chanoclavine-I (CHEBI:3576)

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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

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 )

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 heterotricyclic compound (CHEBI:26979) 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

Last Modified

12 October 2022