Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:14:56 UTC |
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HMDB ID | HMDB0000543 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Benzenebutanoic acid |
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Description | Benzenebutanoic acid (also known as 4-phenylbutyrate, or 4-PBA) is the oral form of butyrate, which is known to be a transcriptional regulator. Sodium-4-PBA has been shown to induce fetal hemoglobin, and it has been used in clinical trials for sickle cell anemia and β-thalassemia. Because gene expression profiles became more differentiated, it is in phase I trials in several different malignant disorders. The potential for therapeutic benefit in cystic fibrosis (CF) resides in an additional mechanism, involving protein folding and the ER (endoplasmic reticulum) environment (PMID 12458151 ). 4-PBA is a drug that was developed to treat elevated blood ammonia in urea cycle disorders, a histone deacetylase inhibitor that promotes mutation ΔF508 cystic fibrosis transmembrane conductance regulator (CFTR) trafficking (PMID 16798551 ). |
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Structure | InChI=1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12) |
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Synonyms | Value | Source |
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4-PHENYL-butanoIC ACID | ChEBI | 4-Phenyl-N-butyric acid | ChEBI | Benzenebutyric acid | ChEBI | gamma-Phenyl-N-butyric acid | ChEBI | gamma-Phenylbutyric acid | ChEBI | Omega-phenylbutanoic acid | ChEBI | Omega-phenylbutyric acid | ChEBI | PBA | ChEBI | 4-PHENYL-butanoate | Generator | 4-Phenyl-N-butyrate | Generator | Benzenebutyrate | Generator | g-Phenyl-N-butyrate | Generator | g-Phenyl-N-butyric acid | Generator | gamma-Phenyl-N-butyrate | Generator | Γ-phenyl-N-butyrate | Generator | Γ-phenyl-N-butyric acid | Generator | g-Phenylbutyrate | Generator | g-Phenylbutyric acid | Generator | gamma-Phenylbutyrate | Generator | Γ-phenylbutyrate | Generator | Γ-phenylbutyric acid | Generator | Omega-phenylbutanoate | Generator | Omega-phenylbutyrate | Generator | Benzenebutanoate | Generator | 4-Phenyl-butyrate | HMDB | 4-Phenyl-butyric acid | HMDB | 4-Phenylbutanoate | HMDB | 4-Phenylbutanoic acid | HMDB | 4-Phenylbutyrate | HMDB | 4-Phenylbutyric acid | HMDB | g-Phenyl-butyrate | HMDB | g-Phenyl-butyric acid | HMDB | g-Phenylbutanoate | HMDB | g-Phenylbutanoic acid | HMDB | gamma-Phenyl-butyrate | HMDB | gamma-Phenyl-butyric acid | HMDB | gamma-Phenylbutanoate | HMDB | gamma-Phenylbutanoic acid | HMDB | W-Phenylbutanoate | HMDB | W-Phenylbutanoic acid | HMDB | 4-Phenylbutyric acid, calcium salt | HMDB | Buphenyl | HMDB | Sodium 4-phenylbutyrate | HMDB | Ammonaps | HMDB | Sodium 4-phenylbutanoate | HMDB | 4-Phenylbutyric acid, sodium salt | HMDB | Sodium phenylbutyrate | HMDB | Phenylbutyrate | HMDB |
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Chemical Formula | C10H12O2 |
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Average Molecular Weight | 164.2011 |
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Monoisotopic Molecular Weight | 164.083729628 |
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IUPAC Name | 4-phenylbutanoic acid |
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Traditional Name | 4-phenylbutyric acid |
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CAS Registry Number | 1821-12-1 |
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SMILES | OC(=O)CCCC1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12) |
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InChI Key | OBKXEAXTFZPCHS-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Not Available |
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Direct Parent | Benzene and substituted derivatives |
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Alternative Parents | |
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Substituents | - Monocyclic benzene moiety
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Benzenebutanoic acid EI-B (Non-derivatized) | splash10-0udl-7900000000-3308656352d708576a12 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Benzenebutanoic acid EI-B (Non-derivatized) | splash10-0udl-7900000000-3308656352d708576a12 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzenebutanoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9600000000-e2844824b9414ffe6a33 | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzenebutanoic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00xu-9600000000-697bd170bbcde4b6eefc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzenebutanoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzenebutanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzenebutanoic acid Quattro_QQQ 10V, Negative-QTOF (Annotated) | splash10-03di-4900000000-2b18919d21183949b0f0 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzenebutanoic acid Quattro_QQQ 25V, Negative-QTOF (Annotated) | splash10-0006-9000000000-6e1432dc108281f8c5fb | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzenebutanoic acid Quattro_QQQ 40V, Negative-QTOF (Annotated) | splash10-0006-9100000000-9477dfafb0c27b1670ab | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzenebutanoic acid 20V, Negative-QTOF | splash10-0006-9100000000-847b406c3e1866a2b19c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzenebutanoic acid 10V, Negative-QTOF | splash10-03dl-8900000000-008ea7253ace5d9b714b | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Benzenebutanoic acid 40V, Negative-QTOF | splash10-0a4l-9000000000-f40db15584357863f25f | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 10V, Positive-QTOF | splash10-014j-0900000000-bf56905d0da6a4541a84 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 20V, Positive-QTOF | splash10-014i-3900000000-8aa8880d8b02b7d0b5ec | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 40V, Positive-QTOF | splash10-054o-9400000000-5ad6828916a1d92c3663 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 10V, Negative-QTOF | splash10-03di-0900000000-765256d50bc87d3eff05 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 20V, Negative-QTOF | splash10-03xr-1900000000-6dfb6698bd016b6dc1df | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 40V, Negative-QTOF | splash10-0aou-9400000000-da376d49262f9db124da | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 10V, Positive-QTOF | splash10-0aor-2900000000-42af6d3b6a736fac50b4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 20V, Positive-QTOF | splash10-05mo-9700000000-3618f3c5894df7c477b6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 40V, Positive-QTOF | splash10-0006-9000000000-8743c8410c72e7bc3241 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 10V, Negative-QTOF | splash10-03di-0900000000-7b5ca54ec317098c43b2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 20V, Negative-QTOF | splash10-07vl-7900000000-834b13602e441659f91c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzenebutanoic acid 40V, Negative-QTOF | splash10-0006-9000000000-c1806dc2d8c81a391a3f | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB06819 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022106 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4611 |
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KEGG Compound ID | Not Available |
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BioCyc ID | CPD-14367 |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 5528 |
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PubChem Compound | 4775 |
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PDB ID | Not Available |
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ChEBI ID | 41500 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1206621 |
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References |
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Synthesis Reference | Galat, Alexander. The reaction of phenylpyruvic acid and related compounds with ammonia. Journal of the American Chemical Society (1950), 72 4436-9. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Koyama M, Watanabe N, Asakawa N: Radioimmunoassay for ubenimex in human serum. J Pharm Biomed Anal. 1992 Feb-Mar;10(2-3):137-40. [PubMed:1391092 ]
- Singh L, Field MJ, Hill DR, Horwell DC, McKnight AT, Roberts E, Tang KW, Woodruff GN: Peptoid CCK receptor antagonists: pharmacological evaluation of CCKA, CCKB and mixed CCKA/B receptor antagonists. Eur J Pharmacol. 1995 Nov 14;286(2):185-91. [PubMed:8605955 ]
- Powell K, Zeitlin PL: Therapeutic approaches to repair defects in deltaF508 CFTR folding and cellular targeting. Adv Drug Deliv Rev. 2002 Dec 5;54(11):1395-408. [PubMed:12458151 ]
- Kerem E: Mutation specific therapy in CF. Paediatr Respir Rev. 2006;7 Suppl 1:S166-9. Epub 2006 Jun 5. [PubMed:16798551 ]
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