You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name3-phenylpropionic acid
Accession NumberDB02024  (EXPT01708)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
3-Phenyl-propionic acid
3-Phenylpropanoic acid
3PP
beta-Phenylpropionic acid
Hydrocinnamic acid
Phenylpropanoate
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII5Q445IN5CU
CAS number501-52-0
WeightAverage: 150.1745
Monoisotopic: 150.068079564
Chemical FormulaC9H10O2
InChI KeyXMIIGOLPHOKFCH-UHFFFAOYSA-N
InChI
InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)
IUPAC Name
3-phenylpropanoic acid
SMILES
OC(=O)CCC1=CC=CC=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Aspartate aminotransferaseProteinunknownNot AvailableEscherichia coli (strain K12)P00509 details
Aromatic-amino-acid aminotransferaseProteinunknownNot AvailableParacoccus denitrificansP95468 details
AminotransferaseProteinunknownNot AvailableThermus thermophilusQ75WK2 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis Reference

Anna M. C. F. Castelijns, Johanna M. Hogeweg, Simon P. J. M. van Nispen, “Process for the preparation of 3-phenylpropionic acid.” U.S. Patent US5786507, issued April, 1964.

US5786507
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9814
Blood Brain Barrier+0.944
Caco-2 permeable+0.837
P-glycoprotein substrateNon-substrate0.7927
P-glycoprotein inhibitor INon-inhibitor0.9723
P-glycoprotein inhibitor IINon-inhibitor0.9873
Renal organic cation transporterNon-inhibitor0.8978
CYP450 2C9 substrateNon-substrate0.8111
CYP450 2D6 substrateNon-substrate0.927
CYP450 3A4 substrateNon-substrate0.7922
CYP450 1A2 substrateNon-inhibitor0.6967
CYP450 2C9 inhibitorNon-inhibitor0.9766
CYP450 2D6 inhibitorNon-inhibitor0.9375
CYP450 2C19 inhibitorNon-inhibitor0.9795
CYP450 3A4 inhibitorNon-inhibitor0.9732
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9812
Ames testNon AMES toxic0.9572
CarcinogenicityNon-carcinogens0.8213
BiodegradationReady biodegradable0.9257
Rat acute toxicity1.9377 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9184
hERG inhibition (predictor II)Non-inhibitor0.9726
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point107 °CPhysProp
boiling point279.8 °CPhysProp
water solubility5900 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.84HANSCH,C ET AL. (1995)
pKa4.66 (at 18 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility1.7 mg/mLALOGPS
logP1.84ALOGPS
logP2.06ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.73ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.97 m3·mol-1ChemAxon
Polarizability15.94 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-1920000000-829ee511cbcb511eaa0dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-6910000000-1df0ef2a35aedd93b1f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-60af9a7ac23f78383156View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9100000000-9009f92e094d3f88cea0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9000000000-1009c57a9a26d3fd03a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0udl-9600000000-f55343cc6dbf913455ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-300) , Positivesplash10-0006-9400000000-6b08d11fe7d8828ea0b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (JEOL JMS-D-300) , Positivesplash10-0udi-0900000000-271b64525610b577f87cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0udl-9300000000-0b08772b626dd7c66febView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-56bd4f79b41d2e676de8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0900000000-7cb5eea800e6e65e5ea1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052b-2900000000-b4b013241fad936a6040View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9100000000-21973848f978136e5896View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-270ffc8363f873d177bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1900000000-add76f4d7844f97853a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-96205e3f347617fff0efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-270ffc8363f873d177bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-1900000000-add76f4d7844f97853a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-96205e3f347617fff0efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd537546837259692View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5b044bdcdf02a8a2de01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-0900000000-c1c19922a709d7d6d7ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-c83fd537546837259692View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Pyridoxal phosphate binding
Specific Function:
Not Available
Gene Name:
aspC
Uniprot ID:
P00509
Molecular Weight:
43572.965 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
unknown
General Function:
Pyridoxal phosphate binding
Specific Function:
Shows activities toward both dicarboxylic and aromatic substrates.
Gene Name:
tyrB
Uniprot ID:
P95468
Molecular Weight:
42731.635 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Thermus thermophilus
Pharmacological action
unknown
General Function:
Transaminase activity
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q75WK2
Molecular Weight:
42270.13 Da
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23