NP-MRD: Showing NP-Card for Cryptochlorogenic acid (NP0045972)

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Record Information

Version

2.0

Created at

2022-03-17 19:46:16 UTC

Updated at

2025-02-11 15:42:39 UTC

NP-MRD ID

NP0045972

Natural Product DOI

https://doi.org/10.57994/0691

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cryptochlorogenic acid

Description

Cryptochlorogenic acid, also known as 4-caffeoylquinic acid or 4-O-(e)-caffeoylquinate, 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. Cryptochlorogenic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cryptochlorogenic acid is found, on average, in the highest concentration within a few different foods, such as coffee, robusta coffee, and arabica coffee and in a lower concentration in apples, tea, and sour cherries. Cryptochlorogenic acid has also been detected, but not quantified in, several different foods, such as strawberries, yali pears, peach (var.), Gooseberries, and eggplants. This could make cryptochlorogenic acid a potential biomarker for the consumption of these foods. Cryptochlorogenic acid is found in Antonia ovata, Camellia sinensis, Carallia brachiata, Centaurea cyanus, Cyclocarya paliurus, Dactylis glomerata, Hypericum perforatum, Ipomoea batatas, Nicotiana tabacum , Peucedanum japonicum, Platycodon grandiflorus, Prunus persica, Solidago canadensis, Viburnum dilatatum, Withania somnifera and Zanthoxylum piperitum. Cryptochlorogenic acid was first documented in 2013 (PMID: 23798877). A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 4-hydroxy group of (+)-quinic acid (PMID: 23829630) (PMID: 23973760) (PMID: 24061869).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218122D          

 25 26  0  0  0  0            999 V2000
    1.4139   -1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4138   -2.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6994   -2.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0151   -2.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0151   -1.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6993   -1.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6993   -0.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    0.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7298    1.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7298    2.2469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6992    1.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0153    3.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7298    3.8969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4443    3.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4443    2.6593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0153    2.6595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6992    2.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7298    4.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4443    5.1344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0154    5.1345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1587    2.2468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7296   -2.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6994   -3.5280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4442    4.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  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
  9 10  1  0  0  0  0
  9 12  2  0  0  0  0
 16 11  1  0  0  0  0
 11 17  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
 13 17  1  0  0  0  0
 17 18  1  1  0  0  0
 14 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 16 22  1  6  0  0  0
  4 23  1  0  0  0  0
  3 24  1  0  0  0  0
 11 10  1  6  0  0  0
 14 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0045972

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
GYFFKZTYYAFCTR-JUHZACGLSA-N

> <FORMULA>
C16H18O9

> <MOLECULAR_WEIGHT>
354.3087

> <EXACT_MASS>
354.095082174

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
34.16285338241827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-0.26852975799999984

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.208578519245334

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3907295079782185

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246160427306884

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
83.23469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.12e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.639  -2.736   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.639  -4.276   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.306  -5.046   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.028  -4.276   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.028  -2.736   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.305  -1.966   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.305  -0.426   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.028   0.344   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.028   1.884   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.362   2.654   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.362   4.194   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.305   2.654   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.029   6.504   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.362   7.274   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.696   6.504   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.696   4.964   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.029   4.964   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.305   4.194   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.362   8.814   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.696   9.584   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.029   9.584   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.030   4.194   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.362  -5.046   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.306  -6.586   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.696   8.044   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   16   17   10                                                  
CONECT   12    9                                                            
CONECT   13   14   17                                                       
CONECT   14   13   15   19   25                                             
CONECT   15   14   16                                                       
CONECT   16   11   15   22                                                  
CONECT   17   11   13   18                                                  
CONECT   18   17                                                            
CONECT   19   14   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16                                                            
CONECT   23    4                                                            
CONECT   24    3                                                            
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
4-(3,4-Dihydroxycinnamoyl)quinic acid	ChEBI
4-Caffeoylquinic acid	ChEBI
4-O-(e)-Caffeoylquinic acid	ChEBI
4-O-Caffeoylquinic acid	ChEBI
4-(3,4-Dihydroxycinnamoyl)quinate	Generator
4-Caffeoylquinate	Generator
4-O-(e)-Caffeoylquinate	Generator
4-O-Caffeoylquinate	Generator
Cryptochlorogenate	Generator
Cryptochlorogenic acid	ChEBI
4-O-trans-Caffeoylquinate	Generator

Chemical Formula

C₁₆H₁₈O₉

Average Mass

354.3087 Da

Monoisotopic Mass

354.09508 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

905-99-7

SMILES

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

InChI Identifier

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

InChI Key

GYFFKZTYYAFCTR-JUHZACGLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2023-06-28	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2023-06-17	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol, simulated)	[email protected]	Oregon State University	BENFRA	2023-06-20	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Antonia ovata	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Carallia brachiata	LOTUS Database	35616633
Centaurea cyanus	LOTUS Database	35616633
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Cyclocarya paliurus	LOTUS Database	35616633
Cydonia oblonga	FooDB	PHENOL EXPLORER
Dactylis glomerata	LOTUS Database	35616633
Daucus carota ssp. sativus	FooDB	PHENOL EXPLORER
Eriobotrya japonica	FooDB	KNAPSACK
Fragaria x ananassa	FooDB	PHENOL EXPLORER
Hypericum perforatum	LOTUS Database	35616633
Ipomoea batatas	LOTUS Database	35616633
Malus pumila	FooDB	PHENOL EXPLORER
Nicotiana tabacum	Plant	KNApSAcK
Peucedanum japonicum	LOTUS Database	35616633
Platycodon grandiflorus	LOTUS Database	35616633
Prunus armeniaca	FooDB	PHENOL EXPLORER
Prunus avium	FooDB	PHENOL EXPLORER
Prunus cerasus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus domestica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus persica	LOTUS Database	35616633
Prunus persica var. persica	FooDB	PHENOL EXPLORER
Pyrus communis	FooDB	18778075
Pyrus pyrifolia	FooDB	18778075
Ribes nigrum	FooDB	PHENOL EXPLORER
Ribes rubrum	FooDB	PHENOL EXPLORER
Ribes uva-crispa	FooDB	PHENOL EXPLORER
Rubus idaeus	FooDB	PHENOL EXPLORER
Solanum lycopersicum var. lycopersicum	FooDB	PHENOL EXPLORER
Solanum melongena	FooDB	Adrian J. Parr, Annie Ng, and Keith W. Waldron Ester-Linked Phenolic Components of Carrot Cell Wa...
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solidago canadensis	LOTUS Database	35616633
Vaccinium corymbosum	FooDB	PHENOL EXPLORER
Viburnum dilatatum	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Withania somnifera	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:75491 )
cyclitol carboxylic acid (CHEBI:75491 )

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	-2.1	ALOGPS
pKa (Strongest Acidic)	3.39	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	34.16 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

HMDB0030653

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002561

KNApSAcK ID

C00029540

Chemspider ID

22912773

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

75491

Good Scents ID

Not Available

References

General References

Fayek NM, Monem AR, Mossa MY, Meselhy MR: New triterpenoid acyl derivatives and biological study of Manilkara zapota (L.) Van Royen fruits. Pharmacognosy Res. 2013 Apr;5(2):55-9. doi: 10.4103/0974-8490.110505. [PubMed:23798877 ]
Amin ZA, Alshawsh MA, Kassim M, Ali HM, Abdulla MA: Gene expression profiling reveals underlying molecular mechanism of hepatoprotective effect of Phyllanthus niruri on thioacetamide-induced hepatotoxicity in Sprague Dawley rats. BMC Complement Altern Med. 2013 Jul 5;13:160. doi: 10.1186/1472-6882-13-160. [PubMed:23829630 ]
An H, Wang H, Lan Y, Hashi Y, Chen S: Simultaneous qualitative and quantitative analysis of phenolic acids and flavonoids for the quality control of Apocynum venetum L. leaves by HPLC-DAD-ESI-IT-TOF-MS and HPLC-DAD. J Pharm Biomed Anal. 2013 Nov;85:295-304. doi: 10.1016/j.jpba.2013.07.005. Epub 2013 Jul 19. [PubMed:23973760 ]
Park JB: Isolation and quantification of major chlorogenic acids in three major instant coffee brands and their potential effects on H2O2-induced mitochondrial membrane depolarization and apoptosis in PC-12 cells. Food Funct. 2013 Nov;4(11):1632-8. doi: 10.1039/c3fo60138b. [PubMed:24061869 ]

Showing NP-Card for Cryptochlorogenic acid (NP0045972)

MOL for NP0045972 (Cryptochlorogenic acid)

3D MOL for NP0045972 (Cryptochlorogenic acid)

3D SDF for NP0045972 (Cryptochlorogenic acid)

3D-SDF for NP0045972 (Cryptochlorogenic acid)

PDB for NP0045972 (Cryptochlorogenic acid)

3D PDB for NP0045972 (Cryptochlorogenic acid)

SMILES for NP0045972 (Cryptochlorogenic acid)

INCHI for NP0045972 (Cryptochlorogenic acid)

Structure for NP0045972 (Cryptochlorogenic acid)

3D Structure for NP0045972 (Cryptochlorogenic acid)