Fusacandin A
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| Category | Antibiotics |
| Catalog number | BBF-01463 |
| CAS | 166407-33-6 |
| Molecular Weight | 1023.12 |
| Molecular Formula | C51H74O21 |
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Description
It is produced by the strain of Fusarium sambucinum. It inhibits (1,3)-β-glucan synthetase and has antifungal properties.
Specification
| Synonyms | D-Glucitol, O-beta-D-galactopyranosyl-(1-2)-O-6-O-((2E,4Z)-1-oxo-2,4-decadienyl)-beta-D-galactopyranosyl-(1-3)-1,5-anhydro-1-C-(2,4-dihydroxy-6-(hydroxymethyl)phenyl)-, 3-((2E,4E,7S,8E,10E)-7-hydroxy-2,4,8,10-hexadecatetraenoate) |
| IUPAC Name | [(2S,3S,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-6-[[(2E,4Z)-deca-2,4-dienoyl]oxymethyl]-4,5-dihydroxy-3-[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[2,4-dihydroxy-6-(hydroxymethyl)phenyl]-3-hydroxy-6-(hydroxymethyl)oxan-4-yl] (2E,4E,8E,10E)-7-hydroxyhexadeca-2,4,8,10-tetraenoate |
| Canonical SMILES | CCCCCC=CC=CC(CC=CC=CC(=O)OC1C(C(OC(C1OC2C(C(C(C(O2)COC(=O)C=CC=CCCCCC)O)O)OC3C(C(C(C(O3)CO)O)O)O)CO)C4=C(C=C(C=C4O)O)CO)O)O |
| InChI | InChI=1S/C51H74O21/c1-3-5-7-9-11-13-16-20-31(55)21-17-15-19-23-38(59)70-48-45(65)47(39-30(26-52)24-32(56)25-33(39)57)67-35(28-54)46(48)71-51-49(72-50-44(64)42(62)40(60)34(27-53)68-50)43(63)41(61)36(69-51)29-66-37(58)22-18-14-12-10-8-6-4-2/h11-20,22-25,31,34-36,40-57,60-65H,3-10,21,26-29H2,1-2H3/b13-11+,14-12-,17-15+,20-16+,22-18+,23-19+/t31?,34-,35+,36+,40-,41-,42-,43-,44+,45-,46+,47-,48+,49+,50-,51-/m0/s1 |
| InChI Key | XRQGNAQBXJWDHO-BPNMBZMZSA-N |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 1163.6°C at 760 mmHg |
| Melting Point | 114-119°C |
| Density | 1.4 g/cm3 |
Reference Reading
1. Fusacandins A and B; novel antifungal antibiotics of the papulacandin class from Fusarium sambucinum. II. Isolation and structural elucidation
J E Hochlowski, D N Whittern, A Buko, L Alder, J B McAlpine J Antibiot (Tokyo). 1995 Jul;48(7):614-8. doi: 10.7164/antibiotics.48.614.
Two novel antifungal compounds of the papulacandin class, named fusacandins A and B, have been isolated from Fusarium sambucinum. Each compound contains two units of galactose and one of glucose, the latter connected as a C-glycoside to an aromatic moiety. Fusacandin A is esterified at two sites with long-chain, unsaturated fatty acids and fusacandin B at only one site. The structures of the fusacandins were elucidated through analysis of mass spectral and 1-D and 2-D homonuclear and heteronuclear NMR data.
2. Fusacandins A and B; novel antifungal antibiotics of the papulacandin class from Fusarium sambucinum. I. Identity of the producing organism, fermentation and biological activity
M Jackson, D J Frost, J P Karwowski, P E Humphrey, S K Dahod, W S Choi, K Brandt, L H Malmberg, R R Rasmussen, M H Scherr, et al. J Antibiot (Tokyo). 1995 Jul;48(7):608-13. doi: 10.7164/antibiotics.48.608.
The fuscandins, antifungal agents of the papulacandin class, are produced by a strain of Fusarium sambucinum. Fermentation yielded 60 mg/liter of fusacandin A and minor amounts of fusacandin B. As expected, the fusacandins inhibit (1,3)-beta-glucan synthesis. Fusacandin A is slightly less active than papulacandin B against Candida albicans and, like papulacandin, loses activity in the presence of serum.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
