tschimganine (CHEBI:142517)

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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

Download	Molfile XML SDF

Formula

C18H24O4

Net Charge

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
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.
Apis mellifera (NCBI:txid7460)	Isolated from propolis (bee glue). See: PubMed

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.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

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 geroprotector (CHEBI:176497) 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 phenols (CHEBI:33853)

IUPAC Name

(1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 4-hydroxy-3-methoxybenzoate

Registry Number	Type	Source
26876325	Reaxys Registry Number	Reaxys

Last Modified

17 August 2023

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.