CHEBI:31738 - jadomycin B

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ChEBI Name jadomycin B
ChEBI ID CHEBI:31738
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H31NO9
Net Charge 0
Average Mass 549.570
Monoisotopic Mass 549.19988
InChI InChI=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
InChIKey BSBSCJRAEMDCHC-LVOPHWFOSA-N
SMILES C1=CC(=C2C(=C1)C(C3=C(C2=O)N4C(C5=C3C(=CC(=C5)C)O)(OC([C@@]4([C@H](CC)C)[H])=O)[H])=O)O[C@@H]6O[C@H]([C@@H]([C@@H](C6)O)O)C
Metabolite of Species Details
Streptomyces venezuelae (NCBI:txid54571) Found in cell suspension culture (BTO:0000221). of strain ISP5230 See: PubMed
Streptomyces venezuelae (NCBI:txid54571) of strain ISP5230 See: PubMed
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via angucycline )
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 B KEGG COMPOUND
Manual Xrefs Databases
C00016835 KNApSAcK
C12395 KEGG COMPOUND
CPD-12934 MetaCyc
View more database links
Registry Numbers Types Sources
149633-99-8 CAS Registry Number KEGG COMPOUND
149633-99-8 CAS Registry Number ChemIDplus
9745667 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11932454 PubMed citation Europe PMC
15070349 PubMed citation Europe PMC
15776503 PubMed citation Europe PMC
16468745 PubMed citation Europe PMC
16568271 PubMed citation Europe PMC
18723485 PubMed citation Europe PMC
19075054 PubMed citation Europe PMC
21565515 PubMed citation Europe PMC
22714025 PubMed citation Europe PMC
23670961 PubMed citation Europe PMC
28904004 PubMed citation Europe PMC
7764672 PubMed citation Europe PMC
8514643 PubMed citation Europe PMC
Last Modified
05 December 2019