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Zaluzanin C

CAT: 0804-HY-N15415Size: 1 EachDry Ice: NoHazardous: No
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Description
Zaluzanin C is a sesquiterpene lactone. Zaluzanin C has anti-inflammatory activity and can inhibit the production of mtROS, block the NF-κB signaling pathway, and reduce the production of TNF-α. In addition, Zaluzanin C can inhibit the differentiation of 3T3-L1 preadipocytes into mature adipocytes[1][2][3].
CAS Number
16838-87-2
UNSPSC
12352005
Target
NF-κB; PPAR; Reactive Oxygen Species (ROS)
Related Pathways
Cell Cycle/DNA Damage; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB; Vitamin D Related/Nuclear Receptor
Field of Research
Inflammation/Immunology
Smiles
C=C1[C@]2([H])[C@]3([H])[C@](CCC([C@]2([H])C[C@@H]1O)=C)([H])C(C(O3)=O)=C
Molecular Formula
C15H18O3
Molecular Weight
246.30
References & Citations
[1]Valkute TR, et al. Synthesis and anticancer studies of Michael adducts and Heck arylation products of sesquiterpene lactones, zaluzanin D and zaluzanin C from Vernonia arborea. RSC Adv. 2018 Nov 14;8 (67) :38289-38304.|[2]Kwak SH, et al. Zaluzanin C Inhibits Differentiation of 3T3-L1 Preadipocytes into Mature Adipocytes. J Obes Metab Syndr. 2019 Jun;28 (2) :105-111.|[3]Jung JW, et al. Zaluzanin C Alleviates Inflammation and Lipid Accumulation in Kupffer Cells and Hepatocytes by Regulating Mitochondrial ROS. Molecules. 2023 Nov 8;28 (22) :7484.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Zaluzanin C

Zaluzanin C is a sesquiterpene lactone that is decahydroazuleno[4,5-b]furan-2(3H)-one substituted by methylidene groups at positions 3, 6 and 9 and a hydroxy group at position 8. It has a role as a metabolite and an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is an organic heterotricyclic compound, a secondary alcohol, a guaiane sesquiterpenoid, a gamma-lactone and a sesquiterpene lactone.

CAS Number16838-87-2
PubChem CID72646
IUPAC Name(3aS,6aR,8S,9aR,9bS)-8-hydroxy-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
Molecular FormulaC15H18O3
Molecular Weight246.30
XLogP1.3
Topological Polar Surface Area46.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Heavy Atom Count18
Formal Charge0
Complexity462
SMILES
C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O)OC(=O)C2=C
InChI
InChI=1S/C15H18O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-14,16H,1-6H2/t10-,11-,12-,13-,14-/m0/s1
InChIKey
XFVLNEYIZGZDHP-PEDHHIEDSA-N
Chemical Structure
2D Structure
2D structure of Zaluzanin C
CAS: 16838-87-2
CID: 72646
Formula: C15H18O3
MW: 246.30
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight246.30
XLogP31.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass246.125594432
Monoisotopic Mass246.125594432
Topological Polar Surface Area46.5 Ų
Heavy Atom Count18
Formal Charge0
Complexity462
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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