CHEBI:30794 - malonic acid

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ChEBI Name malonic acid ChEBI ID CHEBI:30794 Definition An α,ω-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group. Stars This entity has been manually annotated by the ChEBI Team. Secondary ChEBI IDs CHEBI:44060, CHEBI:6660, CHEBI:25132 Supplier Information eMolecules:591716, ZINC000000057152 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License 5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine), also known as O-methylbufotenin or mebufotenin (INNTooltip International Nonproprietary Name), is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad. It may occur naturally in humans as well. Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include five-methoxy, the power, bufo, and toad venom. The drug has been described as the most powerful psychedelic and, by Michael Pollan, as the "Mount Everest of psychedelics". The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT1A and 5-HT2A receptors among others. However, 5-MeO-DMT differs from most other serotonergic psychedelics in having 100- to 1,000-fold higher affinity for the serotonin 5-HT1A receptor over the serotonin 5-HT2A receptor. In relation to this, 5-MeO-DMT has been described as an "atypical" psychedelic and as producing subjective effects notably distinct from those of DMT and other psychedelics, for instance having a relative lack of visual effects. Like DMT, 5-MeO-DMT has a very rapid onset of action and short duration. However, 5-MeO-DMT is 4- to 10-fold more potent than DMT in humans. 5-MeO-DMT was first described by 1936, was first isolated from natural sources by 1959, and was first reported to be hallucinogenic by 1970. The use of 5-MeO-DMT-containing toad venom was first described in 1984. It is a controlled substance in some countries, for instance the United States, United Kingdom, Australia, and New Zealand. The drug is used recreationally and several deaths have been reported in association with its use. 5-MeO-DMT is being developed for potential use in medicine in the treatment of neuropsychiatric disorders such as depression. Read full article at Wikipedia Formula C3H4O4 Net Charge 0 Average Mass 104.06146 Monoisotopic Mass 104.01096 InChI InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) InChIKey OFOBLEOULBTSOW-UHFFFAOYSA-N SMILES OC(=O)CC(O)=O Metabolite of Species Details Homo sapiens (NCBI:txid9606) See: DOI Roles Classification Chemical Role(s): Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid ) Biological Role(s): human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). View more via ChEBI Ontology ChEBI Ontology Outgoing malonic acid (CHEBI:30794) has role human metabolite (CHEBI:77746) malonic acid (CHEBI:30794) is a α,ω-dicarboxylic acid (CHEBI:28383) malonic acid (CHEBI:30794) is conjugate acid of malonate(1−) (CHEBI:30795) Incoming 3-(benzyloxy)-3-oxopropanoic acid (CHEBI:84093) has functional parent malonic acid (CHEBI:30794) 3-oxo-3-ureidopropanoic acid (CHEBI:49049) has functional parent malonic acid (CHEBI:30794) N-malonyltryptophan (CHEBI:142268) has functional parent malonic acid (CHEBI:30794) O-malonyl-D-carnitine (CHEBI:86047) has functional parent malonic acid (CHEBI:30794) O-malonyl-L-carnitine (CHEBI:85470) has functional parent malonic acid (CHEBI:30794) O-malonylcarnitine (CHEBI:73028) has functional parent malonic acid (CHEBI:30794) S-malonyl-4'-phosphopantetheine (CHEBI:132976) has functional parent malonic acid (CHEBI:30794) aminomalonic acid (CHEBI:17475) has functional parent malonic acid (CHEBI:30794) bumadizone (CHEBI:76119) has functional parent malonic acid (CHEBI:30794) elesclomol (CHEBI:79369) has functional parent malonic acid (CHEBI:30794) ethylmalonic acid (CHEBI:741548) has functional parent malonic acid (CHEBI:30794) heptylmalonic acid (CHEBI:70747) has functional parent malonic acid (CHEBI:30794) hydroxymalonic acid (CHEBI:16513) has functional parent malonic acid (CHEBI:30794) isoprothiolane (CHEBI:6047) has functional parent malonic acid (CHEBI:30794) malonamide (CHEBI:48537) has functional parent malonic acid (CHEBI:30794) malonate ester (CHEBI:38083) has functional parent malonic acid (CHEBI:30794) malonyl-CoA methyl ester (CHEBI:71244) has functional parent malonic acid (CHEBI:30794) methylmalonic acid (CHEBI:30860) has functional parent malonic acid (CHEBI:30794) oxomalonic acid (CHEBI:30842) has functional parent malonic acid (CHEBI:30794) malonate(1−) (CHEBI:30795) is conjugate base of malonic acid (CHEBI:30794) carboxyacetyl group (CHEBI:50650) is substituent group from malonic acid (CHEBI:30794) malonyl group (CHEBI:25134) is substituent group from malonic acid (CHEBI:30794) IUPAC Name propanedioic acid Synonyms Sources H2malo IUPAC HOOC‒CH2‒COOH IUPAC Malonic acid KEGG COMPOUND MALONIC ACID PDBeChem Propanedioic acid KEGG COMPOUND Manual Xrefs Databases C00001193 KNApSAcK C00383 KEGG COMPOUND DB02175 DrugBank HMDB0000691 HMDB LMFA01170041 LIPID MAPS MALONATE MetaCyc Malonic_acid Wikipedia MLA PDBeChem View more database links Registry Numbers Types Sources 141-82-2 CAS Registry Number KEGG COMPOUND 141-82-2 CAS Registry Number ChemIDplus 141-82-2 CAS Registry Number NIST Chemistry WebBook 1751370 Reaxys Registry Number Reaxys 2550 Gmelin Registry Number Gmelin Citation Type Source 22770225 PubMed citation Europe PMC Last Modified 18 April 2024