NP-MRD: Showing NP-Card for 3,5-Dicaffeoylquinic acid (NP0044041)

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Record Information

Version

1.0

Created at

2021-11-12 23:46:53 UTC

Updated at

2021-11-26 17:44:45 UTC

NP-MRD ID

NP0044041

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-Dicaffeoylquinic acid

Description

3,5-Dicaffeoylquinic acid is found in Alternaria alternata, Antonia ovata, Arnica montana, Arnica montana cv.ARBO , Artemisia capillaris , Artemisia maritima, Aster indicus, Aster koraiensis, Aster scaber, Baccharis dracunculifolia, Baccharis gaudichaudiana DC, Bidens pilosa, Brickellia cavanillesii, Bridelia ferruginea, Centella asiatica, Chaerophyllum hirsutum, Glebionis coronaria, Chrysanthemum morifolium, Corchorus olitorius, Crassocephalum crepidioides, Cressa cretica, Cussonia arborea, Cydonia oblonga , Daucus carota , Dipsacus asper, Eupatorium perfoliatum, Gardenia jasminoides, Scorzonera latifolia, Hedera rhombea, Helichrysum italicum, Helichrysum stoechas, Hieracium gymnocephalum, Ilex paraguariensis, Ilex taubertiana, Ipomoea batatas , Ipomoea cairica, Ipomoea pes-caprae, Lactuca formosana, Lactuca indica, Lapsana communis, Lonicera japonica , Lonicera somolis, Neurolaena lobata, Ostericum grosseserratum, Ostericum koreanum, Petasites japonicus, Phagnalon rupestre, Psydrax schimperiana, Pyrus communis, Rhaponticum carthamoides, Scorzonera pseudodivaricata, Leontodon autumnalis, Selaginella delicatula, Smallanthus sonchifolius, Solidago canadensis, Sphagneticola calendulacea, Strychnos axillaris, Vaccinium arctostaphylos , Wedelia prostrata, Werneria nubigena, Xanthium strumarium and Youngia japonica. It was first documented in 2002 (PMID: 12494749).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100462D          

 37 39  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7561   -2.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  4  5  1  0  0  0  0
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  5 20  1  0  0  0  0
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  2 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END

     RDKit          3D

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 17 48  1  0
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M  END


  Mrv1652311132100462D          

 37 39  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044041

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1[C@@H](CC(O)(C[C@H]1OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O)OC(=O)\C=C\C1=CC(O)=C(O)C=C1

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

> <INCHI_KEY>
KRZBCHWVBQOTNZ-RDJMKVHDSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.4509

> <EXACT_MASS>
516.126776232

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.56343159261979

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.158230316666666

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.907552884792997

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2760207075026906

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6040694695270155

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999997

> <JCHEM_REFRACTIVITY>
126.76419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-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       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.278  -5.570   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.724  -5.570   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.263  -5.517   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       3.908  -4.264   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   34   35                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19   14                                                            
CONECT   20    5                                                            
CONECT   21    4   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   29                                                            
CONECT   33   28                                                            
CONECT   34    2                                                            
CONECT   35    2   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
3,5-DCQA	MeSH
3,5-Dicaffeoylquinic acid	MeSH

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4509 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1[C@@H](CC(O)(C[C@H]1OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O)OC(=O)\C=C\C1=CC(O)=C(O)C=C1

InChI Identifier

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

InChI Key

KRZBCHWVBQOTNZ-RDJMKVHDSA-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
Alternaria alternata	LOTUS Database	35616633
Antonia ovata	LOTUS Database	35616633
Arnica montana	LOTUS Database	35616633
Arnica montana cv.ARBO	Plant	KNApSAcK
Artemisia capillaris	Plant	KNApSAcK
Artemisia maritima	LOTUS Database	35616633
Aster indicus	LOTUS Database	35616633
Aster koraiensis	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Baccharis gaudichaudiana DC	Plant	KNApSAcK
Bidens pilosa	LOTUS Database	35616633
Brickellia cavanillesii	LOTUS Database	35616633
Bridelia ferruginea	LOTUS Database	35616633
Centella asiatica	LOTUS Database	35616633
Chaerophyllum hirsutum	Plant	KNApSAcK
Chrysanthemum coronarium	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Coffea arabica L.	FooDB	PHYTOHUB
Coffea canephora	FooDB	PHYTOHUB
Corchorus olitorius	LOTUS Database	35616633
Crassocephalum crepidioides	LOTUS Database	35616633
Cressa cretica	LOTUS Database	35616633
Cussonia arborea	LOTUS Database	35616633
Cydonia oblonga	Plant	KNApSAcK
Cynara scolymus	FooDB	PHYTOHUB
Daucus carota	Plant	KNApSAcK
Dipsacus asper	LOTUS Database	35616633
Eupatorium perfoliatum	LOTUS Database	35616633
Gardenia jasminoides	LOTUS Database	35616633
Gelasia latifolia	LOTUS Database	35616633
Hedera rhombea	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Helichrysum stoechas	LOTUS Database	35616633
Hieracium gymnocephalum	LOTUS Database	35616633
Ilex paraguariensis	LOTUS Database	35616633
Ilex taubertiana	LOTUS Database	35616633
Ipomoea batatas	Plant	KNApSAcK
Ipomoea cairica	LOTUS Database	35616633
Ipomoea pes-caprae	LOTUS Database	35616633
Lactuca formosana	LOTUS Database	35616633
Lactuca indica	LOTUS Database	35616633
Lapsana communis L.	LOTUS Database	35616633
Lonicera japonica	Plant	KNApSAcK
Lonicera somolis	Plant	KNApSAcK
Neurolaena lobata	LOTUS Database	35616633
Ostericum grosseserratum	LOTUS Database	35616633
Ostericum koreanum	Plant	KNApSAcK
Petasites japonicus	LOTUS Database	35616633
Phagnalon rupestre	LOTUS Database	35616633
Psydrax schimperiana	LOTUS Database	35616633
Pyrus communis	LOTUS Database	35616633
Rhaponticum carthamoides	LOTUS Database	35616633
Scorzonera pseudodivaricata	LOTUS Database	35616633
Scorzoneroides autumnalis	Plant	KNApSAcK
Selaginella delicatula	LOTUS Database	35616633
Smallanthus sonchifolius	LOTUS Database	35616633
Solidago canadensis	LOTUS Database	35616633
Sphagneticola calendulacea	LOTUS Database	35616633
Strychnos axillaris	LOTUS Database	35616633
Vaccinium arctostaphylos	Plant	KNApSAcK
Wedelia prostrata	LOTUS Database	35616633
Werneria nubigena	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633
Youngia japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as quinic acids and derivatives. These 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)	3.28	ChemAxon
pKa (Strongest Basic)	-3.6	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	49.56 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

6474310

PDB ID

Not Available

ChEBI ID

Not Available

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 ]
Qin S, Wen X: [Simultaneous determination of 6 active components in Chrysanthemum morifolium by HPLC]. Zhongguo Zhong Yao Za Zhi. 2011 Jun;36(11):1474-7. [PubMed:22779181 ]

Showing NP-Card for 3,5-Dicaffeoylquinic acid (NP0044041)

MOL for NP0044041 (3,5-Dicaffeoylquinic acid)

3D MOL for NP0044041 (3,5-Dicaffeoylquinic acid)

3D SDF for NP0044041 (3,5-Dicaffeoylquinic acid)

3D-SDF for NP0044041 (3,5-Dicaffeoylquinic acid)

PDB for NP0044041 (3,5-Dicaffeoylquinic acid)

3D PDB for NP0044041 (3,5-Dicaffeoylquinic acid)

SMILES for NP0044041 (3,5-Dicaffeoylquinic acid)

INCHI for NP0044041 (3,5-Dicaffeoylquinic acid)

Structure for NP0044041 (3,5-Dicaffeoylquinic acid)

3D Structure for NP0044041 (3,5-Dicaffeoylquinic acid)