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Loganin

CAT: 0013-GTR19174632-03Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19174632-03Size:25 mg
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Description
Loganin is an iridoid glucoside that acts as a cyclooxygenase-1 (COX-1) inhibitor and suppresses TNF-α production. It exhibits antioxidant free-radical-scavenging activity and inhibits melanogenesis, making it a compound of interest for research in inflammation, oxidative stress, and dermatology.
CAS Number
18524-94-2
Product Name Alternative
BACE1, BChE, Apoptosis, AChE, Inhibitor, Loganin, Loganoside, inhibit, NF-κB, NFkB, NFκB, NF-kB
Field of Research
Cell Biology, Immunology & Inflammation, Neuroscience, Signal Transduction
Purity
99.01% (May vary between batches)
Solubility
DMSO:250 mg/mL (640.4 mM) ; H2O:20 mg/mL (51.23 mM) ;10% DMSO+40% PEG300+5% Tween 80+45% Saline:2 mg/mL (5.12 mM)
Smiles
COC (=O) C1=CO[C@@H] (O[C@@H]2O[C@H] (CO) [C@@H] (O) [C@H] (O) [C@H]2O) [C@@H]2[C@@H] (C) [C@@H] (O) C[C@H]12
Molecular Formula
C17H26O10
Molecular Weight
390.38
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

(-)-Loganin

Loganin is an iridoid monoterpenoid with formula C17H26O10 that is isolated from several plant species and exhibits neuroprotective and anti-inflammatory properties. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a neuroprotective agent, an anti-inflammatory agent, an EC 3.2.1.20 (alpha-glucosidase) inhibitor, an EC 3.4.23.46 (memapsin 2) inhibitor and a plant metabolite. It is a beta-D-glucoside, a methyl ester, a secondary alcohol, a cyclopentapyran, an iridoid monoterpenoid, an enoate ester and a monosaccharide derivative. It is functionally related to a loganetin.

CAS Number18524-94-2
PubChem CID87691
IUPAC Namemethyl (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-carboxylate
Molecular FormulaC17H26O10
Molecular Weight390.4
XLogP-1.4
Topological Polar Surface Area155
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count5
Heavy Atom Count27
Formal Charge0
Complexity580
SMILES
C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
InChI
InChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1
InChIKey
AMBQHHVBBHTQBF-UOUCRYGSSA-N
Chemical Structure
2D Structure
2D structure of (-)-Loganin
CAS: 18524-94-2
CID: 87691
Formula: C17H26O10
MW: 390.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight390.4
XLogP3-1.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count5
Exact Mass390.15259702
Monoisotopic Mass390.15259702
Topological Polar Surface Area155 Ų
Heavy Atom Count27
Formal Charge0
Complexity580
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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