bryostatin 1 (CHEBI:88353)

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CHEBI:88353 - bryostatin 1

ChEBI ID	CHEBI:88353
ChEBI Name	bryostatin 1
Stars
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.
Last Modified	30 November 2017
Submitter	Gareth Owen
Downloads	Molfile

Formula	C47H68O17
Net Charge	0
Average Mass	905.044
Monoisotopic Mass	904.44565
SMILES	[H][C@@]12C/C(=C\C(=O)OC)[C@H](OC(=O)/C=C/C=C/CCC)[C@@](O)(O1)C(C)(C)/C=C/[C@H]1C/C(=C\C(=O)OC)C[C@@H](C[C@]3(O)O[C@H](C[C@@H](O)CC(=O)O[C@@H]([C@@H](C)O)C2)C[C@H](OC(C)=O)C3(C)C)O1
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

Wikipedia

Species of Metabolite	Component	Source	Comments
Bugula neritina (ncbitaxon:10212)	-	DOI (10.1021/ja00388a092)

Roles Classification

Biological Roles:

protein kinase C agonist An agonist that selectively binds to and activates a protein kinase C receptor

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.

alpha-secretase activator An activator of α-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.

marine metabolite Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.

Application:

antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	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) has role α-secretase activator (CHEBI:88355)
	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[21.3.1.1^3,7.1^11,15]nonacos-8-en-12-yl (2E,4E)-octa-2,4-dienoate

Synonym	Source
bryostatin-1	ChEBI

Manual Xrefs	Databases
Bryostatin	Wikipedia
C00038654	KNApSAcK
C05149	KEGG COMPOUND
DB11752	DrugBank

Registry Numbers	Sources
Reaxys:4349157	Reaxys
CAS:83314-01-6	ChemIDplus
CAS:83314-01-6	KEGG COMPOUND

Citations