Identification

Name
L-Phenylalanine
Accession Number
DB00120  (NUTR00044)
Type
Small Molecule
Groups
Approved, 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 Key
L-Phenylalanine hydrochlorideL6O14A5L6Q 17585-69-2ZAIZDXVMSSDZFA-QRPNPIFTSA-N
Phenylalanine sodiumM67R83MDEE 16480-57-2ZRVUAXXSASAVFG-QRPNPIFTSA-M
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Phenylalanine (140 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (260 mg) + L-Alanine (520 mg) + L-Arginine (290 mg) + L-Histidine (120 mg) + L-Isoleucine (150 mg) + L-Leucine (182.5 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Proline (170 mg) + L-Serine (125 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixL-Phenylalanine (155 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (520 mg) + L-Alanine (520 mg) + L-Arginine (260 mg) + L-Histidine (110 mg) + L-Isoleucine (120 mg) + L-Leucine (155 mg) + L-Lysine (145 mg) + L-Methionine (145 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (115 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixL-Phenylalanine (155 mg) + Glucose (10 g) + Glycine (520 mg) + L-Alanine (520 mg) + L-Arginine (260 mg) + L-Histidine (110 mg) + L-Isoleucine (120 mg) + L-Leucine (155 mg) + L-Lysine (195 mg) + L-Methionine (195 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (115 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexL-Phenylalanine (140 mg) + Dipotassium phosphate (130.5 mg) + Glucose (25 g) + Glycine (260 mg) + L-Alanine (520 mg) + L-Arginine (290 mg) + L-Histidine (120 mg) + L-Isoleucine (150 mg) + L-Leucine (182.5 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Proline (170 mg) + L-Serine (125 mg) + L-Threonine (105 mg) + L-Tryptophan (45 mg) + L-Tyrosine (10 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travas. Amino Acid InJ.W.elecw.25%dexL-Phenylalanine (154 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (283 mg) + L-Alanine (570 mg) + L-Arginine (316 mg) + L-Histidine (132 mg) + L-Isoleucine (165 mg) + L-Leucine (201 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Proline (187 mg) + L-Serine (137.5 mg) + L-Threonine (115.5 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixL-Phenylalanine (170 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (570 mg) + L-Alanine (570 mg) + L-Arginine (285 mg) + L-Histidine (120.5 mg) + L-Isoleucine (131.5 mg) + L-Leucine (170 mg) + L-Lysine (159 mg) + L-Methionine (159 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-02-022007-08-02Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixL-Phenylalanine (170 mg) + Dipotassium phosphate (215.5 mg) + Glucose (5 g) + Glycine (570 mg) + L-Alanine (570 mg) + L-Arginine (285 mg) + L-Histidine (120.5 mg) + L-Isoleucine (131.5 mg) + L-Leucine (170 mg) + L-Lysine (159 mg) + L-Methionine (159 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (256 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312007-08-02Canada
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.L-Phenylalanine (154 mg) + Dipotassium phosphate (261 mg) + Glucose (5 g) + Glycine (283 mg) + L-Alanine (570 mg) + L-Arginine (316 mg) + L-Histidine (132 mg) + L-Isoleucine (165 mg) + L-Leucine (201 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Proline (187 mg) + L-Serine (137.5 mg) + L-Threonine (115.5 mg) + L-Tryptophan (49.5 mg) + L-Tyrosine (11 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215 mg)LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixL-Phenylalanine (263 mg) + Glucose (20 g) + Glycine (880 mg) + L-Alanine (880 mg) + L-Arginine (440 mg) + L-Histidine (186 mg) + L-Isoleucine (203 mg) + L-Leucine (263 mg) + L-Lysine (246 mg) + L-Methionine (246 mg) + L-Proline (178 mg) + L-Threonine (178 mg) + L-Tryptophan (76 mg) + L-Tyrosine (17 mg) + L-Valine (195 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Phenylalanine (238 mg) + Dipotassium phosphate (261 mg) + Glucose (10 g) + Glycine (438 mg) + L-Alanine (880 mg) + L-Arginine (489 mg) + L-Histidine (204 mg) + L-Isoleucine (255 mg) + L-Leucine (310 mg) + L-Lysine (246.5 mg) + L-Methionine (170 mg) + L-Proline (289 mg) + L-Serine (212.5 mg) + L-Threonine (178.5 mg) + L-Tryptophan (76.5 mg) + L-Tyrosine (17 mg) + L-Valine (246.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (77 mg) + Sodium acetate (297 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
Categories
UNII
47E5O17Y3R
CAS number
63-91-2
Weight
Average: 165.1891
Monoisotopic: 165.078978601
Chemical Formula
C9H11NO2
InChI Key
COLNVLDHVKWLRT-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[[email protected]@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

TargetActionsOrganism
UTyrosine aminotransferaseNot AvailableHuman
ULarge neutral amino acids transporter small subunit 2Not AvailableHuman
UPhenylalanine--tRNA ligase alpha subunitNot AvailableHuman
UPhenylalanine-4-hydroxylaseNot AvailableHuman
UPhenylalanine--tRNA ligase, mitochondrialNot AvailableHuman
UPhenylalanine--tRNA ligase beta subunitNot AvailableHuman
UTyrosine 3-monooxygenase
binder
Human
Absorption

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

Volume of distribution
Not Available
Protein binding
Not 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 elimination
Not Available
Half life
Not Available
Clearance
Not 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
PathwayCategory
PhenylketonuriaDisease
Phenylalanine and Tyrosine MetabolismMetabolic
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)Disease
Tyrosinemia Type 3 (TYRO3)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with L-Phenylalanine.Investigational
Clostridium tetani toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Clostridium tetani toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with L-Phenylalanine.Approved
ClozapineThe risk or severity of adverse effects can be increased when L-Phenylalanine is combined with Clozapine.Approved
Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated)The therapeutic efficacy of Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated) can be decreased when used in combination with L-Phenylalanine.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 therapeutic efficacy of G17DT can be decreased when used in combination with L-Phenylalanine.Investigational
GI-5005The therapeutic efficacy of GI-5005 can be decreased when used in combination with L-Phenylalanine.Investigational
INGN 201The therapeutic efficacy of INGN 201 can be decreased when used in combination with L-Phenylalanine.Investigational
INGN 225The therapeutic efficacy of INGN 225 can be decreased when used in combination with L-Phenylalanine.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 virus inactivated antigen, A.Approved
Rabies virus inactivated antigen, AThe therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with L-Phenylalanine.Approved
RindopepimutThe therapeutic efficacy of Rindopepimut can be decreased when used in combination with L-Phenylalanine.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of L-Phenylalanine.Approved
Rotavirus VaccineThe therapeutic efficacy of Rotavirus Vaccine can be decreased when used in combination with L-Phenylalanine.Approved
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with L-Phenylalanine.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with L-Phenylalanine.Approved
SRP 299The therapeutic efficacy of SRP 299 can be decreased when used in combination with L-Phenylalanine.Investigational
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with L-Phenylalanine.Approved, Investigational
TecemotideThe therapeutic efficacy of Tecemotide can be decreased when used in combination with L-Phenylalanine.Investigational
TG4010The therapeutic efficacy of TG4010 can be decreased when used in combination with L-Phenylalanine.Investigational
TofacitinibL-Phenylalanine may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrastuzumabTrastuzumab may increase the neutropenic activities of L-Phenylalanine.Approved, Investigational
Yellow fever vaccineThe therapeutic efficacy of Yellow fever vaccine can be decreased when used in combination with L-Phenylalanine.Approved
Zoster vaccineThe therapeutic efficacy of Zoster vaccine can be decreased when used in combination with L-Phenylalanine.Approved
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00159
KEGG Drug
D00021
KEGG Compound
C00079
PubChem Compound
6140
PubChem Substance
46505708
ChemSpider
5910
BindingDB
18073
ChEBI
17295
ChEMBL
CHEMBL301523
Therapeutic Targets Database
DAP000807
PharmGKB
PA450931
IUPHAR
3313
Guide to Pharmacology
GtP Drug Page
HET
PHE
PDRhealth
PDRhealth Drug Page
Wikipedia
L-Phenylalanine
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Download (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 RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections3
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I6
3CompletedTreatmentCritical Illness1
3CompletedTreatmentHCV Infections / Infection, Human Immunodeficiency Virus I1
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1
3RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
Not AvailableActive Not RecruitingTreatmentMenopause1

Pharmacoeconomics

Manufacturers
Not 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.
Patents
Not Available

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0fr6-1930000000-a37fbccaf826443ef70c
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014l-1940000000-537e2725d621246630c1
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00di-9630000000-ead0919f9a19d2352d80
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-00di-2900000000-cb2d6dc4bf9515150328
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-014l-2960000000-f77489792f0652dd5613
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-014l-0970000000-792b341dd28b9e30bac2
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0fr6-1930000000-a37fbccaf826443ef70c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014l-1940000000-537e2725d621246630c1
GC-MS Spectrum - GC-EI-QQGC-MSsplash10-0ul9-3659000000-b85be4e71798e2fdc47b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9630000000-ead0919f9a19d2352d80
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-2900000000-cb2d6dc4bf9515150328
GC-MS Spectrum - GC-MSGC-MSsplash10-014l-2960000000-f77489792f0652dd5613
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-014i-0900000000-0f3b994108b8a9fd2a56
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0gb9-2900000000-c14d44c8a67621757f3d
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-004i-9300000000-08c642dab7f49c00da43
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0900000000-7dce1e473976f7d2143e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0f6x-9600000000-711557391093b0d8500a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-0900000000-0c25a5c116eac7bb059b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-0900000000-2804f79084ac4e67e155
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0900000000-8a71bb1f8424064d7caf
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0f6x-9800000000-e027ff6bb67ce55e80a5
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0900000000-9f6185e9c7d54189f369
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00di-0900000000-df5f72fe2bba91742427
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0ir3-0988735721-bac229222fe7b52812a8
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0900000000-453477dec847a3672ffe
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4i-0010963000-079a66bf710f6778bceb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-00di-0000009000-62dbe98de4ecde484fb3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-03di-0900000000-80558c17dc1845663c85
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0002-3900000000-e1ee31d41e48824e84b7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0f6x-9500000000-cc11290a37615f24e16e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-1a6020bce0e1a9a14832
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-38c044a112152626962e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-014i-0900000000-9b908abfcb63153d60b3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-1900000000-3ba5964e151bb1d56188
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00di-2900000000-20a7d24da0281f5b3b78
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0udi-5900000000-1800642a835b49f3398a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0fb9-9300000000-f262384c85fb843f8a11
MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , PositiveLC-MS/MSsplash10-014i-0900000000-cb4f1e3bde1f29e264f5
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-014i-0900000000-2ab526c45d7503001dc3
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-01b9-0900000000-ddc97bf483f1a3361fd7
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-01ot-1900000000-8dbbc0673f81b8e1de2a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-80558c17dc1845663c85
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-3900000000-e1ee31d41e48824e84b7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0f6x-9500000000-cc11290a37615f24e16e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-1a6020bce0e1a9a14832
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-38c044a112152626962e
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-37833998cb13dd974fc1
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-01ot-1900000000-8dbbc0673f81b8e1de2a
MS/MS Spectrum - , negativeLC-MS/MSsplash10-01ot-1900000000-6c30a06686190daf5921
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-99b1e46c9ca3032be112
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-c068f70074d7ced6b8b1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-48fb6ee11fb845efdcf3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0900000000-9b908abfcb63153d60b3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-1900000000-3ba5964e151bb1d56188
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-2900000000-20a7d24da0281f5b3b78
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-5900000000-99329db3f395a4f3d593
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0fb9-9300000000-e3023e2a20fe1c5fe987
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-0900000000-1d714b1667871b7d7e82
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-1dd00f428846031939fd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-cf90e5631705754e390f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-88d4b01f6ee598453af9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-20a2bb1d995a8486141c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0f6x-9600000000-b8320b3046aea4d76c6a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-0c25a5c116eac7bb059b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-2804f79084ac4e67e155
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0f6x-9800000000-e027ff6bb67ce55e80a5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-9f6185e9c7d54189f369
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-df5f72fe2bba91742427
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0900000000-2ab526c45d7503001dc3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01b9-0900000000-ddc97bf483f1a3361fd7
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0900000000-969855cae81e0e0b097c
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Organic acids and derivatives
Sub Class
Carboxylic acids and derivatives
Direct Parent
Phenylalanine and derivatives
Alternative Parents
Phenylpropanoic acids / L-alpha-amino acids / Amphetamines and derivatives / Aralkylamines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 2 more
Substituents
Phenylalanine or derivatives / 3-phenylpropanoic-acid / Alpha-amino acid / Amphetamine or derivatives / L-alpha-amino acid / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Amino acid / Carboxylic acid
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
proteinogenic 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...
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 asso...
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)...
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 October 02, 2017 04:31