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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

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:04 UTC

HMDB ID

HMDB0000701

Secondary Accession Numbers

HMDB00701

Metabolite Identification

Common Name

Hexanoylglycine

Description

Hexanoylglycine 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-acylglycineHexanoylglycine is a fatty acid metabolite, it appears in the urine of patients with hereditary medium-chain acyl-CoA dehydrogenase (MCAD) deficiency (PMID 2775902 ), which is a genetic disorder.

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Hexanoylglycine.mol                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       4.235   0.667   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.925  -0.667   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.695   0.667   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.005   2.001   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.005  -0.667   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.385  -0.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.385  -2.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.925  -2.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.695  -0.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.235  -0.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.005   0.667   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.385   0.667   0.000  0.00  0.00           O+0
CONECT    1    3    4    5                                                  
CONECT    2    3    6                                                       
CONECT    3    2    1                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    7   12    2                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0000701
HETATM    1  C1  UNL     1      -4.490  -0.443  -0.454  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.053   0.103  -0.505  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.530   0.008   0.894  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.118   0.509   1.063  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.168  -0.277   0.208  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.235   0.193   0.364  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.468   1.139   1.145  1.00  0.00           O  
HETATM    8  N1  UNL     1       2.299  -0.401  -0.346  1.00  0.00           N  
HETATM    9  C7  UNL     1       3.635   0.098  -0.152  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.636  -0.622  -0.960  1.00  0.00           C  
HETATM   11  O2  UNL     1       4.310  -1.565  -1.723  1.00  0.00           O  
HETATM   12  O3  UNL     1       5.975  -0.272  -0.898  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.402  -1.527  -0.380  1.00  0.00           H  
HETATM   14  H2  UNL     1      -5.068  -0.087  -1.329  1.00  0.00           H  
HETATM   15  H3  UNL     1      -4.917  -0.072   0.502  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.451  -0.561  -1.178  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.046   1.134  -0.911  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.639  -1.047   1.219  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.230   0.588   1.549  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.080   1.587   0.803  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.887   0.414   2.152  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.207  -1.354   0.406  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.512  -0.138  -0.859  1.00  0.00           H  
HETATM   24  H12 UNL     1       2.178  -1.195  -1.016  1.00  0.00           H  
HETATM   25  H13 UNL     1       3.878  -0.047   0.935  1.00  0.00           H  
HETATM   26  H14 UNL     1       3.670   1.190  -0.419  1.00  0.00           H  
HETATM   27  H15 UNL     1       6.513  -0.647  -0.109  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6   22   23
CONECT    6    7    7    8
CONECT    8    9   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
Caproylglycine	ChEBI
N-(1-Oxohexyl)glycine	ChEBI
N-Caproylglycine	ChEBI
N-Hexanoyl-glycine	HMDB
N-Hexanoylglycine	HMDB
Hexanoylglycine	ChEBI

Chemical Formula

C₈H₁₅NO₃

Average Molecular Weight

173.2096

Monoisotopic Molecular Weight

173.105193351

IUPAC Name

2-hexanamidoacetic acid

Traditional Name

hexanoylglycine

CAS Registry Number

24003-67-6

SMILES

CCCCCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C8H15NO3/c1-2-3-4-5-7(10)9-6-8(11)12/h2-6H2,1H3,(H,9,10)(H,11,12)

InChI Key

UPCKIPHSXMXJOX-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
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carbonyl group
Organooxygen compound
Organonitrogen 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:64390 )

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000701)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000701)
Feces (PMID: 27543620)

Source

Endogenous

Endogenous (HMDB: HMDB0000701)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Short-Chain Acyl-CoA Dehydrogenase Deficiency (SCAD Deficiency) (HMDB: HMDB0000701)

Role

Biological role

Metabolite (HMDB: HMDB0000701)
Metabolite (HMDB: HMDB0000701)

Industrial application

Pharmaceutical industry

Biomarker

Medium Chain Acyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00000227)
Ethylmalonic encephalopathy (MarkerDB: MDB00000227)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	144.638	30932474
[M-H]-	Not Available	144.638	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000026

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.61 g/L	ALOGPS
logP	0.9	ALOGPS
logP	0.71	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.25	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	6	ChemAxon
Refractivity	43.88 m³·mol⁻¹	ChemAxon
Polarizability	18.75 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]+	140.37	31661259
DarkChem	[M-H]-	137.627	31661259
AllCCS	[M+H]+	140.94	32859911
AllCCS	[M-H]-	140.438	32859911
DeepCCS	[M+H]+	138.718	30932474
DeepCCS	[M-H]-	134.955	30932474
DeepCCS	[M-2H]-	172.303	30932474
DeepCCS	[M+Na]+	147.55	30932474
AllCCS	[M+H]+	140.9	32859911
AllCCS	[M+H-H2O]+	137.1	32859911
AllCCS	[M+NH4]+	144.5	32859911
AllCCS	[M+Na]+	145.5	32859911
AllCCS	[M-H]-	140.4	32859911
AllCCS	[M+Na-2H]-	142.1	32859911
AllCCS	[M+HCOO]-	144.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hexanoylglycine	CCCCCC(=O)NCC(O)=O	2512.4	Standard polar	33892256
Hexanoylglycine	CCCCCC(=O)NCC(O)=O	1457.4	Standard non polar	33892256
Hexanoylglycine	CCCCCC(=O)NCC(O)=O	1626.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hexanoylglycine,1TMS,isomer #1	CCCCCC(=O)NCC(=O)O[Si](C)(C)C	1612.9	Semi standard non polar	33892256
Hexanoylglycine,1TMS,isomer #2	CCCCCC(=O)N(CC(=O)O)[Si](C)(C)C	1607.0	Semi standard non polar	33892256
Hexanoylglycine,2TMS,isomer #1	CCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1652.1	Semi standard non polar	33892256
Hexanoylglycine,2TMS,isomer #1	CCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1673.1	Standard non polar	33892256
Hexanoylglycine,2TMS,isomer #1	CCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1808.0	Standard polar	33892256
Hexanoylglycine,1TBDMS,isomer #1	CCCCCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	1840.8	Semi standard non polar	33892256
Hexanoylglycine,1TBDMS,isomer #2	CCCCCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	1833.3	Semi standard non polar	33892256
Hexanoylglycine,2TBDMS,isomer #1	CCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2107.7	Semi standard non polar	33892256
Hexanoylglycine,2TBDMS,isomer #1	CCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2066.4	Standard non polar	33892256
Hexanoylglycine,2TBDMS,isomer #1	CCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2076.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hexanoylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdo-9300000000-d63753a58cbed9d64a0b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexanoylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9100000000-73a7c4329504ed705711	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexanoylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexanoylglycine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexanoylglycine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexanoylglycine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylglycine 20V, Negative-QTOF	splash10-00di-9000000000-c2c7c6516a4c26005a3e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylglycine 40V, Negative-QTOF	splash10-00di-9000000000-8edbd20ffcad8e974ad8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylglycine 10V, Negative-QTOF	splash10-00di-9200000000-0f1cc56efc88b769b202	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-9000000000-ae0fac4a19a715861e4a	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-9000000000-0cd5551af50bb9dab102	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9000000000-7b2d1ccb3cfd6637ba94	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylglycine 40V, Positive-QTOF	splash10-0006-9000000000-8ee973dbde07ab2dc7e3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylglycine 20V, Positive-QTOF	splash10-0006-9000000000-0ac5f3602586aca9837a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hexanoylglycine 10V, Positive-QTOF	splash10-00ba-9000000000-146c8038a60ab4b8bbb8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 10V, Negative-QTOF	splash10-00di-0900000000-1b550dc2062741e68381	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 20V, Negative-QTOF	splash10-00di-5900000000-4581a83fc51b5f982245	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 40V, Negative-QTOF	splash10-05fu-9000000000-0bc8374f98e4c0566940	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 10V, Negative-QTOF	splash10-00di-9700000000-62b9b5a0f8d79da36e22	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 20V, Negative-QTOF	splash10-00di-9100000000-c7d2139b876ee8d24df4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 40V, Negative-QTOF	splash10-00di-9000000000-0aea0bfd802824f29c53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 10V, Positive-QTOF	splash10-00fr-6900000000-4965ec5d947be1bb6c1d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 20V, Positive-QTOF	splash10-056r-9200000000-1efeb9e53e85b74b6b65	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 40V, Positive-QTOF	splash10-0adl-9000000000-71afd16555594867855f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 10V, Positive-QTOF	splash10-004i-9200000000-318791dd01dc2494e070	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 20V, Positive-QTOF	splash10-00fr-9000000000-33d20565f405cf67d01f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hexanoylglycine 40V, Positive-QTOF	splash10-0006-9000000000-30720ba72ba1f9743ab2	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	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

Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	0.0213–0.1990 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	0.0268–0.3753 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	0.0338–0.1983 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected but not Quantified	Not Quantified	Adult (24-38years old)	Not Specified	Normal	20971021	details
Urine	Detected and Quantified	0.03-0.62 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	21704015	details
Urine	Detected and Quantified	1.30-13.06 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	The analysis of d...	details
Urine	Detected and Quantified	14.360-70.495 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	The analysis of d...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	<2.88 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	<0.39 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	28853722	details
Urine	Detected and Quantified	<1 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	6616873	details
Urine	Detected and Quantified	<11.7 umol/mmol creatinine	Children (1 - 13 years old)	Female	Normal	9667231	details
Urine	Detected and Quantified	0.900 +/- 0.400 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	7776094	details
Urine	Detected and Quantified	0.41 +/- 1.72 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	18.277-97.910 umol/mmol creatinine	Newborn (0-30 days old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	The analysis of d...	details
Urine	Detected and Quantified	1.958-426.236 umol/mmol creatinine	Newborn (0-30 days old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	The analysis of d...	details
Urine	Detected and Quantified	0.08 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Propionic acidemia	28853722	details
Urine	Detected and Quantified	2.8 umol/mmol creatinine	Children (1 - 13 years old)	Female	Ethylmalonic encephalopathy	9667231	details
Urine	Detected and Quantified	5.222 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	26.762 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	57.441 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	59.399 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	114.881 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	0-3.0679 umol/mmol creatinine	Infant (0-1 year old)	Both	Short chain acyl-CoA dehydrogenase deficiency (SCAD)	7776094	details
Urine	Detected and Quantified	10-169 umol/mmol creatinine	Children (1 - 13 years old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	6616873	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Medium Chain Acyl-CoA Dehydrogenase Deficiency
Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ] Gregersen N, Kolvraa S, Rasmussen K, Mortensen PB, Divry P, David M, Hobolth N: General (medium-chain) acyl-CoA dehydrogenase deficiency (non-ketotic dicarboxylic aciduria): quantitative urinary excretion pattern of 23 biologically significant organic acids in three cases. Clin Chim Acta. 1983 Aug 15;132(2):181-91. [PubMed:6616873 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium. Millington D, Kodo N, Terada N, Roe C, Chace D (1991). The analysis of diagnostic markers of genetic disorders in human blood and urine using tandem mass spectrometry with liquid secondary ion mass spectrometry. Int J Mass Spectrom Ion Proc. 1991;111:211-228. Int J Mass Spectrom Ion Proc..
Propionic acidemia
Riemersma M, Hazebroek MR, Helderman-van den Enden ATJM, Salomons GS, Ferdinandusse S, Brouwers MCGJ, van der Ploeg L, Heymans S, Glatz JFC, van den Wijngaard A, Krapels IPC, Bierau J, Brunner HG: Propionic acidemia as a cause of adult-onset dilated cardiomyopathy. Eur J Hum Genet. 2017 Nov;25(11):1195-1201. doi: 10.1038/ejhg.2017.127. Epub 2017 Aug 30. [PubMed:28853722 ]
Ethylmalonic encephalopathy
Nowaczyk MJ, Lehotay DC, Platt BA, Fisher L, Tan R, Phillips H, Clarke JT: Ethylmalonic and methylsuccinic aciduria in ethylmalonic encephalopathy arise from abnormal isoleucine metabolism. Metabolism. 1998 Jul;47(7):836-9. [PubMed:9667231 ]
Short Chain Acyl-Coa Dehydrogenase Deficiency
Bhala A, Willi SM, Rinaldo P, Bennett MJ, Schmidt-Sommerfeld E, Hale DE: Clinical and biochemical characterization of short-chain acyl-coenzyme A dehydrogenase deficiency. J Pediatr. 1995 Jun;126(6):910-5. [PubMed:7776094 ]

Associated OMIM IDs

114500 (Colorectal cancer)
201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
606054 (Propionic acidemia)
602473 (Ethylmalonic encephalopathy)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022190

KNApSAcK ID

Not Available

Chemspider ID

89859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5669

PubChem Compound

99463

PDB ID

Not Available

ChEBI ID

64390

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000227

Good Scents ID

Not Available

References

Synthesis Reference

Toth, Eugene; Weiss, Benjamine; Banay-Schwartz, Miriam; Lajtha, Abel. Effect of glycine derivatives on behavioral changes induced by 3-mercaptopropionic acid or phencyclidine in mice. Research Communications in Psychology, Psychiatry and Behavior (1986), 11(1), 1-9.

Material Safety Data Sheet (MSDS)

Not Available

General References

Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
Rinaldo P, O'Shea JJ, Welch RD, Tanaka K: Stable isotope dilution analysis of n-hexanoylglycine, 3-phenylpropionylglycine and suberylglycine in human urine using chemical ionization gas chromatography/mass spectrometry selected ion monitoring. Biomed Environ Mass Spectrom. 1989 Jul;18(7):471-7. [PubMed:2775902 ]
Chabrol B, Mancini J, Bertrand C, Vianey-Saban C, Divry P, Livet MO, Pinsard N: [Generalized epilepsy disclosing medium-chain-acyl-CoA dehydrogenase deficiency]. Arch Fr Pediatr. 1993 Jun-Jul;50(6):497-500. [PubMed:8135611 ]
Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]
Yamaguchi S, Shimizu N, Orii T, Fukao T, Suzuki Y, Maeda K, Hashimoto T, Previs SF, Rinaldo P: Prenatal diagnosis and neonatal monitoring of a fetus with glutaric aciduria type II due to electron transfer flavoprotein (beta-subunit) deficiency. Pediatr Res. 1991 Nov;30(5):439-43. [PubMed:1754299 ]

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

Enzyme Details

2. Glycine N-acyltransferase-like protein 1

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:: GLYATL1
Uniprot ID:: Q969I3
Molecular weight:: 35100.895

Enzyme Details

3. Glycine N-acyltransferase-like protein 2

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:: GLYATL2
Uniprot ID:: Q8WU03
Molecular weight:: 34277.055

Enzyme Details

4. Glycine N-acyltransferase-like protein 3

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:: GLYATL3
Uniprot ID:: Q5SZD4
Molecular weight:: 32703.3

Showing metabocard for Hexanoylglycine (HMDB0000701)

MOL for HMDB0000701 (Hexanoylglycine)

3D MOL for HMDB0000701 (Hexanoylglycine)

3D SDF for HMDB0000701 (Hexanoylglycine)

3D-SDF for HMDB0000701 (Hexanoylglycine)

PDB for HMDB0000701 (Hexanoylglycine)

3D PDB for HMDB0000701 (Hexanoylglycine)

SMILES for HMDB0000701 (Hexanoylglycine)

INCHI for HMDB0000701 (Hexanoylglycine)

Structure for HMDB0000701 (Hexanoylglycine)

3D Structure for HMDB0000701 (Hexanoylglycine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes