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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
Structure of Nogalamycin

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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
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

Patents

Sample Use Guides

Nogalamycin inhibited EGFR-tyrosine kinase with IC50 value of 37.71 nM.
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:44:44 GMT 2025
Edited
by admin
on Wed Apr 02 08:44:44 GMT 2025
Record UNII
L059DCD6IP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANTIBIOTIC 205T3
Preferred Name English
Nogalamycin
INN   MI   USAN  
USAN   INN  
Official Name English
U 15167
Code English
NOGALAMYCIN [USAN]
Common Name English
nogalamycin [INN]
Common Name English
U-15167
Code English
NOGALAMYCIN [MI]
Common Name English
NSC-70845
Code English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
Code System Code Type Description
EVMPD
SUB09341MIG
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID20930779
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
NSC
70845
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
MESH
D009621
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
WIKIPEDIA
NOGALAMYCIN
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
CAS
1404-15-5
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
FDA UNII
L059DCD6IP
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
PUBCHEM
5289019
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
INN
1993
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
CHEBI
44504
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
ChEMBL
CHEMBL504459
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
MERCK INDEX
m8028
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C700
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
SMS_ID
100000083565
Created by admin on Wed Apr 02 08:44:44 GMT 2025 , Edited by admin on Wed Apr 02 08:44:44 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY