Australifungin

CAT: 0013-GTR19248371-02Size: 50 mgDry Ice: NoHazardous: No

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CAT#:0013-GTR19248371-02Size:50 mg

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Description

Australifungin is a potent and specific inhibitor of ceramide synthase, exhibiting broad-spectrum antifungal properties. It is a valuable research tool for studying sphingolipid metabolism and fungal pathogenesis in both in vitro and in vivo experimental models.

CAS Number

155468-85-2

Field of Research

Infectious Disease & Virology, Metabolism Research

Smiles

C (/C=C\O) (=O) [C@@]1 (C) [C@]2 ([C@] (C (=O) C (O) =C1[C@@H] (CCCCCC) C) ([C@H] (O) [C@H] (C) C[C@@H]2O) [H]) [H]

Molecular Formula

C23H36O6

Molecular Weight

408.528

Storage Conditions

-20°C

Notes

For research use only.

Chemical Information

Australifungin

Australifungin is a carbobicyclic compound that is 4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one substituted by hydroxy groups at positions 2, 5 and 8, a (2Z)-3-hydroxyprop-2-enoyl group at position 4, methyl groups at positions 4 and 7 and a 2R-octan-2-yl group at position 3 (the 4S,4aR,5S,7R,8R,8aS stereoisomer). It is isolated from the fermentation extracts of Sporormiella australis and exhibits antifungal activity by interfering with the fungal lipid metabolism. It has a role as a metabolite, an antifungal agent, an EC 2.3.1.24 (sphingosine N-acyltransferase) inhibitor and a HIV-1 integrase inhibitor. It is an enol, a secondary alcohol, a carbobicyclic compound and an enone.

CAS Number	155468-85-2
PubChem CID	5276375
IUPAC Name	(4S,4aR,5S,7R,8R,8aS)-2,5,8-trihydroxy-4-[(Z)-3-hydroxyprop-2-enoyl]-4,7-dimethyl-3-[(2R)-octan-2-yl]-4a,5,6,7,8,8a-hexahydronaphthalen-1-one
Molecular Formula	C23H36O6
Molecular Weight	408.5
XLogP	3.9
Topological Polar Surface Area	115
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	8
Heavy Atom Count	29
Formal Charge	0
Complexity	681

SMILES

CCCCCC[C@@H](C)C1=C(C(=O)[C@H]2[C@H]([C@]1(C)C(=O)/C=C\O)[C@H](C[C@H]([C@H]2O)C)O)O

InChI

InChI=1S/C23H36O6/c1-5-6-7-8-9-13(2)18-22(29)21(28)17-19(15(25)12-14(3)20(17)27)23(18,4)16(26)10-11-24/h10-11,13-15,17,19-20,24-25,27,29H,5-9,12H2,1-4H3/b11-10-/t13-,14-,15+,17+,19-,20-,23-/m1/s1

InChIKey

QURROFPXYUFYAZ-GFHGMWMXSA-N

Chemical Structure

2D Structure

CAS: 155468-85-2

CID: 5276375

Formula: C23H36O6

MW: 408.5

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	408.5
XLogP3	3.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	8
Exact Mass	408.25118886
Monoisotopic Mass	408.25118886
Topological Polar Surface Area	115 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	681
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
TN9156-01	Australifungin

Australifungin

Chemical Information

Alternative Products

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