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Loganic acid

CAT: 0804-HY-N0513-03Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0513-03Size:10 mg
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Description
Loganic acid is an iridoid isolated from cornelian cherry fruits. Loganic acid inhibits NF-κB signaling pathway, activates Nrf2 signaling pathway, exhibits anti-inflammatory activity. Loganic acid can modulate diet-induced atherosclerosis and redox status. Loganic acid has strong free radical scavenging activity and remarkable cyto-protective effect against heavy metal mediated toxicity. Loganic acid is orally active[1][2][3][4].
CAS Number
22255-40-9
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Keap1-Nrf2; NF-κB; Phosphatase; Reactive Oxygen Species (ROS)
Type
Natural Products
Related Pathways
Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB
Applications
COVID-19-immunoregulation
Field of Research
Metabolic Disease; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/loganic-acid.html
Concentration
10mM
Purity
99.05
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
O[C@H]([C@@H](O)[C@@H]1O)[C@](O[C@@H]1CO)([H])O[C@H]2[C@@]([C@H]3C)([H])[C@@](C[C@@H]3O)([H])C(C(O)=O)=CO2
Molecular Formula
C16H24O10
Molecular Weight
376.36
Precautions
H302, H315, H319, H335
References & Citations
[1]Sozański T, et al. Loganic acid and anthocyanins from cornelian cherry (Cornus mas L.) fruits modulate diet-induced atherosclerosis and redox status in rabbits. Adv Clin Exp Med. 2018 Nov;27 (11) :1505-1513.|[2]Abirami A, et al. Antioxidant and cytoprotective properties of loganic acid isolated from seeds of Strychnos potatorum L. against heavy metal induced toxicity in PBMC model. Drug Chem Toxicol. 2019 Oct 23:1-11.|[3]Park E, et al., Osteoprotective Effects of Loganic Acid on Osteoblastic and Osteoclastic Cells and Osteoporosis-Induced Mice. Int J Mol Sci. 2020 Dec 28;22 (1) :233. |[4]Prakash AN, et al. Loganic acid protects against ulcerative colitis by inhibiting TLR4/NF-κB mediated inflammation and activating the SIRT1/Nrf2 anti-oxidant responses in-vitro and in-vivo. Int Immunopharmacol. 2023 Sep;122:110585.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Loganic Acid

Loganic acid is a cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by beta-D-glucosyloxy, hydroxy and methyl groups respectively. It has a role as a plant metabolite. It is a glucoside, a cyclopentapyran and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a loganate.

CAS Number22255-40-9
PubChem CID89640
IUPAC Name(1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
Molecular FormulaC16H24O10
Molecular Weight376.36
XLogP-1.7
Topological Polar Surface Area166
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Heavy Atom Count26
Formal Charge0
Complexity565
SMILES
C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
InChI
InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6+,8-,9+,10+,11+,12-,13+,15-,16-/m0/s1
InChIKey
JNNGEAWILNVFFD-CDJYTOATSA-N
Chemical Structure
2D Structure
2D structure of Loganic Acid
CAS: 22255-40-9
CID: 89640
Formula: C16H24O10
MW: 376.36
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight376.36
XLogP3-1.7
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass376.13694696
Monoisotopic Mass376.13694696
Topological Polar Surface Area166 Ų
Heavy Atom Count26
Formal Charge0
Complexity565
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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