Showing Compound N-Acetyl-L-phenylalanine (FDB022084)

Record Information

Version

1.0

Creation date

2011-09-21 00:08:16 UTC

Update date

2015-10-09 22:30:08 UTC

Primary ID

FDB022084

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N-Acetyl-L-phenylalanine

Description

Acetylphenylalanine is a hazardous amphipathic metabolite of phenylalanine. It appears in large amount in urine of patients with phenylketonuria which is a human genetic disorder due to the lack of phenylalanine hydroxylase, the enzyme necessary to metabolize phenylalanine to tyrosine. Acetylphenylalanine is a product of enzyme phenylalanine N-acetyltransferase [EC 2.3.1.53] in the pathway phenylalanine metabolism. (KEGG; Wikipedia) [HMDB]

CAS Number

2018-61-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Acetyl-L-phenylalanine	ChEBI
Acetylphenylalanine	ChEBI
L-N-Acetylphenylalanine	ChEBI
N-Acetylphenylalanine	ChEBI
N-Acetyl-3-phenyl-L-alanine	HMDB
N-Acetyl-L-phenalanine	HMDB
N-Acetylphenylalanine, (D,L)-isomer, 3H-labeled	HMDB
N-Acetylphenylalanine, (L)-isomer	HMDB
N-Acetylphenylalanine, (L)-isomer, 3H-labeled	HMDB
N-Acetylphenylalanine, (D)-isomer	HMDB
N-acetyl-3-phenyl-L-Alanine	hmdb
N-Acetyl-l-phenalanine	hmdb
N-Acetyl-L-phenylalanine	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.97 g/L	ALOGPS
logP	1.11	ALOGPS
logP	0.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.56 m³·mol⁻¹	ChemAxon
Polarizability	21.21 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H13NO3

IUPAC name

(2S)-2-acetamido-3-phenylpropanoic acid

InChI Identifier

InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1

InChI Key

CBQJSKKFNMDLON-JTQLQIEISA-N

Isomeric SMILES

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

Average Molecular Weight

207.2258

Monoisotopic Molecular Weight

207.089543287

Classification

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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Monocyclic benzene moiety
Benzenoid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:16259 )
N-acetylphenylalanine (CHEBI:16259 )
N-acyl-L-phenylalanine (CHEBI:16259 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	N-Acetyl-L-phenylalanine, 2 TMS, GC-MS Spectrum	splash10-00kf-3980000000-205dc96635b498baa46c	Spectrum
GC-MS	N-Acetyl-L-phenylalanine, 1 TMS, GC-MS Spectrum	splash10-00dl-3920000000-50af7cdc34df34b89e91	Spectrum
GC-MS	N-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrum	splash10-00kf-3980000000-205dc96635b498baa46c	Spectrum
GC-MS	N-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrum	splash10-00dl-3920000000-50af7cdc34df34b89e91	Spectrum
GC-MS	N-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrum	splash10-0fr7-1950000000-8c9c63efeb473bcf7625	Spectrum
GC-MS	N-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrum	splash10-00dl-2920000000-f0ce2160cf1eb9d38d56	Spectrum
GC-MS	N-Acetyl-L-phenylalanine, non-derivatized, GC-MS Spectrum	splash10-0f6x-2910000000-33afe725162942dc296a	Spectrum
Predicted GC-MS	N-Acetyl-L-phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9400000000-2c91eb9a78faef00e1da	Spectrum
Predicted GC-MS	N-Acetyl-L-phenylalanine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9110000000-e910d5b4824d2e88d697	Spectrum
Predicted GC-MS	N-Acetyl-L-phenylalanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-L-phenylalanine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-L-phenylalanine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Acetyl-L-phenylalanine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-9e69c187ac8560365826	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-0900000000-04559809a9c6261f18b6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ufr-5900000000-a8bb0fc573e6143527aa	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-0090000000-2dcdf0ed503251026e40	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-2920000000-7447f1e30d868cae5af6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0lxy-8900000000-3b53da8f8106adfdd677	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0pbc-9400000000-1737db9a05bf29f3701a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4l-9100000000-f015dd2066ebbefec15a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0a4l-1960000000-20faf15c3d02bbe80ad2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-0900000000-891ecddb54dab32f4dce	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-1900000000-6867cba730dee8712265	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-2900000000-2e77f5a51bec17ed674e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0udi-4900000000-c9aadc8231b14121aa8c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-02tc-0900000000-ac3b438665d0b035a7e2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0900000000-a426a7fbff06e9213f59	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0900000000-0d8dd7876525745785ff	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0fdo-6900000000-ad4d31f8b5e3e0474416	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0090000000-2dcdf0ed503251026e40	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-2920000000-7447f1e30d868cae5af6	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0btc-2950000000-2865ae294df6193f5a75	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-044l-2900000000-1b1f3d364775a1619b26	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-9bb5ea6eb4c3ab49ee32	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2890000000-293238d6264d01ab86c4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0900-5910000000-b912a04d31d0b03a8552	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9200000000-1b69d466f84616cfe628	2016-09-12	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		Spectrum