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Category Mycotoxins
Catalog number BBF-01575
CAS 75533-14-1
Molecular Weight 294.26
Molecular Formula C13H14N2O6

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U-58431 is an antibiotic isolated from Streptomyces helicus (UC-5837), which is effective against gram-positive and gram-negative bateria, and more potently against streptococcus pneumoniae. It exhibits toxicity.


IUPAC Name (1R,8R,10R,11R)-1,6,11-trihydroxy-4-imino-10-methyl-3-oxo-9-oxatricyclo[,7]dodeca-2(7),5-diene-5-carboxamide
Canonical SMILES CC1C2(C(CC(O1)C3=C2C(=O)C(=N)C(=C3O)C(=O)N)O)O
InChI InChI=1S/C13H14N2O6/c1-3-13(20)5(16)2-4(21-3)6-8(13)11(18)9(14)7(10(6)17)12(15)19/h3-5,14,16-17,20H,2H2,1H3,(H2,15,19)/t3-,4-,5-,13+/m1/s1


Appearance Orange-red Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Melting Point 156-157°C (dec.)

Reference Reading

1. Constitution and absolute stereochemistry of the antibiotic sarubicin A
K Eckardt, D Tresselt, W Ihn, M Kajtár, J Angyán, L Radics, M Hollósi J Antibiot (Tokyo). 1983 Aug;36(8):976-9. doi: 10.7164/antibiotics.36.976.
By spectral (UV-VIS, IR, NMR, MS and CD) methods the quinone antibiotics sarubicin A and U-58,431 were shown to have identical constitution and stereochemistry. Chiroptical data and their theoretical analysis have settled the common absolute configuration as 5S, 6R, 8R, 10R.
2. Fermentation, isolation, characterization and structure of antibiotic U-58,431
L Slechta, C G Chidester, F Reusser J Antibiot (Tokyo). 1980 Sep;33(9):919-23. doi: 10.7164/antibiotics.33.919.
A new antibiotic U-58,431 has been isolated from the fermentation broth of Streptomyces helicus DIETZ and LI, sp. n. (UC-5837) and the structure of this antibiotic, namely, 6-amino-3,4,5,8-tetrahydro-4,9-dihydroxy-3-methyl-5,8-dioxo-1,4-ethano-1H-2-benzopyron-7-carboxamide has been determined by X-ray crystallography. The antibiotic inhibits a variety of Gram-positive and Gram-negative bacteria in vitro. However, it is toxic to mice and does not protect experimentally infected animals when administered at the maximum tolerated dose.

Bio Calculators

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* 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

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40

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