LL-D49194alpha1
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| Category | Antibiotics |
| Catalog number | BBF-03625 |
| CAS | 99755-38-1 |
| Molecular Weight | 993.01 |
| Molecular Formula | C48H64O22 |
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Description
LL-D49194alpha1 is produced by the strain of Streptomyces vinaceusdrappus LL-D49194. It has anti-gram-positive bacteria activity and anti-P388 leukemia and B16 melanoma effect.
Specification
| Synonyms | LL-D 49194 alpha1; NSC-381856; Trioxacarcin A, 13-O-de(4-C-acetyl-2,6-dideoxy-alpha-L-xylo-hexopyranosyl)-16-O-demethyl-16-O-(2,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-xylo-hexopyranosyl)-3-C-methyl-alpha-L-xylo-hexopyranosyl)-13-O-methyl- |
| IUPAC Name | [6-[19-[[5-(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy-4-hydroxy-4,6-dimethyloxan-2-yl]oxy-methoxymethyl]-10,13-dihydroxy-6,17-dimethoxy-3-methyl-11-oxospiro[16,20,22-trioxahexacyclo[17.2.1.02,15.05,14.07,12.017,21]docosa-2(15),3,5(14),6,12-pentaene-18,2'-oxirane]-8-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] acetate |
| Canonical SMILES | CC1C(C(CC(O1)OC2C(OC(CC2(C)O)OC(C34C5(CO5)C6(C(O3)C(O4)C7=C(O6)C8=C(C=C7C)C(=C9C(CC(C(=O)C9=C8O)O)OC1CC(C(C(O1)C)OC(=O)C)(C)O)OC)OC)OC)C)(C)O)O |
| InChI | InChI=1S/C48H64O22/c1-18-12-23-30(34(52)32-31(35(23)57-9)25(13-24(50)33(32)51)65-26-15-44(7,55)39(20(3)62-26)64-22(5)49)36-29(18)37-41-47(59-11,68-36)46(17-60-46)48(69-37,70-41)42(58-10)67-28-16-45(8,56)40(21(4)63-28)66-27-14-43(6,54)38(53)19(2)61-27/h12,19-21,24-28,37-42,50,52-56H,13-17H2,1-11H3 |
| InChI Key | FZSZABYRGYFXRS-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Melting Point | 173-176°C |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Discovery of Druggability-Improved Analogues by Investigation of the LL-D49194α1 Biosynthetic Pathway
Lei Dong, Yi Shen, Xian-Feng Hou, Wen-Jun Li, Gong-Li Tang Org Lett. 2019 Apr 5;21(7):2322-2325. doi: 10.1021/acs.orglett.9b00610. Epub 2019 Mar 11.
The biosynthetic gene cluster of antitumor antibiotic LL-D49194α1 (LLD) was identified and comparatively analyzed with that of trioxacarcins. The tailoring genes encoding glycosyltransferase, methyltransferase and cytochrome P450 were systematically deleted, which led to the discovery of eight compounds from the mutants. Preliminary pharmaceutical evaluation revealed two intermediates exhibiting higher cytotoxicity, stability and solubility. These results highlighted the modification pathway for LLD biosynthesis, and provided highly potent, structurally simplified "unnatural" natural products with improved druggability.
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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 ╳
