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Beauveriolide I

CAT: 0804-HY-N8355Size: 250 µgDry Ice: NoHazardous: No
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CAT#:0804-HY-N8355Size:250 µg
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Description
Beauveriolide I is the metabolite of Entomopathogenic Fungi Beauveria sp.. Beauveriolide I (1) exhibits moderate insecticidal activities against Spodoptera litura and Callosobruchus chinensis[1].
CAS Number
154491-55-1
UNSPSC
12352005
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/beauveriolide-i.html
Solubility
10 mM in DMSO
Smiles
O=C(N[C@H](C(N[C@@H]1CC(C)C)=O)C)[C@@H](NC(C[C@@](OC1=O)([H])[C@@H](C)CCCC)=O)CC2=CC=CC=C2
Molecular Formula
C27H41N3O5
Molecular Weight
487.63
References & Citations
[1]Mochizuki Keiko, et al. The Structures of Bioactive Cyclodepsipeptides, Beauveriolides I and II, Metabolites of Entomopathogenic Fungi Beauveria sp..
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Microbial Metabolite

Chemical Information

Beauveriolide I

Beauveriolide I is a cyclodepsipeptide with formula C27H41N3O5. It was originally isolated from the fungus Beauveria sp. FO-6979 during a screening program for inhibitors of lipid droplet accumulation in murine macrophages. It is an inhibitor of acyl-CoA: cholesterol acyltransferase (ACAT) and effective at reducing atherogenic lesions of the artery and heart in mouse models. It has a role as an antiatherosclerotic agent, a geroprotector, an antiatherogenic agent, an EC 2.3.1.26 (sterol O-acyltransferase) inhibitor and a fungal metabolite. It is a cyclodepsipeptide and a macrocycle.

CAS Number154491-55-1
PubChem CID9913349
IUPAC Name(3R,6S,9S,13S)-9-benzyl-13-[(2S)-hexan-2-yl]-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotridecane-2,5,8,11-tetrone
Molecular FormulaC27H41N3O5
Molecular Weight487.6
XLogP4.8
Topological Polar Surface Area114
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Heavy Atom Count35
Formal Charge0
Complexity720
SMILES
CCCC[C@H](C)[C@@H]1CC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)O1)CC(C)C)C)CC2=CC=CC=C2
InChI
InChI=1S/C27H41N3O5/c1-6-7-11-18(4)23-16-24(31)29-21(15-20-12-9-8-10-13-20)26(33)28-19(5)25(32)30-22(14-17(2)3)27(34)35-23/h8-10,12-13,17-19,21-23H,6-7,11,14-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t18-,19-,21-,22+,23-/m0/s1
InChIKey
ZKSLFHXTWGEITF-JIORRVSTSA-N
Chemical Structure
2D Structure
2D structure of Beauveriolide I
CAS: 154491-55-1
CID: 9913349
Formula: C27H41N3O5
MW: 487.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight487.6
XLogP34.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Exact Mass487.30462142
Monoisotopic Mass487.30462142
Topological Polar Surface Area114 Ų
Heavy Atom Count35
Formal Charge0
Complexity720
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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