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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:35 UTC

Update Date

2023-02-21 17:16:08 UTC

HMDB ID

HMDB0002087

Secondary Accession Numbers

HMDB02087

Metabolite Identification

Common Name

Isovalerylsarcosine

Description

Isovalerylsarcosine, also known as isopentanoylsarcosine, 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. Isovalerylsarcosine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make isovalerylsarcosine a potential biomarker for the consumption of these foods. Isovalerylsarcosine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Isovalerylsarcosine.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      30.475 -18.204   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.808 -20.514   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.809 -16.664   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      34.475 -18.974   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      38.476 -18.204   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.142 -18.204   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      37.143 -18.974   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.475 -20.514   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      39.810 -18.974   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.476 -16.664   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.808 -18.974   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.809 -18.204   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    6    8   12                                                  
CONECT    5    7    9   10                                                  
CONECT    6    4   11                                                       
CONECT    7    5   12                                                       
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    1    2    6                                                  
CONECT   12    3    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0002087
HETATM    1  C1  UNL     1       2.268   0.305   1.178  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.174  -0.290  -0.201  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.221   0.193  -1.144  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.771  -0.091  -0.699  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.212  -0.747   0.178  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.247  -1.369   1.198  1.00  0.00           O  
HETATM    7  N1  UNL     1      -1.611  -0.715  -0.062  1.00  0.00           N  
HETATM    8  C6  UNL     1      -2.508  -1.386   0.849  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.144  -0.025  -1.197  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.448   1.388  -0.880  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.923   2.120  -1.779  1.00  0.00           O  
HETATM   12  O3  UNL     1      -2.200   1.856   0.397  1.00  0.00           O  
HETATM   13  H1  UNL     1       2.721  -0.408   1.887  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.295   0.693   1.547  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.935   1.210   1.082  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.315  -1.404  -0.095  1.00  0.00           H  
HETATM   17  H5  UNL     1       4.084  -0.511  -1.197  1.00  0.00           H  
HETATM   18  H6  UNL     1       3.633   1.152  -0.721  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.862   0.345  -2.178  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.521   1.007  -0.749  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.652  -0.441  -1.761  1.00  0.00           H  
HETATM   22  H10 UNL     1      -3.206  -0.679   1.351  1.00  0.00           H  
HETATM   23  H11 UNL     1      -3.044  -2.165   0.265  1.00  0.00           H  
HETATM   24  H12 UNL     1      -1.932  -1.946   1.639  1.00  0.00           H  
HETATM   25  H13 UNL     1      -1.460  -0.126  -2.064  1.00  0.00           H  
HETATM   26  H14 UNL     1      -3.119  -0.473  -1.552  1.00  0.00           H  
HETATM   27  H15 UNL     1      -2.892   2.508   0.790  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5   20   21
CONECT    5    6    6    7
CONECT    7    8    9
CONECT    8   22   23   24
CONECT    9   10   25   26
CONECT   10   11   11   12
CONECT   12   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3-Methylbutanoyl)sarcosine	ChEBI
Isopentanoylsarcosine	ChEBI
N-(3-Methylbutanoyl)sarcosine	ChEBI
N-Isopentanoylsarcosine	ChEBI
N-Isovalerylsarcosine	HMDB
Isovalerylsarcosine	ChEBI

Chemical Formula

C₈H₁₅NO₃

Average Molecular Weight

173.2096

Monoisotopic Molecular Weight

173.105193351

IUPAC Name

2-(N,3-dimethylbutanamido)acetic acid

Traditional Name

isovalerylsarcosine

CAS Registry Number

88127-29-1

SMILES

CC(C)CC(=O)N(C)CC(O)=O

InChI Identifier

InChI=1S/C8H15NO3/c1-6(2)4-7(10)9(3)5-8(11)12/h6H,4-5H2,1-3H3,(H,11,12)

InChI Key

GPFSWCRCPHKNBU-UHFFFAOYSA-N

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
N-acyl-amine
Tertiary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0002087)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	27.3 g/L	ALOGPS
logP	0.44	ALOGPS
logP	0.33	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-0.86	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	44.12 m³·mol⁻¹	ChemAxon
Polarizability	17.99 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	141.118	31661259
DarkChem	[M-H]-	137.089	31661259
DeepCCS	[M+H]+	141.938	30932474
DeepCCS	[M-H]-	138.106	30932474
DeepCCS	[M-2H]-	175.484	30932474
DeepCCS	[M+Na]+	151.149	30932474
AllCCS	[M+H]+	140.0	32859911
AllCCS	[M+H-H2O]+	136.3	32859911
AllCCS	[M+NH4]+	143.5	32859911
AllCCS	[M+Na]+	144.5	32859911
AllCCS	[M-H]-	139.5	32859911
AllCCS	[M+Na-2H]-	141.3	32859911
AllCCS	[M+HCOO]-	143.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isovalerylsarcosine	CC(C)CC(=O)N(C)CC(O)=O	2194.8	Standard polar	33892256
Isovalerylsarcosine	CC(C)CC(=O)N(C)CC(O)=O	1348.5	Standard non polar	33892256
Isovalerylsarcosine	CC(C)CC(=O)N(C)CC(O)=O	1478.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isovalerylsarcosine,1TMS,isomer #1	CC(C)CC(=O)N(C)CC(=O)O[Si](C)(C)C	1507.0	Semi standard non polar	33892256
Isovalerylsarcosine,1TBDMS,isomer #1	CC(C)CC(=O)N(C)CC(=O)O[Si](C)(C)C(C)(C)C	1731.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylsarcosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ko-9300000000-2abc21fb95df3a641d0e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylsarcosine GC-MS (1 TMS) - 70eV, Positive	splash10-009x-9400000000-b98179bb7f0f3cb48e4d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylsarcosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylsarcosine 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 - Isovalerylsarcosine 10V, Positive-QTOF	splash10-00di-3900000000-85c8cc39698d110da0e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 20V, Positive-QTOF	splash10-0abc-9200000000-40284d92db56052815df	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 40V, Positive-QTOF	splash10-0abc-9000000000-159245318505250d21d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 10V, Negative-QTOF	splash10-00di-0900000000-fad5216b8aa9f3c43d11	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 20V, Negative-QTOF	splash10-00fr-3900000000-e6139a170ba4f2357343	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 40V, Negative-QTOF	splash10-0ab9-9100000000-3d231daac696c7d359e4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 10V, Positive-QTOF	splash10-0076-9300000000-8964b1f70135ed68fdc6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 20V, Positive-QTOF	splash10-000f-9000000000-00a8e4564652edf79ac0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 40V, Positive-QTOF	splash10-0006-9000000000-edab2fb03e52cd059c83	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 10V, Negative-QTOF	splash10-000i-9800000000-d34b4159870ef87bbb9a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 20V, Negative-QTOF	splash10-000i-9200000000-6a3d39369964ccb1cabc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylsarcosine 40V, Negative-QTOF	splash10-00xu-9000000000-dfeb4f4e642a861556ce	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

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

FDB022838

KNApSAcK ID

Not Available

Chemspider ID

121068

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6480

PubChem Compound

137394

PDB ID

Not Available

ChEBI ID

136917

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lehnert W: N-Isovalerylalanine and N-isovalerylsarcosine: two new minor metabolites in isovaleric acidemia. Clin Chim Acta. 1983 Oct 31;134(1-2):207-12. [PubMed:6197208 ]

Enzymes

Enzyme Details

1. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

References

Lehnert W: N-Isovalerylalanine and N-isovalerylsarcosine: two new minor metabolites in isovaleric acidemia. Clin Chim Acta. 1983 Oct 31;134(1-2):207-12. [PubMed:6197208 ]

Showing metabocard for Isovalerylsarcosine (HMDB0002087)

MOL for HMDB0002087 (Isovalerylsarcosine)

3D MOL for HMDB0002087 (Isovalerylsarcosine)

3D SDF for HMDB0002087 (Isovalerylsarcosine)

3D-SDF for HMDB0002087 (Isovalerylsarcosine)

PDB for HMDB0002087 (Isovalerylsarcosine)

3D PDB for HMDB0002087 (Isovalerylsarcosine)

SMILES for HMDB0002087 (Isovalerylsarcosine)

INCHI for HMDB0002087 (Isovalerylsarcosine)

Structure for HMDB0002087 (Isovalerylsarcosine)

3D Structure for HMDB0002087 (Isovalerylsarcosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References