CHEBI:65975 - glomosporin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name glomosporin
ChEBI ID CHEBI:65975
Definition A cyclodepsipeptide consisting of a 3,4-dihydroxy-4-methylhexadecanoyl group attached to the amino terminus of the linear heptapeptide Ser-D-Ala-Asp-Asn-Asn-Ser-D-allo-Thr which is cyclised head-to-tail via the 3-hydroxy group on the hexadecanoyl chain. It is an antifungal drug isolated from the barley solid culture of the fungus Glomospora sp.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C42H71N9O17
Net Charge 0
Average Mass 974.06320
Monoisotopic Mass 973.497
InChI InChI=1S/C42H71N9O17/c1-5-6-7-8-9-10-11-12-13-14-15-42(4,67)29-19-32(57)46-27(20-52)39(64)45-22(2)35(60)47-26(18-33(58)59)38(63)49-24(16-30(43)55)36(61)48-25(17-31(44)56)37(62)50-28(21-53)40(65)51-34(23(3)54)41(66)68-29/h22-29,34,52-54,67H,5-21H2,1-4H3,(H2,43,55)(H2,44,56)(H,45,64)(H,46,57)(H,47,60)(H,48,61)(H,49,63)(H,50,62)(H,51,65)(H,58,59)/t22-,23-,24?,25?,26?,27?,28?,29?,34-,42?/m1/s1
InChIKey INJLZOSCEJMAGG-ADTDQJCQSA-N
SMILES CCCCCCCCCCCCC(C)(O)C1CC(=O)NC(CO)C(=O)N[C@H](C)C(=O)NC(CC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC(N)=O)C(=O)NC(CO)C(=O)N[C@H]([C@@H](C)O)C(=O)O1
Metabolite of Species Details
Glomospora (MB:8365) of strain BAUA 2825 See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via peptide antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing glomosporin (CHEBI:65975) has functional parent 3,4-dihydroxy-4-methylhexadecanoic acid (CHEBI:68513)
glomosporin (CHEBI:65975) has role antifungal agent (CHEBI:35718)
glomosporin (CHEBI:65975) has role fungal metabolite (CHEBI:76946)
glomosporin (CHEBI:65975) is a cyclodepsipeptide (CHEBI:35213)
glomosporin (CHEBI:65975) is a lactam (CHEBI:24995)
glomosporin (CHEBI:65975) is a monocarboxylic acid (CHEBI:25384)
glomosporin (CHEBI:65975) is a peptide antibiotic (CHEBI:25903)
glomosporin (CHEBI:65975) is a primary alcohol (CHEBI:15734)
glomosporin (CHEBI:65975) is a secondary alcohol (CHEBI:35681)
glomosporin (CHEBI:65975) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
[(3R,18R)-9,12-bis(2-amino-2-oxoethyl)-3-[(1R)-1-hydroxyethyl]-6,21-bis(hydroxymethyl)-25-(2-hydroxytetradecan-2-yl)-18-methyl-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosan-15-yl]acetic acid
Synonym Source
2-[(18R)-9,12-bis(2-amino-2-oxoethyl)-3-[(1R)-1-hydroxyethyl]-6,21-bis(hydroxymethyl)-25-(2-hydroxytetradecan-2-yl)-18-methyl-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-15-yl]acetic acid ChEBI
Registry Number Type Source
8672918 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10908117 PubMed citation Europe PMC
10966075 PubMed citation Europe PMC
Last Modified
06 March 2014