CHEBI:16449 - alanine

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ChEBI Name alanine
ChEBI ID CHEBI:16449
Definition An α-amino acid that consists of propionic acid bearing an amino substituent at position 2.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2539, CHEBI:13748, CHEBI:22277
Supplier Information ZINC000003831425
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Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as the prosthetic group of various oxidoreductases, including NADH dehydrogenase, as well as a cofactor in biological blue-light photo receptors. During the catalytic cycle, various oxidoreductases induce reversible interconversions between the oxidized (FMN), semiquinone (FMNH•), and reduced (FMNH2) forms of the isoalloxazine core. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. In its role as blue-light photo receptor, (oxidized) FMN stands out from the 'conventional' photo receptors as the signaling state and not an E/Z isomerization. It is the principal form in which riboflavin is found in cells and tissues. It requires more energy to produce, but is more soluble than riboflavin. In cells, FMN occurs freely circulating but also in several covalently bound forms. Covalently or non-covalently bound FMN is a cofactor of many enzymes playing an important pathophysiological role in cellular metabolism. For example dissociation of flavin mononucleotide from mitochondrial complex I has been shown to occur during ischemia/reperfusion brain injury during stroke.
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Formula C3H7NO2
Net Charge 0
Average Mass 89.09322
Monoisotopic Mass 89.04768
InChI InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)
InChIKey QNAYBMKLOCPYGJ-UHFFFAOYSA-N
SMILES CC(N)C(O)=O
Metabolite of Species Details
Daphnia magna (NCBI:txid35525) See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): fundamental metabolite
Any metabolite produced by all living cells.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing alanine (CHEBI:16449) has functional parent propionic acid (CHEBI:30768)
alanine (CHEBI:16449) has role fundamental metabolite (CHEBI:78675)
alanine (CHEBI:16449) is a α-amino acid (CHEBI:33704)
alanine (CHEBI:16449) is conjugate acid of alaninate (CHEBI:32439)
alanine (CHEBI:16449) is conjugate base of alaninium (CHEBI:32440)
alanine (CHEBI:16449) is tautomer of alanine zwitterion (CHEBI:66916)
Incoming alanine derivative (CHEBI:22278) has functional parent alanine (CHEBI:16449)
alanylalanine (CHEBI:140570) has functional parent alanine (CHEBI:16449)
D-alanine (CHEBI:15570) is a alanine (CHEBI:16449)
L-alanine (CHEBI:16977) is a alanine (CHEBI:16449)
L-alanine-2,3,3,3-d4 (CHEBI:76050) is a alanine (CHEBI:16449)
alanine-2,3,3,3-d4 (CHEBI:143534) is a alanine (CHEBI:16449)
alanine-d7 (CHEBI:132498) is a alanine (CHEBI:16449)
alaninium (CHEBI:32440) is conjugate acid of alanine (CHEBI:16449)
alaninate (CHEBI:32439) is conjugate base of alanine (CHEBI:16449)
alanine residue (CHEBI:32441) is substituent group from alanine (CHEBI:16449)
alanino group (CHEBI:22279) is substituent group from alanine (CHEBI:16449)
alanyl group (CHEBI:22280) is substituent group from alanine (CHEBI:16449)
alanine zwitterion (CHEBI:66916) is tautomer of alanine (CHEBI:16449)
IUPAC Names
2-aminopropanoic acid
alanine
Synonyms Sources
2-Aminopropanoic acid KEGG COMPOUND
2-Aminopropionic acid KEGG COMPOUND
A ChEBI
ALA ChEBI
Alanin ChEBI
alanina ChEBI
Alanine KEGG COMPOUND
Manual Xrefs Databases
4306 DrugCentral
Alanine Wikipedia
C01401 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
2449 Gmelin Registry Number Gmelin
302-72-7 CAS Registry Number NIST Chemistry WebBook
302-72-7 CAS Registry Number ChemIDplus
635807 Reaxys Registry Number Reaxys
Citations Types Sources
17439666 PubMed citation Europe PMC
22264337 PubMed citation Europe PMC
Last Modified
08 August 2024