CHEBI:140441 - 12-epi-hapalindole U

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ChEBI Name 12-epi-hapalindole U
ChEBI ID CHEBI:140441
ChEBI ASCII Name 12-epi-hapalindole U
Definition A tetracyclic hapalindole that is hapalindole U in which the carbon bearing the vinyl group has S configuration instead of R. It is produced by the Stigonematales genus of cyanobacteria.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
Download Molfile XML SDF
Formula C21H24N2
Net Charge 0
Average Mass 304.429
Monoisotopic Mass 304.19395
InChI InChI=1S/C21H24N2/c1-6-21(4)11-10-15-18(19(21)22-5)13-12-23-16-9-7-8-14(17(13)16)20(15,2)3/h6-9,12,15,18-19,23H,1,10-11H2,2-4H3/t15-,18+,19+,21+/m0/s1
InChIKey SLUFHMQYBPOTFZ-BQBKMSKFSA-N
SMILES C12=CC=CC3=C1C([C@@]4([C@](C2(C)C)([H])CC[C@@]([C@@H]4[N+]#[C-])(C)C=C)[H])=CN3
Metabolite of Species Details
Hapalosiphon welwitschii (NCBI:txid1433842) of strain UTEX B1830 See: PubMed
Fischerella ambigua (NCBI:txid230521) of strain UTEX 1903 See: PubMed
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
(via hapalindole )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 12-epi-hapalindole U (CHEBI:140441) has role bacterial metabolite (CHEBI:76969)
12-epi-hapalindole U (CHEBI:140441) is a hapalindole (CHEBI:141617)
12-epi-hapalindole U (CHEBI:140441) is a isocyanide (CHEBI:35353)
12-epi-hapalindole U (CHEBI:140441) is a organic heterotetracyclic compound (CHEBI:38163)
IUPAC Name
(6aS,9S,10R,10aS)-9-ethenyl-10-isocyano-6,6,9-trimethyl-2,2a,6,6a,7,8,9,10,10a,10c-decahydronaphtho[1,2,3-cd]indole
Synonym Source
12-epi-hapalindole U UniProt
Manual Xref Database
CPD-20794 MetaCyc
View more database links
Registry Number Type Source
28957191 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
26629885 PubMed citation SUBMITTER
28225144 PubMed citation Europe PMC
28288107 PubMed citation Europe PMC
28626997 PubMed citation Europe PMC
29531360 PubMed citation Europe PMC
Last Modified
20 August 2018