BASIFUNGIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C60H92N8O11
Molecular Weight	1101.4195
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCCN1C(=O)[C@H](CC3=CC=CC=C3)N(C)C(=O)[C@H](CC4=CC=CC=C4)NC(=O)[C@H](C(C)C)N(C)C(=O)[C@]([H])(OC(=O)[C@@H](N(C)C(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)N(C)C(=O)[C@@]([H])(NC2=O)[C@H](C)CC)C(C)(C)O)[C@H](C)CC

InChI

InChIKey=RLMLFADXHJLPSQ-QKCBWMAHSA-N

InChI=1S/C60H92N8O11/c1-17-38(9)46-57(75)65(14)47(36(5)6)52(70)61-42(32-35(3)4)55(73)67(16)50(60(11,12)78)59(77)79-49(39(10)18-2)58(76)66(15)48(37(7)8)53(71)62-43(33-40-26-21-19-22-27-40)54(72)64(13)45(34-41-28-23-20-24-29-41)56(74)68-31-25-30-44(68)51(69)63-46/h19-24,26-29,35-39,42-50,78H,17-18,25,30-34H2,1-16H3,(H,61,70)(H,62,71)(H,63,69)/t38-,39-,42+,43+,44+,45+,46+,47+,48+,49-,50-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C60H92N8O11
Molecular Weight	1101.4195
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7555208 | https://adisinsight.springer.com/drugs/800004447

Basifungin, previously known as LY 295337 or aureuobacidin A, is an antifungal agent that inhibits phosphorylceramide synthase. The development of basifungin against mycoses was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Antifungal activity of LY295337 in vitro against clinical isolates of Candida spp.	1995 Jul-Aug	7555208
Structures and antifungal activities of new aureobasidins.	1995 Jun	7622442
An alternative animal model for comparison of treatments for cryptococcal meningitis.	1999 Feb	9925548
Antifungal peptides: novel therapeutic compounds against emerging pathogens.	1999 Jan	9869556
Emerging novel antifungal agents.	2000 Jan	10637546
Inhibition of inositol phosphorylceramide synthase by aureobasidin A in Candida and Aspergillus species.	2000 Mar	10681333
Yatakemycin, a novel antifungal antibiotic produced by Streptomyces sp. TP-A0356.	2003 Feb	12715869
IPC synthase as a useful target for antifungal drugs.	2004 Dec	15578972
Inhibitory effect of aureobasidin A on Toxoplasma gondii.	2005 May	15855498
Pleofungins, novel inositol phosphorylceramide synthase inhibitors, from Phoma sp. SANK 13899. I. Taxonomy, fermentation, isolation, and biological activities.	2007 Feb	17420564

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:52:41 UTC 2023` Edited by `admin` on `Fri Dec 15 15:52:41 UTC 2023`
Record UNII	VV0USO6I6U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BASIFUNGIN

Official Name

English

LY295337

Code

English

N-((2R,3R)-2-HYDROXY-3-METHYLVALERYL)-N-METHYL-L-VALYL-L-PHENYLALANYL-N-METHYL-L-PHENYLALANYL-L-PROLYL-L-ALLOISOLEUCYL-N-METHYL-L-VALYL-L-LEUCYL-3-HYDROXY-N-METHYL-L-VALINE .ALPHA.(SUB 1)-LACTONE

Common Name

English

AUREOBASIDIN A

Common Name

English

R-106-1

Code

English

NK-204

Code

English

LY-295337

Code

English

BASIFUNGIN [USAN]

Common Name

English

basifungin [INN]

Common Name

English

R106-1

Code

English

NK 204

Code

English

R106 1

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C514