EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:41791 - calyculin A

ChEBI IDCHEBI:41791
ChEBI Namecalyculin A
Stars
DefinitionA natural product with formula C50H81N4O15P. It is a cytotoxic compound isolated from the Japanese marine sponge Discodermia calyx.
Secondary ChEBI IDCHEBI:3335
Last Modified30 January 2025
DownloadsMolfile
FormulaC50H81N4O15P
Net Charge0
Average Mass1009.185
Monoisotopic Mass1008.54360
SMILES[H][C@]1([C@H](C[C@H](O)[C@H](C)[C@H](O)[C@H](C)/C=C(C)/C(C)=C/C=C/C(C)=C\C#N)OC)O[C@]2(C[C@@H](O)[C@H](C)[C@H](C/C=C/c3coc([C@@H](C)CCNC(=O)[C@@H](O)[C@@H](O)[C@H](COC)N(C)C)n3)O2)C(C)(C)[C@H]1OP(=O)(O)O
InChIInChI=1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m0/s1
InChIKeyFKAWLXNLHHIHLA-YCBIHMBMSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Discodermia calyx (WORMS:190926) - PubMed (24974231)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor  Any EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of phosphoprotein phosphatase (EC 3.1.3.16).
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
ChEBI Ontology
Outgoing Relation(s)
calyculin A (CHEBI:41791) has role animal metabolite (CHEBI:75767)
calyculin A (CHEBI:41791) has role EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor (CHEBI:37153)
calyculin A (CHEBI:41791) has role marine metabolite (CHEBI:76507)
calyculin A (CHEBI:41791) is a 1,3-oxazoles (CHEBI:46812)
calyculin A (CHEBI:41791) is a ether (CHEBI:25698)
calyculin A (CHEBI:41791) is a nitrile (CHEBI:18379)
calyculin A (CHEBI:41791) is a olefinic compound (CHEBI:78840)
calyculin A (CHEBI:41791) is a organic phosphate (CHEBI:25703)
calyculin A (CHEBI:41791) is a oxaspiro compound (CHEBI:37948)
calyculin A (CHEBI:41791) is a secondary alcohol (CHEBI:35681)
calyculin A (CHEBI:41791) is a secondary carboxamide (CHEBI:140325)
calyculin A (CHEBI:41791) is a tertiary amino compound (CHEBI:50996)
Synonyms  Source
calyculin-AChEBI
CLAChEBI
N-[(3S)-3-[4-[(1E)-3-[(2R,3R,5R,7S,8S,9R)-2-[(1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-Cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraen-1-yl]-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propen-1-yl]-2-oxazolyl]butyl]-4-deoxy-4-(dimethylamino)-5-O-methyl-L-ribonamideChEBI
(−)-calyculin AChEBI
Manual XrefsDatabases
C05370KEGG COMPOUND
CYUPDBeChem
C00038685KNApSAcK
DB02860DrugBank
CalyculinWikipedia
Registry NumbersSources
Reaxys:4903216Reaxys
CAS:101932-71-2KEGG COMPOUND
Citations