Saccharocarcin A
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| Category | Antibiotics |
| Catalog number | BBF-02640 |
| CAS | 158475-32-2 |
| Molecular Weight | 1240.51 |
| Molecular Formula | C67H101NO20 |
| Purity | >95% by HPLC |
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Description
An unusual tetronic acid structurally related to kijanimicin, chlorothricin, tetrocarcin and versipelostatin; has pronounced activity against gram positive bacteria and chlamydia trachomatis; inhibits transcription from the promoter of GRP78; appears to target the phosphatidylinositide-3-kinase/akt signalling pathway.
Specification
| Synonyms | 10-[[4-(acetylamino)-2,4,6-trideoxy-3-C-methylhexopyranosyl]oxy]-4-[[O-2,6-dideoxyhexopyranosyl-(1→4)-O-2,6-dideoxy-3-O-(tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)hexopyranosyl-(1→4)-2,6-dideoxyhexopyranosyl]oxy]-15-ethyl-2,3,4,4a,6a,9,10,12a,15,16,20a,20b-dodecahydro-21-hydroxy-1,3,7,9,11,20a-hexamethyl-18H-16a,19-metheno-16aH-benzo[b]naphth[2,1-j]oxacyclotetradecin-18,20(1H)-dione |
| Storage | Store at -20°C |
| IUPAC Name | N-[(2S,3S,4S,6R)-6-[[(1S,3R,6S,7E,9S,11E,13S,16S,17S,18S,20S,21R,22S,23E)-17-[(2S,4R,5R,6R)-5-[(2R,4R,5S,6R)-5-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-[(2S,5R,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-3-ethyl-23-hydroxy-8,10,12,18,20,22-hexamethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-4,7,11,14,23-pentaen-9-yl]oxy]-4-hydroxy-2,4-dimethyloxan-3-yl]acetamide |
| Canonical SMILES | CCC1CC23C(C=C1)C=C(C(C(C=C(C4C=CC5C(C4(C(=C(C2=O)C(=O)O3)O)C)C(CC(C5OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)O)O)O)OC9CCC(C(O9)C)O)C)C)C)C)OC1CC(C(C(O1)C)NC(=O)C)(C)O)C |
| InChI | InChI=1S/C67H101NO20/c1-15-41-16-17-42-24-34(6)57(87-53-29-65(13,77)61(39(11)82-53)68-40(12)69)32(4)22-30(2)44-19-18-43-55(66(44,14)62(74)54-63(75)67(42,28-41)88-64(54)76)31(3)23-33(5)58(43)84-52-27-48(83-49-21-20-45(70)35(7)78-49)60(38(10)81-52)86-51-26-47(72)59(37(9)80-51)85-50-25-46(71)56(73)36(8)79-50/h16-19,22,24,31-33,35-39,41-53,55-61,70-74,77H,15,20-21,23,25-29H2,1-14H3,(H,68,69)/b30-22+,34-24+,62-54+/t31-,32?,33-,35-,36+,37+,38+,39-,41-,42-,43-,44-,45+,46+,47+,48+,49-,50+,51+,52+,53-,55+,56+,57-,58-,59+,60+,61-,65-,66+,67-/m0/s1 |
| InChI Key | QQZJNABARVXBJD-IXCNRNCNSA-N |
| Source | Amycolatopsis sp. |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 220°C |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1. A family of novel macrocyclic lactones, the saccharocarcins produced by Saccharothrix aerocolonigenes subsp. antibiotica. I. Taxonomy, fermentation, isolation and biological properties
K Cardaci, A C Horan, M Nimeck, A King, V Hedge, B C Brodsky, M L Beyazova, R Berrie, M C Shearer J Antibiot (Tokyo) . 1997 Feb;50(2):119-25. doi: 10.7164/antibiotics.50.119.
A nocardioform actinomycete, SCC 1886, isolated from a soil sample collected in Ohio was found to produce, in fermentation, six novel macrocyclic lactones, the saccharocarcins. The producing culture was identified as Saccharothrix aerocolonigenes subsp. antibiotica based on the formation of fragmenting substrate mycelia, aerial mycelia that coalesce to form aerial colonies, whole-cell hydrolysates that contain meso-diaminopimelic acid, galactose and rhamnose and physiological comparisons to type species of the genus. Peak production of the saccharocarcins occurred after 95 hours of fermentation in a starch rich medium. The compounds were isolated from the fermentation broth by solvent extraction and purified by HPLC. Isolated compounds were active against Micrococcus luteus, Staphylococcus aureus and Chlamydia trachomatis; none were cytotoxic at concentrations up to 1.0 microgram/ml.
2. A family of novel macrocyclic lactones, the saccharocarcins produced by Saccharothrix aerocolonigenes subsp. antibiotica. II. Physico-chemical properties and structure determination
M G Patel, B Pramanik, M S Puar, V R Hegde, P R Das J Antibiot (Tokyo) . 1997 Feb;50(2):126-34. doi: 10.7164/antibiotics.50.126.
Six novel tetronic acid analogs were isolated from the fermentation broth of the actinomycete Saccharothrix aerocolongenes subsp. antibiotica SCC1886. The structures of these saccharocarcins were determined by their spectral data, and chemical degradation. All six compounds are derived from two modified tetronic acid homologs which differ from other tetronic acids by having an ethyl or propyl side chain at C-23 and a methyl group at C-16. They are all characterized by a novel sugar-amide at C-17.
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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 ╳
