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CHEBI:17295 - L-phenylalanine
| Formula | C9H11NO2 |
| Net Charge | 0 |
| Average Mass | 165.192 |
| Monoisotopic Mass | 165.07898 |
| SMILES | N[C@@H](Cc1ccccc1)C(=O)O |
| 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)/t8-/m0/s1 |
| InChIKey | COLNVLDHVKWLRT-QMMMGPOBSA-N |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Homo sapiens (ncbitaxon:9606) | |||
| - | DOI (10.1038/nbt.2488) | ||
| blood serum (BTO:0000133) | MetaboLights (MTBLS90) | ||
| Saccharomyces cerevisiae (ncbitaxon:4932) | |||
| - | PubMed (24733517) | ||
| - | PubMed (24678285) | Source: yeast.sf.net | |
| Escherichia coli (ncbitaxon:562) | |||
| - | PubMed (24966042) | ||
| - | PubMed (21988831) | ||
| Chlamydomonas reinhardtii (ncbitaxon:3055) | - | PubMed (25515814) | |
| Mus musculus (ncbitaxon:10090) | - | PubMed (19425150) | Source: BioModels - MODEL1507180067 |
| Roles Classification |
|---|
| Chemical Roles: | Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). |
| Biological Roles: | Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. EC 3.1.3.1 (alkaline phosphatase) inhibitor An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of alkaline phosphatase (EC 3.1.3.1). Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans. Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. |
| Application: | nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| L-phenylalanine (CHEBI:17295) has role Escherichia coli metabolite (CHEBI:76971) |
| L-phenylalanine (CHEBI:17295) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) |
| L-phenylalanine (CHEBI:17295) has role algal metabolite (CHEBI:84735) |
| L-phenylalanine (CHEBI:17295) has role EC 3.1.3.1 (alkaline phosphatase) inhibitor (CHEBI:63332) |
| L-phenylalanine (CHEBI:17295) has role human xenobiotic metabolite (CHEBI:76967) |
| L-phenylalanine (CHEBI:17295) has role micronutrient (CHEBI:27027) |
| L-phenylalanine (CHEBI:17295) has role mouse metabolite (CHEBI:75771) |
| L-phenylalanine (CHEBI:17295) has role nutraceutical (CHEBI:50733) |
| L-phenylalanine (CHEBI:17295) has role plant metabolite (CHEBI:76924) |
| L-phenylalanine (CHEBI:17295) is a L-α-amino acid (CHEBI:15705) |
| L-phenylalanine (CHEBI:17295) is a erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:73690) |
| L-phenylalanine (CHEBI:17295) is a phenylalanine (CHEBI:28044) |
| L-phenylalanine (CHEBI:17295) is a proteinogenic amino acid (CHEBI:83813) |
| L-phenylalanine (CHEBI:17295) is conjugate acid of L-phenylalaninate (CHEBI:32486) |
| L-phenylalanine (CHEBI:17295) is conjugate base of L-phenylalaninium (CHEBI:32487) |
| L-phenylalanine (CHEBI:17295) is enantiomer of D-phenylalanine (CHEBI:16998) |
| L-phenylalanine (CHEBI:17295) is tautomer of L-phenylalanine zwitterion (CHEBI:58095) |
| Incoming Relation(s) |
| (2S,3S)-β-methylphenylalanine (CHEBI:77031) has functional parent L-phenylalanine (CHEBI:17295) |
| N-formyl-L-methionyl-L-leucyl-L-phenylalanine (CHEBI:53490) has functional parent L-phenylalanine (CHEBI:17295) |
| N-phenylacetylphenylalanine (CHEBI:141030) has functional parent L-phenylalanine (CHEBI:17295) |
| L-Phe-L-Phe-Gly-L-Leu-L-Met-NH2 (CHEBI:191176) has functional parent L-phenylalanine (CHEBI:17295) |
| L-Phe-Gly-L-Leu-L-Met-NH2 (CHEBI:191175) has functional parent L-phenylalanine (CHEBI:17295) |
| L-phenylalanine derivative (CHEBI:84144) has functional parent L-phenylalanine (CHEBI:17295) |
| Ala-Phe-Thr-Ser (CHEBI:73377) has functional parent L-phenylalanine (CHEBI:17295) |
| Ala-Phe-Trp-Asn (CHEBI:73379) has functional parent L-phenylalanine (CHEBI:17295) |
| Arg-Phe-Phe-Cys (CHEBI:73402) has functional parent L-phenylalanine (CHEBI:17295) |
| Asn-Leu-Phe-Asp (CHEBI:73411) has functional parent L-phenylalanine (CHEBI:17295) |
| Asn-Phe (CHEBI:141424) has functional parent L-phenylalanine (CHEBI:17295) |
| Asp-Leu-Phe-Val (CHEBI:73431) has functional parent L-phenylalanine (CHEBI:17295) |
| Asp-Phe-Asp-Gln (CHEBI:73437) has functional parent L-phenylalanine (CHEBI:17295) |
| Asp-Phe-Val-Tyr (CHEBI:73293) has functional parent L-phenylalanine (CHEBI:17295) |
| Asp-Phe-Val-Val (CHEBI:73438) has functional parent L-phenylalanine (CHEBI:17295) |
| Cys-Met-Phe-His (CHEBI:138508) has functional parent L-phenylalanine (CHEBI:17295) |
| Cys-Phe-Phe-Gly (CHEBI:73460) has functional parent L-phenylalanine (CHEBI:17295) |
| DON-10-phenylalanine (CHEBI:149457) has functional parent L-phenylalanine (CHEBI:17295) |
| Gln-Phe (CHEBI:141430) has functional parent L-phenylalanine (CHEBI:17295) |
| Gln-Phe-Trp-Tyr (CHEBI:73464) has functional parent L-phenylalanine (CHEBI:17295) |
| Gln-Phe-Tyr (CHEBI:156250) has functional parent L-phenylalanine (CHEBI:17295) |
| Glu-Gly-Phe (CHEBI:140739) has functional parent L-phenylalanine (CHEBI:17295) |
| Glu-Ile-Phe (CHEBI:73497) has functional parent L-phenylalanine (CHEBI:17295) |
| Glu-Leu-Phe-Ala (CHEBI:73485) has functional parent L-phenylalanine (CHEBI:17295) |
| Glu-Phe-Gln-Gln (CHEBI:73488) has functional parent L-phenylalanine (CHEBI:17295) |
| Glu-Phe-Val (CHEBI:73501) has functional parent L-phenylalanine (CHEBI:17295) |
| His-Phe (CHEBI:141438) has functional parent L-phenylalanine (CHEBI:17295) |
| Leu-enkephalin (CHEBI:89656) has functional parent L-phenylalanine (CHEBI:17295) |
| Leu-Phe (CHEBI:73585) has functional parent L-phenylalanine (CHEBI:17295) |
| Leu-Phe-Asn (CHEBI:73570) has functional parent L-phenylalanine (CHEBI:17295) |
| Leu-Phe-Asp (CHEBI:73571) has functional parent L-phenylalanine (CHEBI:17295) |
| Lys-Phe (CHEBI:73605) has functional parent L-phenylalanine (CHEBI:17295) |
| Met-enkephalin (CHEBI:6618) has functional parent L-phenylalanine (CHEBI:17295) |
| Met-Phe-Met (CHEBI:160990) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Ala (CHEBI:73630) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Ala-Asp (CHEBI:73627) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Ala-Gly (CHEBI:73628) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Ala-Pro (CHEBI:73617) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Arg (CHEBI:73632) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Arg-Thr (CHEBI:144556) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Asn (CHEBI:73633) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Asp (CHEBI:73631) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Asp-Cys (CHEBI:73629) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-FMDP (CHEBI:74492) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Gly (CHEBI:73635) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-His (CHEBI:73634) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Lys (CHEBI:141443) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Phe (CHEBI:72723) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Phe-Asp (CHEBI:73643) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Pro-Pro (CHEBI:73644) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Pro-Thr (CHEBI:138789) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Ser (CHEBI:71032) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Thr (CHEBI:73636) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Trp-Ala (CHEBI:73640) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Trp-Trp (CHEBI:73642) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Tyr (CHEBI:73637) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Tyr-Asp (CHEBI:84102) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Val (CHEBI:73638) has functional parent L-phenylalanine (CHEBI:17295) |
| Phe-Val-Asp (CHEBI:73639) has functional parent L-phenylalanine (CHEBI:17295) |
| Ser-Phe (CHEBI:71029) has functional parent L-phenylalanine (CHEBI:17295) |
| L-phenylalanine-d5 (CHEBI:192084) is a L-phenylalanine (CHEBI:17295) |
| L-phenylalaninium (CHEBI:32487) is conjugate acid of L-phenylalanine (CHEBI:17295) |
| L-phenylalaninate (CHEBI:32486) is conjugate base of L-phenylalanine (CHEBI:17295) |
| D-phenylalanine (CHEBI:16998) is enantiomer of L-phenylalanine (CHEBI:17295) |
| L-phenylalanine residue (CHEBI:29997) is substituent group from L-phenylalanine (CHEBI:17295) |
| L-phenylalanino group (CHEBI:32501) is substituent group from L-phenylalanine (CHEBI:17295) |
| L-phenylalanyl group (CHEBI:32496) is substituent group from L-phenylalanine (CHEBI:17295) |
| L-phenylalanine zwitterion (CHEBI:58095) is tautomer of L-phenylalanine (CHEBI:17295) |
| IUPAC Names |
|---|
| L-phenylalanine |
| (2S)-2-amino-3-phenylpropanoic acid |
| Synonyms | Source |
|---|---|
| L-Phenylalanine | KEGG COMPOUND |
| F | ChEBI |
| Phe | ChEBI |
| 3-phenyl-L-alanine | NIST Chemistry WebBook |
| β-phenyl-L-alanine | NIST Chemistry WebBook |
| (S)-alpha-Amino-beta-phenylpropionic acid | KEGG COMPOUND |
| Manual Xrefs | Databases |
|---|---|
| C00079 | KEGG COMPOUND |
| PHE | PDBeChem |
| Phenylalanine | Wikipedia |
| D00021 | KEGG DRUG |
| DB00120 | DrugBank |
| HMDB0000159 | HMDB |
| PHE | MetaCyc |
| YMDB00304 | YMDB |
| ECMDB00159 | ECMDB |
| C00001386 | KNApSAcK |
| 2144 | DrugCentral |
| Citations |
|---|