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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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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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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
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
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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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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