D-Phenylalanine

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
Weight
Average: 165.1891
Monoisotopic: 165.078978601
Chemical Formula
C9H11NO2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UKynurenine--oxoglutarate transaminase 1Not AvailableHumans
UCorticoliberinNot AvailableHumans
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
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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
  1. 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]
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 163 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility2.82E+004 mg/L (at 16 °C)MERCK INDEX (1996)
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
Polarizability17.13 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)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-006x-9600000000-df38fcb743d8f44fb876
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-0900000000-ca3fc81971fbdc14b192
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-2367708ffcc91ccace49
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-bc72353d2f7da9c791d2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6x-9800000000-e67542c736bd407aa451
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kdl-9800000000-8c73276b79f2b885610b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9300000000-ad6d862c26d145115900
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-139.0717691
predicted
DarkChem Lite v0.1.0
[M-H]-138.8867691
predicted
DarkChem Lite v0.1.0
[M-H]-129.84201
predicted
DeepCCS 1.0 (2019)
[M+H]+139.7221691
predicted
DarkChem Lite v0.1.0
[M+H]+139.7028691
predicted
DarkChem Lite v0.1.0
[M+H]+133.30418
predicted
DeepCCS 1.0 (2019)
[M+Na]+138.8984691
predicted
DarkChem Lite v0.1.0
[M+Na]+139.1432691
predicted
DarkChem Lite v0.1.0
[M+Na]+142.71825
predicted
DeepCCS 1.0 (2019)

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
  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]
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
  1. 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
Substrate
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, 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]
  2. 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
  1. 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