U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H31NO4
Molecular Weight 433.5393
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ILICICOLIN H

SMILES

[H][C@]12C[C@@H](C)CC[C@]1([H])C(C)=C[C@H]([C@@H]2\C=C\C)C(=O)C3=C(O)C(=CNC3=O)C4=CC=C(O)C=C4

InChI

InChIKey=BYVVOONSAAQMKI-RFKCMYLBSA-N
InChI=1S/C27H31NO4/c1-4-5-20-21-12-15(2)6-11-19(21)16(3)13-22(20)25(30)24-26(31)23(14-28-27(24)32)17-7-9-18(29)10-8-17/h4-5,7-10,13-15,19-22,29H,6,11-12H2,1-3H3,(H2,28,31,32)/b5-4+/t15-,19+,20+,21-,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H31NO4
Molecular Weight 433.5393
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 1
Optical Activity UNSPECIFIED

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 12:46:35 GMT 2023
Edited
by admin
on Sat Dec 16 12:46:35 GMT 2023
Record UNII
XG38FSS45W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ILICICOLIN H
Common Name English
ILICICOLIN-H
Common Name English
ILLICICOLIN H
Common Name English
4-HYDROXY-5-(4-HYDROXYPHENYL)-3-(((1R,2S,4AS,7S,8AR)-1,2,4A,5,6,7,8,8A-OCTAHYDRO-4,7-DIMETHYL-1-(1E)-1-PROPEN-1-YL-2-NAPHTHALENYL)CARBONYL)-2(1H)-PYRIDINONE
Systematic Name English
2(1H)-PYRIDINONE, 4-HYDROXY-5-(4-HYDROXYPHENYL)-3-(((1R,2S,4AS,7S,8AR)-1,2,4A,5,6,7,8,8A-OCTAHYDRO-4,7-DIMETHYL-1-(1E)-1-PROPEN-1-YL-2-NAPHTHALENYL)CARBONYL)-
Systematic Name English
Code System Code Type Description
MANUFACTURER PRODUCT INFORMATION
ILICICOLIN H
Created by admin on Sat Dec 16 12:46:35 GMT 2023 , Edited by admin on Sat Dec 16 12:46:35 GMT 2023
PRIMARY
CHEBI
77772
Created by admin on Sat Dec 16 12:46:35 GMT 2023 , Edited by admin on Sat Dec 16 12:46:35 GMT 2023
PRIMARY
CAS
12689-26-8
Created by admin on Sat Dec 16 12:46:35 GMT 2023 , Edited by admin on Sat Dec 16 12:46:35 GMT 2023
PRIMARY
FDA UNII
XG38FSS45W
Created by admin on Sat Dec 16 12:46:35 GMT 2023 , Edited by admin on Sat Dec 16 12:46:35 GMT 2023
PRIMARY
PUBCHEM
54704283
Created by admin on Sat Dec 16 12:46:35 GMT 2023 , Edited by admin on Sat Dec 16 12:46:35 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY
ABSTRACT: Ilicicolin H is a polyketide nonribosomal peptide synthase (NRPS)natural product isolated from Gliocadium roseum, which exhibits potent and broad spectrum antifungal activity, with sub-.MU.g/mL MICs against Candida spp., Aspergillus f umigatus, and Cryptococcus spp. It showed a novel mode of action, potent inhibition (IC50 = 23 ng/mL) of the mitochondrial cytochrome bc1 reductase, and over 1000-fold selectivity relative to rat liver cytochrome bc1 reductase. Ilicicolin H exhibited in vivo efficacy in murine models of Candida albicans and Cryptococcus neoformans infections, but efficacy may have been limited by high plasma protein binding.