NP-MRD: Showing NP-Card for Glutarylglycine (NP0001328)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:22:34 UTC

NP-MRD ID

NP0001328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glutarylglycine

Description

Glutarylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) Which is an enzyme that catalyzes the chemical reaction:. Acyl-CoA + glycine < -- > CoA + N-acylglycine. Glutarylglycine is involved in lysine metabolism. An elevated level of glutarylglycine occurs in patients with glutaric acidemia type II, which is an autosomal recessive inborn error of metabolism due to a mitochondrial respiratory electron chain transport defect. (Http://Www.Pediatricneuro.Com/alfonso/pg75.Htm).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.949  -8.916   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.282  -8.146   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.616  -8.916   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.950  -8.146   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.283  -8.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.617  -8.146   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.951  -8.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.284  -8.146   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.950  -6.606   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.949 -10.456   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.615  -8.146   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      13.284  -6.606   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      14.618  -8.916   0.000  0.00  0.00           O+0
CONECT    1    2   10   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   12   13                                                  
CONECT    9    4                                                            
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
5-[(Carboxymethyl)amino]-5-oxo-pentanoate	HMDB
5-[(Carboxymethyl)amino]-5-oxo-pentanoic acid	HMDB
N-(Carboxymethyl)-glutaramic acid	HMDB
4-[(Carboxymethyl)-C-hydroxycarbonimidoyl]butanoate	HMDB

Chemical Formula

C₇H₁₁NO₅

Average Mass

189.1659 Da

Monoisotopic Mass

189.06372 Da

IUPAC Name

4-[(carboxymethyl)carbamoyl]butanoic acid

Traditional Name

4-(carboxymethylcarbamoyl)butanoic acid

CAS Registry Number

17686-38-3

SMILES

OC(=O)CCCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C7H11NO5/c9-5(8-4-7(12)13)2-1-3-6(10)11/h1-4H2,(H,8,9)(H,10,11)(H,12,13)

InChI Key

NBLKTRLPZFCMJG-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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	¹³C NMR Spectrum (1D, 252 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	¹³C NMR Spectrum (1D, 75 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	¹³C NMR Spectrum (1D, 126 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	¹³C NMR Spectrum (1D, 176 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	¹³C NMR Spectrum (1D, 226 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 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
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Fatty acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

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
Water Solubility	12.4 g/L	ALOGPS
logP	-0.82	ALOGPS
logP	-1.1	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	40.94 m³·mol⁻¹	ChemAxon
Polarizability	17.68 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

HMDB0000590

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022131

KNApSAcK ID

Not Available

Chemspider ID

19712034

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5569

PubChem Compound

23592950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ohie T, Fu X, Iga M, Kimura M, Yamaguchi S: Gas chromatography-mass spectrometry with tert.-butyldimethylsilyl derivation: use of the simplified sample preparations and the automated data system to screen for organic acidemias. J Chromatogr B Biomed Sci Appl. 2000 Sep 1;746(1):63-73. [PubMed:11048741 ]
Gron I, Gregersen N, Kolvraa S, Rasmussen K: Formation of N-dicarboxyl-mono-glycines catalyzed by glycine-N-acylase. Biochem Med. 1978 Feb;19(1):133-48. [PubMed:623642 ]
Gregersen N, Kolvraa S, Rasmussen K, Gron I: Demonstration of N-dicarboxyl-mono-glycines in dicarboxylic acidurias by mass fragmentography. Clin Chim Acta. 1977 Jul 15;78(2):173-82. [PubMed:884855 ]
Bonafe L, Troxler H, Kuster T, Heizmann CW, Chamoles NA, Burlina AB, Blau N: Evaluation of urinary acylglycines by electrospray tandem mass spectrometry in mitochondrial energy metabolism defects and organic acidurias. Mol Genet Metab. 2000 Apr;69(4):302-11. [PubMed:10870848 ]
Gregersen N, Gron I, Rasmussen K, Kolvraa S: Gas chromatographic mass spectrometric identification of N-dicarboxylmonoglycines. Biomed Mass Spectrom. 1978 Jan;5(1):80-3. [PubMed:623898 ]
(). Asai, Kiyofumi. Urinary glutarylglycine in a patient with glutaric aciduria type I. Quantification of urinary glutarylglycine by a carboxylic acid analyzer and its clinical application. Nagoya-shiritsu Daigaku Igakkai Zasshi (1989), 40(4), 743-58. .
(). Curtius, T., Hechtenberg, Wihelm. Synthesis of -aminobutyric acid from glutarylglycine ester. Journal fuer Praktische Chemie (Leipzig) (1923), 105 319-26. .
(). Fujita, A. Synthesis of anemoninic acid. Yakugaku Zasshi (1923), No. 492 67-75. .
(). Paul, L., Dittmar, A., Rusch, Christel. Synthesis of maleoyl- and glutarylglycyl chlorides. Chemische Berichte (1967), 100(8), 2757-60. .

Showing NP-Card for Glutarylglycine (NP0001328)

MOL for NP0001328 (Glutarylglycine)

3D MOL for NP0001328 (Glutarylglycine)

3D SDF for NP0001328 (Glutarylglycine)

3D-SDF for NP0001328 (Glutarylglycine)

PDB for NP0001328 (Glutarylglycine)

3D PDB for NP0001328 (Glutarylglycine)

SMILES for NP0001328 (Glutarylglycine)

INCHI for NP0001328 (Glutarylglycine)

Structure for NP0001328 (Glutarylglycine)

3D Structure for NP0001328 (Glutarylglycine)