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Avenacin A-1

CAT: 0804-HY-N7723Size: InquireDry Ice: NoHazardous: No
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CAS Number
90547-90-3
UNSPSC Description
Avenacin A-1 exhibits antifungal activity, which inhibits growth of Culvularia sp, Drechslera victoriae, Rhizoctonia solani, Fusarium spp.. Avenacin A-1 affects the bilayer permeability[1].
Target Antigen
Endogenous Metabolite; Fungal
Type
Natural Products
Related Pathways
Anti-infection;Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/avenacin-a-1.html
Smiles
O[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)[C@H]1O[C@@H]2CO[C@H]([C@H](O[C@@H]3[C@H](O)[C@H](O)[C@H](O)[C@H](CO)O3)[C@@H]2O)O[C@@H]4[C@@](CO)([C@@H]5[C@@](C)(CC4)[C@@H]6[C@@]([C@]7([C@]8([C@@H]9[C@@]([C@H](C7)O)(C[C@H](OC(C%10=CC=CC=C%10NC)=O)[C@@](C=O)(C9)C)C)O[C@@H]8C6)C)(C)CC5)C
Molecular Weight
1094.24
References & Citations
[1]Armah CN, et al., The membrane-permeabilizing effect of avenacin A-1 involves the reorganization of bilayer cholesterol. Biophys J. 1999 Jan;76(1 Pt 1):281-90.|[2]TÜRK F M, et al., Avenacin A-1 content of some local oat genotypes and the in vitro effect of avenacins on several soil-borne fungal pathogens of cereals[J]. Turkish journal of agriculture and forestry, 2005, 29(3): 157-164.
Shipping Conditions
Room temperature
Clinical Information
No Development Reported

Chemical Information

Avenacin A 1

Avenacin A-1 is a triterpenoid saponin and a trisaccharide derivative. It derives from a hydride of an oleanane.

CAS Number90547-90-3
PubChem CID441907
IUPAC Name[(1S,3R,5R,6R,9S,10R,11R,14R,15S,17S,18S,20S,21R,23R)-21-formyl-17-hydroxy-9-[(2S,3R,4S,5S)-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-10-(hydroxymethyl)-6,10,14,15,18,21-hexamethyl-2-oxahexacyclo[13.8.0.01,3.05,14.06,11.018,23]tricosan-20-yl] 2-(methylamino)benzoate
Molecular FormulaC55H83NO21
Molecular Weight1094.2
XLogP1.3
Topological Polar Surface Area346
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count22
Rotatable Bond Count14
Heavy Atom Count77
Formal Charge0
Complexity2150
SMILES
C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2C[C@@H]4[C@]5([C@]3(C[C@@H]([C@@]6([C@H]5C[C@@]([C@H](C6)OC(=O)C7=CC=CC=C7NC)(C)C=O)C)O)C)O4)C)(C)CO)O[C@H]8[C@@H]([C@H]([C@H](CO8)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
InChI
InChI=1S/C55H83NO21/c1-49(23-59)17-32-51(3,19-36(49)74-45(69)25-10-8-9-11-26(25)56-7)33(61)18-54(6)53(5)15-12-30-50(2,31(53)16-35-55(32,54)77-35)14-13-34(52(30,4)24-60)75-48-44(76-47-43(68)41(66)38(63)28(21-58)72-47)39(64)29(22-70-48)73-46-42(67)40(65)37(62)27(20-57)71-46/h8-11,23,27-44,46-48,56-58,60-68H,12-22,24H2,1-7H3/t27-,28-,29+,30-,31-,32-,33+,34+,35-,36+,37-,38-,39+,40+,41+,42-,43-,44-,46+,47+,48+,49+,50+,51+,52+,53-,54+,55-/m1/s1
InChIKey
SYXUBXTYGFJFEH-PFTGTSLFSA-N
Chemical Structure
2D Structure
2D structure of Avenacin A 1
CAS: 90547-90-3
CID: 441907
Formula: C55H83NO21
MW: 1094.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1094.2
XLogP31.3
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count22
Rotatable Bond Count14
Exact Mass1093.54575866
Monoisotopic Mass1093.54575866
Topological Polar Surface Area346 Ų
Heavy Atom Count77
Formal Charge0
Complexity2150
Isotope Atom Count0
Defined Atom Stereocenter Count28
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
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