eseroline (CHEBI:48845)

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ChEBI Name	eseroline

ChEBI ID	CHEBI:48845

Definition	A pyrroloindole that is 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole substituted by methyl groups at positions 1, 3a and 8 and a hydroxy group at position 5. It is a metabolite of physostigmine and causes neuronal cell death by a mechanism involving loss of cell ATP.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C13H18N2O

Net Charge

Average Mass

218.29480

Monoisotopic Mass

218.14191

InChI

InChI=1S/C13H18N2O/c1-13-6-7-14(2)12(13)15(3)11-5-4-9(16)8-10(11)13/h4-5,8,12,16H,6-7H2,1-3H3/t12-,13+/m1/s1

InChIKey

HKGWQUVGHPDEBZ-OLZOCXBDSA-N

SMILES

CN1CC[C@]2(C)[C@H]1N(C)c1ccc(O)cc21

Roles Classification
Biological Role(s):	human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans. opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.

Application(s):	opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.

ChEBI Ontology
Outgoing	eseroline (CHEBI:48845) has role human xenobiotic metabolite (CHEBI:76967) eseroline (CHEBI:48845) has role opioid analgesic (CHEBI:35482) eseroline (CHEBI:48845) is a phenols (CHEBI:33853) eseroline (CHEBI:48845) is a pyrroloindole (CHEBI:48133)

Incoming	5-O-[8-(cis-2,6-dimethylmorpholino)octylcarbamoyl]eseroline (CHEBI:43927) has functional parent eseroline (CHEBI:48845)

IUPAC Name

(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol

Last Modified

26 February 2016