BASIFUNGIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C60H92N8O11
Molecular Weight	1101.4218
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

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
Pleofungins, novel inositol phosphorylceramide synthase inhibitors, from Phoma sp. SANK 13899. I. Taxonomy, fermentation, isolation, and biological activities.	2007-02	17420564
Inhibitory effect of aureobasidin A on Toxoplasma gondii.	2005-05	15855498
IPC synthase as a useful target for antifungal drugs.	2004-12	15578972
Yatakemycin, a novel antifungal antibiotic produced by Streptomyces sp. TP-A0356.	2003-02	12715869
Inhibition of inositol phosphorylceramide synthase by aureobasidin A in Candida and Aspergillus species.	2000-03	10681333
Emerging novel antifungal agents.	2000-01	10637546
An alternative animal model for comparison of treatments for cryptococcal meningitis.	1999-02	9925548
Antifungal peptides: novel therapeutic compounds against emerging pathogens.	1999-01	9869556
Antifungal activity of LY295337 in vitro against clinical isolates of Candida spp.	1995-07-01	7555208
Structures and antifungal activities of new aureobasidins.	1995-06	7622442

Name

Type

Language

LY-295337

Preferred Name

English

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

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