EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:66695 - metachromin S

ChEBI IDCHEBI:66695
ChEBI Namemetachromin S
Stars
DefinitionA sesquiterpenoid that is 5-amino-2-hydroxy-3-methyl-1,4-benzoquinone in which one of the hydrogens of the methyl group is replaced by a 2-methyl-4-[(1R,2S)-1,2,3-trimethylcyclohex-3-en-1-yl]but-1-en-1-yl group and one of the hydrogens attached to the nitrogen is replaced by a 3-methylbutyl group. It is isolated from an Okinawan sponge Spongia sp.SS-1037 and exhibits moderate cytotoxicity against L1210 murine leukemia and KB human epidermoid carcinoma cells.
Last Modified2 June 2016
DownloadsMolfile
FormulaC26H39NO3
Net Charge0
Average Mass413.602
Monoisotopic Mass413.29299
SMILESCC1=CCC[C@](C)(CC/C(C)=C/CC2=C(O)C(=O)C=C(NCCC(C)C)C2=O)[C@@H]1C
InChIInChI=1S/C26H39NO3/c1-17(2)12-15-27-22-16-23(28)25(30)21(24(22)29)10-9-18(3)11-14-26(6)13-7-8-19(4)20(26)5/h8-9,16-17,20,27,30H,7,10-15H2,1-6H3/b18-9+/t20-,26-/m1/s1
InChIKeyYBVKKXUZRPNHQO-JEJCENLRSA-N
Species of MetaboliteComponentSourceComments
Spongia (ncbitaxon:121489) - PubMed (18057748) Strain: SS 1037
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)
metachromin S (CHEBI:66695) has role antineoplastic agent (CHEBI:35610)
metachromin S (CHEBI:66695) has role metabolite (CHEBI:25212)
metachromin S (CHEBI:66695) is a monohydroxy-1,4-benzoquinones (CHEBI:67273)
metachromin S (CHEBI:66695) is a secondary amino compound (CHEBI:50995)
metachromin S (CHEBI:66695) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name 
2-hydroxy-5-[(3-methylbutyl)amino]-3-{(2E)-3-methyl-5-[(1R,2S)-1,2,3-trimethylcyclohex-3-en-1-yl]pent-2-en-1-yl}cyclohexa-2,5-diene-1,4-dione
Manual XrefsDatabases
23076805ChemSpider
Registry NumbersSources
Reaxys:18556301Reaxys
Citations