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CHEBI:65421 - apratoxin D

ChEBI IDCHEBI:65421
ChEBI Nameapratoxin D
Stars
DefinitionAn aprotoxin having the common aprotoxin cyclodepsipeptide skeleton where the isoleucyl residue carries an N-methyl substituent and the side-chain adjacent to the lactone is (2R)-4,4-dimethylpentan-2-yl. It is isolateed from Lyngbya majuscula and Lyngbya sordida and exhibits anticancer properties.
Last Modified21 February 2013
DownloadsMolfile
FormulaC48H75N5O8S
Net Charge0
Average Mass882.222
Monoisotopic Mass881.53364
SMILESCC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=O)O[C@H]([C@@H](C)CC(C)(C)C)C[C@@H](C)C[C@H](O)[C@H](C)C2=N[C@@H](/C=C(\C)C(=O)N[C@@H](Cc3ccc(OC)cc3)C(=O)N(C)[C@@H](C)C(=O)N1C)CS2
InChIInChI=1S/C48H75N5O8S/c1-14-29(3)41-46(58)53-21-15-16-38(53)47(59)61-40(31(5)26-48(8,9)10)23-28(2)22-39(54)32(6)43-49-35(27-62-43)24-30(4)42(55)50-37(25-34-17-19-36(60-13)20-18-34)45(57)51(11)33(7)44(56)52(41)12/h17-20,24,28-29,31-33,35,37-41,54H,14-16,21-23,25-27H2,1-13H3,(H,50,55)/b30-24+/t28-,29-,31-,32-,33-,35-,37-,38-,39-,40-,41-/m0/s1
InChIKeyOFUDGDJEKOUEKG-MBNNSLKJSA-N
Species of MetaboliteComponentSourceComments
Lyngbya majuscula (ncbitaxon:158786) - PubMed (18444683)
Lyngbya sordida (ncbitaxon:748015) - PubMed (18444683)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
apratoxin D (CHEBI:65421) has role antineoplastic agent (CHEBI:35610)
apratoxin D (CHEBI:65421) has role metabolite (CHEBI:25212)
apratoxin D (CHEBI:65421) is a apratoxin (CHEBI:35214)
IUPAC Name 
(3S,5S,7S,8S,12S,13E,17S,20S,23S,28aS)-23-[(2S)-butan-2-yl]-3-[(2S)-4,4-dimethylpentan-2-yl]-7-hydroxy-17-(4-methoxybenzyl)-5,8,14,19,20,22-hexamethyl-3,4,5,6,7,8,11,12,16,17,19,20,22,23,26,27,28,28a-octadecahydro-1H-12,9-(azeno)pyrrolo[2,1-c][1,19,4,7,10,13]oxathiatetraazacyclohexacosine-1,15,18,21,24-pentone
Registry NumbersSources
Reaxys:18840921Reaxys
Citations