CHEBI:65421 - apratoxin D

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ChEBI Name apratoxin D
ChEBI ID CHEBI:65421
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C48H75N5O8S
Net Charge 0
Average Mass 882.20300
Monoisotopic Mass 881.53364
InChI InChI=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
InChIKey OFUDGDJEKOUEKG-MBNNSLKJSA-N
SMILES CC[C@H](C)[C@@H]1N(C)C(=O)[C@H](C)N(C)C(=O)[C@H](Cc2ccc(OC)cc2)NC(=O)\C(C)=C\[C@H]2CSC(=N2)[C@@H](C)[C@@H](O)C[C@H](C)C[C@H](OC(=O)[C@@H]2CCCN2C1=O)[C@@H](C)CC(C)(C)C
Metabolite of Species Details
Lyngbya majuscula (NCBI:txid158786) See: PubMed
Lyngbya sordida (NCBI:txid748015) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
18840921 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18444683 PubMed citation Europe PMC
23057680 PubMed citation Europe PMC
Last Modified
21 February 2013