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CHEBI:136555 - 1-O-caffeoylquinic acid
| Formula | C16H18O9 |
| Net Charge | 0 |
| Average Mass | 354.311 |
| Monoisotopic Mass | 354.09508 |
| SMILES | O=C(/C=C/c1ccc(O)c(O)c1)O[C@]1(C(=O)O)C[C@@H](O)[C@H](O)[C@H](O)C1 |
| InChI | InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-16(15(23)24)6-11(19)14(22)12(20)7-16/h1-5,11-12,14,17-20,22H,6-7H2,(H,23,24)/b4-2+/t11-,12-,14-,16+/m1/s1 |
| InChIKey | GWTUHAXUUFROTF-JUHZACGLSA-N |
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Camellia sinensis (ncbitaxon:4442) | - | MetaboLights (MTBLS403) | |
| Canna edulis (ncbitaxon:4628) | - | DOI (10.1016/j.lwt.2011.05.021) | Obtained from water-soluble extracts |
| Tetrastigma hemsleyanum (ncbitaxon:1006121) | leaf (BTO:0000713) | PubMed (24151872) | |
| Cynara cardunculus var. scolymus (ncbitaxon:59895) | - | PubMed (28873750) | |
| Xanthium (ncbitaxon:36590) | fruit (BTO:0000486) | PubMed (19185132) | |
| Lonicera japonica (ncbitaxon:105884) | flower bud (BTO:0000470) | PubMed (18830958) | |
| Crepidiastrum sonchifolium (ncbitaxon:77563) | - | PubMed (24228586) | |
| Cyclocarya paliurus (ncbitaxon:117167) | leaf (BTO:0000713) | DOI (10.1016/j.foodchem.2009.09.031) |
| Roles Classification |
|---|
| Chemical Roles: | antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). |
| Biological Roles: | Camellia sinensis metabolite Any plant metabolite that is produced by Camellia sinensis. NF-kappaB inhibitor An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| Application: | antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| 1-O-caffeoylquinic acid (CHEBI:136555) has functional parent trans-caffeic acid (CHEBI:16433) |
| 1-O-caffeoylquinic acid (CHEBI:136555) has parent hydride (−)-quinic acid (CHEBI:17521) |
| 1-O-caffeoylquinic acid (CHEBI:136555) has role Camellia sinensis metabolite (CHEBI:140160) |
| 1-O-caffeoylquinic acid (CHEBI:136555) has role antineoplastic agent (CHEBI:35610) |
| 1-O-caffeoylquinic acid (CHEBI:136555) has role antioxidant (CHEBI:22586) |
| 1-O-caffeoylquinic acid (CHEBI:136555) has role NF-κB inhibitor (CHEBI:73240) |
| 1-O-caffeoylquinic acid (CHEBI:136555) is a alkyl caffeate ester (CHEBI:65331) |
| 1-O-caffeoylquinic acid (CHEBI:136555) is a quinic acid (CHEBI:26493) |
| IUPAC Name |
|---|
| (1S,3R,4S,5R)-1-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4,5-trihydroxycyclohexane-1-carboxylic acid |
| Synonyms | Source |
|---|---|
| 1-Caffeoylquinic acid | ChemIDplus |
| trans-1-o-Caffeoylquinic acid | ChemIDplus |
| 1-O-(trans-caffeoyl)quinic acid | ChEBI |
| Registry Numbers | Sources |
|---|---|
| Reaxys:3173163 | Reaxys |
| CAS:928005-87-2 | ChemIDplus |
| Citations |
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