Indanomycin
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| Category | Antibiotics |
| Catalog number | BBF-01902 |
| CAS | 66513-28-8 |
| Molecular Weight | 493.68 |
| Molecular Formula | C31H43NO4 |
| Purity | >95% by HPLC |
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Description
Indanomycin is an antibiotic of the pyrroloketoindane class produced by Streptomyces sp. It is an unusual pyrollic ionophore that is active against gram-positive bacteria and insects. It has antihypertensive properties. It is a growth promoter in ruminants.
Specification
| Synonyms | X-14547A; X 14547A; 2H-Pyran-2-acetic acid, 6-(1-ethyl-4-(1-ethyl-2,3,3a,4,5,7a-hexahydro-4-(1H-pyrrol-2-ylcarbonyl)-1H-inden-5-yl)-1,3-butadienyl)tetrahydro-alpha, 5-dimethyl-, (1S-(1-alpha,3-alpha,beta,4-beta,5-beta(1E(2S*(S*),5R*,6S*),3E),7a-alpha))-; Antibiotic X-14547A |
| Storage | Store at -20°C |
| IUPAC Name | (2R)-2-[(2R,5S,6R)-6-[(3E,5E)-6-[(1S,3aR,4S,5S,7aS)-1-ethyl-4-(1H-pyrrole-2-carbonyl)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]hexa-3,5-dien-3-yl]-5-methyloxan-2-yl]propanoic acid |
| Canonical SMILES | CCC1CCC2C1C=CC(C2C(=O)C3=CC=CN3)C=CC=C(CC)C4C(CCC(O4)C(C)C(=O)O)C |
| InChI | InChI=1S/C31H43NO4/c1-5-21-13-16-25-24(21)15-14-23(28(25)29(33)26-11-8-18-32-26)10-7-9-22(6-2)30-19(3)12-17-27(36-30)20(4)31(34)35/h7-11,14-15,18-21,23-25,27-28,30,32H,5-6,12-13,16-17H2,1-4H3,(H,34,35)/b10-7+,22-9+/t19-,20+,21-,23+,24+,25+,27+,28+,30+/m0/s1 |
| InChI Key | BAIPOTOKPGDCHA-MWBHXQFBSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Light Tan Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; parasites |
| Boiling Point | 654°C at 760 mmHg |
| Melting Point | 138-141°C |
| Density | 1.115 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Indanomycin-related antibiotics from marine Streptomyces antibioticus PTZ0016
Xiao-Yuan Lian, Zhizhen Zhang Nat Prod Res . 2013;27(23):2161-7. doi: 10.1080/14786419.2013.793688.
Four indanomycin-related antibiotics 2-5 were isolated from the cultured broth of marine Streptomyces antibioticus strain PTZ0016. Their structures were characterised as 16-deethylindanomycin (2), iso-16-deethylindanomycin (3), 16-deethylindanomycin methyl ester (4) and iso-16-deethylindanomycin methyl ester (5) on the basis of NMR, HR-ESI-MS and CD evidences. Compounds 3-5 are new additions to the class of indanomycin antibiotics. All isolated compounds showed in vitro activity against Staphylococcus aureus with minimal inhibitory concentration at 4.0-8.0 μg/ml.
2. [Kafamycin--a new pyrrol ether antibiotic]
T N Drobysheva, M K Kudinova, T P Korobkova, N V Murenets, N A Kliuev Antibiot Med Biotekhnol . 1987 Nov;32(11):811-4.
Cafamycin is a novel polyether antibiotic active against gram-positive bacteria. It was isolated from the culture fluid of Streptomyces sp., an organism producing the anthracycline antibiotic galtamycin. The structure of cafamycin was assessed by spectral analysis: UV, PMR, mass spectroscopy and CD. Physico-chemical and biological properties of the antibiotic are described. Cafamycin was shown to be an analog of indanomycin (X-14547A), a pyrrol ether antibiotic.
3. Syntheses of the hexahydroindene cores of indanomycin and stawamycin by combinations of iridium-catalyzed asymmetric allylic alkylations and intramolecular Diels-Alder reactions
Günter Helmchen, Martin Gärtner, Gedu Satyanarayana, Sebastian Förster Chemistry . 2013 Jan 2;19(1):400-5. doi: 10.1002/chem.201202822.
Short and concise syntheses of the hexahydroindene cores of the antibiotics indanomycin (X-14547 A) and stawamycin are presented. Key methods used are an asymmetric iridium-catalyzed allylic alkylation, a modified Julia olefination, a Suzuki-Miyaura coupling, and an intramolecular Diels-Alder reaction.
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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 ╳
