Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C39H49NO16 |
| Molecular Weight | 787.8035 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 13 / 13 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CO[C@H]1[C@H](C)O[C@@H](O[C@H]2C[C@](C)(O)[C@H](C(=O)OC)C3=CC4=C(C(=O)C5=C(C4=O)C6=C(C=C5O)[C@@]7(C)O[C@@H](O6)[C@@H](O)[C@@H]([C@H]7O)N(C)C)C(O)=C23)[C@H](OC)[C@]1(C)OC
InChI
InChIKey=KGTDRFCXGRULNK-JYOBTZKQSA-N
InChI=1S/C39H49NO16/c1-14-32(49-7)39(4,52-10)33(50-8)36(53-14)54-19-13-37(2,48)24(34(47)51-9)15-11-16-21(27(43)20(15)19)28(44)22-18(41)12-17-30(23(22)26(16)42)55-35-29(45)25(40(5)6)31(46)38(17,3)56-35/h11-12,14,19,24-25,29,31-33,35-36,41,43,45-46,48H,13H2,1-10H3/t14-,19-,24-,25-,29-,31+,32-,33-,35+,36-,37-,38+,39+/m0/s1
| Molecular Formula | C39H49NO16 |
| Molecular Weight | 787.8035 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 13 / 13 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Nogalamycin is an unusual anthracycline antineoplastic antibiotic isolated from the bacterium Streptomyces nogalater. Nogalamycin intercalates into DNA and interacts with topoisomerase I, thereby inhibiting DNA replication and repair and RNA and protein synthesis. Nogalamycin contains two saccharides. The neutral monosaccharide attaches to the D ring, similar to the aminoglycoside moieties of the doxorubicin class, while the second, basic saccharide attaches to the phenolic group on the A ring in the ortho position to form a unique family of hexacyclic anthracyclines. Nogalamycin is potent antibacterial and antitumor agent. Nogalamycin was markedly cytotoxic in vitro and was active against several tumor systems in vivo.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Crystal structure of the glycosyltransferase SnogD from the biosynthetic pathway of nogalamycin in Streptomyces nogalater. | 2012-09 |
|
| Discovery of a two-component monooxygenase SnoaW/SnoaL2 involved in nogalamycin biosynthesis. | 2012-05-25 |
|
| Identification of late-stage glycosylation steps in the biosynthetic pathway of the anthracycline nogalamycin. | 2012-01-02 |
|
| Human mismatch repair and G*T mismatch binding by hMutSalpha in vitro is inhibited by adriamycin, actinomycin D, and nogalamycin. | 2001-03-30 |
|
| [Effects of chromomycine A 3 and nogalamycin on embryonal cells of amphibians in differentiation in vitro]. | 1972-06-26 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30324706
Nogalamycin inhibited EGFR-tyrosine kinase with IC50 value of 37.71 nM.
| Substance Class |
Chemical
Created
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admin
on
Edited
Wed Apr 02 08:44:44 GMT 2025
by
admin
on
Wed Apr 02 08:44:44 GMT 2025
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| Record UNII |
L059DCD6IP
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Validated (UNII)
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NCI_THESAURUS |
C1594
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SUB09341MIG
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NOGALAMYCIN
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m8028
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C700
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100000083565
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