Natural Product (NP) Details

General Information of the NP (ID: NP6934)
Name
Chlorogenic acid
Synonyms
CHLOROGENIC ACID; 327-97-9; 3-Caffeoylquinic acid; 3-O-Caffeoylquinic acid; 3-(3,4-Dihydroxycinnamoyl)quinic acid; Chlorogenate; Heriguard; Hlorogenic acid; Caffeoyl quinic acid; NSC-407296; 3-Caffeoylquinate; UNII-318ADP12RI; 5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid; CCRIS 1400; Chlorogenic acid (8CI); EINECS 206-325-6; NSC 70861; NSC 407296; 3-trans-Caffeoylquinic acid; CHEMBL284616; 318ADP12RI; CHEBI:16112; 1,3,4,5-tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate); 3-(3,4-Dihydroxycinnamoyl)quinate
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Species Origin Imperata cylindrica ...     Click to Show/Hide
Imperata cylindrica
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Poales
Family: Poaceae
Genus: Imperata
Species: Imperata cylindrica
Prunus mume
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Rosales
Family: Rosaceae
Genus: Prunus
Species: Prunus mume
Vachellia nilotica
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Vachellia
Species: Vachellia nilotica
Disease Ulcerative colitis [ICD-11: DD71] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.426
 
MDCK Permeability
 -5.158
 
PAMPA
 +++
 
HIA
 - -
 
Distribution
VDss
 -0.012
 
PPB
 64.8%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 - - -
 
Excretion
CLplasma
 3.34
 
T1/2
 2.758
Toxicity
DILI
 - -
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 -
 
Respiratory
 - -
 
Human Hepatotoxicity
 +
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 -
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C16H18O9
PubChem CID
1794427
Canonical SMILES
C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
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
InChIKey
CWVRJTMFETXNAD-JUHZACGLSA-N
CAS Number
CAS 202650-88-2
ChEBI ID
CHEBI:16112
Herb ID
HBIN020363
ETMC ID
1550
SymMap ID
SMIT01671
TCMSP ID
MOL003871
TTD Drug ID
D02HCQ
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Regorafenib      Colorectal cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-xL  Molecule Info 
Pathway MAP
Up-regulation Expression CASP7  Molecule Info 
Pathway MAP
                    In-vitro Model PLC/PRF/5 CVCL_0485 Adult hepatocellular carcinoma Homo sapiens
Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Co-treatment with Regorafenib and CGA enhanced Regorafenib action, reducing its cytotoxicity in HCC cells.
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK2  Molecule Info 
Pathway MAP
                    In-vitro Model Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
Hep 3B2.1-7 CVCL_0326 Childhood hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Chlorogenic acid enhances the effects of 5-fluorouracil in human hepatocellular carcinoma cells through the inhibition of extracellular signal-regulated kinases.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Methotrexate      Leukaemia     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression GPT  Molecule Info 
Pathway MAP
Down-regulation Expression GPT  Molecule Info 
Pathway MAP
Down-regulation Expression LDHA  Molecule Info 
Pathway MAP
Down-regulation Expression NOS2  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Attennuation Pro-inflammatory and apoptotic mediators
Improvement Antioxidant competence
                    In-vivo Model 6-8 weeks old Male Wistar rats (150-200 g) were use in this study.
                    Experimental
                    Result(s)		 CGA has perfective effect against MTX-induced liver injury.
Target and Pathway
Target(s) Glucose-6-phosphate translocase (SLC37A4)  Molecule Info  [5]
KEGG Pathway Carbohydrate digestion and absorption Click to Show/Hide
Pathwhiz Pathway Gluconeogenesis Click to Show/Hide
2 Mitochondrial Electron Transport Chain
Reactome Glucose transport Click to Show/Hide
WikiPathways Metabolism of carbohydrates Click to Show/Hide
2 Hexose transport
References
Reference 1 Chlorogenic Acid Attenuates Dextran Sodium Sulfate-Induced Ulcerative Colitis in Mice through MAPK/ERK/JNK Pathway. Biomed Res Int. 2019 Apr 18;2019:6769789.
Reference 2 Chlorogenic Acid Improves the Regorafenib Effects in Human Hepatocellular Carcinoma Cells. Int J Mol Sci. 2018 May 19;19(5):1518.
Reference 3 Chlorogenic acid enhances the effects of 5-fluorouracil in human hepatocellular carcinoma cells through the inhibition of extracellular signal-regulated kinases. Anticancer Drugs. 2015 Jun;26(5):540-6.
Reference 4 Protective effect of Chlorogenic acid against methotrexate induced oxidative stress, inflammation and apoptosis in rat liver: An experimental approach. Chem Biol Interact. 2017 Jun 25;272:80-91.
Reference 5 Chlorogenic acid and synthetic chlorogenic acid derivatives: novel inhibitors of hepatic glucose-6-phosphate translocase. J Med Chem. 1997 Jan 17;40(2):137-45.
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