NP-MRD: Showing NP-Card for (2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid (NP0183556)

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Record Information

Version

2.0

Created at

2022-09-03 22:29:17 UTC

Updated at

2022-09-03 22:29:17 UTC

NP-MRD ID

NP0183556

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid

Description

Gamma-Glutamyl-beta-aminopropiononitrile 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. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Gamma-Glutamyl-beta-aminopropiononitrile is a very strong basic compound (based on its pKa). (2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid is found in Apis cerana. Gamma-Glutamyl-beta-aminopropiononitrile exists in all living organisms, ranging from bacteria to humans.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08131209302D          

 15 14  0  0  0  0            999 V2000
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  4  3  0  0  0  0
  6 10  1  1  0  0  0
 11  5  1  4  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
  6 15  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0183556

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](N)(CCC(O)=NCCC#N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H13N3O3/c9-4-1-5-11-7(12)3-2-6(10)8(13)14/h6H,1-3,5,10H2,(H,11,12)(H,13,14)/t6-/m0/s1

> <INCHI_KEY>
VQPVVWAFTIFKDD-LURJTMIESA-N

> <FORMULA>
C8H13N3O3

> <MOLECULAR_WEIGHT>
199.2071

> <EXACT_MASS>
199.095691297

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
20.084176651374424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-[(2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid

> <ALOGPS_LOGP>
-2.44

> <JCHEM_LOGP>
-3.225940732736835

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.1862125812007696

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5023139462839143

> <JCHEM_PKA_STRONGEST_BASIC>
9.538122137864855

> <JCHEM_POLAR_SURFACE_AREA>
119.7

> <JCHEM_REFRACTIVITY>
48.2916

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-[(2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    4    5                                                       
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    1    9                                                       
CONECT    5    1   11                                                       
CONECT    6    2    8   10   15                                             
CONECT    7    3   11   12                                                  
CONECT    8    6   13   14                                                  
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    5    7                                                       
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    6                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
gamma-Glutamyl-3-aminopropiononitrile	ChEBI
g-Glutamyl-3-aminopropiononitrile	Generator
Γ-glutamyl-3-aminopropiononitrile	Generator
g-Glutamyl-b-aminopropiononitrile	Generator
Γ-glutamyl-β-aminopropiononitrile	Generator

Chemical Formula

C₈H₁₃N₃O₃

Average Mass

199.2071 Da

Monoisotopic Mass

199.09569 Da

IUPAC Name

(2S)-2-amino-4-[(2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid

Traditional Name

(2S)-2-amino-4-[(2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CCC(O)=NCCC#N)C(O)=O

InChI Identifier

InChI=1S/C8H13N3O3/c9-4-1-5-11-7(12)3-2-6(10)8(13)14/h6H,1-3,5,10H2,(H,11,12)(H,13,14)/t6-/m0/s1

InChI Key

VQPVVWAFTIFKDD-LURJTMIESA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Apis cerana	LOTUS Database	35616633

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
Alpha-amino acid
L-alpha-amino acid
Fatty amide
Fatty acyl
Fatty acid
N-acyl-amine
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonitrile
Nitrile
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:28092 )
L-glutamine derivative (CHEBI:28092 )
aliphatic nitrile (CHEBI:28092 )
carboxamide (CHEBI:28092 )

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	-2.4	ALOGPS
logP	-3.2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.5	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	48.29 m³·mol⁻¹	ChemAxon
Polarizability	20.08 Å³	ChemAxon
Number of Rings	0	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

HMDB0060477

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

389750

KEGG Compound ID

C06114

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440920

PDB ID

Not Available

ChEBI ID

28092

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid (NP0183556)

MOL for NP0183556 ((2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D MOL for NP0183556 ((2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D SDF for NP0183556 ((2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D-SDF for NP0183556 ((2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

PDB for NP0183556 ((2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D PDB for NP0183556 ((2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

SMILES for NP0183556 ((2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

INCHI for NP0183556 ((2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

Structure for NP0183556 ((2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D Structure for NP0183556 ((2s)-2-amino-4-[(2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)