CHEBI:65814 - durhamycin A

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name durhamycin A
ChEBI ID CHEBI:65814
Definition An aureolic acid that consists of tetrasaccharide and disaccharide moieties attached to the tricyclic aglycone. Isolated from Actinoplanes durhamensis, it exhibits anti-HIV activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C62H92O28
Net Charge 0
Average Mass 1285.37710
Monoisotopic Mass 1284.57751
InChI InChI=1S/C62H92O28/c1-12-22(2)47-36(85-43-18-37(53(70)26(6)80-43)86-41-16-34(65)51(68)24(4)78-41)15-32-13-31-14-33(61(77-11)59(76)50(67)23(3)63)62(58(75)49(31)57(74)48(32)56(47)73)90-46-20-39(55(72)28(8)82-46)88-45-21-40(60(29(9)83-45)84-30(10)64)89-44-19-38(54(71)27(7)81-44)87-42-17-35(66)52(69)25(5)79-42/h13,15,22-29,33-35,37-46,50-55,60-63,65-74H,12,14,16-21H2,1-11H3/t22?,23?,24-,25-,26-,27-,28-,29-,33-,34-,35-,37-,38-,39-,40-,41+,42+,43+,44+,45+,46+,50?,51-,52-,53-,54-,55-,60+,61?,62-/m1/s1
InChIKey GKQPKEYSNFSHDQ-JVYPXMHJSA-N
SMILES [H][C@@]1(Cc2cc3cc(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)c3c(O)c2C(=O)[C@]1([H])O[C@H]1C[C@@H](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](O)[C@@H](C)O3)[C@@H](OC(C)=O)[C@@H](C)O2)[C@H](O)[C@@H](C)O1)C(OC)C(=O)C(O)C(C)O
Metabolite of Species Details
Actinoplanes durhamensis (NCBI:txid113563) Methylethylketone extract of fermentation broth of Actinoplanes durhamensis See: PubMed
Roles Classification
Biological Role(s): 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.
(via carbohydrate-containing antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing durhamycin A (CHEBI:65814) has role anti-HIV agent (CHEBI:64946)
durhamycin A (CHEBI:65814) has role metabolite (CHEBI:25212)
durhamycin A (CHEBI:65814) is a acetate ester (CHEBI:47622)
durhamycin A (CHEBI:65814) is a aureolic acid (CHEBI:52513)
durhamycin A (CHEBI:65814) is a carbohydrate-containing antibiotic (CHEBI:23007)
durhamycin A (CHEBI:65814) is a carbotricyclic compound (CHEBI:38032)
durhamycin A (CHEBI:65814) 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)-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 Number Type Source
9250588 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12193009 PubMed citation Europe PMC
12762675 PubMed citation Europe PMC
Last Modified
01 August 2013