CHEBI:65404 - amomol A

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ChEBI Name amomol A
ChEBI ID CHEBI:65404
Definition An oxaspiro compound that is 1-oxaspiro[4.5]deca-6,9-dien-8-one substituted by a (2R)-2-hydroxyheptadecyl moiety and a methoxy group at position 2. It is isolated from the leaves of Amomum aculeatum and exhibits anticancerous efficacy against human lung carcinoma, hormone-dependent human prostate carcinoma and human breast carcinoma.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C27H46O4
Net Charge 0
Average Mass 434.65170
Monoisotopic Mass 434.33961
InChI InChI=1S/C27H46O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-25(29)23-27(30-2)22-21-26(31-27)19-17-24(28)18-20-26/h17-20,25,29H,3-16,21-23H2,1-2H3/t25-,27?/m1/s1
InChIKey LOBKLUVDTHVJSR-CSMDKSQMSA-N
SMILES CCCCCCCCCCCCCCC[C@@H](O)CC1(CCC2(O1)C=CC(=O)C=C2)OC
Metabolite of Species Details
Amomum aculeatum (NCBI:txid1076729) Found in leaf (BTO:0000713). See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing amomol A (CHEBI:65404) has role antineoplastic agent (CHEBI:35610)
amomol A (CHEBI:65404) has role plant metabolite (CHEBI:76924)
amomol A (CHEBI:65404) is a cyclic ketal (CHEBI:59779)
amomol A (CHEBI:65404) is a enone (CHEBI:51689)
amomol A (CHEBI:65404) is a oxaspiro compound (CHEBI:37948)
amomol A (CHEBI:65404) is a secondary alcohol (CHEBI:35681)
IUPAC Name
2-[(2R)-2-hydroxyheptadecyl]-2-methoxy-1-oxaspiro[4.5]deca-6,9-dien-8-one
Synonyms Sources
(−)-amomol A ChEBI
2ξ,12R-2-(2-hydroxyheptadecyl)-2-methoxy-1-oxaspiro[4.5]deca-6,9-dien-8-one ChEBI
Registry Number Type Source
18832055 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18260638 PubMed citation Europe PMC
20046887 PubMed citation Europe PMC
21650152 PubMed citation Europe PMC
Last Modified
13 January 2020
General Comment
2020-01-13 The stereochemistry at position 2 of the oxaspiro ring is unknown according to PMID:18260638. The optical rotation of this compound is opposite to that of amomol B (CHEBI:65405).