fisetin

fisetin
Compound Structure:
Synonyms: 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one; 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one; 2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one; 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-chromen-4-one
Compound ID: NMPC-1053
PubChem ID:

5281614
Molecular Formula: C15H10O6
Canonical SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
InChIKey: XHEFDIBZLJXQHF-UHFFFAOYSA-N
About the compound:

Fisetin is a 7-hydroxyflavonol with additional hydroxy groups at positions 3, 3' and 4'. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an antioxidant, an anti-inflammatory agent, a metabolite, a plant metabolite and a geroprotector. It is a 3'-hydroxyflavonoid, a 7-hydroxyflavonol and a tetrahydroxyflavone. It is a conjugate acid of a fisetin(1-). Fisetin is an orally bioavailable naturally occurring polyphenol found in many fruits and vegetables, with potential antioxidant, neuroprotective, anti-inflammatory, antineoplastic, senolytic, and longevity promoting activities. Upon administration, fisetin, as an antioxidant, scavenges free radicals, protect cells from oxidative stress, and is able to upregulate glutathione. It inhibits pro-inflammatory mediators, such as tumor necrosis factor alpha (TNF-a), interleukin-6 (IL-6), and nuclear factor kappa B (NF-kB). Fisetin promotes cellular metabolism, reduces senescence, regulates sirtuin function and may promote longevity. Fisetin also exerts anti-cancer activity by inhibiting certain signaling pathways. It also inhibits certain anti-apoptotic proteins and induces apoptosis in susceptible cells.

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

• H335 (85.71%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

286.24 g/mol

XLogP3-AA

2

Hydrogen Bond Donor Count

4

Hydrogen Bond Acceptor Count

6

Rotatable Bond Count

1

Exact Mass

286.04773803 g/mol

Monoisotopic Mass

286.04773803 g/mol

Topological Polar Surface Area

107Ų

Heavy Atom Count

21

Formal Charge

0

Complexity

459

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source: PubChem                        
Source Species: Garcinia kola
Erythrina sigmoidea.
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