3-phenylpropionic acid

Identification

Name
3-phenylpropionic acid
Accession Number
DB02024  (EXPT01708)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 3-Phenyl-propionic acid
  • 3-Phenylpropanoic acid
  • 3PP
  • beta-Phenylpropionic acid
  • Hydrocinnamic acid
  • Phenylpropanoate
External IDs
FEMA NO. 2889 / NSC-9272
Categories
UNII
5Q445IN5CU
CAS number
501-52-0
Weight
Average: 150.1745
Monoisotopic: 150.068079564
Chemical Formula
C9H10O2
InChI Key
XMIIGOLPHOKFCH-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

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAspartate aminotransferaseNot AvailableEscherichia coli (strain K12)
UAromatic-amino-acid aminotransferaseNot AvailableParacoccus denitrificans
UAminotransferaseNot AvailableThermus thermophilus
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00764
KEGG Compound
C05629
PubChem Compound
107
PubChem Substance
46506078
ChemSpider
10181339
BindingDB
50304072
ChEBI
28631
ChEMBL
CHEMBL851
HET
HCI
PDB Entries
1ahx / 1ay8 / 1bxg / 1tog / 1toi / 1toj / 1v2f / 3ayi / 4e67 / 4gm7
show 3 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)107 °CPhysProp
boiling point (°C)279.8 °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-2ALOGPS
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0udi-1920000000-829ee511cbcb511eaa0d
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0udi-6910000000-1df0ef2a35aedd93b1f0
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0udl-9600000000-685b73e7f17a8be64f76
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9400000000-6b08d11fe7d8828ea0b4
GC-MS Spectrum - CI-BGC-MSsplash10-0udi-0900000000-271b64525610b577f87c
GC-MS Spectrum - EI-BGC-MSsplash10-0udl-9300000000-faf8506e70502be88599
GC-MS Spectrum - EI-BGC-MSsplash10-0f6x-9800000000-6d3e3634b1663556c431
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-1940000000-4bdbde45f0dac2b3ec59
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-1920000000-829ee511cbcb511eaa0d
GC-MS Spectrum - GC-MSGC-MSsplash10-0udi-6910000000-1df0ef2a35aedd93b1f0
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-2910000000-b14f8ca2c631d87eb834
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0udi-0900000000-60af9a7ac23f78383156
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0006-9100000000-9009f92e094d3f88cea0
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-000f-9000000000-1009c57a9a26d3fd03a1
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-0udl-9600000000-f55343cc6dbf913455ec
MS/MS Spectrum - EI-B (JEOL JMS-D-300) , PositiveLC-MS/MSsplash10-0006-9400000000-6b08d11fe7d8828ea0b4
MS/MS Spectrum - CI-B (JEOL JMS-D-300) , PositiveLC-MS/MSsplash10-0udi-0900000000-271b64525610b577f87c
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-0udl-9300000000-0b08772b626dd7c66feb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0002-0900000000-56bd4f79b41d2e676de8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0002-0900000000-7cb5eea800e6e65e5ea1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-052b-2900000000-b4b013241fad936a6040
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9100000000-21973848f978136e5896
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-270ffc8363f873d177bd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-1900000000-add76f4d7844f97853a1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pdi-9700000000-96205e3f347617fff0ef
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-270ffc8363f873d177bd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-1900000000-add76f4d7844f97853a1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pdi-9700000000-96205e3f347617fff0ef
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-5b044bdcdf02a8a2de01
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0532-0900000000-c1c19922a709d7d6d7ce
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-3900000000-c83fd537546837259692
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-5b044bdcdf02a8a2de01
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0532-0900000000-c1c19922a709d7d6d7ce
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-3900000000-c83fd537546837259692
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-56bd4f79b41d2e676de8
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-7cb5eea800e6e65e5ea1
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-052b-2900000000-b4b013241fad936a6040
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9100000000-21973848f978136e5896
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0a4i-0900000000-b8bb01617b312682874b
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Phenylpropanoic acids
Sub Class
Not Available
Direct Parent
Phenylpropanoic acids
Alternative Parents
Benzene and substituted derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
3-phenylpropanoic-acid / Benzenoid / Monocyclic benzene moiety / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid, benzenes (CHEBI:28631)

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
Uniprot Name
Aspartate aminotransferase
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
Uniprot Name
Aromatic-amino-acid aminotransferase
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
Uniprot Name
Aminotransferase
Molecular Weight
42270.13 Da

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:08