CHEBI:41977 - daunorubicin

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ChEBI Name daunorubicin
ChEBI ID CHEBI:41977
Definition A natural product found in Actinomadura roseola.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41970, CHEBI:65723, CHEBI:4330, CHEBI:23560
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Formula C27H29NO10
Net Charge 0
Average Mass 527.51990
Monoisotopic Mass 527.179
InChI InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
InChIKey STQGQHZAVUOBTE-VGBVRHCVSA-N
SMILES COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(C)=O
Metabolite of Species Details
Actinomadura roseola (NCBI:46179) of strain Ao108 See: PubMed
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via anthracycline )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via carbohydrate-containing antibiotic )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing daunorubicin (CHEBI:41977) has parent hydride tetracene (CHEBI:32600)
daunorubicin (CHEBI:41977) has role antineoplastic agent (CHEBI:35610)
daunorubicin (CHEBI:41977) has role bacterial metabolite (CHEBI:76969)
daunorubicin (CHEBI:41977) is a p-quinones (CHEBI:25830)
daunorubicin (CHEBI:41977) is a aminoglycoside antibiotic (CHEBI:22507)
daunorubicin (CHEBI:41977) is a anthracycline (CHEBI:48120)
daunorubicin (CHEBI:41977) is a tetracenequinones (CHEBI:51286)
daunorubicin (CHEBI:41977) is conjugate base of daunorubicin(1+) (CHEBI:64677)
Incoming 10-carboxy-13-deoxydaunorubicin (CHEBI:77195) has functional parent daunorubicin (CHEBI:41977)
daunorubicin(1+) (CHEBI:64677) is conjugate acid of daunorubicin (CHEBI:41977)
IUPAC Name
(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
INNs Sources
daunorubicin ChemIDplus
daunorubicinum ChemIDplus
Synonyms Sources
(+)-daunomycin ChemIDplus
(8S-cis)-8-acetyl-10-((3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione ChemIDplus
acetyladriamycin ChemIDplus
Daunomycin KEGG COMPOUND
DAUNOMYCIN PDBeChem
Daunorubicin KEGG COMPOUND
leukaemomycin C ChemIDplus
Database Links Databases
C01907 KEGG COMPOUND
D07776 KEGG DRUG
Daunorubicin Wikipedia
DB00694 DrugBank
DM1 PDBeChem
LMPK13050002 LIPID MAPS
LSM-2962 LINCS
View more database links
Registry Numbers Types Sources
1445583 Beilstein Registry Number ChemIDplus
1445583 Reaxys Registry Number Reaxys
20830-81-3 CAS Registry Number KEGG COMPOUND
20830-81-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10820108 PubMed citation Europe PMC
23414337 PubMed citation Europe PMC
23900905 PubMed citation Europe PMC
24396448 PubMed citation Europe PMC
Last Modified
06 June 2016