4-Phenylbutanoic acid (CED0005352)

Record Information
Version1.0
Creation Date2016-05-26 05:18:58 UTC
Update Date2026-08-17 23:47:04 UTC
Accession NumberCHEM034900
Identification
Common Name4-Phenylbutanoic acid
ClassSmall Molecule
Description
4-Phenylbutanoic acid (C10H12O2) is an organic compound with an average molecular weight of 164.20 g/mol. 4-Phenylbutanoic acid belongs to the benzene and substituted derivatives, a class of benzenoids within the organic compounds. This compound is found in or released from 23 recorded sources across several sectors. Within healthcare, pharmaceuticals, and veterinary products, it is associated with unclassified nervous system drugs and alimentary tract and metabolism products. In the food, food processing, and cookware sector, it is linked to the preparation of vinegar, the preparation of wine or sparkling wine, fermentation processes for beer, the preparation of wort, and food preservation. Recorded sources in household cleaning and consumer products include bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non-electric simulated smoking devices, and pipe accessories. Additionally, it is found in building and construction materials such as stairs and ramps, and in electrical and electronic equipment including antennas, conductors or conductive bodies characterised by the conductive materials, electrodes, emergency protective devices, and electrically stimulated smoking devices. The recorded route of exposure for this compound is oral. At the molecular level, 4-phenylbutanoic acid interacts with 11 recorded protein targets. It acts as a binder, inhibitor, or modulator of histone deacetylase 1 (HDAC1), histone deacetylase 3 (HDAC3), histone deacetylase 4 (HDAC4), and aromatic-amino-acid aminotransferase (tyrB), among 7 other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
4-PHENYL-butanoIC ACIDChEBI
4-Phenyl-N-butyric acidChEBI
Benzenebutyric acidChEBI
gamma-Phenyl-N-butyric acidChEBI
gamma-Phenylbutyric acidChEBI
Omega-phenylbutanoic acidChEBI
Omega-phenylbutyric acidChEBI
PBAChEBI
4-PHENYL-butanoateGenerator
4-Phenyl-N-butyrateGenerator
BenzenebutyrateGenerator
g-Phenyl-N-butyrateGenerator
g-Phenyl-N-butyric acidGenerator
gamma-Phenyl-N-butyrateGenerator
Γ-phenyl-N-butyrateGenerator
Γ-phenyl-N-butyric acidGenerator
g-PhenylbutyrateGenerator
g-Phenylbutyric acidGenerator
gamma-PhenylbutyrateGenerator
Γ-phenylbutyrateGenerator
Γ-phenylbutyric acidGenerator
Omega-phenylbutanoateGenerator
Omega-phenylbutyrateGenerator
BenzenebutanoateGenerator
4-Phenyl-butyrateHMDB
4-Phenyl-butyric acidHMDB
4-PhenylbutanoateHMDB
4-Phenylbutanoic acidHMDB
4-PhenylbutyrateHMDB
4-Phenylbutyric acidHMDB
g-Phenyl-butyrateHMDB
g-Phenyl-butyric acidHMDB
g-PhenylbutanoateHMDB
g-Phenylbutanoic acidHMDB
gamma-Phenyl-butyrateHMDB
gamma-Phenyl-butyric acidHMDB
gamma-PhenylbutanoateHMDB
gamma-Phenylbutanoic acidHMDB
W-PhenylbutanoateHMDB
W-Phenylbutanoic acidHMDB
4-Phenylbutyric acid, calcium saltHMDB
BuphenylHMDB
Sodium 4-phenylbutyrateHMDB
AmmonapsHMDB
Sodium 4-phenylbutanoateHMDB
4-Phenylbutyric acid, sodium saltHMDB
Sodium phenylbutyrateHMDB
PhenylbutyrateHMDB
Chemical FormulaC10H12O2
Average Molecular Mass164.201 g/mol
Monoisotopic Mass164.084 g/mol
CAS Registry Number1821-12-1
IUPAC Name4-phenylbutanoic acid
Traditional Name4-phenylbutyric acid
SMILESOC(=O)CCCC1=CC=CC=C1
InChI IdentifierInChI=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)
InChI KeyOBKXEAXTFZPCHS-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
logP2.29ALOGPS
logP2.5ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4.81ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity46.57 m³·mol⁻¹ChemAxon
Polarizability17.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0udl-7900000000-3308656352d708576a12Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0udl-7900000000-3308656352d708576a12Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9600000000-e2844824b9414ffe6a33Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00xu-9600000000-697bd170bbcde4b6eefcNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-4900000000-2b18919d21183949b0f0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-6e1432dc108281f8c5fbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9100000000-9477dfafb0c27b1670abNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9100000000-847b406c3e1866a2b19cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-8900000000-008ea7253ace5d9b714bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4l-9000000000-f40db15584357863f25fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014j-0900000000-bf56905d0da6a4541a84Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-3900000000-8aa8880d8b02b7d0b5ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-054o-9400000000-5ad6828916a1d92c3663Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-765256d50bc87d3eff05Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03xr-1900000000-6dfb6698bd016b6dc1dfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aou-9400000000-da376d49262f9db124daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-2900000000-42af6d3b6a736fac50b4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05mo-9700000000-3618f3c5894df7c477b6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-8743c8410c72e7bc3241Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-7b5ca54ec317098c43b2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-07vl-7900000000-834b13602e441659f91cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-c1806dc2d8c81a391a3fNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2666.0Log mg/kg[1500:4700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
272Alimentary tract and metabolism productsHealthcare, pharmaceuticals & veterinary productsNot Available
384Unclassified nervous system drugsHealthcare, pharmaceuticals & veterinary productsNot Available
500Stairs And RampsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureGlutamyl aminopeptidaseP16406Mus musculusPredicted (SEA)0.544945
Click to view 3D structureMast cell carboxypeptidase AP15088HumansPredicted (SEA)0.778492
Click to view 3D structureDiacylglycerol lipase-alphaQ9Y4D2HumansPredicted (SEA)4.20386
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)12.2223
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)9.18621
Liver carboxylesterase 1 structureClick to view 3D structureLiver carboxylesterase 1P23141HumansPredicted (SEA)5.2159
Free fatty acid receptor 4 structureClick to view 3D structureFree fatty acid receptor 4Q5NUL3HumansPredicted (SEA)5.3716
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)18.4503
Click to view 3D structureGIM-1 proteinQ704V1Pseudomonas aeruginosaPredicted (SEA)0.389246
Phospholipase A and acyltransferase 4 structureClick to view 3D structurePhospholipase A and acyltransferase 4Q9UL19HumansPredicted (SEA)2.49118
Click to view 3D structurePhospholipase A and acyltransferase 5Q96KN8HumansPredicted (SEA)2.49118
Phospholipase A and acyltransferase 3 structureClick to view 3D structurePhospholipase A and acyltransferase 3P53816HumansPredicted (SEA)2.49118
Phospholipase A and acyltransferase 2 structureClick to view 3D structurePhospholipase A and acyltransferase 2Q9NWW9HumansPredicted (SEA)2.49118
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)0.389246
Click to view 3D structureFatty-acid amide hydrolase 1O08914Mus musculusPredicted (SEA)11.4438
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)89.838
Neutrophil collagenase structureClick to view 3D structureNeutrophil collagenaseP22894HumansPredicted (SEA)65.2376
Click to view 3D structureCarboxypeptidase A1P00730Bos taurusPredicted (SEA)1.47914
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)201.785
Click to view 3D structureProlyl endopeptidaseP23687Sus scrofaPredicted (SEA)3.19182
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)155.621
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)64.9263
Macrophage metalloelastase structureClick to view 3D structureMacrophage metalloelastaseP39900HumansPredicted (SEA)48.1887
Collagenase 3 structureClick to view 3D structureCollagenase 3P45452HumansPredicted (SEA)69.3637
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)88.9038
Concentrations
Not Available
External Links
DrugBank IDDB06819
HMDB IDHMDB0000543
FooDB IDFDB022106
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-14367
METLIN ID5528
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4611
ChEBI ID41500
PubChem Compound ID4775
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19918981
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20399799
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21237159
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21726539
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21887297
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21894430
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22101259
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22359472
9. Galat, Alexander. The reaction of phenylpyruvic acid and related compounds with ammonia. Journal of the American Chemical Society (1950), 72 4436-9.
10. Koyama M, Watanabe N, Asakawa N: Radioimmunoassay for ubenimex in human serum. J Pharm Biomed Anal. 1992 Feb-Mar;10(2-3):137-40.
11. 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.
12. 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.
13. Kerem E: Mutation specific therapy in CF. Paediatr Respir Rev. 2006;7 Suppl 1:S166-9. Epub 2006 Jun 5.