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CHEBI:31738 - jadomycin B

ChEBI IDCHEBI:31738
ChEBI Namejadomycin B
Stars
DefinitionA jadomycin that is jadomycin A in which the phenolic hydroxy group at position 12 has been converted to the corresponding 2,6-dideoxy-α-L-ribo-hexopyranoside, isolated from Streptomyces venezuelae. It exists as a diastereoisomeric mixture consisting of both 3aS and 3aR isomers.
Last Modified5 December 2019
DownloadsMolfile
FormulaC30H31NO9
Net Charge0
Average Mass549.576
Monoisotopic Mass549.19988
SMILES[H]C12OC(=O)[C@]([H])([C@@H](C)CC)N1C1=C(C(=O)c3cccc(O[C@H]4C[C@@H](O)[C@@H](O)[C@H](C)O4)c3C1=O)c1c(O)cc(C)cc12
InChIInChI=1S/C30H31NO9/c1-5-13(3)24-30(37)40-29-16-9-12(2)10-17(32)21(16)23-25(31(24)29)28(36)22-15(27(23)35)7-6-8-19(22)39-20-11-18(33)26(34)14(4)38-20/h6-10,13-14,18,20,24,26,29,32-34H,5,11H2,1-4H3/t13-,14-,18+,20-,24-,26-,29?/m0/s1
InChIKeyBSBSCJRAEMDCHC-LVOPHWFOSA-N
Species of MetaboliteComponentSourceComments
Streptomyces venezuelae (ncbitaxon:54571)
cell suspension culture (BTO:0000221) PubMed (21565515) Strain: ISP5230
- PubMed (8514643) Strain: ISP5230
Roles Classification
Biological Roles:
Aurora kinase inhibitor  Any protein kinase inhibitor that inhibits the action of an Aurora kinase (a group of serine/threonine kinases that are essential for cell proliferation).
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
jadomycin B (CHEBI:31738) has functional parent jadomycin A (CHEBI:81887)
jadomycin B (CHEBI:31738) has role antibacterial agent (CHEBI:33282)
jadomycin B (CHEBI:31738) has role antineoplastic agent (CHEBI:35610)
jadomycin B (CHEBI:31738) has role apoptosis inducer (CHEBI:68495)
jadomycin B (CHEBI:31738) has role Aurora kinase inhibitor (CHEBI:70770)
jadomycin B (CHEBI:31738) has role bacterial metabolite (CHEBI:76969)
jadomycin B (CHEBI:31738) is a glycoside (CHEBI:24400)
jadomycin B (CHEBI:31738) is a jadomycin (CHEBI:48217)
jadomycin B (CHEBI:31738) is a organic heteropentacyclic compound (CHEBI:38164)
IUPAC Name 
(1S)-1-[(2S)-butan-2-yl]-7-hydroxy-5-methyl-2,8,13-trioxo-1,2,8,13-tetrahydro-3aH-benzo[b][1,3]oxazolo[3,2-f]phenanthridin-12-yl 2,6-dideoxy-α-L-ribo-hexopyranoside
Synonym  Source
jadomycin BKEGG COMPOUND
Manual XrefsDatabases
C12395KEGG COMPOUND
C00016835KNApSAcK
CPD-12934MetaCyc
Registry NumbersSources
Reaxys:9745667Reaxys
CAS:149633-99-8KEGG COMPOUND
CAS:149633-99-8ChemIDplus
Citations