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:

metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

anti-HIV agent An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.

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