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Record Information |
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Version | 4.0 |
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Status | Detected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-01-11 19:14:44 UTC |
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HMDB ID | HMDB0000563 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | D-Phenyllactic acid |
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Description | Phenyllactic acid is a product of phenylalanine catabolism. An elevated level of phenyllactic acid is found in body fluids of patients with or phenylketonuria. |
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Structure | |
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Synonyms | Value | Source |
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ALPHA-HYDROXY-BETA-phenyl-propionIC ACID | ChEBI | L-(-)-3-Phenyllactic acid | ChEBI | L-3-Phenyllactic acid | ChEBI | L-beta-Phenyllactic acid | ChEBI | a-HYDROXY-b-phenyl-propionate | Generator | a-HYDROXY-b-phenyl-propionic acid | Generator | alpha-HYDROXY-beta-phenyl-propionate | Generator | α-hydroxy-β-phenyl-propionate | Generator | α-hydroxy-β-phenyl-propionic acid | Generator | D-Phenyllactate | Generator | L-(-)-3-Phenyllactate | Generator | L-3-Phenyllactate | Generator | L-b-Phenyllactate | Generator | L-b-Phenyllactic acid | Generator | L-beta-Phenyllactate | Generator | L-β-phenyllactate | Generator | L-β-phenyllactic acid | Generator | (+)-2-Hydroxy-3-phenylpropionate | HMDB | (+)-2-Hydroxy-3-phenylpropionic acid | HMDB | (+)-3-Phenyllactate | HMDB | (+)-3-Phenyllactic acid | HMDB | (+)-b-Phenyllactate | HMDB | (+)-b-Phenyllactic acid | HMDB | (+)-beta-Phenyllactate | HMDB | (+)-beta-Phenyllactic acid | HMDB | (2R)-2-Hydroxy-2-phenylpropanoate | HMDB | (2R)-2-Hydroxy-2-phenylpropanoic acid | HMDB | (2R)-2-Hydroxy-2-phenylpropionate | HMDB | (2R)-2-Hydroxy-2-phenylpropionic acid | HMDB | (R)-2-Hydroxy-2-phenylpropionate | HMDB | (R)-2-Hydroxy-2-phenylpropionic acid | HMDB | (R)-2-Phenyl-2-hydroxypropanoate | HMDB | (R)-2-Phenyl-2-hydroxypropanoic acid | HMDB | (R)-3-Phenyl-lactate | HMDB | (R)-3-Phenyl-lactic acid | HMDB | (R)-3-Phenyllactate | HMDB | (R)-3-Phenyllactic acid | HMDB | (R)-a-Hydroxy-3-phenylpropionate | HMDB | (R)-a-Hydroxy-3-phenylpropionic acid | HMDB | (R)-a-Hydroxy-benzenepropanoate | HMDB | (R)-a-Hydroxy-benzenepropanoic acid | HMDB | (R)-alpha-Hydroxy-3-phenylpropionate | HMDB | (R)-alpha-Hydroxy-3-phenylpropionic acid | HMDB | (R)-alpha-Hydroxy-benzenepropanoate | HMDB | (R)-alpha-Hydroxy-benzenepropanoic acid | HMDB | (R)-b-Phenyllactate | HMDB | (R)-b-Phenyllactic acid | HMDB | (R)-beta-Phenyllactate | HMDB | (R)-beta-Phenyllactic acid | HMDB | (R)-Phenyllactate | HMDB | (R)-Phenyllactic acid | HMDB | b-Phenyl-D-lactate | HMDB | b-Phenyl-D-lactic acid | HMDB | beta-Phenyl-delta-lactate | HMDB | beta-Phenyl-delta-lactic acid | HMDB | D-2-Hydroxy-3-phenylpropionate | HMDB | D-2-Hydroxy-3-phenylpropionic acid | HMDB | D-3-Phenyllactate | HMDB | D-3-Phenyllactic acid | HMDB | D-b-Phenyllactate | HMDB | D-b-Phenyllactic acid | HMDB | delta-2-Hydroxy-3-phenylpropionate | HMDB | delta-2-Hydroxy-3-phenylpropionic acid | HMDB | delta-3-Phenyllactate | HMDB | delta-3-Phenyllactic acid | HMDB | delta-beta-Phenyllactate | HMDB | delta-beta-Phenyllactic acid | HMDB | delta-Phenyllactate | HMDB | delta-Phenyllactic acid | HMDB |
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Chemical Formula | C9H10O3 |
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Average Molecular Weight | 166.1739 |
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Monoisotopic Molecular Weight | 166.062994186 |
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IUPAC Name | (2S)-2-hydroxy-3-phenylpropanoic acid |
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Traditional Name | L-3-phenyllactic acid |
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CAS Registry Number | 7326-19-4 |
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SMILES | [H][C@](O)(CC1=CC=CC=C1)C(O)=O |
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InChI Identifier | InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/m0/s1 |
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InChI Key | VOXXWSYKYCBWHO-QMMMGPOBSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Phenylpropanoic acids |
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Sub Class | Not Available |
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Direct Parent | Phenylpropanoic acids |
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Alternative Parents | |
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Substituents | - 3-phenylpropanoic-acid
- Alpha-hydroxy acid
- Monocyclic benzene moiety
- Hydroxy acid
- Benzenoid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 122-124 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 1.184 | Not Available |
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Predicted Properties | |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB02494 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | C05607 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 5547 |
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PubChem Compound | 444718 |
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PDB ID | HFA |
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ChEBI ID | 43065 |
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References |
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Synthesis Reference | Kamata, Masahiro; Toyomasu, Ryuta; Suzuki, Eiichiro; Tanaka, Takashi. D-Phenyllactic acid production by Brevibacterium or Corynebacterium. Jpn. Kokai Tokkyo Koho (1986), 4 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | Not Available |
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