Identification
- Generic Name
- D-Phenylalanine
- DrugBank Accession Number
- DB02556
- Background
An essential aromatic amino acid that is a precursor of melanin; dopamine; noradrenalin (norepinephrine), and thyroxine. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for D-Phenylalanine (DB02556)
- Weight
- Average: 165.1891
Monoisotopic: 165.078978601 - Chemical Formula
- C9H11NO2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UKynurenine--oxoglutarate transaminase 1 Not Available Humans UCorticoliberin Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- 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 / D-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
- D-alpha-amino acid, phenylalanine (CHEBI:16998) / Other amino acids (C02265)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 032K16VRCU
- CAS number
- 673-06-3
- InChI Key
- COLNVLDHVKWLRT-MRVPVSSYSA-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-/m1/s1
- IUPAC Name
- (2R)-2-amino-3-phenylpropanoic acid
- SMILES
- N[C@H](CC1=CC=CC=C1)C(O)=O
References
- Synthesis Reference
Dennis P. Bauer, "Process for producing N-acyl-D-phenylalanine ester." U.S. Patent US4262092, issued November, 1977.
US4262092- General References
- Yanagida O, Kanai Y, Chairoungdua A, Kim DK, Segawa H, Nii T, Cha SH, Matsuo H, Fukushima J, Fukasawa Y, Tani Y, Taketani Y, Uchino H, Kim JY, Inatomi J, Okayasu I, Miyamoto K, Takeda E, Goya T, Endou H: Human L-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines. Biochim Biophys Acta. 2001 Oct 1;1514(2):291-302. [Article]
- External Links
- KEGG Compound
- C02265
- PubChem Compound
- 71567
- PubChem Substance
- 46505758
- ChemSpider
- 64639
- ChEBI
- 57981
- ChEMBL
- CHEMBL379630
- ZINC
- ZINC000000001927
- PDBe Ligand
- DPN
- Wikipedia
- Phenylalanine
- PDB Entries
- 1abi / 1b0q / 1bfw / 1go9 / 1goe / 1ihs / 1iht / 1mcb / 1mcc / 1mcd … show 149 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 2.82E+004 mg/L (at 16 °C) MERCK INDEX (1996) - 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 17.13 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transaminase activity
- Specific Function
- Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to ...
- Gene Name
- CCBL1
- Uniprot ID
- Q16773
- Uniprot Name
- Kynurenine--oxoglutarate transaminase 1
- Molecular Weight
- 47874.765 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor binding
- Specific Function
- Hormone regulating the release of corticotropin from pituitary gland (By similarity). Induces NLRP6 in intestinal epithelial cells, hence may influence gut microbiota profile (By similarity).
- Gene Name
- CRH
- Uniprot ID
- P06850
- Uniprot Name
- Corticoliberin
- Molecular Weight
- 21421.505 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Peptide antigen binding
- Specific Function
- Sodium-independent, high-affinity transport of large neutral amino acids such as phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Involved in cellular a...
- Gene Name
- SLC7A5
- Uniprot ID
- Q01650
- Uniprot Name
- Large neutral amino acids transporter small subunit 1
- Molecular Weight
- 55009.62 Da
References
- Yanagida O, Kanai Y, Chairoungdua A, Kim DK, Segawa H, Nii T, Cha SH, Matsuo H, Fukushima J, Fukasawa Y, Tani Y, Taketani Y, Uchino H, Kim JY, Inatomi J, Okayasu I, Miyamoto K, Takeda E, Goya T, Endou H: Human L-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines. Biochim Biophys Acta. 2001 Oct 1;1514(2):291-302. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:43