CHEBI:566274 - malonaldehyde

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ChEBI Name malonaldehyde
ChEBI ID CHEBI:566274
Definition A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43895
Supplier Information ChemicalBook:CB11236081, eMolecules:6758733, ZINC000005178380
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Formula C3H4O2
Net Charge 0
Average Mass 72.06270
Monoisotopic Mass 72.02113
InChI InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2
InChIKey WSMYVTOQOOLQHP-UHFFFAOYSA-N
SMILES O=CCC=O
Roles Classification
Application(s): biomarker
A substance used as an indicator of a biological state.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing malonaldehyde (CHEBI:566274) has role biomarker (CHEBI:59163)
malonaldehyde (CHEBI:566274) is a dialdehyde (CHEBI:38124)
IUPAC Name
propanedial
Synonyms Sources
1,3-Propanedial ChemIDplus
1,3-Propanedialdehyde ChemIDplus
1,3-Propanedione ChemIDplus
malonaldehyde UniProt
Malondialdehyde KEGG COMPOUND
Malondialdehyde ChemIDplus
Malonic aldehyde ChemIDplus
Malonic dialdehyde ChemIDplus
Malonodialdehyde ChemIDplus
Malonyldialdehyde ChemIDplus
MDA ChEBI
MDD ChEBI
Manual Xrefs Databases
C19440 KEGG COMPOUND
DB03057 DrugBank
MDD PDBeChem
View more database links
Registry Numbers Types Sources
1209262 Reaxys Registry Number Reaxys
362229 Gmelin Registry Number Gmelin
542-78-9 CAS Registry Number ChemIDplus
542-78-9 CAS Registry Number NIST Chemistry WebBook
Citations
Jouyban A, Khoubnasabjafari M (2018)
Comments on "Malondialdehyde: A novel predictive biomarker for post-stroke depression".
Journal of affective disorders 225, 52-53 [PubMed:28783520]
[show Abstract]
Senders ML, Que X, Cho YS, Yeang C, Groenen H, Fay F, Calcagno C, Meerwaldt AE, Green S, Miu P, Lobatto ME, Reiner T, Fayad ZA, Witztum JL, Mulder WJM, Pérez-Medina C, Tsimikas S (2018)
PET/MR Imaging of Malondialdehyde-Acetaldehyde Epitopes With a Human Antibody Detects Clinically Relevant Atherothrombosis.
Journal of the American College of Cardiology 71, 321-335 [PubMed:29348025]
[show Abstract]
Liu Z, Zhu Z, Zhao J, Ren W, Cai Y, Wang Q, Luan X, Zhao K, He J (2017)
Malondialdehyde: A novel predictive biomarker for post-stroke depression.
Journal of affective disorders 220, 95-101 [PubMed:28600933]
[show Abstract]
Roomruangwong C, Kanchanatawan B, Sirivichayakul S, Anderson G, Carvalho AF, Duleu S, Geffard M, Maes M (2017)
IgM-mediated autoimmune responses to oxidative specific epitopes, but not nitrosylated adducts, are significantly decreased in pregnancy: association with bacterial translocation, perinatal and lifetime major depression and the tryptophan catabolite (TRYCAT) pathway.
Metabolic brain disease 32, 1571-1583 [PubMed:28600633]
[show Abstract]
Kummu O, Turunen SP, Prus P, Lehtimäki J, Veneskoski M, Wang C, Hörkkö S (2014)
Human monoclonal Fab and human plasma antibodies to carbamyl-epitopes cross-react with malondialdehyde-adducts.
Immunology 141, 416-430 [PubMed:24168430]
[show Abstract]
Wang C, Turunen SP, Kummu O, Veneskoski M, Lehtimäki J, Nissinen AE, Hörkkö S (2013)
Natural antibodies of newborns recognize oxidative stress-related malondialdehyde acetaldehyde adducts on apoptotic cells and atherosclerotic plaques.
International immunology 25, 575-587 [PubMed:23900424]
[show Abstract]
Bellia F, Amorini AM, La Mendola D, Vecchio G, Tavazzi B, Giardina B, Di Pietro V, Lazzarino G, Rizzarelli E (2008)
New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.
European journal of medicinal chemistry 43, 373-380 (Source: ChEMBL) [PubMed:17548130]
[show Abstract]
Lykkesfeldt J (2007)
Malondialdehyde as biomarker of oxidative damage to lipids caused by smoking.
Clinica chimica acta; international journal of clinical chemistry 380, 50-58 [PubMed:17336279]
[show Abstract]
Shukla R, Rajani M, Srivastava N, Barthwal MK, Dikshit M (2006)
Nitrite and malondialdehyde content in cerebrospinal fluid of patients with Parkinson's disease.
The International journal of neuroscience 116, 1391-1402 [PubMed:17145675]
[show Abstract]
Chang MK, Binder CJ, Miller YI, Subbanagounder G, Silverman GJ, Berliner JA, Witztum JL (2004)
Apoptotic cells with oxidation-specific epitopes are immunogenic and proinflammatory.
The Journal of experimental medicine 200, 1359-1370 [PubMed:15583011]
[show Abstract]
Agarwal R, Chase SD (2002)
Rapid, fluorimetric-liquid chromatographic determination of malondialdehyde in biological samples.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 775, 121-126 [PubMed:12101069]
[show Abstract]
Last Modified
09 February 2018