Viranamycin B

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Viranamycin B
Category Antibiotics
Catalog number BBF-02965
CAS 139595-04-3
Molecular Weight 840.05
Molecular Formula C44H73NO14

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Description

It is produced by the strain of Str. sp. CH 41. It can inhibit the growth of murine leukemia cell P388 with IC50 of 2.8 ng/mL, and it can also inhibit KB human multi-squamous cell carcinoma cells with IC50 of 1.9 ng/mL.

Specification

Synonyms Concanamycin A, 25-de(1-propenyl)-25-methyl-
IUPAC Name [(2R,3R,4S,6S)-6-[(2R,4S,5R,6R)-2-[(2S,3S,4R)-4-[(2S,3S,4E,6E,9R,10S,11R,12R,13S,14E,16Z)-11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6,14,16-tetraen-2-yl]-3-hydroxypentan-2-yl]-2-hydroxy-5,6-dimethyloxan-4-yl]oxy-4-hydroxy-2-methyloxan-3-yl] carbamate
Canonical SMILES CCC1C(C(CC(=CC=CC(C(OC(=O)C(=CC(=CC(C1O)C)C)OC)C(C)C(C(C)C2(CC(C(C(O2)C)C)OC3CC(C(C(O3)C)OC(=O)N)O)O)O)OC)C)C)O
InChI InChI=1S/C44H73NO14/c1-13-31-37(47)24(4)17-22(2)15-14-16-33(53-11)40(57-42(50)34(54-12)19-23(3)18-25(5)38(31)48)27(7)39(49)28(8)44(52)21-35(26(6)29(9)59-44)56-36-20-32(46)41(30(10)55-36)58-43(45)51/h14-16,18-19,24-33,35-41,46-49,52H,13,17,20-21H2,1-12H3,(H2,45,51)/b16-14+,22-15+,23-18+,34-19-/t24-,25+,26-,27-,28+,29-,30-,31-,32+,33+,35+,36-,37+,38-,39+,40+,41+,44-/m1/s1
InChI Key IQDQMKRHOJUEEN-IFQPHJMCSA-N

Properties

Appearance Colorless Powder
Antibiotic Activity Spectrum Neoplastics (Tumor)
Boiling Point 956.2±65.0°C at 760 mmHg
Melting Point 108-109°C
Density 1.2±0.1 g/cm3
Solubility Soluble in Methanol, Chloroform

Reference Reading

1. Isolation and structural elucidation of new 18-membered macrolide antibiotics, viranamycins A and B
Y Hayakawa, K Takaku, K Furihata, K Nagai, H Seto J Antibiot (Tokyo). 1991 Dec;44(12):1294-9. doi: 10.7164/antibiotics.44.1294.
Two cytotoxic antibiotics, designated viranamycins A and B, were isolated from the culture broth of Streptomyces sp. CH41. Their structures were elucidated as new 18-membered macrolides related to virustomycin A and concanamycin A from NMR spectral analysis. Viranamycins A and B inhibited the growth of P388 mouse leukemia and KB human squamous-cell-carcinoma cells.

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