CHEBI:44504 - nogalamycin

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ChEBI Name nogalamycin
ChEBI ID CHEBI:44504
Definition An anthracycline antibiotic isolated from Streptomyces nogalater. It is a DNA intercalator and exhibits anticancer properties.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C39H49NO16
Net Charge 0
Average Mass 739.80530
Monoisotopic Mass 739.32039
InChI 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
InChIKey KGTDRFCXGRULNK-JYOBTZKQSA-N
SMILES [H][C@@]12OC3=C(C=C(O)C4=C3C(=O)C3=C(C(O)=C5[C@H](C[C@](C)(O)[C@H](C(=O)OC)C5=C3)O[C@@H]3O[C@@H](C)[C@H](OC)[C@@](C)(OC)[C@H]3OC)C4=O)[C@@](C)(O1)[C@H](O)[C@H]([C@@H]2O)N(C)C
Metabolite of Species Details
Streptomyces nogalater (NCBI:txid38314) of strain Lv65 See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): cardiotoxic agent
A role played by a chemical compound exihibiting itself through the ability to induce damage to the heart and cardiomyocytes.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
intercalator
A role played by a chemical agent which exhibits the capability of occupying space between DNA base pairs due to particular properties in size, shape and charge. Intercalation of chemical compounds in DNA helix can result in replication errors (shift, mutation) or DNA damages.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via anthracycline antibiotic )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via anthracycline )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing nogalamycin (CHEBI:44504) has role antineoplastic agent (CHEBI:35610)
nogalamycin (CHEBI:44504) has role bacterial metabolite (CHEBI:76969)
nogalamycin (CHEBI:44504) has role cardiotoxic agent (CHEBI:50912)
nogalamycin (CHEBI:44504) has role intercalator (CHEBI:24853)
nogalamycin (CHEBI:44504) is a anthracycline antibiotic (CHEBI:49322)
nogalamycin (CHEBI:44504) is a methyl ester (CHEBI:25248)
nogalamycin (CHEBI:44504) is a monosaccharide derivative (CHEBI:63367)
nogalamycin (CHEBI:44504) is a organic heterohexacyclic compound (CHEBI:51914)
nogalamycin (CHEBI:44504) is a polyketide (CHEBI:26188)
nogalamycin (CHEBI:44504) is a tertiary amino compound (CHEBI:50996)
nogalamycin (CHEBI:44504) is a tetrol (CHEBI:33573)
IUPAC Name
methyl (2R,3S,4R,5R,6R,11S,13S,14R)-11-[(6-deoxy-3-C-methyl-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-4-(dimethylamino)-3,5,8,10,13-pentahydroxy-6,13-dimethyl-9,16-dioxo-3,4,5,6,9,11,12,13,14,16-decahydro-2H-2,6-epoxytetraceno[1,2-b]oxocine-14-carboxylate
INNs Sources
nogalamicina WHO MedNet
nogalamycin WHO MedNet
nogalamycine WHO MedNet
nogalamycinum WHO MedNet
Synonyms Sources
antibiotic 205t3 ChemIDplus
U 15167 ChemIDplus
U-15167 ChemIDplus
Manual Xrefs Databases
4451071 ChemSpider
C18633 KEGG COMPOUND
CPD-15795 MetaCyc
D05198 KEGG DRUG
NGM PDBeChem
Nogalamycin Wikipedia
View more database links
Registry Numbers Types Sources
1404-15-5 CAS Registry Number KEGG COMPOUND
1404-15-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
23 November 2020