CHEBI:88353 - bryostatin 1

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ChEBI Name bryostatin 1
ChEBI ID CHEBI:88353
Definition A member of the class of bryostatins that is (17E)-2-oxooxacyclohexacos-17-ene which is substituted by hydroxy groups at positions 4, 10, and 20; an acetoxy group at position 8; methyl groups at positions 9, 9, 18, and 19; 2-methoxy-2-oxoethylidene groups at positions 14 and 24; an (E,E)-octa-2,4-dienoyloxy group at position 21; and with oxygen bridges linking positions 6 to 10, 12 to 16, and 20 to 24. It is one of the most abundant member of the class of bryostatins.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C47H68O17
Net Charge 0
Average Mass 905.034
Monoisotopic Mass 904.446
InChI InChI=1S/C47H68O17/c1-10-11-12-13-14-15-39(51)62-43-31(22-41(53)58-9)21-34-25-37(28(2)48)61-42(54)24-32(50)23-35-26-38(59-29(3)49)45(6,7)46(55,63-35)27-36-19-30(20-40(52)57-8)18-33(60-36)16-17-44(4,5)47(43,56)64-34/h12-17,20,22,28,32-38,43,48,50,55-56H,10-11,18-19,21,23-27H2,1-9H3/b13-12+,15-14+,17-16+,30-20+,31-22+/t28-,32-,33+,34+,35-,36+,37-,38+,43+,46+,47-/m1/s1
InChIKey MJQUEDHRCUIRLF-TVIXENOKSA-N
SMILES C/1(\C[C@H]2O[C@@H](C1)C[C@]3(C([C@H](C[C@@H](C[C@H](CC(O[C@@H]([C@@H](C)O)C[C@@]4(C\C(\[C@@H]([C@](C(C=C2)(C)C)(O4)O)OC(/C=C/C=C/CCC)=O)=C/C(OC)=O)[H])=O)O)O3)OC(C)=O)(C)C)O)=C\C(OC)=O
Metabolite of Species Details
Bugula neritina (NCBI:txid10212) See: DOI
Roles Classification
Biological Role(s): marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
protein kinase C agonist
An agonist that selectively binds to and activates a protein kinase C receptor
alpha-secretase activator
An activator of alpha-secretase, one of the three endopeptidases that are specific for amyloid protein precursor and which have been identified based upon the region of the amyloid protein precursor which they cleave.
anti-HIV-1 agent
An anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bryostatin 1 (CHEBI:88353) has role α-secretase activator (CHEBI:88355)
bryostatin 1 (CHEBI:88353) has role anti-HIV-1 agent (CHEBI:64947)
bryostatin 1 (CHEBI:88353) has role antineoplastic agent (CHEBI:35610)
bryostatin 1 (CHEBI:88353) has role marine metabolite (CHEBI:76507)
bryostatin 1 (CHEBI:88353) has role protein kinase C agonist (CHEBI:64018)
bryostatin 1 (CHEBI:88353) is a acetate ester (CHEBI:47622)
bryostatin 1 (CHEBI:88353) is a bryostatins (CHEBI:3200)
bryostatin 1 (CHEBI:88353) is a cyclic hemiketal (CHEBI:59780)
bryostatin 1 (CHEBI:88353) is a enoate ester (CHEBI:51702)
bryostatin 1 (CHEBI:88353) is a methyl ester (CHEBI:25248)
bryostatin 1 (CHEBI:88353) is a organic heterotetracyclic compound (CHEBI:38163)
bryostatin 1 (CHEBI:88353) is a secondary alcohol (CHEBI:35681)
IUPAC Name
(1S,3S,5Z,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-25-(acetyloxy)-1,11,21-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl (2E,4E)-octa-2,4-dienoate
Synonym Source
bryostatin-1 ChEBI
Database Links Databases
Bryostatin Wikipedia
C00038654 KNApSAcK
C05149 KEGG COMPOUND
DB11752 DrugBank
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Registry Numbers Types Sources
4349157 Reaxys Registry Number Reaxys
83314-01-6 CAS Registry Number ChemIDplus
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Last Modified
30 November 2017