Identification
NameL-Phenylalanine
Accession NumberDB00120  (NUTR00044)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

An essential aromatic amino acid that is a precursor of melanin; dopamine; noradrenalin (norepinephrine), and thyroxine. [PubChem]

Structure
Thumb
Synonyms
(S)-2-Amino-3-phenylpropionic acid
(S)-alpha-Amino-beta-phenylpropionic acid
3-phenyl-L-alanine
beta-Phenyl-L-alanine
F
Phe
Phenylalanine
β-phenyl-L-alanine
External IDs FEMA NO. 3585
Product Ingredients
IngredientUNIICASInChI KeyDetails
L-Phenylalanine hydrochlorideL6O14A5L6Q 17585-69-2ZAIZDXVMSSDZFA-QRPNPIFTSA-NDetails
Phenylalanine sodiumM67R83MDEE 16480-57-2ZRVUAXXSASAVFG-QRPNPIFTSA-MDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexLiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travas. Amino Acid InJ.W.elecw.25%dexLiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-02-022007-08-02Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312007-08-02Canada
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 20% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 20% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 25% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection Without Electrlytes In 10% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
4.25% Travasol Amino Acid Injection Without Electrolytes In 20% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection Without Electrolytes In 25% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
4.25% Travasol Amino Acid Without Electrolytes In 5% Dextrose QuickmixSolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25%trav. Amino Acid InJ.W.O.elect.5%dext.LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
4.25%travasol Amino Acid InJ.W.elecw.5%dex.LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
5% Travasol Amino Acid Injection With Electrolytes In 20% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
5% Travasol Amino Acid Injection Without Electrolytes In 20% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
5% Travasol Amino Acid Injection Without Electrolytes In 25% DextroseSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312007-08-02Canada
AminosynInjection, solutionIntravenousHospira, Inc.2012-03-06Not applicableUs
Aminosyn 10%SolutionIntravenousHospira, Inc.1979-12-31Not applicableCanada
Aminosyn 10% W ElectrolytesLiquidIntravenousAbbott1984-12-311999-08-09Canada
Aminosyn 3.5% MLiquidIntravenousAbbott1980-12-311999-08-09Canada
Aminosyn 5%SolutionIntravenousHospira, Inc.1977-12-312016-07-29Canada
Aminosyn 7%SolutionIntravenousHospira, Inc.1979-12-312016-07-29Canada
Aminosyn 8.5%SolutionIntravenousHospira, Inc.1984-12-312016-07-29Canada
Aminosyn 8.5% Injection With ElectrolytesSolutionIntravenousHospira, Inc.1984-12-312012-08-03Canada
Aminosyn IIInjection, solutionIntravenousHospira, Inc.1986-04-032017-05-18Us
Aminosyn II 10%SolutionIntravenousHospira, Inc.1987-12-31Not applicableCanada
Aminosyn II 10% With ElectrolytesSolutionIntravenousHospira, Inc.1991-12-312016-07-29Canada
Aminosyn II 15%SolutionIntravenousHospira, Inc.1995-12-31Not applicableCanada
Aminosyn II 5% InjLiquidIntravenousAbbott1988-12-311999-08-09Canada
Aminosyn II 7% InjectionSolutionIntravenousHospira, Inc.1987-12-312016-07-29Canada
Aminosyn II 7% M In 10% Dextrose(dual Chamber)SolutionIntravenousHospira, Inc.1987-12-312012-08-03Canada
Aminosyn II 7% With 10% DextroseSolutionIntravenousHospira, Inc.1988-12-312012-08-03Canada
Aminosyn II 7% With 50% DextroseSolutionIntravenousHospira, Inc.1988-12-312012-08-03Canada
Aminosyn II 8.5% InjectionSolutionIntravenousHospira, Inc.1987-12-312016-07-29Canada
Aminosyn II 8.5% M In 20% Dextrose (dual Chamber)SolutionIntravenousHospira, Inc.1987-12-312012-08-03Canada
Aminosyn II 8.5% With 50% DextroseSolutionIntravenousHospira, Inc.1988-12-312012-08-03Canada
Aminosyn II In Dextrose InjectionSolutionIntravenousHospira, Inc.1987-12-312012-08-03Canada
Aminosyn II With ElectrolytesInjection, solutionIntravenousHospira, Inc.1986-04-03Not applicableUs
Aminosyn RFInjection, solutionIntravenousHospira, Inc.2011-02-18Not applicableUs
Aminosyn RF InjectionSolutionIntravenousHospira, Inc.1986-12-312016-07-29Canada
Aminosyn Sulfite FreeInjection, solutionIntravenousHospira, Inc.2011-10-27Not applicableUs
Aminosyn-PFInjection, solutionIntravenousHospira, Inc.1985-09-06Not applicableUs
Aminosyn-PF 10%SolutionIntravenousHospira, Inc.1990-12-312016-07-29Canada
Aminosyn-PF 7%SolutionIntravenousHospira, Inc.1990-12-312016-07-29Canada
ClinimixInjectionIntravenousBaxter Laboratories1997-09-29Not applicableUs
Clinimix 2.5% Travasol Aa Without Electrolytes In 10% Dextrose InjecSolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312007-08-02Canada
Clinimix EInjectionIntravenousBaxter Laboratories1997-03-26Not applicableUs
ClinisolInjection, solutionIntravenousBaxter Laboratories1996-08-30Not applicableUs
HepatamineInjection, solutionIntravenousB. Braun Medical Inc.1982-08-03Not applicableUs
NephramineInjection, solutionIntravenousB. Braun Medical Inc.1978-02-24Not applicableUs
NovamineInjection, solution, concentrateIntravenousHospira, Inc.2011-11-22Not applicableUs
Olimel 3.3% EEmulsionIntravenousBaxter LaboratoriesNot applicableNot applicableCanada
Olimel 4.4%EmulsionIntravenousBaxter Laboratories2011-09-29Not applicableCanada
Olimel 4.4% EEmulsionIntravenousBaxter Laboratories2011-02-26Not applicableCanada
Olimel 5.7%EmulsionIntravenousBaxter Laboratories2011-03-01Not applicableCanada
Olimel 5.7% EEmulsionIntravenousBaxter Laboratories2011-01-19Not applicableCanada
Periolimel 2.5% EEmulsionIntravenousBaxter Laboratories2011-02-28Not applicableCanada
PlenamineSolutionIntravenousB. Braun Medical Inc.2015-01-30Not applicableUs
Premasol - Sulfite-free (amino Acid)Injection, solutionIntravenousBaxter Laboratories2003-06-19Not applicableUs
Primene 10%LiquidIntravenousBaxter Laboratories1997-11-14Not applicableCanada
Primene 10%-liq IVLiquidIntravenousClintec Nutrition Company1995-12-311998-08-13Canada
ProsolInjection, solutionIntravenousBaxter Laboratories1998-08-26Not applicableUs
Quick Mix 2.5% Travasol Aa With Electrolytes With 25% Dextrose InjecLiquidIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312000-07-20Canada
Renamin (amino Acids) InjectionSolutionIntravenousBaxter Laboratories1996-02-022011-05-10Canada
TravasolInjectionIntravenousBaxter Laboratories1984-08-23Not applicableUs
Travasol Amino Acid Inj 5.5%SolutionIntravenousBaxter Laboratories1981-12-312007-08-02Canada
Travasol Amino Acid Inj 8.5%SolutionIntravenousBaxter Laboratories1980-12-312008-03-26Canada
Travasol ESolutionIntravenousBaxter Laboratories1974-12-31Not applicableCanada
Travasol Inj Without Electrolytes 5.5%SolutionIntravenousBaxter Laboratories1978-12-312007-08-02Canada
TrophamineSolutionIntravenousB. Braun Medical Inc.1984-07-20Not applicableUs
Vamin 18 Electrolyte-freeSolutionIntravenousFresenius Kabi Ab1996-12-302006-07-17Canada
Vamin NSolutionIntravenousFresenius Kabi Ab1995-12-312006-07-17Canada
Categories
UNII47E5O17Y3R
CAS number63-91-2
WeightAverage: 165.1891
Monoisotopic: 165.078978601
Chemical FormulaC9H11NO2
InChI KeyCOLNVLDHVKWLRT-QMMMGPOBSA-N
InChI
InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1
IUPAC Name
(2S)-2-amino-3-phenylpropanoic acid
SMILES
N[C@@H](CC1=CC=CC=C1)C(O)=O
Pharmacology
Indication

L-phenylalanine may be helpful in some with depression. It may also be useful in the treatment of vitiligo. There is some evidence that L-phenylalanine may exacerbate tardive dyskinesia in some schizophrenic patients and in some who have used neuroleptic drugs.

Structured Indications Not Available
Pharmacodynamics

Used by the brain to produce Norepinephrine, a chemical that transmits signals between nerve cells and the brain; keeps you awake and alert; reduces hunger pains; functions as an antidepressant and helps improve memory.

Mechanism of action

The mechanism of L-phenylalanine's putative antidepressant activity may be accounted for by its precursor role in the synthesis of the neurotransmitters norepinephrine and dopamine. Elevated brain norepinephrine and dopamine levels are thought to be associated with antidepressant effects.
The mechanism of L-phenylalanine's possible antivitiligo activity is not well understood. It is thought that L-phenylalanine may stimulate the production of melanin in the affected skin

TargetKindPharmacological actionActionsOrganismUniProt ID
Tyrosine aminotransferaseProteinunknownNot AvailableHumanP17735 details
Large neutral amino acids transporter small subunit 2ProteinunknownNot AvailableHumanQ9UHI5 details
Phenylalanine--tRNA ligase alpha subunitProteinunknownNot AvailableHumanQ9Y285 details
Phenylalanine-4-hydroxylaseProteinunknownNot AvailableHumanP00439 details
Phenylalanine--tRNA ligase, mitochondrialProteinunknownNot AvailableHumanO95363 details
Phenylalanine--tRNA ligase beta subunitProteinunknownNot AvailableHumanQ9NSD9 details
Tyrosine 3-monooxygenaseProteinunknown
binder
HumanP07101 details
Related Articles
Absorption

Absorbed from the small intestine by a sodium dependent active transport process.

Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. L-phenylalanine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body, where it undergoes metabolic reactions similar to those that take place in the liver.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity

L-phenylalanine will exacerbate symptoms of phenylketonuria if used by phenylketonurics. L-phenylalanine was reported to exacerbate tardive dyskinesia when used by some with schizophrenia.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
PhenylketonuriaDiseaseSMP00206
Phenylalanine and Tyrosine MetabolismMetabolicSMP00008
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)DiseaseSMP00369
Tyrosinemia Type 3 (TYRO3)DiseaseSMP00370
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
BCG vaccineThe therapeutic efficacy of Bcg can be decreased when used in combination with L-Phenylalanine.Investigational
ClozapineThe risk or severity of adverse effects can be increased when L-Phenylalanine is combined with Clozapine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with L-Phenylalanine.Approved
FingolimodL-Phenylalanine may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
G17DTThe risk or severity of adverse effects can be increased when L-Phenylalanine is combined with G17DT.Investigational
GI-5005The risk or severity of adverse effects can be increased when L-Phenylalanine is combined with GI-5005.Investigational
INGN 201The risk or severity of adverse effects can be increased when L-Phenylalanine is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when L-Phenylalanine is combined with INGN 225.Investigational
LeflunomideThe risk or severity of adverse effects can be increased when L-Phenylalanine is combined with Leflunomide.Approved, Investigational
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with L-Phenylalanine.Withdrawn
NatalizumabThe risk or severity of adverse effects can be increased when L-Phenylalanine is combined with Natalizumab.Approved, Investigational
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with L-Phenylalanine.Approved, Investigational
Rabies virus inactivated antigen, AThe risk or severity of adverse effects can be increased when L-Phenylalanine is combined with Rabies vaccine.Approved
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies vaccine can be decreased when used in combination with L-Phenylalanine.Approved
RindopepimutThe risk or severity of adverse effects can be increased when L-Phenylalanine is combined with CDX-110.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of L-Phenylalanine.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with L-Phenylalanine.Approved
SRP 299The risk or severity of adverse effects can be increased when L-Phenylalanine is combined with SRP 299.Investigational
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with L-Phenylalanine.Approved, Investigational
TG4010The risk or severity of adverse effects can be increased when L-Phenylalanine is combined with TG4010.Investigational
TofacitinibL-Phenylalanine may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrastuzumabTrastuzumab may increase the neutropenic activities of L-Phenylalanine.Approved, Investigational
Food InteractionsNot Available
References
Synthesis Reference

Gerald L. Bachman, "Recovery of L-phenylalanine and L-aspartic acid during preparation of .alpha.-L-aspartyl-L-phenylalanine methyl ester." U.S. Patent US4348317, issued January, 1967.

US4348317
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (72.5 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingSupportive CareProtein Feeding in Post-traumatic Injury Patients1
2Active Not RecruitingTreatmentCarcinoid Tumors / Medulloblastomas / Neuroblastomas / Neuroendocrine Tumors1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections2
2CompletedTreatmentB-cell Chronic Lymphocytic Leukemia CLL1
2RecruitingPreventionMuscle Wasting / Quality of Life1
2, 3Active Not RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHCV Infections / Infection, Human Immunodeficiency Virus I1
3Active Not RecruitingTreatmentHIV Disease / Human Immunodeficiency Virus (HIV) Infections3
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I6
3CompletedTreatmentCritical Illness1
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1
3RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
Not AvailableActive Not RecruitingTreatmentMenopause1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntravenous
Injection, solution, concentrateIntravenous
EmulsionIntravenous
SolutionIntravenous
LiquidIntravenous
InjectionIntravenous
Prices
Unit descriptionCostUnit
L-phenylalanine 500 mg tablet0.11USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)283 dec °CPhysProp
water solubility2.69E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.38AVDEEF,A (1997)
pKa1.24 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility4.14 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.12 m3·mol-1ChemAxon
Polarizability17.03 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9733
Blood Brain Barrier+0.5902
Caco-2 permeable+0.8129
P-glycoprotein substrateNon-substrate0.721
P-glycoprotein inhibitor INon-inhibitor0.9916
P-glycoprotein inhibitor IINon-inhibitor0.9941
Renal organic cation transporterNon-inhibitor0.9204
CYP450 2C9 substrateNon-substrate0.8512
CYP450 2D6 substrateNon-substrate0.8296
CYP450 3A4 substrateNon-substrate0.8378
CYP450 1A2 substrateNon-inhibitor0.9448
CYP450 2C9 inhibitorNon-inhibitor0.9792
CYP450 2D6 inhibitorNon-inhibitor0.9674
CYP450 2C19 inhibitorNon-inhibitor0.9797
CYP450 3A4 inhibitorNon-inhibitor0.9278
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9896
Ames testNon AMES toxic0.9211
CarcinogenicityNon-carcinogens0.8441
BiodegradationReady biodegradable0.7562
Rat acute toxicity1.9053 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9805
hERG inhibition (predictor II)Non-inhibitor0.9737
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Download (8.46 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0fr6-1930000000-a37fbccaf826443ef70cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014l-1940000000-537e2725d621246630c1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9630000000-ead0919f9a19d2352d80View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-2900000000-cb2d6dc4bf9515150328View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014l-2960000000-f77489792f0652dd5613View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-014l-0970000000-792b341dd28b9e30bac2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQsplash10-0ul9-3659000000-b85be4e71798e2fdc47bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-0f3b994108b8a9fd2a56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0gb9-2900000000-c14d44c8a67621757f3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9300000000-08c642dab7f49c00da43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-7dce1e473976f7d2143eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f6x-9600000000-711557391093b0d8500aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-0c25a5c116eac7bb059bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-2804f79084ac4e67e155View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-8a71bb1f8424064d7cafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0f6x-9800000000-e027ff6bb67ce55e80a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-9f6185e9c7d54189f369View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-df5f72fe2bba91742427View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0ir3-0988735721-bac229222fe7b52812a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-453477dec847a3672ffeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0010963000-079a66bf710f6778bcebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-62dbe98de4ecde484fb3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-80558c17dc1845663c85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-3900000000-e1ee31d41e48824e84b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0f6x-9500000000-cc11290a37615f24e16eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-1a6020bce0e1a9a14832View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-38c044a112152626962eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0900000000-9b908abfcb63153d60b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-3ba5964e151bb1d56188View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-2900000000-20a7d24da0281f5b3b78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0udi-5900000000-1800642a835b49f3398aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0fb9-9300000000-f262384c85fb843f8a11View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentPhenylalanine and derivatives
Alternative ParentsPhenylpropanoic acids / L-alpha-amino acids / Amphetamines and derivatives / Aralkylamines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines
SubstituentsPhenylalanine or derivatives / 3-phenylpropanoic-acid / Alpha-amino acid / Amphetamine or derivatives / L-alpha-amino acid / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Amino acid / Carboxylic acid
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorsproteinogenic amino acid, L-alpha-amino acid, phenylalanine, erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:17295 ) / Common amino acids (C00079 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Pyridoxal phosphate binding
Specific Function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:
TAT
Uniprot ID:
P17735
Uniprot Name:
Tyrosine aminotransferase
Molecular Weight:
50398.895 Da
References
  1. Luong TN, Kirsch JF: A continuous coupled spectrophotometric assay for tyrosine aminotransferase activity with aromatic and other nonpolar amino acids. Anal Biochem. 1997 Nov 1;253(1):46-9. [PubMed:9356140 ]
  2. Rege AA: Purification and characterization of a tyrosine aminotransferase from Crithidia fasciculata. Mol Biochem Parasitol. 1987 Aug;25(1):1-9. [PubMed:2890101 ]
  3. De-Eknamkul W, Ellis BE: Behavior of Free Aromatic Amino Acid Pools in Rosmarinic Acid-Producing Cell Cultures of Anchusa officinalis L. Plant Physiol. 1989 Feb;89(2):429-33. [PubMed:16666560 ]
  4. Patrizio M, Colucci M, Levi G: Human immunodeficiency virus type 1 Tat protein decreases cyclic AMP synthesis in rat microglia cultures. J Neurochem. 2001 Apr;77(2):399-407. [PubMed:11299302 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxin transporter activity
Specific Function:
Sodium-independent, high-affinity transport of small and large neutral amino acids such as alanine, serine, threonine, cysteine, phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Acts as an amino acid exchanger. Has higher affinity for L-phenylalanine than LAT1 but lower affinity for glutamine and serine. L-alanine is transported at physiological conc...
Gene Name:
SLC7A8
Uniprot ID:
Q9UHI5
Uniprot Name:
Large neutral amino acids transporter small subunit 2
Molecular Weight:
58381.12 Da
References
  1. Shennan DB, Calvert DT, Travers MT, Kudo Y, Boyd CA: A study of L-leucine, L-phenylalanine and L-alanine transport in the perfused rat mammary gland: possible involvement of LAT1 and LAT2. Biochim Biophys Acta. 2002 Aug 19;1564(1):133-9. [PubMed:12101005 ]
  2. Rossier G, Meier C, Bauch C, Summa V, Sordat B, Verrey F, Kuhn LC: LAT2, a new basolateral 4F2hc/CD98-associated amino acid transporter of kidney and intestine. J Biol Chem. 1999 Dec 3;274(49):34948-54. [PubMed:10574970 ]
  3. Babu E, Kanai Y, Chairoungdua A, Kim DK, Iribe Y, Tangtrongsup S, Jutabha P, Li Y, Ahmed N, Sakamoto S, Anzai N, Nagamori S, Endou H: Identification of a novel system L amino acid transporter structurally distinct from heterodimeric amino acid transporters. J Biol Chem. 2003 Oct 31;278(44):43838-45. Epub 2003 Aug 20. [PubMed:12930836 ]
  4. Satoh S, Kimura T, Toda M, Maekawa M, Ono S, Narita H, Miyazaki H, Murayama T, Nomura Y: Involvement of L-type-like amino acid transporters in S-nitrosocysteine-stimulated noradrenaline release in the rat hippocampus. J Neurochem. 1997 Nov;69(5):2197-205. [PubMed:9349567 ]
  5. Nemoto T, Shimma N, Horie S, Saito T, Okuma Y, Nomura Y, Murayama T: Involvement of the system L amino acid transporter on uptake of S-nitroso-L-cysteine, an endogenous S-nitrosothiol, in PC12 cells. Eur J Pharmacol. 2003 Jan 1;458(1-2):17-24. [PubMed:12498902 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Trna binding
Specific Function:
Not Available
Gene Name:
FARSA
Uniprot ID:
Q9Y285
Uniprot Name:
Phenylalanine--tRNA ligase alpha subunit
Molecular Weight:
57563.225 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 ]
  3. Kodama K, Fukuzawa S, Sakamoto K, Nakayama H, Kigawa T, Yabuki T, Matsuda N, Shirouzu M, Takio K, Tachibana K, Yokoyama S: A new protein engineering approach combining chemistry and biology, part I; site-specific incorporation of 4-iodo-L-phenylalanine in vitro by using misacylated suppressor tRNAPhe. Chembiochem. 2006 Oct;7(10):1577-81. [PubMed:16969782 ]
  4. Kotik-Kogan O, Moor N, Tworowski D, Safro M: Structural basis for discrimination of L-phenylalanine from L-tyrosine by phenylalanyl-tRNA synthetase. Structure. 2005 Dec;13(12):1799-807. [PubMed:16338408 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Phenylalanine 4-monooxygenase activity
Specific Function:
Not Available
Gene Name:
PAH
Uniprot ID:
P00439
Uniprot Name:
Phenylalanine-4-hydroxylase
Molecular Weight:
51861.565 Da
References
  1. Thorolfsson M, Ibarra-Molero B, Fojan P, Petersen SB, Sanchez-Ruiz JM, Martinez A: L-phenylalanine binding and domain organization in human phenylalanine hydroxylase: a differential scanning calorimetry study. Biochemistry. 2002 Jun 18;41(24):7573-85. [PubMed:12056888 ]
  2. Pueschel SM, Boylan J, Ellenbogen R: Studies on experimentally induced hyperphenylalaninemia. J Ment Defic Res. 1988 Aug;32 ( Pt 4):309-19. [PubMed:2975336 ]
  3. Nagasaki Y, Matsubara Y, Takano H, Fujii K, Senoo M, Akanuma J, Takahashi K, Kure S, Hara M, Kanegae Y, Saito I, Narisawa K: Reversal of hypopigmentation in phenylketonuria mice by adenovirus-mediated gene transfer. Pediatr Res. 1999 Apr;45(4 Pt 1):465-73. [PubMed:10203136 ]
  4. Fusetti F, Erlandsen H, Flatmark T, Stevens RC: Structure of tetrameric human phenylalanine hydroxylase and its implications for phenylketonuria. J Biol Chem. 1998 Jul 3;273(27):16962-7. [PubMed:9642259 ]
  5. Stokka AJ, Flatmark T: Substrate-induced conformational transition in human phenylalanine hydroxylase as studied by surface plasmon resonance analyses: the effect of terminal deletions, substrate analogues and phosphorylation. Biochem J. 2003 Feb 1;369(Pt 3):509-18. [PubMed:12379147 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Trna binding
Specific Function:
Is responsible for the charging of tRNA(Phe) with phenylalanine in mitochondrial translation. To a lesser extent, also catalyzes direct attachment of m-Tyr (an oxidized version of Phe) to tRNA(Phe), thereby opening the way for delivery of the misacylated tRNA to the ribosome and incorporation of ROS-damaged amino acid into proteins.
Gene Name:
FARS2
Uniprot ID:
O95363
Uniprot Name:
Phenylalanine--tRNA ligase, mitochondrial
Molecular Weight:
52356.21 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 ]
  3. Kodama K, Fukuzawa S, Sakamoto K, Nakayama H, Kigawa T, Yabuki T, Matsuda N, Shirouzu M, Takio K, Tachibana K, Yokoyama S: A new protein engineering approach combining chemistry and biology, part I; site-specific incorporation of 4-iodo-L-phenylalanine in vitro by using misacylated suppressor tRNAPhe. Chembiochem. 2006 Oct;7(10):1577-81. [PubMed:16969782 ]
  4. Kotik-Kogan O, Moor N, Tworowski D, Safro M: Structural basis for discrimination of L-phenylalanine from L-tyrosine by phenylalanyl-tRNA synthetase. Structure. 2005 Dec;13(12):1799-807. [PubMed:16338408 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Rna binding
Specific Function:
Not Available
Gene Name:
FARSB
Uniprot ID:
Q9NSD9
Uniprot Name:
Phenylalanine--tRNA ligase beta subunit
Molecular Weight:
66114.93 Da
References
  1. Kotik-Kogan O, Moor N, Tworowski D, Safro M: Structural basis for discrimination of L-phenylalanine from L-tyrosine by phenylalanyl-tRNA synthetase. Structure. 2005 Dec;13(12):1799-807. [PubMed:16338408 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Tyrosine 3-monooxygenase activity
Specific Function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
TH
Uniprot ID:
P07101
Uniprot Name:
Tyrosine 3-monooxygenase
Molecular Weight:
58599.545 Da
References
  1. Fukami MH, Haavik J, Flatmark T: Phenylalanine as substrate for tyrosine hydroxylase in bovine adrenal chromaffin cells. Biochem J. 1990 Jun 1;268(2):525-8. [PubMed:1973034 ]
  2. Ogawa S, Ichinose H: Effect of metals and phenylalanine on the activity of human tryptophan hydroxylase-2: comparison with that on tyrosine hydroxylase activity. Neurosci Lett. 2006 Jul 3;401(3):261-5. Epub 2006 Apr 11. [PubMed:16581181 ]
  3. Schallreuter KU, Kothari S, Hasse S, Kauser S, Lindsey NJ, Gibbons NC, Hibberts N, Wood JM: In situ and in vitro evidence for DCoH/HNF-1 alpha transcription of tyrosinase in human skin melanocytes. Biochem Biophys Res Commun. 2003 Feb 7;301(2):610-6. [PubMed:12565907 ]
  4. McQuade PS, Juorio AV: The effect of various amino acids and drugs on the para- and meta-hydroxyphenylacetic acid concentrations in the mouse caudate nucleus. Neurochem Res. 1983 Jul;8(7):903-12. [PubMed:6621777 ]
  5. Fusetti F, Erlandsen H, Flatmark T, Stevens RC: Structure of tetrameric human phenylalanine hydroxylase and its implications for phenylketonuria. J Biol Chem. 1998 Jul 3;273(27):16962-7. [PubMed:9642259 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
Specific Function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Uniprot Name:
Monocarboxylate transporter 10
Molecular Weight:
55492.07 Da
References
  1. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. [PubMed:11827462 ]
  2. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]
Drug created on June 13, 2005 07:24 / Updated on August 02, 2017 16:20