D-Phenylalanine (YMDB00995)

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Identification

YMDB ID

YMDB00995

Name

D-Phenylalanine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

D-Phenylalanine, also known as D-phe or DPN, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives 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. D-Phenylalanine is a very strong basic compound (based on its pKa). D-Phenylalanine may be a unique S. cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(-)-beta-Phenylalanine
(L)-Phenylalanine
(S)-(-)-Phenylalanine
(S)-2-amino-3-phenylpropanoate
(S)-2-amino-3-phenylpropanoic acid
(S)-2-Amino-3-phenylpropionate
(S)-2-Amino-3-phenylpropionic acid
(S)-alpha-Amino-benzenepropanoate
(S)-alpha-Amino-benzenepropanoic acid
(S)-alpha-Amino-beta-phenylpropionate
(S)-alpha-Amino-beta-phenylpropionic acid
(S)-alpha-Aminobenzenepropanoate
(S)-alpha-Aminobenzenepropanoic acid
(S)-alpha-Aminohydrocinnamate
(S)-alpha-Aminohydrocinnamic acid
(S)-Phenylalanine
3-Phenyl-L-alanine
Alanine, phenyl-, D-
alpha-Aminohydrocinnamate
alpha-Aminohydrocinnamic acid
beta-Phenyl-alpha-alanine
beta-Phenyl-L-alanine
beta-Phenylalanine
D-alpha-Amino-beta-phenylpropionic acid
D-Phenylalanine
L-2-Amino-3-phenylpropionate
L-2-Amino-3-phenylpropionic acid
L-Phenylalanine
Phe
phenyl-Alanine
Phenylalamine
Phenylalanine
Sabiden
D-Phe
DPN
Phenylalanine D-form
D-a-Amino-b-phenylpropionate
D-a-Amino-b-phenylpropionic acid
D-alpha-Amino-beta-phenylpropionate
D-Α-amino-β-phenylpropionate
D-Α-amino-β-phenylpropionic acid

CAS number

673-06-3

Weight

Average: 165.1891
Monoisotopic: 165.078978601

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

Traditional IUPAC Name

D-phenylalanine

Chemical Formula

C₉H₁₁NO₂

SMILES

N[C@H](CC1=CC=CC=C1)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives 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

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
D-alpha-amino acid
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:16998 )
phenylalanine (CHEBI:16998 )
Other amino acids (C02265 )

Physical Properties

State

Solid

Charge

Melting point

283 °C

Experimental Properties

Property	Value	Reference
Water Solubility	26.9 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-1.38 [AVDEEF,A (1997)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	4.14 g/L	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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Odorless	Not Available

SMPDB Pathways

Methionine metabolism and salvage	PW002384
Phenylalanine metabolism	PW002437
Tryptophan metabolism	PW002442

KEGG Pathways

Phenylalanine metabolism	ec00360
Tryptophan metabolism	ec00380

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9600000000-df38fcb743d8f44fb876	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00xr-1900000000-0716c626d7af27ede0c6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-c28830f82e77d9fd325c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-59ef5064d5616752bdcb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-73d3e9e338ef63c2f358	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03k9-3900000000-09edb34ae30afc47be75	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9400000000-bc289705a957b79378ba	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Yow, G. Y., Uo, T., Yoshimura, T., Esaki, N. (2004). "D-amino acid N-acetyltransferase of Saccharomyces cerevisiae: a close homologue of histone acetyltransferase Hpa2p acting exclusively on free D-amino acids." Arch Microbiol 182:396-403.15375647

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16998
HMDB ID	HMDB00159
Pubchem Compound ID	6140
Kegg ID	C02265
ChemSpider ID	64639
FOODB ID	Not Available
Wikipedia	Phenylalanine
BioCyc ID	PHE

Enzymes

Protein Details

1. N-acetyltransferase HPA3

General function:: Involved in N-acetyltransferase activity
Specific function:: N-acetyltransferase whose physiological acetyl acceptor substrate is still unknown. In vitro, histone acetylation is very weak
Gene Name:: HPA3
Uniprot ID:: P39979
Molecular weight:: 20698.5

Reactions

acetyl-CoA + a D-amino acid → CoA + an N-acetyl-D-amino acid

Structure for #<Compound:0x054e08a4>

Enzymes

Reactions