10-Decarbomethoxyaclacinomycin A
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| Category | Antibiotics |
| Catalog number | BBF-02013 |
| CAS | 76264-91-0 |
| Molecular Weight | 753.83 |
| Molecular Formula | C40H51NO13 |
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Description
10-Decarbomethoxyaclacinomycin A is an anthracycline antibiotic produced by Streptomyces galilaeus MA144-Mlt mutant strain KE303. It has anti-tumor and gram-positive bacteria activity.
Specification
| Synonyms | 7-epi-10-Decarbomethoxyaclacinomycin A |
| IUPAC Name | 7-[4-(dimethylamino)-5-[4-hydroxy-6-methyl-5-(6-methyl-5-oxooxan-2-yl)oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-9-ethyl-4,6,9-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione |
| Canonical SMILES | CCC1(CC(C2=C(C3=C(C=C2C1)C(=O)C4=C(C3=O)C(=CC=C4)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)O |
| InChI | InChI=1S/C40H51NO13/c1-7-40(48)16-21-13-23-34(37(47)33-22(35(23)45)9-8-10-26(33)43)36(46)32(21)28(17-40)52-30-14-24(41(5)6)38(19(3)50-30)54-31-15-27(44)39(20(4)51-31)53-29-12-11-25(42)18(2)49-29/h8-10,13,18-20,24,27-31,38-39,43-44,46,48H,7,11-12,14-17H2,1-6H3 |
| InChI Key | OXPCRXLITLBLEY-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 876.9±65.0°C at 760 mmHg |
| Melting Point | 139-141°C |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Modification of aklavinone and aclacinomycins in vitro and in vivo by rhodomycin biosynthesis gene products
Yulong Wang, Jarmo Niemi, Pekka Mäntsälä FEMS Microbiol Lett. 2002 Feb 19;208(1):117-22. doi: 10.1111/j.1574-6968.2002.tb11070.x.
The rdm genes B, C and E from Streptomyces purpurascens encode enzymes that tailor aklavinone and aclacinomycins. We report that in addition to hydroxylation of aklavinone to epsilon-rhodomycinone, RdmE (aklavinone-11-hydroxylase) hydroxylated 11-deoxy-beta-rhodomycinone to beta-rhodomycinone both in vivo and in vitro. 15-Demethoxyaklavinone and decarbomethoxyaklavinone did not serve as substrates. RdmC (aclacinomycin methyl esterase) converted aclacinomycin T (AcmT) to 15-demethoxyaclacinomycin T, which was in turn converted to 10-decarbomethoxyaclacinomycin T and then to rhodomycin B by RdmB (aclacinomycin-10-hydroxylase). RdmC and RdmB were most active on AcmT, the one-sugar derivative, with their activity decreasing by 70-90% on two- and three-sugar aclacinomycins. Aclacinomycin A competitively inhibited the AcmT modifications at C-10. The results presented here suggest that in vivo the modifications at C-10 take place principally after addition of the first sugar.
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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 ╳
