Naphthomycin H
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| Category | Antibiotics |
| Catalog number | BBF-01988 |
| CAS | 98525-20-3 |
| Molecular Weight | 706.22 |
| Molecular Formula | C39H44ClNO9 |
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Description
Naphthomycin H is a macrolide (Ansa family) antibiotic produced by strains such as Str.collinus Tv105, Str. galbus subsp. griseosporeus Tv 353, Str. diastatochromogene, Str. sp. Y83 40369. It has activity against gram-positive bacteria and fungi.
Specification
| Synonyms | Naphthoquinomycin C |
| IUPAC Name | (7E,9S,10S,11S,12E,14S,16E,20S,21S,22E,24Z,26E)-31-chloro-4,10,14,20-tetrahydroxy-3,7,9,11,17,21-hexamethyl-29-azatricyclo[28.3.1.05,33]tetratriaconta-1(33),2,4,7,12,16,22,24,26,30-decaene-6,18,28,32,34-pentone |
| Canonical SMILES | CC1C=CC=CC=CC(=O)NC2=C(C(=O)C3=C(C2=O)C=C(C(=C3C(=O)C(=CC(C(C(C=CC(CC=C(C(=O)CC1O)C)O)C)O)C)C)O)C)Cl |
| InChI | InChI=1S/C39H44ClNO9/c1-20-11-9-7-8-10-12-30(45)41-34-33(40)39(50)31-27(38(34)49)18-25(6)37(48)32(31)36(47)24(5)17-23(4)35(46)22(3)14-16-26(42)15-13-21(2)29(44)19-28(20)43/h7-14,16-18,20,22-23,26,28,35,42-43,46,48H,15,19H2,1-6H3,(H,41,45)/b8-7-,11-9+,12-10+,16-14+,21-13+,24-17+/t20-,22-,23-,26-,28-,35-/m0/s1 |
| InChI Key | PGLCKEFYXCGUGA-IAIMMSNWSA-N |
Properties
| Appearance | Brown Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Boiling Point | 974.3±65.0°C at 760 mmHg |
| Melting Point | 150°C (dec.) |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. 3-amino-5-hydroxybenzoic acid in antibiotic biosynthesis. XI. Biological origins and semisynthesis of thionaphthomycins, and the structures of naphthomycins I and J
A M Hooper, R W Rickards J Antibiot (Tokyo). 1998 Sep;51(9):845-51. doi: 10.7164/antibiotics.51.845.
Fermentations of Streptomyces sp. E/784 produce low levels of the novel C-30 alkylthio-substituted ansamycin antibiotics naphthomycins J (9) and I (10), in addition to the more abundant C-30 hydroxylated analogues actamycin (1) and naphthomycin D (2) and C-30 chlorinated analogues naphthomycins H (3) and A (4). The addition of N-acetyl-L-cysteine to the fermentation medium substantially increases the production of the thionaphthomycins J and I at the expense of their chloro analogues H and A. Other thiols and thiol progenitors are similarly utilised, including N-acetyl-L-cysteine methyl ester which affords the known naphthomycin F (8) and its novel 2-demethyl homologue (7). The formation of thioansamycins from chloroansamycins and thiols in vivo is probably non-enzymic since similar conversions can be effected in vitro.
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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 ╳
