Fungichromin
Basic information
- CAS
6834-98-6- Standard SMILES
CCCCC[C@@H](O)[C@H]1C(=O)O[C@H](C)[C@@H](O)/C=C/C=C/C=C/C=C/C=C(\C)[C@@H](O)[C@H](O)[C@H](O)C[C@H](O)C[C@H](O)C[C@H](O)C[C@H](O)C[C@@H]1O- InChIKey
AGJUUQSLGVCRQA-SWOUQTJZSA-N- Molecular formula
- C35H58O12
- Average molar mass
- 670.8 g/mol
- Monoisotopic mass
- 670.39282728
Overview
Fungichromin is a macrolide and an antibiotic antifungal drug.
Names & identifiers
- Preferred name
- Fungichromin
- IUPAC
- (3R,4S,6S,8S,10R,12R,14R,15R,16R,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,15,16,27-nonahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
- English name
- Fungichromin
- Molecular formula
- C35H58O12
- Molecular weight
- 670.83
Names & synonyms
FungichrominLagosinCogomycinPentamycinAntibiotic A-246CantricinFungchrominAntibiotic A 246FemifectNSC-1053886834-98-6Pruri-ex
Show more names
Lagosin【antibiotic】Oxacyclooctacosa-17,19,21,23,25-pentaen-2-one, 4,6,8,10,12,14,15,16,27-nonahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-, (3R,4S,6S,8S,10R,12R,14R,15R,16R,17E,19E,21E,23E,25E,27S,28R)-
1JB340D58SNSC-276732(3R,4S,6S,8S,10R,12R,14R,15R,16R,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,15,16,27-nonahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-oneDTXCID2026866(3R,4S,6S,8S,10R,12R,14R,15R,16R,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,15,16,27-nonahydroxy-3-((1R)-1-hydroxyhexyl)-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-oneRefChem:141718229-913-4DTXSID4046866
Database identifiers
- CAS
6834-98-6- PubChem CID
- 5282200
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 229 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 5
- Heavy atoms
- 47
- Formal charge
- 0
- Complexity
- 1,020
Physicochemical properties
- Melting point
- 157 · 157-162° (dec)
- alpha
- 20 · D20 -227.7° (c = 0.53 in DMF)
- Boiling point
- 914 · 914.0±65.0 °C(Predicted)
- Density
- 1.196 · 1.196±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in DMSO
- form
- solid
- pka
- 12.77 · 12.77±0.70(Predicted)
- color
- Light yellow to yellow
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 JB340D58S · 1JB340D58S
- Toxicity
- 50 in · LD50 in mice (mg/kg): 1624 orally; 33.3 i.p. (Umezawa, Tanaka)
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
- Toxicity
- LD50 in mice (mg/kg): 1624 orally; 33.3 i.p. (Umezawa, Tanaka)
Chemistry & industry
Pharmacology
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Applications
UsesLagosin is a pentaene antifungal produced by Streptomyces, first isolated in 1958 by researchers at MIT in the USA. The discovery was soon followed by several independent isolations as lagosin and cogomyin. Initially these metabolites were thought to be isomeric, but Pandey and colleagues at NCI definitively demonstrated they were identical. Structurally, lagosin is 14-hydroxyfilipin III and the most polar member of the filipin family of fungicides. Lagosin exhibits broad spectrum antifungal and antitumor activity and, like filipin, acts via interaction with cell membrane sterols.
Additional notes
DefinitionChEBI: Fungichromin is a macrolide and an antibiotic antifungal drug.
Related reactions
4 records
Compound notes
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