Chicoric acid

Chicoric acid
Compound Structure:
Synonyms: Chicoric acid;Cichoric Acid;L-Chicoric acid;(-)-Chicoric acid;dicaffeoyltartaric acid;(2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
Compound ID: NMPC-743
PubChem ID:

5281764

Molecular Formula: C22H18O12
Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)OC(C(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)C(=O)O)O)O
InChIKey: YDDGKXBLOXEEMN-IABMMNSOSA-N
About the compound:

Chicoric acid, also known as cichoric acid, is an organooxygen compound with notable roles as an HIV-1 integrase inhibitor and a geroprotector, functionally related to tetracarboxylic acids. Belonging to the hydroxycinnamic acid class, it's an organic compound within the phenylpropanoid family and is derived from both caffeic and tartaric acids. First isolated from Cichorium intybus (chicory), chicoric acid is also found in significant amounts in Echinacea (particularly E. purpurea), dandelion leaves, basil, lemon balm, and various aquatic plants, including algae and seagrasses. In research studies, chicoric acid has demonstrated the ability to stimulate phagocytosis both in vitro and in vivo. Additionally, it inhibits the activity of hyaluronidase, an enzyme that breaks down hyaluronic acid in the human body. Chicoric acid also helps in protecting collagen from damage caused by free radicals and inhibits the function of HIV-1 integrase.https://en.wikipedia.org/wiki/Chicoric_acid

GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H334 (100%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

474.4 g/mol

XLogP3-AA

2

Hydrogen Bond Donor Count

6

Hydrogen Bond Acceptor Count

12

Rotatable Bond Count

11

Exact Mass

474.07982601 g/mol

Monoisotopic Mass

474.07982601 g/mol

Topological Polar Surface Area

208Ų

Heavy Atom Count

34

Formal Charge

0

Complexity

740

Isotope Atom Count

0

Defined Atom Stereocenter Count

2

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

2

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid

Source: PubChem

Source Species: Echinacea purpurea
Eichhornia crassipes
Talinum triangulare
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