Elaiophylin
Basic information
- CAS
37318-06-2- Standard SMILES
CC[C@@H]1[C@@H](C)O[C@@](O)([C@@H](C)[C@H](O)[C@H](C)[C@H]2OC(=O)/C=C/C=C/[C@H](C)[C@@H]([C@@H](C)[C@@H](O)[C@H](C)[C@@]3(O)C[C@@H](O[C@H]4C[C@H](O)[C@H](O)[C@H](C)O4)[C@H](CC)[C@@H](C)O3)OC(=O)/C=C/C=C/[C@@H]2C)C[C@H]1O[C@H]1C[C@H](O)[C@H](O)[C@H](C)O1- InChIKey
OSERMIPXNLXAPD-MJMYBOKFSA-N- Molecular formula
- C54H88O18
- Average molar mass
- 1,025.3 g/mol
- Monoisotopic mass
- 1,024.59706595
Overview
Elaiophylin is a macrodiolide that is isolated from several bacteria including Streptomyces violaceoniger and other soil actinomycetes. It has a role as an antifungal agent, a bacterial metabolite and an autophagy inhibitor. It is a macrodiolide, a lactol and a monosaccharide derivative.
Names & identifiers
- Preferred name
- Elaiophylin
- IUPAC
- (3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(2S,3R,4S)-4-[(2R,4R,5R,6R)-4-[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-ethyl-2-hydroxy-6-methyloxan-2-yl]-3-hydroxypentan-2-yl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
- English name
- elaiophylin
- Molecular formula
- C54H88O18
- Molecular weight
- 1025.27
Names & synonyms
Elaiophylin37318-06-2Azalomycin BGopalamicinAntibiotic 5001BAntibiotic 56-62Elayofilin1CAF8865TMCHEBI:77879DTXSID001318254(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(2S,3R,4S)-4-[(2R,4R,5R,6R)-4-[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-ethyl-2-hydroxy-6-methyloxan-2-yl]-3-hydroxypentan-2-yl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis((2S,3R,4S)-4-((2R,4R,5R,6R)-4-((2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl)oxy-5-ethyl-2-hydroxy-6-methyloxan-2-yl)-3-hydroxypentan-2-yl)-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
Show more names
ElaiophilinOlive leaf hormoneElaiophylin (>85%)Elaiophylin (Azalomycin B)
RefChem:136444DTXCID301748040Azalomycin-BSalbomycinElaiofilinEfomycin EEFOMYCINE EANTIBIOTIC A-164AB
Properties
Computed structural properties
- XLogP
- 7
- Topological polar surface area
- 270 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 18
- Rotatable bonds
- 14
- Heavy atoms
- 72
- Formal charge
- 0
- Complexity
- 1,730
Physicochemical properties
- Melting point
- 179 · 179-182℃
- Boiling point
- 1080.5 · 1080.5±65.0 °C(Predicted)
- Density
- 1.25 · 1.25
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 12.18 · 12.18±0.70(Predicted)
- form
- White to off-white solid.
- color
- White to Off-White
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 CAF8865TM · 1CAF8865TM
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332
- Precautionary statements
- 261 · P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P321-P330-P362+P364-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302+H312+H332
- Precautionary statements
- P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P321-P330-P362+P364-P501
Chemistry & industry
Applications
UsesElaiophyllin is a highly characteristic metabolite produced by Streptomyces hygroscopicus. Elaiophylin inhibits testosterone 5-reductase. Elaiophylin is synergistic with its co-metabolite, rapamycin, as an antifungal. Elaiophylin also has anthelminthic and immunosuppressive activity and inhibits NO synthesis. Elaiophylin displays broad, albeit weak, biological activity against bacteria, nematodes, protozoa and mammalian tumour cells.
UsesElaiophylin is a highly characteristic metabolite produced by Streptomyces hygroscopicus. Elaiophylin inhibits testosterone 5-reductase. Elaiophylin is synergistic with its co-metabolite, rapamycin, as an antifungal. Elaiophylin also has anthelmintic and immunosuppressive activity and inhibits NO synthesis. Elaiophylin displays broad, albeit weak, biological activity against bacteria, nematodes, protozoa and mammalian tumor cells.
UsesElaiophylin is a macrodiolide antibiotic that can be isolated from various strains of Streptomyces. It displays in vitro anti-protozoal activity against both Plasmodium and Trypanosoma (IC50s = 370 and 460 ng/ml, respectively) and cytotoxicity against human fetal lung fibroblast MRC-5 cells (IC50 = 870 ng/ml). Elaiophylin alone has no activity against Candida, although it enhances the anti-fungal activity of rapamycin . Elaiophylin also forms stable, long-lasting ion channels in bilayer membranes that are selective for cations.
Additional notes
DefinitionChEBI: A macrolide that is isolated from several bacteria including Streptomyces violaceoniger and other soil actinomycetes.
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