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Tetracenomycin C information


Tetracenomycin C
Names
IUPAC name
Methyl (6aR,7S,10aR)-6a,7,10a,12-tetrahydroxy-3,8-dimethoxy-1-methyl-6,10,11-trioxo-6,6a,7,10,10a,11-hexahydrotetracene-2-carboxylate
Identifiers
CAS Number
  • 71135-22-3
3D model (JSmol)
  • Interactive image
Beilstein Reference
4774234
ChEBI
  • CHEBI:9470
ChemSpider
  • 66294
KEGG
  • C06801
PubChem CID
  • 73632
InChI
  • InChI=1S/C23H20O11/c1-8-14-9(6-11(32-2)15(8)21(29)34-4)5-10-16(17(14)25)20(28)22(30)13(24)7-12(33-3)19(27)23(22,31)18(10)26/h5-7,19,25,27,30-31H,1-4H3/t19-,22-,23-/m1/s1
    Key: ULHJWHCSSAEMLW-UEVCKROQSA-N
SMILES
  • O=C1C=2C(C(=O)[C@@]3(O)[C@]1(O)[C@H](O)C(OC)=CC3=O)=C(O)C=4C(C2)=CC(OC)=C(C(OC)=O)C4C
Properties
Chemical formula
C23H20O11
Molar mass 472.402 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetracenomycin C is an antitumor anthracycline-like antibiotic produced by Streptomyces glaucescens GLA.0.[1] The pale-yellow antibiotic is active against some gram-positive bacteria, especially against streptomycetes. Gram-negative bacteria and fungi are not inhibited. In considering the differences of biological activity and the functional groups of the molecule, tetracenomycin C is not a member of the tetracycline or anthracyclinone group of antibiotics.[2] Tetracenomycin C is notable for its broad activity against actinomycetes. As in other anthracycline antibiotics, the framework is synthesized by a polyketide synthase and subsequently modified by other enzymes.

  1. ^ Weber, W; Zahner, H; Siebers, J; Schroder, K; Zeeck, A (1979). "Metabolic products of microorganisms". Arch. Microbiol. 121 (2): 111–116. doi:10.1007/bf00689973. PMID 485765. S2CID 32884198.
  2. ^ Weber, W; Zahner, H; Siebers, J; Schroder, K; Zeeck, A (1979). "Proceeding of the fourth International Symposium on the Actinomycete Biology". Actinomycetes: 465.

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Tetracenomycin C

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Tetracenomycin C is an antitumor anthracycline-like antibiotic produced by Streptomyces glaucescens GLA.0. The pale-yellow antibiotic is active against...

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Streptomyces glaucescens

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isolated from soil. Streptomyces glaucescens produces tetracenomycin C, tetracenomycin D and tetracenomycin E. BAUMANN, R.; HUTTER, R.; HOPWOOD, D. A. (1 April...

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Polyketide synthesis cyclase family

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catalyses an aromatic rearrangement in the biosynthetic pathway of tetracenomycin C from Streptomyces coelicolor. The protein is a homodimer where each...

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Biosynthesis of doxorubicin

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PMID 8022857. Hutchinson CR (1997). "Biosynthetic Studies of Daunorubicin and Tetracenomycin C". Chemical Reviews. 97 (7): 2525–2536. doi:10.1021/cr960022x. PMID 11851469...

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Streptomyces canus

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isolated from soil in the US. Streptomyces canus produces resistomycin, tetracenomycin D, amphomycin, aspartocin D and aspartocin E. List of Streptomyces species...

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