Caffeoylmalic Acid
PubChem CID
6124299
Structure
Molecular Formula
Synonyms
- Caffeoylmalic Acid
- Coumaroyl malic acid
- 2-O-Caffeoylmalic acid
- 2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxybutanedioic acid
- 8EY7S5QS7D
Molecular Weight
296.23 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
- Create:2005-09-15
- Modify:2025-01-04
Description
Caffeoylmalic acid is a hydroxycinnamic acid.
Caffeoylmalic Acid has been reported in Marrubium velutinum with data available.
Chemical Structure Depiction
2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxybutanedioic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)
InChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)/b4-2+
Computed by InChI 1.0.5 (PubChem release 2019.06.18)
PMKQSEYPLQIEAY-DUXPYHPUSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)
C1=CC(=C(C=C1/C=C/C(=O)OC(CC(=O)O)C(=O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C13H12O8
Computed by PubChem 2.1 (PubChem release 2019.06.18)
92344-57-5
39015-77-5
53755-04-7
caffeoylmalic acid
- Caffeoylmalic Acid
- Coumaroyl malic acid
- 2-O-Caffeoylmalic acid
- 2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxybutanedioic acid
- 8EY7S5QS7D
- 149197-97-7
- 92344-57-5
- 2-((3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)butanedioic acid
- Butanedioic acid, ((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-
- 2-(((2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)butanedioic acid
- Butanedioic acid, 2-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-
- Butanedioic acid, 2-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-
- 2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
- (-)-Phaselic acid
- 2-((3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)butanedioate
- 2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioate
- 2-(((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)butanedioic acid
- 2-((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxybutanedioic acid
- Phaseolic acid?
- (S)-Phaselic acid
- UNII-8EY7S5QS7D
- CHEMBL393293
- 2-O-(trans-caffeoyl)malic acid
- SCHEMBL19894754
- CHEBI:169040
- DTXSID301031926
- AKOS040734961
- Q18379746
- (E)-2-((3-(3,4-Dihydroxyphenyl)acryloyl)oxy)succinicacid
- (E)-2-((3-(3,4-Dihydroxyphenyl)acryloyl)oxy)succinic acid
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
296.23 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
0.6
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
296.05321734 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
296.05321734 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
141 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
21
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
430
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
- Cytoplasm
- Extracellular
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=PMKQSEYPLQIEAY-DUXPYHPUSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- ChEBICaffeoylmalic acidhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:169040
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Caffeoylmalic Acidhttps://www.wikidata.org/wiki/Q18379746LOTUS Treehttps://lotus.naturalproducts.net/
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSToxCaffeoylmalic acidhttps://comptox.epa.gov/dashboard/DTXSID301031926CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linkingCAFFEOYLMALIC ACIDhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/8EY7S5QS7D
- Human Metabolome Database (HMDB)LICENSEHMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.http://www.hmdb.ca/citingCaffeoylmalic acidhttp://www.hmdb.ca/metabolites/HMDB0029318
- FooDBLICENSEFooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.https://foodb.ca/aboutL-Malic acid caffeatehttps://foodb.ca/compounds/FDB000379
- Japan Chemical Substance Dictionary (Nikkaji)
- Natural Product Activity and Species Source (NPASS)Caffeoylmalic Acidhttps://bidd.group/NPASS/compound.php?compoundID=NPC132921
- Metabolomics WorkbenchCaffeoylmalic acidhttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=43771
- SpectraBasePHASELIC-ACID;TRANS-CAFFEOYL-MALIC-ACIDhttps://spectrabase.com/spectrum/B7GEhysgrfP(+)-(E)-CAFFEOYL-L-MALIC_ACIDhttps://spectrabase.com/spectrum/Azq2LnISrQ1
- Springer Nature
- WikidataCaffeoylmalic acidhttps://www.wikidata.org/wiki/Q18379746
- WikipediaDiethyl phenylmalonatehttps://en.wikipedia.org/wiki/Diethyl_phenylmalonateCaffeoylmalic acidhttps://en.wikipedia.org/wiki/Caffeoylmalic_acid
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlcaffeoylmalic acidhttps://www.ncbi.nlm.nih.gov/mesh/67099798
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 390256707https://pubchem.ncbi.nlm.nih.gov/substance/390256707
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