Delaminomycin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00804 |
| CAS | 149779-38-4 |
| Molecular Weight | 501.65 |
| Molecular Formula | C29H43NO6 |
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Description
Delaminomycin A is an extracellular Matrix receptor antagonist and immunomodulator produced by Streptomyces albulus MJ202-72F3. It inhibits cell adhesion ECM (Extracellular matrix), reduces immune response activity, and inhibits Gram-positive bacteria.
Specification
| Synonyms | 2H-Imidazol-2-one, 3-((2-(2,8-dihydroxy-7-methyl-3,5-decadienyl)-1,2,4a,5,6,7,8,8a-octahydro-1,6,8-trimethyl-1-naphthalenyl)carbonyl)-1,5-dihydro-4,5-dihydroxy-5-methoxy-; 2H-Pyrrol-2-one, 1,5-dihydro-4,5-dihydroxy-3-((2-(2,8-dihydroxy-7-methyl-3,5-decadienyl)-1,2,4a,5,6,7,8,8a-octahydrox-1,6,8-trimethyl-1-naphthalenyl)carbonyl)- |
| IUPAC Name | (3Z)-3-[[2-[(3E,5E)-2,8-dihydroxy-7-methyldeca-3,5-dienyl]-1,6,8-trimethyl-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-hydroxymethylidene]-5-hydroxypyrrolidine-2,4-dione |
| Canonical SMILES | CCC(C(C)C=CC=CC(CC1C=CC2CC(CC(C2C1(C)C(=C3C(=O)C(NC3=O)O)O)C)C)O)O |
| InChI | InChI=1S/C29H43NO6/c1-6-22(32)17(3)9-7-8-10-21(31)15-20-12-11-19-14-16(2)13-18(4)24(19)29(20,5)26(34)23-25(33)28(36)30-27(23)35/h7-12,16-22,24,28,31-32,34,36H,6,13-15H2,1-5H3,(H,30,35)/b9-7+,10-8+,26-23- |
| InChI Key | AEZPXPDCVAUXRV-XBBTVXHCSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 692.6°C at 760 mmHg |
| Density | 1.162 g/cm3 |
| Solubility | Soluble in Methanol, DMSO |
Reference Reading
1. Low molecular weight immunomodulators produced by microorganisms
M Ishizuka, M Kawatsu, T Yamashita, M Ueno, T Takeuchi Int J Immunopharmacol. 1995 Feb;17(2):133-39. doi: 10.1016/0192-0561(94)00086-4.
In order to develop a new class of low molecular weight immunomodulators for the treatment of incurable diseases involving cancer, hematologic diseases and inflammation, we have sought cytokine inducers and inhibitors of cell adhesion to the extracellular matrix among the low molecular compounds produced by microorganisms. Cytogenin, cytoblastin (a monokine inducer), conagenin (a lymphokine inducer) and delaminomycins and IC-101 (inhibitors of cell adhesion to extracellular matrices) have been recently found in our institute. In this report, we describe the principles of screening and structures, and discuss their biological activities.
2. Delaminomycins, novel extracellular matrix receptor antagonists. V. Biosynthesis
M Ueno, I Yoshinaga, M Amemiya, T Someno, H Iinuma, M Ishizuaka, T Takeuchi J Antibiot (Tokyo). 1993 Sep;46(9):1390-6. doi: 10.7164/antibiotics.46.1390.
The biosynthesis of delaminomycin A, produced by Streptomyces albulus MJ202-72F3, was investigated by feeding 13C-labeled compounds followed by 13C NMR analyses. The results indicate that delaminomycin A is derived from six acetate units, five propionate units and one glycine unit.
3. Alchivemycin A, a bioactive polycyclic polyketide with an unprecedented skeleton from Streptomyces sp
Yasuhiro Igarashi, Youngju Kim, Yasuko In, Toshimasa Ishida, Yukiko Kan, Tsuyoshi Fujita, Takashi Iwashita, Hirokazu Tabata, Hiroyasu Onaka, Tamotsu Furumai Org Lett. 2010 Aug 6;12(15):3402-5. doi: 10.1021/ol1012982.
Alchivemycin A, a novel polycyclic polyketide, was isolated from the culture extract of a plant-derived actinomycete Streptomyces sp. The structure and relative configuration were elucidated by spectroscopic analysis and X-ray crystallography, and the absolute configuration was determined by a (1)H NMR anisotropy method using MPA ester derivatization. The new compound contains an unprecedented heterocyclic ring system, 2H-tetrahydro-4,6-dioxo-1,2-oxazine. Alchivemycin A showed potent antimicrobial activity against Micrococcus luteus and inhibitory effects on tumor cell invasion.
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Bio Calculators
* 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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
