Pradimicin M

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Category Enzyme inhibitors
Catalog number BBF-02055
CAS 132971-63-2
Molecular Weight 464.38
Molecular Formula C24H16O10

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Description

Pradimicin M is an antibiotic produced by Actinomadura hibisca. α-glycosidase and β-galactosidase inhibitor.

Specification

Synonyms 11-O-Demethylpradinone; (5S,6S)-1,5,6,9,11,14-hexahydroxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carboxylic acid
IUPAC Name (5S,6S)-1,5,6,9,11,14-hexahydroxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carboxylic acid
Canonical SMILES CC1=CC2=C(C3=C(C4=C(C=C3C(C2O)O)C(=O)C5=C(C4=O)C=C(C=C5O)O)O)C(=C1C(=O)O)O
InChI InChI=1S/C24H16O10/c1-6-2-8-15(22(31)13(6)24(33)34)16-10(21(30)20(8)29)5-11-17(23(16)32)19(28)9-3-7(25)4-12(26)14(9)18(11)27/h2-5,20-21,25-26,29-32H,1H3,(H,33,34)/t20-,21-/m0/s1
InChI Key ROFMCMXCPNFONV-SFTDATJTSA-N

Properties

Boiling Point 870.9±65.0°C at 760 mmHg
Density 1.8±0.1 g/cm3

Reference Reading

1. Pradimicins M, N, O and P, new dihydrobenzo[a]naphthacenequinones produced by blocked mutants of Actinomadura hibisca P157-2
Y Sawada, T Tsuno, H Yamamoto, M Nishio, M Konishi, T Oki J Antibiot (Tokyo). 1990 Nov;43(11):1367-74. doi: 10.7164/antibiotics.43.1367.
Four blocked mutants which accumulated new dihydrobenzo[a]naphthacenequinone metabolites, designated pradimicins M, N, O and P, have been isolated from cultures of mutants of Actinomadura hibisca P157-2 resulting from treatment with N-methyl-N'-nitro-N-nitrosoguanidine. The structures of the four compounds were determined by spectral analysis. Pradimicins N, O and P contain D-alanine, while pradimicin M does not. The conformations at C-5 and C-6 of these compounds are different from those of the original pradimicins.

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