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Identification
NameD-Phenylalanine
Accession NumberDB02556  (EXPT01257)
TypeSmall Molecule
GroupsExperimental
Description

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

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number673-06-3
WeightAverage: 165.1891
Monoisotopic: 165.078978601
Chemical FormulaC9H11NO2
InChI KeyCOLNVLDHVKWLRT-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassPhenylpropanoic Acids
SubclassNot Available
Direct parentPhenylpropanoic Acids
Alternative parentsAlpha Amino Acids and Derivatives; Amphetamines and Derivatives; Amino Fatty Acids; Carboxylic Acids; Enolates; Polyamines; Monoalkylamines
Substituentsbenzene; carboxylic acid; enolate; polyamine; carboxylic acid derivative; amine; primary amine; primary aliphatic amine; organonitrogen compound
Classification descriptionThis compound belongs to the phenylpropanoic acids. These are compounds whose structure contain a benzene ring conjugated to a propanoic acid.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9792
CYP450 2D6 substrate Non-inhibitor 0.9674
CYP450 2C19 substrate Non-inhibitor 0.9797
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubility2.82E+004 mg/L (at 16 °C)MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility4.14ALOGPS
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
Spectra
SpectraNot Available
References
Synthesis Reference

Dennis P. Bauer, “Process for producing N-acyl-D-phenylalanine ester.” U.S. Patent US4262092, issued November, 1977.

US4262092
General Reference
  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. Pubmed
External Links
ResourceLink
KEGG CompoundC02265
ChEBI16998
ChEMBL
HETDPN
Drug Product Database285528
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Kynurenine--oxoglutarate transaminase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Kynurenine--oxoglutarate transaminase 1 Q16773 Details

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
  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

2. Corticoliberin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Corticoliberin P06850 Details

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. Pubmed

Transporters

1. Monocarboxylate transporter 10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 10 Q8TF71 Details

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. Pubmed
  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. Pubmed

2. Large neutral amino acids transporter small subunit 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Large neutral amino acids transporter small subunit 1 Q01650 Details

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. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18