durhamycin A (CHEBI:65814)

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CHEBI:65814 - durhamycin A

ChEBI ID	CHEBI:65814
ChEBI Name	durhamycin A
Stars
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.
Last Modified	1 August 2013
Downloads	Molfile

Formula	C62H92O28
Net Charge	0
Average Mass	1285.390
Monoisotopic Mass	1284.57751
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]5C[C@@H](O)[C@H](O)[C@@H](C)O5)[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
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

Species of Metabolite	Component	Source	Comments
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 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

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 Numbers	Sources
Reaxys:9250588	Reaxys

Citations