NP-MRD: Showing NP-Card for Isovalerylglycine (NP0001489)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-03 04:19:10 UTC

NP-MRD ID

NP0001489

Natural Product DOI

https://doi.org/10.57994/1654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isovalerylglycine

Description

Isovalerylglycine (IVG) 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. Isovalerylglycine is a byproduct of the catabolism of the aminoacid leucine. Accumulation of isovalerylglycine occurs in Isovaleric Acidemia (IVA). IVA (OMIM/ McKusick 243500) is an autosomal recessive disorder caused by mutations in the isovaleryl-CoA dehydrogenase (EC 1.3.99.10) Gene. The deficiency of this enzyme in the metabolism of leucine leads to the accumulation of a series of isovaleryl-CoA metabolites, such as isovalerylglycine. It is very important to caution for false positive results when screening for isovaleric acidemia by tandem mass spectrometry based on dried blood-spot levels of C5-acylcarnitines, including isovalerylcarnitine and its isomer, pivaloylcarnitine; pivaloylcarnitine is derived from pivalate-generating antibiotics, and has caused many false-positive results (PMID: 17850781 ). Isovalerylglycine is a biomarker for the consumption of cheese.

Structure

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


  Mrv1652307272003222D          

 24 23  0  0  0  0            999 V2000
    0.3316    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1047    0.6917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8453    0.6917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9887    2.5787    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2482    2.5787    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2609    1.0446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8724    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2609    2.6383    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -0.2211    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    0.6039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001489

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])N([H])C(=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO3/c1-5(2)3-6(9)8-4-7(10)11/h5H,3-4H2,1-2H3,(H,8,9)(H,10,11)

> <INCHI_KEY>
ZRQXMKMBBMNNQC-UHFFFAOYSA-N

> <FORMULA>
C7H13NO3

> <MOLECULAR_WEIGHT>
159.183

> <EXACT_MASS>
159.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.39546018458692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-methylbutanamido)acetic acid

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.10349465433333323

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.905941443928317

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.166378508060191

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7399347523033928

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
39.2237

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isovalerylglycine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-JUL-20         0                                  
HETATM    1  H   UNK     0       0.619   3.437   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0       1.953   2.667   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.286   4.977   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       3.929   1.291   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0       5.311   1.291   0.000  0.00  0.00           H+0
HETATM    8  N   UNK     0       5.954   3.437   0.000  0.00  0.00           N+0
HETATM    9  H   UNK     0       5.954   4.977   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       9.312   4.814   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       7.930   4.814   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       9.955   4.207   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      11.288   3.437   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      11.687   1.950   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      12.828   3.437   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0      11.687   4.925   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       9.955   1.127   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       8.415   1.127   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       9.955  -0.413   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      11.495   1.127   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21   15   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

View in JSmol

Synonyms

Value	Source
2-(3-Methylbutanoylamino)ethanoic acid	ChEBI
Isopentanoylglycine	ChEBI
N-Isopentanoylglycine	ChEBI
N-Isovaleroylglycine	ChEBI
2-(3-Methylbutanoylamino)ethanoate	Generator
3-Methylbutyrylglycine	HMDB
N-Isovaleryl-glycine	HMDB
[(3-Methylbutanoyl)amino]acetate	HMDB
[(3-Methylbutanoyl)amino]acetic acid	HMDB
N-Isovalerylglycine	HMDB
Isovalerylglycine	ChEBI

Chemical Formula

C₇H₁₃NO₃

Average Mass

159.1830 Da

Monoisotopic Mass

159.08954 Da

IUPAC Name

2-(3-methylbutanamido)acetic acid

Traditional Name

isovalerylglycine

CAS Registry Number

16284-60-9

SMILES

[H]OC(=O)C([H])([H])N([H])C(=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C7H13NO3/c1-5(2)3-6(9)8-4-7(10)11/h5H,3-4H2,1-2H3,(H,8,9)(H,10,11)

InChI Key

ZRQXMKMBBMNNQC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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

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

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

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
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
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

N-acylglycine (CHEBI:70984 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	87 - 90 °C	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	6.5 g/L	ALOGPS
logP	0.35	ALOGPS
logP	0.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	39.22 m³·mol⁻¹	ChemAxon
Polarizability	16.4 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

HMDB0000678

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022177

KNApSAcK ID

C00052329

Chemspider ID

475516

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5647

PubChem Compound

546304

PDB ID

Not Available

ChEBI ID

70984

Good Scents ID

Not Available

References

General References

Fries MH, Rinaldo P, Schmidt-Sommerfeld E, Jurecki E, Packman S: Isovaleric acidemia: response to a leucine load after three weeks of supplementation with glycine, L-carnitine, and combined glycine-carnitine therapy. J Pediatr. 1996 Sep;129(3):449-52. [PubMed:8804338 ]
Goodman SI, McCabe ER, Fennessey PV, Mace JW: Multiple acyl-CoA dehydrogenase deficiency (glutaric aciduria type II) with transient hypersarcosinemia and sarcosinuria; possible inherited deficiency of an electron transfer flavoprotein. Pediatr Res. 1980 Jan;14(1):12-7. [PubMed:7360517 ]
Hine DG, Hack AM, Goodman SI, Tanaka K: Stable isotope dilution analysis of isovalerylglycine in amniotic fluid and urine and its application for the prenatal diagnosis of isovaleric acidemia. Pediatr Res. 1986 Mar;20(3):222-6. [PubMed:3703611 ]
Shigematsu Y, Hata I, Tanaka Y: Stable-isotope dilution measurement of isovalerylglycine by tandem mass spectrometry in newborn screening for isovaleric acidemia. Clin Chim Acta. 2007 Nov-Dec;386(1-2):82-6. Epub 2007 Aug 19. [PubMed:17850781 ]
Slupsky CM, Cheypesh A, Chao DV, Fu H, Rankin KN, Marrie TJ, Lacy P: Streptococcus pneumoniae and Staphylococcus aureus pneumonia induce distinct metabolic responses. J Proteome Res. 2009 Jun;8(6):3029-36. doi: 10.1021/pr900103y. [PubMed:19368345 ]

Showing NP-Card for Isovalerylglycine (NP0001489)

MOL for NP0001489 (Isovalerylglycine)

3D MOL for NP0001489 (Isovalerylglycine)

3D SDF for NP0001489 (Isovalerylglycine)

3D-SDF for NP0001489 (Isovalerylglycine)

PDB for NP0001489 (Isovalerylglycine)

3D PDB for NP0001489 (Isovalerylglycine)

SMILES for NP0001489 (Isovalerylglycine)

INCHI for NP0001489 (Isovalerylglycine)

Structure for NP0001489 (Isovalerylglycine)

3D Structure for NP0001489 (Isovalerylglycine)