CHEBI:3576 - chanoclavine-I

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ChEBI Name chanoclavine-I
ChEBI ID CHEBI:3576
Definition An organic tricyclic compound that is 1,3,4,5-tetrahydrobenzo[cd]indole which is substituted at position 4 by a methylamino group and at position 5 by a 3-hydroxy-2-methylprop-1-en-1-yl group (the 4R,5R,E diastereoisomer). It is a precursor of the tetracyclic ergolines agroclavine, elymoclavine and lysergic acid amide.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C16H20N2O
Net Charge 0
Average Mass 256.34280
Monoisotopic Mass 256.15756
InChI InChI=1S/C16H20N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8,13,15,17-19H,7,9H2,1-2H3/b10-6+/t13-,15-/m1/s1
InChIKey SAHHMCVYMGARBT-HEESEWQSSA-N
SMILES CN[C@@H]1Cc2c[nH]c3cccc([C@H]1\C=C(/C)CO)c23
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.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing chanoclavine-I (CHEBI:3576) is a benzoindole (CHEBI:38111)
chanoclavine-I (CHEBI:3576) is a ergot alkaloid (CHEBI:23943)
chanoclavine-I (CHEBI:3576) is a organic tricyclic compound (CHEBI:51959)
chanoclavine-I (CHEBI:3576) is a primary alcohol (CHEBI:15734)
chanoclavine-I (CHEBI:3576) is a secondary amino compound (CHEBI:50995)
chanoclavine-I (CHEBI:3576) is conjugate base of chanoclavine-I(1+) (CHEBI:72949)
Incoming chanoclavine-I aldehyde (CHEBI:64429) has functional parent chanoclavine-I (CHEBI:3576)
chanoclavine-I(1+) (CHEBI:72949) is conjugate acid of chanoclavine-I (CHEBI:3576)
IUPAC Name
(2E)-2-methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol
Synonyms Sources
chanoclavin-I ChemIDplus
chanoclavine ChemIDplus
Manual Xrefs Databases
C00001707 KNApSAcK
C09131 KEGG COMPOUND
CPD-12356 MetaCyc
View more database links
Registry Numbers Types Sources
2390-99-0 CAS Registry Number KEGG COMPOUND
2390-99-0 CAS Registry Number ChemIDplus
28050 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20039019 PubMed citation Europe PMC
20102147 PubMed citation Europe PMC
20118373 PubMed citation Europe PMC
20435769 PubMed citation Europe PMC
447932 PubMed citation Europe PMC
5588727 PubMed citation Europe PMC
Last Modified
28 July 2014