Phenylalanine

Identification

Summary

Phenylalanine is an amino acid commonly found as a component of total parenteral nutrition.

Brand Names
Aminosyn II 7 %, Sulfite-free, Aminosyn-PF 7%, Clinimix 2.75/5, Clinimix E 2.75/5, Clinisol 15, Freamine 6.9, Freamine III 10, Hepatamine 8, Nephramine, Olimel, Periolimel, Plenamine, Premasol, Primene, Procalamine 3, Prosol, Travasol 10, Trophamine 10 %
Generic Name
Phenylalanine
DrugBank Accession Number
DB00120
Background

Phenylalanine is an essential aromatic amino acid that is a precursor of melanin, dopamine, noradrenalin (norepinephrine), and thyroxine.

Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Structure
Weight
Average: 165.1891
Monoisotopic: 165.078978601
Chemical Formula
C9H11NO2
Synonyms
  • (S)-2-Amino-3-phenylpropionic acid
  • (S)-alpha-Amino-beta-phenylpropionic acid
  • 3-phenyl-L-alanine
  • beta-Phenyl-L-alanine
  • F
  • Fenilalanina
  • L-Phenylalanine
  • Phe
  • Phenylalanine
  • Phenylalaninum
  • β-phenyl-L-alanine
External IDs
  • FEMA NO. 3585

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.

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Associated Therapies
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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 supposed antidepressant effects of L-phenylalanine may be due to its role as a precursor 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

Target Actions Organism
UTyrosine aminotransferase Not Available Humans
ULarge neutral amino acids transporter small subunit 2 Not Available Humans
UPhenylalanine--tRNA ligase alpha subunit Not Available Humans
UPhenylalanine-4-hydroxylase Not Available Humans
UPhenylalanine--tRNA ligase, mitochondrial Not Available Humans
UPhenylalanine--tRNA ligase beta subunit Not Available Humans
UTyrosine 3-monooxygenase
binder
Humans
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

Adverse Effects
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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.

Pathways
Pathway Category
Tyrosinemia Type 3 (TYRO3) Disease
Phenylketonuria Disease
Phenylalanine and Tyrosine Metabolism Metabolic
Tyrosinemia Type 2 (or Richner-Hanhart Syndrome) Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction
Abatacept The risk or severity of adverse effects can be increased when Phenylalanine is combined with Abatacept.
Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Phenylalanine.
Acenocoumarol The risk or severity of bleeding can be increased when Acenocoumarol is combined with Phenylalanine.
Acetylsalicylic acid The risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Phenylalanine.
Adalimumab The risk or severity of adverse effects can be increased when Adalimumab is combined with Phenylalanine.
Food Interactions
Not Available

Products

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Product Ingredients
Ingredient UNII CAS InChI Key
Phenylalanine hydrochloride L6O14A5L6Q 17585-69-2 ZAIZDXVMSSDZFA-QRPNPIFTSA-N
Phenylalanine sodium M67R83MDEE 16480-57-2 ZRVUAXXSASAVFG-QRPNPIFTSA-M
Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose Phenylalanine (140 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (290 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (260 mg / 100 mL) + Histidine (120 mg / 100 mL) + Isoleucine (150 mg / 100 mL) + Leucine (182.5 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (100 mg / 100 mL) + Proline (170 mg / 100 mL) + Serine (125 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (145 mg / 100 mL) Solution Intravenous Baxter Corporation Clintec Nutrition Division 1996-12-31 2015-08-05 Canada flag
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose Clinimix Phenylalanine hydrochloride (155 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (260 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (520 mg / 100 mL) + Histidine (110 mg / 100 mL) + Isoleucine (120 mg / 100 mL) + L-Leucine hydrochloride (155 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (145 mg / 100 mL) + Proline (105 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (115 mg / 100 mL) Solution Intravenous Baxter Corporation Clintec Nutrition Division 1993-12-31 2015-08-05 Canada flag
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose Quickmix Phenylalanine hydrochloride (155 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (260 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Glycine (520 mg / 100 mL) + Histidine (110 mg / 100 mL) + Isoleucine (120 mg / 100 mL) + L-Leucine hydrochloride (155 mg / 100 mL) + Lysine hydrochloride (195 mg / 100 mL) + Methionine (195 mg / 100 mL) + Proline (105 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (115 mg / 100 mL) Solution Intravenous Baxter Corporation Clintec Nutrition Division 1995-12-31 2007-08-02 Canada flag
2.5%travasol Amino Acid InJ.W.eleC.W.25%dex Phenylalanine (140 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (290 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (260 mg / 100 mL) + Histidine (120 mg / 100 mL) + Isoleucine (150 mg / 100 mL) + Leucine (182.5 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (100 mg / 100 mL) + Proline (170 mg / 100 mL) + Serine (125 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tryptophan (45 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (145 mg / 100 mL) Liquid Intravenous Clintec Nutrition Company 1996-07-30 1998-08-13 Canada flag
2.75% Travas. Amino Acid InJ.W.elecw.25%dex Phenylalanine (154 mg / 100 mL) + Alanine (570 mg / 100 mL) + Arginine (316 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (261 mg / 100 mL) + Glycine (283 mg / 100 mL) + Histidine (132 mg / 100 mL) + Isoleucine (165 mg / 100 mL) + Leucine (201 mg / 100 mL) + Lysine hydrochloride (159.5 mg / 100 mL) + Magnesium chloride (51 mg / 100 mL) + Methionine (110 mg / 100 mL) + Proline (187 mg / 100 mL) + Serine (137.5 mg / 100 mL) + Sodium acetate (215.5 mg / 100 mL) + Sodium chloride (112 mg / 100 mL) + Threonine (115.5 mg / 100 mL) + Tryptophan (49.5 mg / 100 mL) + Tyrosine (11 mg / 100 mL) + Valine (159.5 mg / 100 mL) Liquid Intravenous Clintec Nutrition Company 1996-07-30 1998-08-13 Canada flag
Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
Clinimix Phenylalanine (1.54 g/1L) + Alanine (5.70 g/1L) + Arginine (3.17 g/1L) + Calcium chloride dihydrate (0.33 g/1L) + D-glucose monohydrate (100.00 g/1L) + Dipotassium phosphate (2.61 g/1L) + Glycine (2.84 g/1L) + Histidine (1.32 g/1L) + Isoleucine (1.65 g/1L) + Leucine (2.01 g/1L) + Lysine (2.00 g/1L) + Magnesium chloride hexahydrate (0.51 g/1L) + Methionine (1.10 g/1L) + Proline (1.87 g/1L) + Serine (1.38 g/1L) + Sodium acetate trihydrate (2.16 g/1L) + Sodium chloride (1.12 g/1L) + Threonine (1.16 g/1L) + Tryptophan (0.50 g/1L) + Tyrosine (0.11 g/1L) + Valine (1.60 g/1L) Solution Intravenous Baxter Healthcare Corporation 2017-10-25 2019-11-30 US flag
Clinimix Phenylalanine (4.76 g/2L) + Alanine (17.60 g/2L) + Arginine (9.78 g/2L) + Calcium chloride dihydrate (0.66 g/2L) + D-glucose monohydrate (300.00 g/2L) + Dipotassium phosphate (5.22 g/2L) + Glycine (8.76 g/2L) + Histidine (4.08 g/2L) + Isoleucine (5.10 g/2L) + Leucine (6.20 g/2L) + Lysine (4.93 g/2L) + Magnesium chloride hexahydrate (1.02 g/2L) + Methionine (3.40 g/2L) + Proline (5.78 g/2L) + Serine (4.25 g/2L) + Sodium acetate trihydrate (5.94 g/2L) + Sodium chloride (1.54 g/2L) + Threonine (3.57 g/2L) + Tryptophan (1.53 g/2L) + Tyrosine (0.34 g/2L) + Valine (4.93 g/2L) Solution Intravenous Baxter Healthcare Corporation 2017-10-25 2019-11-30 US flag
Clinimix Phenylalanine (1.54 g/1L) + Alanine (5.70 g/1L) + Arginine (3.17 g/1L) + Calcium chloride dihydrate (0.33 g/1L) + D-glucose monohydrate (75.00 g/1L) + Dipotassium phosphate (2.61 g/1L) + Glycine (2.84 g/1L) + Histidine (1.32 g/1L) + Isoleucine (1.65 g/1L) + Leucine (2.01 g/1L) + Lysine (2.00 g/1L) + Magnesium chloride hexahydrate (0.51 g/1L) + Methionine (1.10 g/1L) + Proline (1.87 g/1L) + Serine (1.38 g/1L) + Sodium acetate trihydrate (2.16 g/1L) + Sodium chloride (1.12 g/1L) + Threonine (1.16 g/1L) + Tryptophan (0.50 g/1L) + Tyrosine (0.11 g/1L) + Valine (1.60 g/1L) Solution Intravenous Baxter Healthcare Corporation 2017-10-25 2019-11-30 US flag
FREAMINE III %10 1000 ML(SETLI) Phenylalanine (0.56 %) + Alanine (0.71 %) + Arginine (0.95 %) + Cysteine (0.016 %) + Glycine (1.4 %) + Histidine (0.28 %) + Isoleucine (0.69 %) + Leucine (0.91 %) + Lysine (0.73 %) + Methionine (0.53 %) + Proline (1.12 %) + Serine (0.59 %) + Threonine (0.4 %) + Tryptophan (0.15 %) + Valine (0.66 %) Solution Intravenous ECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş. 2013-01-29 2024-01-23 Turkey flag
FREAMINE III %10 1000 ML(SETSIZ) Phenylalanine (0.56 %) + Alanine (0.71 %) + Arginine (0.95 %) + Cysteine (0.016 %) + Glycine (1.4 %) + Histidine (0.28 %) + Isoleucine (0.69 %) + Leucine (0.91 %) + Lysine (0.73 %) + Methionine (0.53 %) + Proline (1.12 %) + Serine (0.59 %) + Threonine (0.4 %) + Tryptophan (0.15 %) + Valine (0.66 %) Solution Intravenous ECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş. 2013-01-29 2024-01-23 Turkey flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds 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
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
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
3-phenylpropanoic-acid / Alpha-amino acid / Amine / Amino acid / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / 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)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
47E5O17Y3R
CAS number
63-91-2
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[C@@H](CC1=CC=CC=C1)C(O)=O

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
Human Metabolome Database
HMDB0000159
KEGG Drug
D00021
KEGG Compound
C00079
PubChem Compound
6140
PubChem Substance
46505708
ChemSpider
5910
BindingDB
18073
RxNav
8156
ChEBI
58095
ChEMBL
CHEMBL301523
ZINC
ZINC000000105196
Therapeutic Targets Database
DAP000807
PharmGKB
PA450931
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
PHE
PDRhealth
PDRhealth Drug Page
Wikipedia
Phenylalanine
MSDS
Download (72.5 KB)

Clinical Trials

Clinical Trials
Phase Status Purpose Conditions Count
4 Active Not Recruiting Treatment Critically Ill Patients / Starvation 1
4 Recruiting Basic Science Healthy Volunteers (HV) / Obesity / Type 2 Diabetes Mellitus 1
4 Recruiting Prevention Intestinal Obstruction / Laparotomy / Mesenteric vascular insufficiency 1
4 Terminated Supportive Care Cancer-related Malnutrition 1
4 Terminated Supportive Care Critically Ill Patients 1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Magno-Humphries Laboratories
Dosage Forms
Form Route Strength
Solution Parenteral
Tablet Oral
Solution Intravenous 10.50 g/1000ml
Injection Intravenous 0.5 g/l
Injection Intravenous 0.25 g/1000ml
Solution, concentrate Intravenous
Injection Intravenous 0.52 g/l
Injection, solution Intravenous
Injection Intravenous 11.000 g/1000ml
Solution Intravenous 18.5 g/L
Injection Intravenous 5.5 g/1000ml
Injection, emulsion Intravenous
Emulsion Intravenous 0.468 g
Injection Intravenous 16 g/1000ml
Emulsion Parenteral 20.000 g
Injection Intravenous 1.6 g/l
Tablet Oral
Injection Intravenous 0.37 g/l
Injection, solution, concentrate Intravenous
Injection, emulsion Parenteral
Emulsion Intravenous 0.466 g
Injection, emulsion; injection, solution Intravenous
Emulsion Parenteral
Emulsion Intravenous
Injection, solution
Injection, emulsion Intravenous 4.656 g/1000ml
Injection, emulsion Intravenous 6.792 g/1000ml
Solution Intraperitoneal
Injection, solution Intraperitoneal
Liquid Hemodialysis
Solution Intraperitoneal 0.184 g/l
Emulsion Intravenous 176 g/l
Emulsion Intravenous 4 g
Emulsion Intravenous 3 g
Solution Intravenous
Injection Intravenous 4 g/l
Injection Intravenous 0.21 g/100ml
Liquid Intravenous
Emulsion Intravenous 13.000 g
Emulsion Parenteral 42.00 g
Injection, emulsion Intravenous 14 g/1000ml
Injection Intravenous 10.30 g/l
Injection Intravenous
Prices
Unit description Cost Unit
L-phenylalanine 500 mg tablet 0.11USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Property Value Source
melting point (°C) 283 dec °C PhysProp
water solubility 2.69E+004 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP -1.38 AVDEEF,A (1997)
pKa 1.24 (at 25 °C) KORTUM,G ET AL (1961)
Predicted Properties
Property Value Source
Water Solubility 4.14 mg/mL ALOGPS
logP -1.4 ALOGPS
logP -1.2 Chemaxon
logS -1.6 ALOGPS
pKa (Strongest Acidic) 2.47 Chemaxon
pKa (Strongest Basic) 9.45 Chemaxon
Physiological Charge 0 Chemaxon
Hydrogen Acceptor Count 3 Chemaxon
Hydrogen Donor Count 2 Chemaxon
Polar Surface Area 63.32 Å2 Chemaxon
Rotatable Bond Count 3 Chemaxon
Refractivity 45.12 m3·mol-1 Chemaxon
Polarizability 17.03 Å3 Chemaxon
Number of Rings 1 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter No Chemaxon
Veber's Rule No Chemaxon
MDDR-like Rule No Chemaxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 0.9733
Blood Brain Barrier + 0.5902
Caco-2 permeable + 0.8129
P-glycoprotein substrate Non-substrate 0.721
P-glycoprotein inhibitor I Non-inhibitor 0.9916
P-glycoprotein inhibitor II Non-inhibitor 0.9941
Renal organic cation transporter Non-inhibitor 0.9204
CYP450 2C9 substrate Non-substrate 0.8512
CYP450 2D6 substrate Non-substrate 0.8296
CYP450 3A4 substrate Non-substrate 0.8378
CYP450 1A2 substrate Non-inhibitor 0.9448
CYP450 2C9 inhibitor Non-inhibitor 0.9792
CYP450 2D6 inhibitor Non-inhibitor 0.9674
CYP450 2C19 inhibitor Non-inhibitor 0.9797
CYP450 3A4 inhibitor Non-inhibitor 0.9278
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9896
Ames test Non AMES toxic 0.9211
Carcinogenicity Non-carcinogens 0.8441
Biodegradation Ready biodegradable 0.7562
Rat acute toxicity 1.9053 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9805
hERG inhibition (predictor II) Non-inhibitor 0.9737
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 Spectrum Type Splash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) GC-MS splash10-0fr6-1930000000-a37fbccaf826443ef70c
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) GC-MS splash10-014l-1940000000-537e2725d621246630c1
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) GC-MS splash10-00di-9630000000-ead0919f9a19d2352d80
GC-MS Spectrum - GC-MS (1 TMS) GC-MS splash10-00di-2900000000-cb2d6dc4bf9515150328
GC-MS Spectrum - GC-MS (2 TMS) GC-MS splash10-014l-2960000000-f77489792f0652dd5613
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-006x-9600000000-df38fcb743d8f44fb876
GC-MS Spectrum - EI-B GC-MS splash10-014l-0970000000-792b341dd28b9e30bac2
GC-MS Spectrum - GC-EI-TOF GC-MS splash10-0fr6-1930000000-a37fbccaf826443ef70c
GC-MS Spectrum - GC-EI-TOF GC-MS splash10-014l-1940000000-537e2725d621246630c1
GC-MS Spectrum - GC-EI-QQ GC-MS splash10-0ul9-3659000000-b85be4e71798e2fdc47b
GC-MS Spectrum - GC-EI-TOF GC-MS splash10-00di-9630000000-ead0919f9a19d2352d80
GC-MS Spectrum - GC-MS GC-MS splash10-00di-2900000000-cb2d6dc4bf9515150328
GC-MS Spectrum - GC-MS GC-MS splash10-014l-2960000000-f77489792f0652dd5613
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) LC-MS/MS splash10-014i-0900000000-0f3b994108b8a9fd2a56
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) LC-MS/MS splash10-0gb9-2900000000-c14d44c8a67621757f3d
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) LC-MS/MS splash10-004i-9300000000-08c642dab7f49c00da43
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive LC-MS/MS splash10-014i-0900000000-7dce1e473976f7d2143e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive LC-MS/MS splash10-0f6x-9600000000-711557391093b0d8500a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive LC-MS/MS splash10-00di-0900000000-0c25a5c116eac7bb059b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive LC-MS/MS splash10-00di-0900000000-2804f79084ac4e67e155
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive LC-MS/MS splash10-014i-0900000000-8a71bb1f8424064d7caf
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive LC-MS/MS splash10-0f6x-9800000000-e027ff6bb67ce55e80a5
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive LC-MS/MS splash10-014i-0900000000-9f6185e9c7d54189f369
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive LC-MS/MS splash10-00di-0900000000-df5f72fe2bba91742427
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative LC-MS/MS splash10-0ir3-0988735721-bac229222fe7b52812a8
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative LC-MS/MS splash10-0002-0900000000-453477dec847a3672ffe
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative LC-MS/MS splash10-0a4i-0010963000-079a66bf710f6778bceb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative LC-MS/MS splash10-00di-0000009000-62dbe98de4ecde484fb3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative LC-MS/MS splash10-03di-0900000000-80558c17dc1845663c85
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative LC-MS/MS splash10-0002-3900000000-e1ee31d41e48824e84b7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative LC-MS/MS splash10-0f6x-9500000000-cc11290a37615f24e16e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative LC-MS/MS splash10-0006-9000000000-1a6020bce0e1a9a14832
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative LC-MS/MS splash10-0006-9000000000-38c044a112152626962e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive LC-MS/MS splash10-014i-0900000000-9b908abfcb63153d60b3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive LC-MS/MS splash10-00di-1900000000-3ba5964e151bb1d56188
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive LC-MS/MS splash10-00di-2900000000-20a7d24da0281f5b3b78
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive LC-MS/MS splash10-0udi-5900000000-1800642a835b49f3398a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive LC-MS/MS splash10-0fb9-9300000000-f262384c85fb843f8a11
MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive LC-MS/MS splash10-014i-0900000000-cb4f1e3bde1f29e264f5
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive LC-MS/MS splash10-014i-0900000000-2ab526c45d7503001dc3
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive LC-MS/MS splash10-01b9-0900000000-ddc97bf483f1a3361fd7
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative LC-MS/MS splash10-01ot-1900000000-8dbbc0673f81b8e1de2a
LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-03di-0900000000-80558c17dc1845663c85
LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-0002-3900000000-e1ee31d41e48824e84b7
LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-0f6x-9500000000-cc11290a37615f24e16e
LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-0006-9000000000-1a6020bce0e1a9a14832
LC-MS/MS Spectrum - LC-ESI-QQ , negative LC-MS/MS splash10-0006-9000000000-38c044a112152626962e
LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-0002-0900000000-37833998cb13dd974fc1
LC-MS/MS Spectrum - LC-ESI-QTOF , negative LC-MS/MS splash10-01ot-1900000000-8dbbc0673f81b8e1de2a
MS/MS Spectrum - , negative LC-MS/MS splash10-01ot-1900000000-6c30a06686190daf5921
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-00di-0900000000-99b1e46c9ca3032be112
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-00di-0900000000-c068f70074d7ced6b8b1
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-00di-0900000000-48fb6ee11fb845efdcf3
LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-014i-0900000000-9b908abfcb63153d60b3
LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-00di-1900000000-3ba5964e151bb1d56188
LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-00di-2900000000-20a7d24da0281f5b3b78
LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-0udi-5900000000-99329db3f395a4f3d593
LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-0fb9-9300000000-e3023e2a20fe1c5fe987
LC-MS/MS Spectrum - LC-ESI-IT , positive LC-MS/MS splash10-00di-0900000000-1d714b1667871b7d7e82
LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-00di-0900000000-1dd00f428846031939fd
LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-00di-0900000000-cf90e5631705754e390f
LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-00di-0900000000-88d4b01f6ee598453af9
LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-00di-0900000000-20a2bb1d995a8486141c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0f6x-9600000000-b8320b3046aea4d76c6a
LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-00di-0900000000-0c25a5c116eac7bb059b
LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-00di-0900000000-2804f79084ac4e67e155
LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0f6x-9800000000-e027ff6bb67ce55e80a5
LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-014i-0900000000-9f6185e9c7d54189f369
LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-00di-0900000000-df5f72fe2bba91742427
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-014i-0900000000-2ab526c45d7503001dc3
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-01b9-0900000000-ddc97bf483f1a3361fd7
MS/MS Spectrum - , positive LC-MS/MS splash10-00di-0900000000-969855cae81e0e0b097c
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0uk9-0900000000-ca3fc81971fbdc14b192
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-1900000000-2367708ffcc91ccace49
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0f6x-9800000000-e67542c736bd407aa451
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0900000000-bc72353d2f7da9c791d2
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0kdl-9800000000-8c73276b79f2b885610b
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9300000000-ad6d862c26d145115900
1H NMR Spectrum 1D NMR Not Applicable
13C NMR Spectrum 1D NMR Not Applicable
Predicted 1H NMR Spectrum 1D NMR Not Applicable
Predicted 13C NMR Spectrum 1D NMR Not Applicable
[1H,1H] 2D NMR Spectrum 2D NMR Not Applicable
[1H,13C] 2D NMR Spectrum 2D NMR Not Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source
[M-H]- 139.3087691
predicted
DarkChem Lite v0.1.0
[M-H]- 139.256643
predicted
DarkChem Standard v0.1.0
[M-H]- 139.3193691
predicted
DarkChem Lite v0.1.0
[M-H]- 139.4458691
predicted
DarkChem Lite v0.1.0
[M-H]- 139.2625691
predicted
DarkChem Lite v0.1.0
[M-H]- 130.50636
predicted
DeepCCS 1.0 (2019)
[M+H]+ 139.5540691
predicted
DarkChem Lite v0.1.0
[M+H]+ 140.2779703
predicted
DarkChem Standard v0.1.0
[M+H]+ 139.9188691
predicted
DarkChem Lite v0.1.0
[M+H]+ 139.9879691
predicted
DarkChem Lite v0.1.0
[M+H]+ 139.9518691
predicted
DarkChem Lite v0.1.0
[M+H]+ 133.92598
predicted
DeepCCS 1.0 (2019)
[M+Na]+ 139.0270691
predicted
DarkChem Lite v0.1.0
[M+Na]+ 139.0861691
predicted
DarkChem Lite v0.1.0
[M+Na]+ 139.2070691
predicted
DarkChem Lite v0.1.0
[M+Na]+ 138.9690691
predicted
DarkChem Lite v0.1.0
[M+Na]+ 139.1394691
predicted
DarkChem Lite v0.1.0
[M+Na]+ 143.25589
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  2. Rege AA: Purification and characterization of a tyrosine aminotransferase from Crithidia fasciculata. Mol Biochem Parasitol. 1987 Aug;25(1):1-9. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  2. Pueschel SM, Boylan J, Ellenbogen R: Studies on experimentally induced hyperphenylalaninemia. J Ment Defic Res. 1988 Aug;32 ( Pt 4):309-19. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Transporters

Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:42