Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C7H12O6 |
Molecular Weight | 192.1666 |
Optical Activity | ( - ) |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O
InChI
InChIKey=AAWZDTNXLSGCEK-WYWMIBKRSA-N
InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1
Molecular Formula | C7H12O6 |
Molecular Weight | 192.1666 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Quinic acid is an acid obtained from cinchona bark, coffee beans, tobacco leaves, carrot leaves, apples, etc. For over 50 years, hippuric/quinic acids were believed to have no biological efficacy, but in 2009th these components were identified as major dietary components, and not simply originating from environmental pollution as previously had been thought. Quinic acid has been shown to possess radioprotection, anti-neuroinflammatory, and anti-oxidant activities. It also inhibits the TNF-α-stimulated induction of vascular cell adhesion molecule-1 (VCAM-1) by inhibiting the MAP kinase and NF-κB signaling pathways, which may explain the ability of QA to inhibit vascular inflammation such as atherosclerosis.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: map04010 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29032340 |
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Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29032340 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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The anti-HIV activity and mechanisms of action of pure compounds isolated from Rosa damascena. | 1996 Dec 4 |
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Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase. | 1996 Jun 25 |
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Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. | 1998 Jan |
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Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication. | 1999 Feb 11 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18844285
hippuric/quinic acids were identified as major dietary components, and not simply originating from environmental pollution as previously had been thought.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29032340
Quinic acid (QA) inhibits the TNF-α-stimulated induction of vascular cell adhesion molecule-1 (VCAM-1) in VSMC by inhibiting the MAP kinase and NF-κB signaling pathways and the adhesion capacity of VSMC, which may explain the ability of QA to inhibit vascular inflammation such as atherosclerosis. Pre-incubation of MOVAS cells, the mouse vascular smooth muscle cell line for 2h with QA (0.1, 1 and 10 μg/mL) dose-dependently inhibits TNF-α-induced mRNA and protein expression of VCAM-1 and monocyte adhesion.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 14:59:39 GMT 2023
by
admin
on
Fri Dec 15 14:59:39 GMT 2023
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Record UNII |
058C04BGYI
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
227 (Number of products:2)
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m9445
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77-95-2
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QUINIC ACID
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1427232
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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