CHEBI:142517 - tschimganine

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ChEBI Name tschimganine
ChEBI ID CHEBI:142517
Definition A benzoate ester resulting from the formal condensation of the carboxy group of vanillic acid with the hydroxy group of (−)-borneol. A metabolite isolated from Ferula dissecta.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H24O4
Net Charge 0
Average Mass 304.381
Monoisotopic Mass 304.16746
InChI InChI=1S/C18H24O4/c1-17(2)12-7-8-18(17,3)15(10-12)22-16(20)11-5-6-13(19)14(9-11)21-4/h5-6,9,12,15,19H,7-8,10H2,1-4H3/t12-,15+,18+/m0/s1
InChIKey KTOAGBIQQPGNIR-WBHUJUFNSA-N
SMILES C(C1=CC(=C(C=C1)O)OC)(=O)O[C@@H]2C[C@@]3(CC[C@]2(C3(C)C)C)[H]
Metabolite of Species Details
Apis mellifera Isolated from propolis (bee glue). See: PubMed
Ferula dissecta (NCBI:txid371337) Found in root (BTO:0001188). See: Wang, Z.Q., Huang, C., Huang, J., Han, H.Y., Li, G.Y., Wang, J.H. and Sun, T.M. (2014) The stereochemistry of two monoterpenoid diastereomers from Ferula dissecta. RSC Adv., 4, 14373-14377.
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
animal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
disinfectant
An antimicrobial agent that is applied to non-living objects to destroy harmful microorganisms or to inhibit their activity.
(via phenol )
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via phenol )
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
(via phenol )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antiseptic drug
A substance used locally on humans and other animals to destroy harmful microorganisms or to inhibit their activity (cf. disinfectants, which destroy microorganisms found on non-living objects, and antibiotics, which can be transported through the lymphatic system to destroy bacteria within the body).
(via phenol )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tschimganine (CHEBI:142517) has functional parent (−)-borneol (CHEBI:15394)
tschimganine (CHEBI:142517) has functional parent vanillic acid (CHEBI:30816)
tschimganine (CHEBI:142517) has role animal metabolite (CHEBI:75767)
tschimganine (CHEBI:142517) has role antimicrobial agent (CHEBI:33281)
tschimganine (CHEBI:142517) has role antineoplastic agent (CHEBI:35610)
tschimganine (CHEBI:142517) has role plant metabolite (CHEBI:76924)
tschimganine (CHEBI:142517) is a benzoate ester (CHEBI:36054)
tschimganine (CHEBI:142517) is a carbobicyclic compound (CHEBI:36785)
tschimganine (CHEBI:142517) is a monomethoxybenzene (CHEBI:25235)
tschimganine (CHEBI:142517) is a monoterpenoid (CHEBI:25409)
tschimganine (CHEBI:142517) is a phenol (CHEBI:15882)
IUPAC Name
(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 4-hydroxy-3-methoxybenzoate
Synonyms Sources
chimganin ChEBI
tschimganin ChEBI
tschimganine ChEBI
Registry Number Type Source
26876325 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20350297 PubMed citation Europe PMC
21589808 PubMed citation Europe PMC
23521895 PubMed citation Europe PMC
29900664 PubMed citation Europe PMC
29912155 PubMed citation Europe PMC
Last Modified
16 November 2018
General Comment
2018-11-07 Relevant Articles: Wang, Z.Q., Huang, C., Huang, J., Han, H.Y., Li, G.Y., Wang, J.H. and Sun, T.M. (2014) The stereochemistry of two monoterpenoid diastereomers from Ferula dissecta. RSC Adv., 4, 14373-14377.