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CHEBI:94770 - pirarubicin

ChEBI IDCHEBI:94770
ChEBI Namepirarubicin
Stars
DefinitionAn anthracycline that is doxorubicin in which the hydroxy group at position 4' is replaced by a (2R)-tetrahydro-2H-pyran-2-yloxy group.
Secondary ChEBI IDCHEBI:32011
Last Modified9 June 2025
DownloadsMolfile
FormulaC32H37NO12
Net Charge0
Average Mass627.643
Monoisotopic Mass627.23158
SMILESCOc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O[C@@H]2CCCCO2)[C@H](C)O1
InChIInChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1
InChIKeyKMSKQZKKOZQFFG-YXRRJAAWSA-N
Wikipedia
Roles Classification
Biological Roles:
cardiotoxic agent  A role played by a chemical compound exhibiting itself through the ability to induce damage to the heart and cardiomyocytes.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
pirarubicin (CHEBI:94770) has functional parent doxorubicin (CHEBI:28748)
pirarubicin (CHEBI:94770) has role antineoplastic agent (CHEBI:35610)
pirarubicin (CHEBI:94770) has role cardiotoxic agent (CHEBI:50912)
pirarubicin (CHEBI:94770) is a p-quinones (CHEBI:25830)
pirarubicin (CHEBI:94770) is a aminoglycoside (CHEBI:47779)
pirarubicin (CHEBI:94770) is a anthracycline (CHEBI:48120)
pirarubicin (CHEBI:94770) is a deoxy hexoside (CHEBI:35315)
pirarubicin (CHEBI:94770) is a monosaccharide derivative (CHEBI:63367)
pirarubicin (CHEBI:94770) is a oxanes (CHEBI:46942)
pirarubicin (CHEBI:94770) is a primary α-hydroxy ketone (CHEBI:139590)
pirarubicin (CHEBI:94770) is a tertiary α-hydroxy ketone (CHEBI:139592)
pirarubicin (CHEBI:94770) is a tetracenequinones (CHEBI:51286)
IUPAC Name 
(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranoside
INNs  Source
pirarubicinWHO MedNet
pirarubicinumWHO MedNet
pirarubicinaWHO MedNet
pirarubicineWHO MedNet
Synonyms  Source
therarubicinDrugCentral
(2''R)-4'-O-tetrahydropyranyldoxorubicinChEBI
(2''R)-4'-O-tetrahydropyranyladriamycinChEBI
THP-adriamycinChEBI
4'-O-tetrahydropyranyladriamycinChEBI
(8S,10S)-10-[[3-Amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedioneChEBI
Manual XrefsDatabases
D01885KEGG DRUG
LSM-5899LINCS
2198DrugCentral
DB11616DrugBank
PirarubicinWikipedia
Registry NumbersSources
CAS:72496-41-4ChEBI
Citations