CHEBI:66695 - metachromin S

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ChEBI Name metachromin S
ChEBI ID CHEBI:66695
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C26H39NO3
Net Charge 0
Average Mass 413.59280
Monoisotopic Mass 413.29299
InChI InChI=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
InChIKey YBVKKXUZRPNHQO-JEJCENLRSA-N
SMILES CC(C)CCNC1=CC(=O)C(O)=C(C\C=C(/C)CC[C@@]2(C)CCC=C(C)[C@H]2C)C1=O
Metabolite of Species Details
Spongia (NCBI:txid121489) of strain SS 1037 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 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 Xref Database
23076805 ChemSpider
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Registry Number Type Source
18556301 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18057748 PubMed citation Europe PMC
Last Modified
02 June 2016