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CHEBI:2992 - barbinine

ChEBI IDCHEBI:2992
ChEBI Namebarbinine
Stars
DefinitionA diterpene alkaloid that is a phytotoxin produced by several Delphinium species.
Last Modified12 February 2015
DownloadsMolfile
FormulaC36H46N2O10
Net Charge0
Average Mass666.768
Monoisotopic Mass666.31525
SMILES[H][C@@]12C[C@@]3([H])C(=O)[C@]1([H])[C@](O)(C[C@@H]3OC)[C@]1(O)C3N(CC)C[C@]4(COC(=O)c5ccccc5N5C(=O)C[C@H](C)C5=O)CC[C@H](OC)[C@@]32[C@]4([H])[C@@H]1OC
InChIInChI=1S/C36H46N2O10/c1-6-37-16-33(17-48-31(42)19-9-7-8-10-22(19)38-25(39)13-18(2)30(38)41)12-11-24(46-4)35-21-14-20-23(45-3)15-34(43,26(21)27(20)40)36(44,32(35)37)29(47-5)28(33)35/h7-10,18,20-21,23-24,26,28-29,32,43-44H,6,11-17H2,1-5H3/t18-,20+,21+,23-,24-,26+,28+,29-,32?,33-,34+,35-,36+/m0/s1
InChIKeyVBFGMIUWGBSAGV-UCFHPTPSSA-N
Species of MetaboliteComponentSourceComments
Delphinium nuttallianum (ncbitaxon:136334) - PubMed (19012276)
Delphinium andersonii (ncbitaxon:136314) - PubMed (19012276)
Delphinium glaucescens (ncbitaxon:136323) - DOI (10.1021/jf00025a020)
Delphinium barbeyi (ncbitaxon:136316) - DOI (10.1021/jf00025a020)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
phytotoxin  Any toxin produced by a plant.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
barbinine (CHEBI:2992) has parent hydride aconitane (CHEBI:35911)
barbinine (CHEBI:2992) has role phytotoxin (CHEBI:38231)
barbinine (CHEBI:2992) is a benzoate ester (CHEBI:36054)
barbinine (CHEBI:2992) is a dicarboximide (CHEBI:35356)
barbinine (CHEBI:2992) is a diterpene alkaloid (CHEBI:23847)
barbinine (CHEBI:2992) is a ether (CHEBI:25698)
barbinine (CHEBI:2992) is a organic heteropolycyclic compound (CHEBI:38166)
barbinine (CHEBI:2992) is a pyrrolidinone (CHEBI:38275)
barbinine (CHEBI:2992) is a tertiary alcohol (CHEBI:26878)
barbinine (CHEBI:2992) is a tertiary amino compound (CHEBI:50996)
IUPAC Name 
(20-ethyl-7,8-dihydroxy-1α,6β,16β-trimethoxy-14-oxoaconitan-4-yl)methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate
Synonyms  Source
BarbinineKEGG COMPOUND
Aconitan-14-one, 7,8-dihydroxy-20-ethyl-4-(((2-(3-methyl-2,5-dioxo-1-pyrrolidinyl)benzoyl)oxy)methyl)-1,6,16-trimethoxy-, (1-alpha,4(S),6-beta,16-beta)-KEGG COMPOUND
Manual XrefsDatabases
C08662KEGG COMPOUND
C00001618KNApSAcK
Registry NumbersSources
Reaxys:8181881Reaxys
Reaxys:10753152Reaxys
CAS:123497-99-4KEGG COMPOUND
CAS:123497-99-4ChemIDplus
Citations