NP-MRD: Showing NP-Card for Phenylacetylglutamine (NP0083595)

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Record Information

Version

1.0

Created at

2022-04-29 04:35:21 UTC

Updated at

2022-04-29 04:35:21 UTC

NP-MRD ID

NP0083595

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenylacetylglutamine

Description

Phenylacetylglutamine belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Phenylacetylglutamine is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylacetylglutamine can be biosynthesized from phenylacetyl-CoA and L-glutamine; which is catalyzed by the enzyme glycine N-acyltransferase. An a N(2)-phenylacetylglutamine having L-configuration. Phenylacetylglutamine is found in Homo sapiens (Urine). It was first documented in 1983 (PMID: 6420430). In humans, phenylacetylglutamine is involved in phenylacetate metabolism (PMID: 22770225) (PMID: 32033212) (PMID: 2791363) (PMID: 8972626) (PMID: 26241311) (PMID: 14709615).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -5.1523    1.9609    0.5127 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8431    1.5019    0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0022    2.2490    1.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4838    0.0937    0.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0433   -0.1313    0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -1.5355    0.5011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1763   -1.6168    0.9319 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223   -0.8275    0.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5494   -0.0152   -0.5637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2283   -0.9584    0.8459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -0.0201    0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    1.2536    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0223    2.1263   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6070    1.7113   -1.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4198    0.4277   -1.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6404   -0.4576   -1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340   -1.8665   -0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5716   -2.1527   -1.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7890   -1.9030   -1.6902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2985    2.9867    0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9246    1.2808    0.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056   -0.0105   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1321   -0.6063    0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931    0.0400    1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4598    0.6529    0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449   -2.2518    1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0903   -2.2929    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960   -1.9800    0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556   -0.7444    1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942    1.6287    1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595    3.1338    0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2133    2.3813   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8985    0.1383   -2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5104   -1.4544   -1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2981   -2.7419   -1.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 19  1  0
 17 18  2  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  1
  7 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 19 35  1  0
M  END

      
  Mrv1652305301819242D          

 19 19  0  0  0  0            999 V2000
10001.922210001.1927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.207410001.6046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.493310001.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.779310001.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.493310000.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.634810001.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.349810001.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.062610001.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.777510001.1927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.062610002.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.922210000.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6348 9999.9557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2074 9999.9557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.065510001.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.350910001.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.636310001.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.636310000.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3509 9999.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.065610000.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 11  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
  4 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083595

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1

> <INCHI_KEY>
JFLIEFSWGNOPJJ-JTQLQIEISA-N

> <FORMULA>
C13H16N2O4

> <MOLECULAR_WEIGHT>
264.2771

> <EXACT_MASS>
264.11100701

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.55439529399692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid

> <ALOGPS_LOGP>
-0.35

> <JCHEM_LOGP>
-0.08561821066666678

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.01470691027999

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8975375279453566

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5334406653959398

> <JCHEM_POLAR_SURFACE_AREA>
109.49

> <JCHEM_REFRACTIVITY>
67.27560000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylacetylglutamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAY-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-18         0                                  
HETATM    1  C   UNK     0    8670.2558668.893   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8668.9208669.662   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8667.5878668.893   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.2558669.662   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8667.5878667.355   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8671.5858669.662   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8672.9208668.893   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8674.2508669.662   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8675.5858668.893   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0    8674.2508671.200   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8670.2558667.355   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8671.5858666.584   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8668.9208666.584   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8664.9228668.894   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.5888669.664   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.2548668.894   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.2548667.354   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.5888666.584   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.9228667.354   0.000  0.00  0.00           C+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3   14                                                       
CONECT    5    3                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   15   19    4                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
alpha-N-Phenylacetyl-L-glutamine	ChEBI
Phenylacetyl-L-glutamine	ChEBI
N2-(2-Phenylacetyl)-L-glutamine	Kegg
a-N-Phenylacetyl-L-glutamine	Generator
Α-N-phenylacetyl-L-glutamine	Generator
N(2)-(Phenylacetyl)-L-glutamine	HMDB
N(2)-(2-Phenylacetyl)-L-glutamine	HMDB
N-Phenylacetylglutamine	HMDB
N2-(Phenylacetyl)-L-glutamine	HMDB
Α-N-phenylacetylglutamine	HMDB
alpha-N-Phenylacetylglutamine	HMDB
Phenylacetylglutamine	ChEBI

Chemical Formula

C₁₃H₁₆N₂O₄

Average Mass

264.2771 Da

Monoisotopic Mass

264.11101 Da

IUPAC Name

(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acid

Traditional Name

phenylacetylglutamine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1

InChI Key

JFLIEFSWGNOPJJ-JTQLQIEISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens (Urine)	Animalia	KNApSAcK
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N(2)-phenylacetylglutamine (CHEBI:17884 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.35	ALOGPS
logP	-0.086	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.9	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.49 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	67.28 m³·mol⁻¹	ChemAxon
Polarizability	26.55 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

External Links

HMDB ID

HMDB0006344

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023896

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Phenylacetylglutamine

METLIN ID

Not Available

PubChem Compound

92258

PDB ID

Not Available

ChEBI ID

17884

Good Scents ID

Not Available

References

General References

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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Showing NP-Card for Phenylacetylglutamine (NP0083595)

MOL for NP0083595 (Phenylacetylglutamine)

3D MOL for NP0083595 (Phenylacetylglutamine)

3D SDF for NP0083595 (Phenylacetylglutamine)

3D-SDF for NP0083595 (Phenylacetylglutamine)

PDB for NP0083595 (Phenylacetylglutamine)

3D PDB for NP0083595 (Phenylacetylglutamine)

SMILES for NP0083595 (Phenylacetylglutamine)

INCHI for NP0083595 (Phenylacetylglutamine)

Structure for NP0083595 (Phenylacetylglutamine)

3D Structure for NP0083595 (Phenylacetylglutamine)