia spp.	Plant	KNApSAcK
Aster koraiensis	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Athyrium filix-femina	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633
Centaurea bracteata	LOTUS Database	35616633
Centaurea bracteata Scop.	Plant	KNApSAcK
Centella asiatica	LOTUS Database	35616633
Chrysothamnus paniculatus	Plant	KNApSAcK
Coffea arabica L.	Plant	KNApSAcK
Coffea canephora	Plant	KNApSAcK
Cuscuta chinensis	LOTUS Database	35616633
Cussonia arborea	LOTUS Database	35616633
Cynara scolymus	FooDB	PHYTOHUB
Echinacea pallida	LOTUS Database	35616633
Gardenia jasminoides	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Ilex dumosa	LOTUS Database	35616633
Ipomoea batatas	LOTUS Database	35616633
Isertia pittieri	LOTUS Database	35616633
Lactuca indica	LOTUS Database	35616633
Neurolaena lobata	LOTUS Database	35616633
Nicotiana tabacum	Plant	KNApSAcK
Phagnalon rupestre	LOTUS Database	35616633
Pluchea sagittalis	Plant	KNApSAcK
Psydrax schimperiana	LOTUS Database	35616633
Pterocaulon virgatum	Plant	KNApSAcK
Rhaponticum carthamoides	LOTUS Database	35616633
Selaginella delicatula	LOTUS Database	35616633
Simira rubescens	LOTUS Database	35616633
Solidago canadensis	Plant	KNApSAcK
Sphagneticola calendulacea	LOTUS Database	35616633
Stevia rebaudiana	LOTUS Database	35616633
Streptocaulon juventas	LOTUS Database	35616633
Strychnos axillaris	LOTUS Database	35616633
Tessaria integrifolia	LOTUS Database	35616633
Withania somnifera	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
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.05	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	ALOGPS
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	49.96 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

HMDB0030707

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002629

KNApSAcK ID

C00034768

Chemspider ID

4976335

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6474309

PDB ID

Not Available

ChEBI ID

390480

Good Scents ID

Not Available

References

General References

Tolonen A, Joutsamo T, Mattlla S, Kamarainen T, Jalonen J: Identification of isomeric dicaffeoylquinic acids from Eleutherococcus senticosus using HPLC-ESI/TOF/MS and 1H-NMR methods. Phytochem Anal. 2002 Nov-Dec;13(6):316-28. doi: 10.1002/pca.663. [PubMed:12494749 ]

Showing NP-Card for 4,5-Dicaffeoylquinic acid (NP0044042)

MOL for NP0044042 (4,5-Dicaffeoylquinic acid)

3D MOL for NP0044042 (4,5-Dicaffeoylquinic acid)

3D SDF for NP0044042 (4,5-Dicaffeoylquinic acid)

3D-SDF for NP0044042 (4,5-Dicaffeoylquinic acid)

PDB for NP0044042 (4,5-Dicaffeoylquinic acid)

3D PDB for NP0044042 (4,5-Dicaffeoylquinic acid)

SMILES for NP0044042 (4,5-Dicaffeoylquinic acid)

INCHI for NP0044042 (4,5-Dicaffeoylquinic acid)

Structure for NP0044042 (4,5-Dicaffeoylquinic acid)

3D Structure for NP0044042 (4,5-Dicaffeoylquinic acid)