NP-MRD: Showing NP-Card for gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine (NP0334052)

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Record Information

Version

2.0

Created at

2024-09-09 21:50:15 UTC

Updated at

2024-09-09 21:50:16 UTC

NP-MRD ID

NP0334052

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine

Description

Constituent of Lens culinaris (lentil). Gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine is found in pulses.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920442D          

 23 23  0  0  1  0            999 V2000
    4.9820   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2676   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1980   -2.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6090   -2.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6965   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1242   -1.7309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5531   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6105   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4110   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1242   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6965   -0.4934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8386   -1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952   -1.7309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5531   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4310   -1.9222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1255   -1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4110   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8386   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -1.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6965   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  6  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
  7 13  1  1  0  0  0
 13  8  2  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
  8 15  1  4  0  0  0
 16  9  2  0  0  0  0
 17 10  2  0  0  0  0
 18 10  1  0  0  0  0
 19 11  2  0  0  0  0
 20 11  1  0  0  0  0
 21  9  1  0  0  0  0
 21 14  1  0  0  0  0
 22  6  1  0  0  0  0
  7 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334052

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(N)(CCC(O)=N[C@@]([H])(CN1OC(=O)C=C1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N3O7/c12-6(10(17)18)1-2-8(15)13-7(11(19)20)5-14-4-3-9(16)21-14/h3-4,6-7H,1-2,5,12H2,(H,13,15)(H,17,18)(H,19,20)/t6?,7-/m0/s1

> <INCHI_KEY>
XXZPYJHULCBZPT-MLWJPKLSSA-N

> <FORMULA>
C11H15N3O7

> <MOLECULAR_WEIGHT>
301.2527

> <EXACT_MASS>
301.090999849

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.421192394397373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-{[(1S)-1-carboxy-2-(5-oxo-2,5-dihydro-1,2-oxazol-2-yl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <ALOGPS_LOGP>
-3.13

> <JCHEM_LOGP>
-3.6838990710019126

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.6148208047698556

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6920167176402678

> <JCHEM_PKA_STRONGEST_BASIC>
9.536116958372443

> <JCHEM_POLAR_SURFACE_AREA>
162.74999999999997

> <JCHEM_REFRACTIVITY>
66.36280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-{[(1S)-1-carboxy-2-(5-oxo-1,2-oxazol-2-yl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       9.300  -3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.966  -2.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.370  -5.083   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.137  -4.763   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.631  -2.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.633  -2.461   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.965  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.632  -3.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.140  -3.749   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.967  -3.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.965  -4.771   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      10.633  -0.921   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       5.299  -2.461   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       1.298  -3.231   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       6.632  -4.771   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.671  -3.588   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      13.301  -2.461   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      11.967  -4.771   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.299  -5.541   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.631  -5.541   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.109  -2.605   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      10.633  -4.001   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.631  -4.001   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    8                                                       
CONECT    3    4    9                                                       
CONECT    4    3   14                                                       
CONECT    5    7   14                                                       
CONECT    6    1   10   12   22                                             
CONECT    7    5   11   13   23                                             
CONECT    8    2   13   15                                                  
CONECT    9    3   16   21                                                  
CONECT   10    6   17   18                                                  
CONECT   11    7   19   20                                                  
CONECT   12    6                                                            
CONECT   13    7    8                                                       
CONECT   14    4    5   21                                                  
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   11                                                            
CONECT   21    9   14                                                       
CONECT   22    6                                                            
CONECT   23    7                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
g-Glutamyl-b-(isoxazolin-5-on-2-yl)alanine	Generator
Γ-glutamyl-β-(isoxazolin-5-on-2-yl)alanine	Generator

Chemical Formula

C₁₁H₁₅N₃O₇

Average Mass

301.2527 Da

Monoisotopic Mass

301.09100 Da

IUPAC Name

2-amino-4-{[(1S)-1-carboxy-2-(5-oxo-2,5-dihydro-1,2-oxazol-2-yl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid

Traditional Name

2-amino-4-{[(1S)-1-carboxy-2-(5-oxo-1,2-oxazol-2-yl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

[H]C(N)(CCC(O)=N[C@@]([H])(CN1OC(=O)C=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H15N3O7/c12-6(10(17)18)1-2-8(15)13-7(11(19)20)5-14-4-3-9(16)21-14/h3-4,6-7H,1-2,5,12H2,(H,13,15)(H,17,18)(H,19,20)/t6?,7-/m0/s1

InChI Key

XXZPYJHULCBZPT-MLWJPKLSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Alpha-amino acid
Fatty acyl
N-acyl-amine
Fatty amide
Dicarboxylic acid or derivatives
Heteroaromatic compound
Vinylogous amide
Isoxazole
Azole
Amino acid
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-3.1	ALOGPS
logP	-3.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.69	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	162.75 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	66.36 m³·mol⁻¹	ChemAxon
Polarizability	27.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020281

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine (NP0334052)

MOL for NP0334052 (gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine)

3D MOL for NP0334052 (gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine)

3D SDF for NP0334052 (gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine)

3D-SDF for NP0334052 (gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine)

PDB for NP0334052 (gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine)

3D PDB for NP0334052 (gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine)

SMILES for NP0334052 (gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine)

INCHI for NP0334052 (gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine)

Structure for NP0334052 (gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine)

3D Structure for NP0334052 (gamma-Glutamyl-beta-(isoxazolin-5-on-2-yl)alanine)