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CHEBI:65815 - durhamycin B

ChEBI IDCHEBI:65815
ChEBI Namedurhamycin B
Stars
DefinitionAn aureolic acid that consists of trisaccharide and disaccharide moieties attached to the tricyclic aglycone. Isolated from Actinoplanes durhamensis, it exhibits anti-HIV activity.
Last Modified1 August 2013
DownloadsMolfile
FormulaC56H82O25
Net Charge0
Average Mass1155.247
Monoisotopic Mass1154.51452
SMILES[H][C@]1(O[C@H]2C[C@@H](O[C@H]3C[C@@H](O[C@H]4C[C@@H](O)[C@H](O)[C@@H](C)O4)[C@@H](OC(C)=O)[C@@H](C)O3)[C@H](O)[C@@H](C)O2)C(=O)c2c(cc3cc(O[C@H]4C[C@@H](O[C@H]5C[C@@H](O)[C@H](O)[C@@H](C)O5)[C@H](O)[C@@H](C)O4)c(C(C)CC)c(O)c3c2O)C[C@]1([H])C(OC)C(=O)C(O)C(C)O
InChIInChI=1S/C56H82O25/c1-11-20(2)42-33(77-39-17-34(48(64)24(6)73-39)78-37-15-31(59)46(62)22(4)71-37)14-29-12-28-13-30(55(70-10)53(69)45(61)21(3)57)56(52(68)44(28)51(67)43(29)50(42)66)81-41-18-35(49(65)25(7)74-41)79-40-19-36(54(26(8)75-40)76-27(9)58)80-38-16-32(60)47(63)23(5)72-38/h12,14,20-26,30-32,34-41,45-49,54-57,59-67H,11,13,15-19H2,1-10H3/t20?,21?,22-,23-,24-,25-,26-,30-,31-,32-,34-,35-,36-,37+,38+,39+,40+,41+,45?,46-,47-,48-,49-,54+,55?,56-/m1/s1
InChIKeyICFBIVXFINBMRC-SRFJPACDSA-N
Species of MetaboliteComponentSourceComments
Actinoplanes durhamensis (ncbitaxon:113563) - PubMed (12193009) Methylethylketone extract of fermentation broth of Actinoplanes durhamensis
Roles Classification
Biological Roles:
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ChEBI Ontology
Outgoing Relation(s)
durhamycin B (CHEBI:65815) has role anti-HIV agent (CHEBI:64946)
durhamycin B (CHEBI:65815) has role metabolite (CHEBI:25212)
durhamycin B (CHEBI:65815) is a acetate ester (CHEBI:47622)
durhamycin B (CHEBI:65815) is a aureolic acid (CHEBI:52513)
durhamycin B (CHEBI:65815) is a carbohydrate-containing antibiotic (CHEBI:23007)
durhamycin B (CHEBI:65815) is a carbotricyclic compound (CHEBI:38032)
durhamycin B (CHEBI:65815) is a dideoxyhexose derivative (CHEBI:63347)
IUPAC Name 
1-C-[(2R*,3R*)-6-(butan-2-yl)-7-{[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy}-3-{[2,6-dideoxy-β-D-arabino-hexopyranosyl-(1→3)-4-O-acetyl-2,6-dideoxy-β-D-lyxo-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy}-5,10-dihydroxy-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl]-5-deoxy-1-O-methylpent-2-ulose
Registry NumbersSources
Reaxys:9250229Reaxys
Citations