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37318-06-2 molecular structure
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(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(2S,3R,4S)-4-[(2R,4R,5R,6R)-4-{[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-ethyl-2-hydroxy-6-methyloxan-2-yl]-3-hydroxypentan-2-yl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione

ChemBase ID: 72682
Molecular Formular: C54H88O18
Molecular Mass: 1025.26572
Monoisotopic Mass: 1024.59706598
SMILES and InChIs

SMILES:
[C@H]1([C@@H]([C@@H](O[C@H](C1)O[C@H]1[C@H](CC)[C@H](O[C@](C1)([C@H]([C@@H]([C@@H]([C@H]1OC(=O)/C=C/C=C/[C@@H]([C@H](OC(=O)/C=C/C=C/[C@@H]1C)[C@H]([C@H]([C@@H]([C@]1(C[C@H]([C@@H]([C@H](O1)C)CC)O[C@H]1C[C@@H]([C@@H]([C@@H](O1)C)O)O)O)C)O)C)C)C)O)C)O)C)C)O)O
Canonical SMILES:
CC[C@H]1[C@H](O[C@H]2C[C@H](O)[C@@H]([C@@H](O2)C)O)C[C@](O[C@@H]1C)(O)[C@H]([C@@H]([C@@H]([C@H]1OC(=O)/C=C/C=C/[C@H](C)[C@H](OC(=O)/C=C/C=C/[C@@H]1C)[C@H]([C@H]([C@@H]([C@@]1(O)C[C@@H](O[C@H]2C[C@H](O)[C@@H]([C@@H](O2)C)O)[C@@H]([C@H](O1)C)CC)C)O)C)C)O)C
InChI:
InChI=1S/C54H88O18/c1-13-37-33(9)71-53(63,25-41(37)67-45-23-39(55)49(61)35(11)65-45)31(7)47(59)29(5)51-27(3)19-15-17-22-44(58)70-52(28(4)20-16-18-21-43(57)69-51)30(6)48(60)32(8)54(64)26-42(38(14-2)34(10)72-54)68-46-24-40(56)50(62)36(12)66-46/h15-22,27-42,45-52,55-56,59-64H,13-14,23-26H2,1-12H3/b19-15+,20-16+,21-18+,22-17+/t27-,28-,29-,30-,31-,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42+,45-,46-,47+,48+,49+,50+,51-,52-,53+,54+/m0/s1
InChIKey:
OSERMIPXNLXAPD-MJMYBOKFSA-N

Cite this record

CBID:72682 http://www.chembase.cn/molecule-72682.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(2S,3R,4S)-4-[(2R,4R,5R,6R)-4-{[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-ethyl-2-hydroxy-6-methyloxan-2-yl]-3-hydroxypentan-2-yl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
IUPAC Traditional name
(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(2S,3R,4S)-4-[(2R,4R,5R,6R)-4-{[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-5-ethyl-2-hydroxy-6-methyloxan-2-yl]-3-hydroxypentan-2-yl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
Synonyms
Elaiophylin
Salbomycin
Gopalamicin
SNA 4606-3
Azalomycin-B
CAS Number
37318-06-2
PubChem SID
162037603
PubChem CID
6444206

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S1448 external link Add to cart Please log in.
Data Source Data ID
PubChem 6444206 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.373988  H Acceptors 16 
H Donor LogD (pH = 5.5) 6.398651 
LogD (pH = 7.4) 6.398606  Log P 6.3986516 
Molar Refractivity 266.1378 cm3 Polarizability 106.37813 Å3
Polar Surface Area 269.82 Å2 Rotatable Bonds 14 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Storage Condition
-20°C expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S1448 external link
Research Area
Description Infection
Biological Activity
Description Azalomycin-B (Elaiophylin) shows antiprotozoal activity against Plasmodium falciparum K1a and Trypanosoma brucei brucei GUTat 3.1 strains with IC50 of 0.36 μM and 0.45 μM, respectively.
Targets
IC50
In Vitro Azalomycin-B possesses an antibacterial activity against Gram-positive bacteria. The minimum inhibitory concentration (MIC) of Azalomycin-B against Staphylococcus aureus (SG 511, 285 and 503) is 1.52 μM. The MIC of Azalomycin-B against Streptococcus pyogenes is 0.76 μM and 1.52 μM for strains 306A, and 77A, respectively. The MIC of Azalomycin-B against S. faecium A is 3.05 μM. [1] In vitro, Azalomycin-B shows an antibiotic activity as a rumen fermentation efficiency enhancer and also inhibits lactic acid production in the rumen fluid with IC5O of 2.14 μM. [2] Azalomycin-B inhibits P-type ATPases such as the P-type, K+-dependent ATPase from Escherichia coli, without affecting F-type and V-type ATPases at all. [3] Azalomycin-B shows the potent cytotoxic effect on L929 mouse fibroblast cells, K562 human leukemia cells and HeLa cell cultures with IC50 of 0.29 μM, 0.19 μM and 0.29 μg/mL, respectively. [4] Moreover, Azalomycin-B also produces the cytotoxicity in MRC-5 cells with IC50 of 0.85 μM. [5]
In Vivo
Clinical Trials
Features Azalomycin-B is a macrolide antibiotic showing the antiprotozoal activity against Plasmodium falciparum K1a and Trypanosoma brucei brucei GUTat 3.1 strains.
Combination Therapy
Description Azalomycin-B (μg/mL) markedly enhances Rapamycin (μg/mL)'s antifungal activity against Candida albicans ATCC 11651 as high as 219%. [6]
Protocol
Cell Assay [4]
Cell Lines L92, K562 and HeLa cells
Concentrations 0-10 μM
Incubation Time 72 hours
Methods The adherent mouse fibroblast cell line L-929 is cultured in Eagle's MEM with 0.35 mg/mL sodium bicarbonate, 100 units/mL penicillin/100 μg/mL streptomycin, 10 mM HEPES, and 10% heat-inactivated FBS at 37 °C in culture flasks. The adherent cells are harvested at the logarithmic growth phase after trypsination using 0.05% trypsin in phosphate-buffered saline (PBS) containing 0.02% EDTA. The nonadherent human leukemia cell line K-562, is cultured in RPMI 1640 medium, supplemented with 100 units/mL penicillin/100 μg/mL streptomycin and 10% FBS in culture flasks. L-929 and K-562 cells are inoculated in 0.1 mL culture medium, containing NaHCO3 without HEPES, per well of the 96-well microplates. The plates are previously prepared with dilutions of the Azalomycin-B in 0.1 mL medium. The microplates are kept for 72 hour at 37 °C in a humidified atmosphere containing 5% CO2. The adherent human cell line HeLa is cultured in MEM Eagle with 100 units/mL penicillin/100 μg/mL streptomycin, 10% FBS, and 2 mM l-glutamine in vented culture flasks. The adherent cells are harvested during the logarithmic growth phase after trypsination with 0.4% trypsin in PBS containing 0.02% EDTA. These cells are seeded with in 0.1 mL culture medium per well of the 96-well microplates. HeLa cells are preincubated 48 hours without Azalomycin-B. The dilutions of Azalomycin-B are carried out on the monolayer of HeLa cells after preincubation time. After incubation, the monolayer of the adherent L-929 and HeLa cells are fixed by glutaraldehyde and stained with a 0.05% solution of methylene blue for 15 minutes. After washing the stain is eluted by 0.2 mL of 0.33 N HCl in the wells. The optical densities are measured at 630 nm in a Dynatech MR 7000 microplate reader. After incubation, the K-562 cells are analyzed using an electronic cell analyzer system CASY 1 and software CASYSTAT for determination of IC50 values. The IC50 values are determined by integrated software CASYSTAT.
References
[1] Hammann P, et al. J Antibiot (Tokyo). 1990, 43(11), 1431-1440.
[2] Liu CM, et al. J Antibiot (Tokyo). 1993, 46(2), 350-352.
[3] Dröse S, et al. Biochemistry. 1993, 32(15), 3902-3906.
[4] Ritzau M, et al. J Nat Prod. 1998, 61(11), 1337-1339.
[5] Otoguro K, et al. J Antibiot (Tokyo). 2010, 63(5), 275-277.
[6] Fang A, et al. J Antibiot (Tokyo). 2000, 53(2), 158-162.

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PATENTS

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