D788-1
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| Category | Antibiotics |
| Catalog number | BBF-02799 |
| CAS | 97583-07-8 |
| Molecular Weight | 543.52 |
| Molecular Formula | C27H29NO11 |
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Description
D788-1 is produced by the strain of Streptomyces sp. D788. It had inhibitory activity against L1210 with IC50 of 0.027 μg/mL.
Specification
| Synonyms | 10-Carboxy-13-deoxycarminomycin; D-788-1; Carbolbicin; 4-[(3-Amino-2,3,6-trideoxyhexopyranosyl)oxy]-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid |
| IUPAC Name | (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylic acid |
| Canonical SMILES | CCC1(CC(C2=C(C1C(=O)O)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)O)OC5CC(C(C(O5)C)O)N)O |
| InChI | InChI=1S/C27H29NO11/c1-3-27(37)8-13(39-14-7-11(28)21(30)9(2)38-14)16-17(20(27)26(35)36)25(34)18-19(24(16)33)23(32)15-10(22(18)31)5-4-6-12(15)29/h4-6,9,11,13-14,20-21,29-30,33-34,37H,3,7-8,28H2,1-2H3,(H,35,36)/t9-,11-,13-,14-,20-,21+,27+/m0/s1 |
| InChI Key | MMYTYGXIKKVLES-AGMCFEMXSA-N |
Properties
| Appearance | Red Crystalline Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 745.5°C at 760 mmHg |
| Melting Point | 161-163°C |
| Density | 1.65 g/cm3 |
Reference Reading
1. Anthracycline metabolites from baumycin-producing Streptomyces sp. D788. II. New anthracycline metabolites produced by a blocked mutant strain RPM-5
A Yoshimoto, S Fujii, O Johdo, K Kubo, H Nishida, R Okamoto, T Takeuchi J Antibiot (Tokyo). 1993 Jan;46(1):56-64. doi: 10.7164/antibiotics.46.56.
A daunorubicin-blocked mutant strain RPM-5 derived from a new baumycin-producing Streptomyces sp. D788 accumulated a major precursor metabolite D788-1 (10-carboxyl-13-deoxocarminomycin) and nine minor metabolites in the culture broth. Five among them were new with a substituent at C-10 or the altered side chains at C-9. Isolation, purification and identification of all anthracycline metabolites produced by strain RPM-5 are described with their antitumor activities against L1210 cells.
2. New anthracycline antibiotics 10-epi-oxaunomycin and 10-epi-11-deoxyoxaunomycin
O Johdo, H Nishida, R Okamoto, A Yoshimoto, T Takeuchi J Antibiot (Tokyo). 1995 Oct;48(10):1153-8. doi: 10.7164/antibiotics.48.1153.
Two new anthracycline antibiotics, 10-epi-oxaunomycin and 10-epi-11-deoxyoxaunomycin, were photochemically obtained from anthracycline metabolites D788-1 (10-carboxy-13-deoxocarminomy-cin) and D788-3 (10-carboxy-11-deoxy-13-deoxocarminomycin) and were examined for their growth inhibitory activities on cultured L1210 leukemic cells. Effects of the S configuration of C-10 and a hydroxyl group at C-11 on the bioactivity are discussed in comparison with oxaunomycin and 11-deoxyoxaunomycin.
3. Anthracycline metabolites from baumycin-producing Streptomyces sp. D788. I. Isolation of antibiotic-blocked mutants and their characterization
A Yoshimoto, O Johdo, S Fujii, K Kubo, H Nishida, R Okamoto, T Takeuchi J Antibiot (Tokyo). 1992 Aug;45(8):1255-67. doi: 10.7164/antibiotics.45.1255.
Biosynthetically blocked mutants were obtained from a baumycin-producing Streptomyces sp. D788 newly isolated from soil. The first mutant isolated was a baumycin-negative but daunorubicin-accumulating mutant with a loss of 4'-substitution activity, from which all other blocked mutants were successively derived. These included a known 11-deoxydaunorubicin-producing mutant and several new types of mutants which produced mainly 10-carboxy-13-deoxocarminomycin, 10-methoxycarbonyl-13-deoxocarminomycin, their 11-deoxy derivatives or a precursor aglycone, respectively. In this paper, all the anthracycline components produced by the parent strain and its two known blocked mutants, a daunorubicin producer and a 11-deoxydaunorubicin producer, are also determined by HPLC and five new components are isolated. Cytotoxicities in vitro of all the components against L1210 cell culture are also described.
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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 ╳
