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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:23:38 UTC

Update Date

2022-03-07 03:17:45 UTC

HMDB ID

HMDB0060477

Secondary Accession Numbers

HMDB60477

Metabolite Identification

Common Name

gamma-Glutamyl-beta-aminopropiononitrile

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). gamma-Glutamyl-beta-aminopropiononitrile exists in all living organisms, ranging from bacteria to humans.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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>
HMDB0060477

> <DATABASE_NAME>
hmdb

> <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

COMPND    HMDB0060477
HETATM    1  N1  UNL     1       2.486   2.055   1.948  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.086   1.313   1.277  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.852   0.394   0.457  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.968  -0.157  -0.669  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.851  -0.846  -0.074  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.682  -0.338   0.136  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.514   0.972  -0.250  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.349  -1.175   0.753  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.537  -1.508  -0.051  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.401  -0.418  -0.548  1.00  0.00           C  
HETATM   11  N3  UNL     1      -1.813   0.547  -1.411  1.00  0.00           N  
HETATM   12  C8  UNL     1      -3.157   0.273   0.525  1.00  0.00           C  
HETATM   13  O2  UNL     1      -3.752  -0.386   1.391  1.00  0.00           O  
HETATM   14  O3  UNL     1      -3.197   1.645   0.555  1.00  0.00           O  
HETATM   15  H1  UNL     1       4.684   0.953  -0.015  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.252  -0.437   1.057  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.575  -0.850  -1.315  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.656   0.661  -1.317  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.807   1.415  -1.082  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.132  -2.162   1.025  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.637  -0.774   1.778  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.208  -2.213  -0.865  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.192  -2.161   0.602  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.210  -0.926  -1.168  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.026   0.383  -2.433  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.022   1.537  -1.153  1.00  0.00           H  
HETATM   27  H13 UNL     1      -4.045   2.203   0.519  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6    6
CONECT    6    7    8
CONECT    7   19
CONECT    8    9   20   21
CONECT    9   10   22   23
CONECT   10   11   12   24
CONECT   11   25   26
CONECT   12   13   13   14
CONECT   14   27
END

View in JSmol View NMR Assignments View Stereo Labels

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 Molecular Weight

199.2071

Monoisotopic Molecular Weight

199.095691297

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

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 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060477)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.8 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	146.214	31661259
DarkChem	[M-H]-	145.211	31661259
DeepCCS	[M+H]+	141.395	30932474
DeepCCS	[M-H]-	138.999	30932474
DeepCCS	[M-2H]-	174.476	30932474
DeepCCS	[M+Na]+	148.956	30932474
AllCCS	[M+H]+	143.5	32859911
AllCCS	[M+H-H2O]+	139.9	32859911
AllCCS	[M+NH4]+	146.7	32859911
AllCCS	[M+Na]+	147.7	32859911
AllCCS	[M-H]-	143.8	32859911
AllCCS	[M+Na-2H]-	144.8	32859911
AllCCS	[M+HCOO]-	146.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.21 minutes	32390414
Predicted by Siyang on May 30, 2022	8.7419 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	384.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	253.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	55.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	48.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	275.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	234.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	771.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	549.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	39.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	619.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	181.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	694.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	515.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	359.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamyl-beta-aminopropiononitrile	[H][C@](N)(CCC(O)=NCCC#N)C(O)=O	2440.1	Standard polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile	[H][C@](N)(CCC(O)=NCCC#N)C(O)=O	2038.1	Standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile	[H][C@](N)(CCC(O)=NCCC#N)C(O)=O	2248.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Glutamyl-beta-aminopropiononitrile,1TMS,isomer #1	C[Si](C)(C)OC(CC[C@H](N)C(=O)O)=NCCC#N	2072.3	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CCC(O)=NCCC#N	2018.0	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(O)=NCCC#N)C(=O)O	2104.9	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=NCCC#N)O[Si](C)(C)C	1995.7	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=NCCC#N)O[Si](C)(C)C)C(=O)O	2116.7	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(O)=NCCC#N)C(=O)O[Si](C)(C)C	2075.1	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CCC(O)=NCCC#N)C(=O)O)[Si](C)(C)C	2214.9	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=NCCC#N)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2072.5	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=NCCC#N)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2068.1	Standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=NCCC#N)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2769.2	Standard polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TMS,isomer #2	C[Si](C)(C)OC(CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=NCCC#N	2206.1	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TMS,isomer #2	C[Si](C)(C)OC(CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=NCCC#N	2143.0	Standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TMS,isomer #2	C[Si](C)(C)OC(CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=NCCC#N	2903.4	Standard polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC(O)=NCCC#N)N([Si](C)(C)C)[Si](C)(C)C	2174.2	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC(O)=NCCC#N)N([Si](C)(C)C)[Si](C)(C)C	2106.5	Standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC(O)=NCCC#N)N([Si](C)(C)C)[Si](C)(C)C	2969.6	Standard polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC(=NCCC#N)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2183.3	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC(=NCCC#N)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2174.5	Standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC(=NCCC#N)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2570.9	Standard polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CC[C@H](N)C(=O)O)=NCCC#N	2279.8	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(O)=NCCC#N	2213.8	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(O)=NCCC#N)C(=O)O	2308.6	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=NCCC#N)O[Si](C)(C)C(C)(C)C	2357.4	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=NCCC#N)O[Si](C)(C)C(C)(C)C)C(=O)O	2497.5	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(O)=NCCC#N)C(=O)O[Si](C)(C)C(C)(C)C	2455.8	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CCC(O)=NCCC#N)C(=O)O)[Si](C)(C)C(C)(C)C	2611.3	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=NCCC#N)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2608.2	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=NCCC#N)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2618.5	Standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=NCCC#N)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2905.9	Standard polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NCCC#N	2801.5	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NCCC#N	2682.7	Standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NCCC#N	2973.1	Standard polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(O)=NCCC#N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2790.4	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(O)=NCCC#N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2739.5	Standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(O)=NCCC#N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3063.3	Standard polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=NCCC#N)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2981.2	Semi standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=NCCC#N)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2859.7	Standard non polar	33892256
gamma-Glutamyl-beta-aminopropiononitrile,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=NCCC#N)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2839.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uec-9200000000-f218d4c91166ca03ce38	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile GC-MS (2 TMS) - 70eV, Positive	splash10-004i-4290000000-3a1d60db995aff45ffa3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 10V, Positive-QTOF	splash10-0gb9-9810000000-a233576842f26de13176	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 20V, Positive-QTOF	splash10-0gb9-9200000000-a6db4bf10b3c15dfd50f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 40V, Positive-QTOF	splash10-0uxr-9000000000-917dcb7053cf2f990749	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 10V, Negative-QTOF	splash10-0002-0900000000-9d0a6c69667f7d6a86fd	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 20V, Negative-QTOF	splash10-00l2-4900000000-e2cc039bb0175e6b7161	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 40V, Negative-QTOF	splash10-0006-9100000000-cc0e7eb8ba343b858c49	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 10V, Positive-QTOF	splash10-0udi-4590000000-0a447d1b6cfc6063f94b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 20V, Positive-QTOF	splash10-000i-9400000000-c22ed552944f5df105f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 40V, Positive-QTOF	splash10-0zg0-9000000000-97712e263528b7044832	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 10V, Negative-QTOF	splash10-001i-1900000000-496e5c0ed03ca00229a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 20V, Negative-QTOF	splash10-00ur-9700000000-d3f6caee9c201874729a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 40V, Negative-QTOF	splash10-00kf-9200000000-b077f442c50f547f7366	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

HC01700

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Gamma-glutamyltranspeptidase 1

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:: GGT1
Uniprot ID:: P19440
Molecular weight:: 61409.67

Reactions

Beta-Aminopropionitrile + Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Water	details

Enzyme Details

2. Gamma-glutamyltransferase 7

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Cleaves glutathione conjugates (By similarity).
Gene Name:: GGT7
Uniprot ID:: Q9UJ14
Molecular weight:: 70466.015

Reactions

Beta-Aminopropionitrile + Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Water	details

Enzyme Details

3. Gamma-glutamyltransferase 6

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Cleaves glutathione conjugates (By similarity).
Gene Name:: GGT6
Uniprot ID:: Q6P531
Molecular weight:: 50508.83

Reactions

Beta-Aminopropionitrile + Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Water	details

Enzyme Details

4. Gamma-glutamyltransferase 5

General function:: Involved in gamma-glutamyltransferase activity
Specific function:: Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:: GGT5
Uniprot ID:: P36269
Molecular weight:: 62331.75

Reactions

Beta-Aminopropionitrile + Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Water	details

Showing metabocard for gamma-Glutamyl-beta-aminopropiononitrile (HMDB0060477)

MOL for HMDB0060477 (gamma-Glutamyl-beta-aminopropiononitrile)

3D MOL for HMDB0060477 (gamma-Glutamyl-beta-aminopropiononitrile)

3D SDF for HMDB0060477 (gamma-Glutamyl-beta-aminopropiononitrile)

3D-SDF for HMDB0060477 (gamma-Glutamyl-beta-aminopropiononitrile)

PDB for HMDB0060477 (gamma-Glutamyl-beta-aminopropiononitrile)

3D PDB for HMDB0060477 (gamma-Glutamyl-beta-aminopropiononitrile)

SMILES for HMDB0060477 (gamma-Glutamyl-beta-aminopropiononitrile)

INCHI for HMDB0060477 (gamma-Glutamyl-beta-aminopropiononitrile)

Structure for HMDB0060477 (gamma-Glutamyl-beta-aminopropiononitrile)

3D Structure for HMDB0060477 (gamma-Glutamyl-beta-aminopropiononitrile)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions