phenylalanine (CHEBI:28044)

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ChEBI Name	phenylalanine

ChEBI ID	CHEBI:28044

Definition	An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:8089, CHEBI:25984

Supplier Information	ZINC000003831425

Download	Molfile XML SDF

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Wikipedia	License
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

C9H11NO2

Net Charge

Average Mass

165.18918

Monoisotopic Mass

165.07898

InChI

InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)

InChIKey

COLNVLDHVKWLRT-UHFFFAOYSA-N

SMILES

NC(Cc1ccccc1)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):	Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna.

ChEBI Ontology
Outgoing	phenylalanine (CHEBI:28044) has part benzyl group (CHEBI:22744) phenylalanine (CHEBI:28044) has role Daphnia magna metabolite (CHEBI:83056) phenylalanine (CHEBI:28044) is a α-amino acid (CHEBI:33704) phenylalanine (CHEBI:28044) is a aromatic amino acid (CHEBI:33856) phenylalanine (CHEBI:28044) is conjugate acid of phenylalaninate (CHEBI:32504) phenylalanine (CHEBI:28044) is conjugate base of phenylalaninium (CHEBI:32505)

Incoming	γ-glutamylphenylalanine (CHEBI:82966) has functional parent phenylalanine (CHEBI:28044) 4-nitrophenylalanine (CHEBI:48496) has functional parent phenylalanine (CHEBI:28044) methyl 4-amino-N-(tert-butoxycarbonyl)phenylalaninate (CHEBI:48493) has functional parent phenylalanine (CHEBI:28044) phenylalanine derivative (CHEBI:25985) has functional parent phenylalanine (CHEBI:28044) D-phenylalanine (CHEBI:16998) is a phenylalanine (CHEBI:28044) L-phenylalanine (CHEBI:17295) is a phenylalanine (CHEBI:28044) phenylalaninium (CHEBI:32505) is conjugate acid of phenylalanine (CHEBI:28044) phenylalaninate (CHEBI:32504) is conjugate base of phenylalanine (CHEBI:28044) phenylalanine residue (CHEBI:32503) is substituent group from phenylalanine (CHEBI:28044) phenylalanino group (CHEBI:25986) is substituent group from phenylalanine (CHEBI:28044) phenylalanyl group (CHEBI:25987) is substituent group from phenylalanine (CHEBI:28044)

IUPAC Names

2-amino-3-phenylpropanoic acid

phenylalanine

Synonyms	Sources
alpha-Amino-beta-phenylpropionic acid	KEGG COMPOUND
DL-Phenylalanine	KEGG COMPOUND
F	ChEBI
fenilalanina	ChEBI
PHE	ChEBI
Phenylalanin	ChEBI
Phenylalanine	KEGG COMPOUND
phénylalanine	ChEBI

Last Modified

19 December 2014