NP-MRD: Showing NP-Card for Phenylbutyrylglutamine (NP0091558)

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Record Information

Version

2.0

Created at

2022-05-11 18:41:17 UTC

Updated at

2022-05-11 18:41:17 UTC

NP-MRD ID

NP0091558

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenylbutyrylglutamine

Description

Phenylbutyrylglutamine belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Phenylbutyrylglutamine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    6.9746    1.0804    0.9524 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5581    1.1468    1.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0191    2.0541    1.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7898    0.0683    0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3458    0.3457    0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -0.6113   -0.0613 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0492   -0.1595    0.2949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0809    0.1994   -0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883    0.1246   -1.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2687    0.6550   -0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504    0.9566   -1.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416    1.4274   -1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2222    0.4473   -0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1500    0.4932    0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8531   -0.3923    1.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6462   -1.3465    1.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7439   -1.4240   -0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0269   -0.5216   -1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5251   -2.0063    0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991   -2.6046    0.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7129   -2.6698    0.1704 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4277    0.1471    0.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5860    1.9147    0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1461   -0.9086    0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0371    0.2025   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1358    0.3583    1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1195    1.3529    0.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355   -0.5988   -1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8108   -0.1039    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8014   -0.0835    0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1274    1.6255    0.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0112    0.1574   -2.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5328    1.8428   -2.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3207    2.3595   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951    1.6904   -2.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306    1.2368    1.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7994   -0.3592    2.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1938   -2.0367    1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3617   -2.1668   -0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0646   -0.5346   -2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -3.3589    0.8482 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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  6 19  1  0
 19 21  1  0
 19 20  2  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  6
  7 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 21 41  1  0
M  END


  Mrv0541 02241201502D          

 21 21  0  0  0  0            999 V2000
    9.9478   -8.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3603   -9.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1228   -8.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9478  -10.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7103   -9.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1228  -10.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3603   -8.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1853   -8.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5978   -7.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4228   -7.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8353   -8.0730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8353   -6.6440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6603   -6.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0728   -7.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0728   -5.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8978   -5.9296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6603   -5.2151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6603   -8.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0728   -8.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6603   -9.5020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8978   -8.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 19  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091558

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)CCC(NC(=O)CCCC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20N2O4/c16-13(18)10-9-12(15(20)21)17-14(19)8-4-7-11-5-2-1-3-6-11/h1-3,5-6,12H,4,7-10H2,(H2,16,18)(H,17,19)(H,20,21)

> <INCHI_KEY>
XKQKXKRCMAJADR-UHFFFAOYSA-N

> <FORMULA>
C15H20N2O4

> <MOLECULAR_WEIGHT>
292.3303

> <EXACT_MASS>
292.142307138

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.50610072212152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-carbamoyl-2-(4-phenylbutanamido)butanoic acid

> <ALOGPS_LOGP>
0.65

> <JCHEM_LOGP>
0.8035191193333332

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.347598251745865

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8746090309136254

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5642088469050045

> <JCHEM_POLAR_SURFACE_AREA>
109.49000000000001

> <JCHEM_REFRACTIVITY>
76.4776

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-carbamoyl-2-(4-phenylbutanamido)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      18.569 -16.403   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.339 -17.737   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.029 -16.403   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.569 -19.071   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.259 -17.737   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.029 -19.071   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.339 -15.070   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.879 -15.070   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.649 -13.736   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.189 -13.736   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      23.959 -15.070   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      23.959 -12.402   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      25.499 -12.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.269 -13.736   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.269 -11.069   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      27.809 -11.069   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      25.499  -9.735   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      25.499 -15.070   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.269 -16.403   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      25.499 -17.737   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      27.809 -16.403   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   14   15   12                                                  
CONECT   14   13   18                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
2-[(1-Hydroxy-4-phenylbutylidene)amino]-4-(C-hydroxycarbonimidoyl)butanoate	HMDB
Phenylbutyrylglutamine	MeSH

Chemical Formula

C₁₅H₂₀N₂O₄

Average Mass

292.3303 Da

Monoisotopic Mass

292.14231 Da

IUPAC Name

4-carbamoyl-2-(4-phenylbutanamido)butanoic acid

Traditional Name

4-carbamoyl-2-(4-phenylbutanamido)butanoic acid

CAS Registry Number

Not Available

SMILES

NC(=O)CCC(NC(=O)CCCC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C15H20N2O4/c16-13(18)10-9-12(15(20)21)17-14(19)8-4-7-11-5-2-1-3-6-11/h1-3,5-6,12H,4,7-10H2,(H2,16,18)(H,17,19)(H,20,21)

InChI Key

XKQKXKRCMAJADR-UHFFFAOYSA-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
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 glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine 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

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Primary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
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

Not Available

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	0.65	ALOGPS
logP	0.8	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-0.56	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	9	ChemAxon
Refractivity	76.48 m³·mol⁻¹	ChemAxon
Polarizability	30.51 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

HMDB0011687

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028374

KNApSAcK ID

Not Available

Chemspider ID

8119529

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9943917

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phenylbutyrylglutamine (NP0091558)

MOL for NP0091558 (Phenylbutyrylglutamine)

3D MOL for NP0091558 (Phenylbutyrylglutamine)

3D SDF for NP0091558 (Phenylbutyrylglutamine)

3D-SDF for NP0091558 (Phenylbutyrylglutamine)

PDB for NP0091558 (Phenylbutyrylglutamine)

3D PDB for NP0091558 (Phenylbutyrylglutamine)

SMILES for NP0091558 (Phenylbutyrylglutamine)

INCHI for NP0091558 (Phenylbutyrylglutamine)

Structure for NP0091558 (Phenylbutyrylglutamine)

3D Structure for NP0091558 (Phenylbutyrylglutamine)