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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-11-30 15:51:59 UTC

Update Date

2020-02-26 21:38:25 UTC

HMDB ID

HMDB0013267

Secondary Accession Numbers

HMDB13267

Metabolite Identification

Common Name

N-Decanoylglycine

Description

N-Decanoylglycine is an acylglycine with C-10 fatty acid group as the acyl moiety. Acylglycines 1 possess a common amidoacetic acid moiety and are normally minor metabolites of fatty acids. Elevated levels of certain acylglycines appear in the urine and blood of patients with various fatty acid oxidation disorders. They are normally produced through the action of glycine N-acyltransferase which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine ↔ CoA + N-acylglycine.

Structure

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

HMDB0013267
     RDKit          3D
N-Decanoylglycine
 39 38  0  0  0  0  0  0  0  0999 V2000
   -6.5054   -0.4861   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4077   -1.3032   -0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0524   -0.9822   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7720    0.4806   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669    0.9321    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    0.2011   -0.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0434    0.7638    0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    0.0800   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4481    0.6388    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6751   -0.0173   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -0.9139   -0.9195 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292    0.3652    0.4427 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1252   -0.2794   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3465    0.2440    0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2874    1.1535    1.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5779   -0.2611    0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3836   -1.1401    0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8684    0.3009   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2318   -0.0345    0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643   -1.0701   -1.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6289   -2.3719   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2966   -1.6571   -0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1756   -1.1838    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5739    1.0430    0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8484    0.7728   -1.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    2.0076   -0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735    0.9303    1.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982   -0.8784   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763    0.3786   -1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029    0.7075    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0639    1.8640    0.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    0.1999   -1.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1366   -0.9967    0.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4906    1.7462    0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3597    0.4247    1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0093    1.1094    1.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1260   -0.1750   -1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0128   -1.3723    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6776   -1.2206   -0.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 16 39  1  0
M  END

  Mrv1652303102016512D          

 16 15  0  0  0  0            999 V2000
    8.6857  -14.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4001  -14.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1146  -14.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8291  -14.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5435  -14.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2580  -14.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9725  -14.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6870  -14.5133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9725  -15.7508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9712  -14.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1159  -14.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1159  -13.6883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8304  -14.9258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4015  -14.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2567  -14.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5422  -14.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  2  0  0  0  0
 10  1  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  1  0  0  0  0
 14 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013267

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H23NO3/c1-2-3-4-5-6-7-8-9-11(14)13-10-12(15)16/h2-10H2,1H3,(H,13,14)(H,15,16)

> <INCHI_KEY>
WRRYZYASRAUROW-UHFFFAOYSA-N

> <FORMULA>
C12H23NO3

> <MOLECULAR_WEIGHT>
229.3159

> <EXACT_MASS>
229.167793607

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.07472179728099

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-decanamidoacetic acid

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.483887548

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.99380161601848

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.046618031780419

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6781963755393616

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
62.281099999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
decanamidoacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013267
     RDKit          3D
N-Decanoylglycine
 39 38  0  0  0  0  0  0  0  0999 V2000
   -6.5054   -0.4861   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4077   -1.3032   -0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0524   -0.9822   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7720    0.4806   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669    0.9321    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    0.2011   -0.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0434    0.7638    0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    0.0800   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4481    0.6388    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6751   -0.0173   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -0.9139   -0.9195 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292    0.3652    0.4427 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1252   -0.2794   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3465    0.2440    0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2874    1.1535    1.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5779   -0.2611    0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3836   -1.1401    0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8684    0.3009   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2318   -0.0345    0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643   -1.0701   -1.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6289   -2.3719   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2966   -1.6571   -0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1756   -1.1838    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5739    1.0430    0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8484    0.7728   -1.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    2.0076   -0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735    0.9303    1.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982   -0.8784   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763    0.3786   -1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029    0.7075    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0639    1.8640    0.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    0.1999   -1.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1366   -0.9967    0.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4906    1.7462    0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3597    0.4247    1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0093    1.1094    1.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1260   -0.1750   -1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0128   -1.3723    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6776   -1.2206   -0.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 16 39  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      16.213 -27.861   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.547 -27.091   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.881 -27.861   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.214 -27.091   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.548 -27.861   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.882 -27.091   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.215 -27.861   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      25.549 -27.091   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      24.215 -29.401   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.880 -27.091   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.216 -27.091   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      28.216 -25.551   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      29.550 -27.861   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      26.883 -27.861   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.546 -27.861   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.212 -27.091   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   14                                                       
CONECT    9    7                                                            
CONECT   10    1   15                                                       
CONECT   11   12   13   14                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11    8                                                       
CONECT   15   10   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0013267
HETATM    1  C1  UNL     1      -6.505  -0.486  -0.165  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.408  -1.303  -0.764  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.052  -0.982  -0.134  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.772   0.481  -0.375  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.467   0.932   0.193  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.279   0.201  -0.376  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.043   0.764   0.291  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.206   0.080  -0.226  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.448   0.639   0.438  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.675  -0.017  -0.056  1.00  0.00           C  
HETATM   11  O1  UNL     1       3.582  -0.914  -0.920  1.00  0.00           O  
HETATM   12  N1  UNL     1       4.929   0.365   0.443  1.00  0.00           N  
HETATM   13  C11 UNL     1       6.125  -0.279  -0.043  1.00  0.00           C  
HETATM   14  C12 UNL     1       7.346   0.244   0.586  1.00  0.00           C  
HETATM   15  O2  UNL     1       7.287   1.153   1.446  1.00  0.00           O  
HETATM   16  O3  UNL     1       8.578  -0.261   0.236  1.00  0.00           O  
HETATM   17  H1  UNL     1      -7.384  -1.140   0.011  1.00  0.00           H  
HETATM   18  H2  UNL     1      -6.868   0.301  -0.882  1.00  0.00           H  
HETATM   19  H3  UNL     1      -6.232  -0.035   0.810  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.364  -1.070  -1.857  1.00  0.00           H  
HETATM   21  H5  UNL     1      -5.629  -2.372  -0.683  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.297  -1.657  -0.526  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.176  -1.184   0.949  1.00  0.00           H  
HETATM   24  H8  UNL     1      -4.574   1.043   0.174  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.848   0.773  -1.419  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.342   2.008  -0.100  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.474   0.930   1.300  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.298  -0.878  -0.222  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.176   0.379  -1.466  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.103   0.707   1.395  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.064   1.864   0.058  1.00  0.00           H  
HETATM   32  H16 UNL     1       1.237   0.200  -1.326  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.137  -0.997   0.009  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.491   1.746   0.318  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.360   0.425   1.527  1.00  0.00           H  
HETATM   36  H20 UNL     1       5.009   1.109   1.160  1.00  0.00           H  
HETATM   37  H21 UNL     1       6.126  -0.175  -1.159  1.00  0.00           H  
HETATM   38  H22 UNL     1       6.013  -1.372   0.219  1.00  0.00           H  
HETATM   39  H23 UNL     1       8.678  -1.221  -0.097  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   11   11   12
CONECT   12   13   36
CONECT   13   14   37   38
CONECT   14   15   15   16
CONECT   16   39
END

HMDB0013267
     RDKit          3D
N-Decanoylglycine
 39 38  0  0  0  0  0  0  0  0999 V2000
   -6.5054   -0.4861   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4077   -1.3032   -0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0524   -0.9822   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7720    0.4806   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669    0.9321    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    0.2011   -0.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0434    0.7638    0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    0.0800   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4481    0.6388    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6751   -0.0173   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -0.9139   -0.9195 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292    0.3652    0.4427 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1252   -0.2794   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3465    0.2440    0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2874    1.1535    1.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5779   -0.2611    0.2364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3836   -1.1401    0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8684    0.3009   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2318   -0.0345    0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643   -1.0701   -1.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6289   -2.3719   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2966   -1.6571   -0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1756   -1.1838    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5739    1.0430    0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8484    0.7728   -1.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    2.0076   -0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4735    0.9303    1.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982   -0.8784   -0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763    0.3786   -1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029    0.7075    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0639    1.8640    0.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    0.1999   -1.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1366   -0.9967    0.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4906    1.7462    0.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3597    0.4247    1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0093    1.1094    1.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1260   -0.1750   -1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0128   -1.3723    0.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6776   -1.2206   -0.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 16 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Acylglycine c:10	ChEBI
Caprylglycine	ChEBI
Decanoylglycine	HMDB

Chemical Formula

C₁₂H₂₃NO₃

Average Molecular Weight

229.3159

Monoisotopic Molecular Weight

229.167793607

IUPAC Name

2-decanamidoacetic acid

Traditional Name

decanamidoacetic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C12H23NO3/c1-2-3-4-5-6-7-8-9-11(14)13-10-12(15)16/h2-10H2,1H3,(H,13,14)(H,15,16)

InChI Key

WRRYZYASRAUROW-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
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

fatty amide (CHEBI:74430 )
N-acylglycine (CHEBI:74430 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0013267)
Cell membrane (HMDB: HMDB0013267)

Source

Endogenous

Endogenous (HMDB: HMDB0013267)

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	0.16 g/L	ALOGPS
logP	3.03	ALOGPS
logP	2.48	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.05	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	10	ChemAxon
Refractivity	62.28 m³·mol⁻¹	ChemAxon
Polarizability	27.07 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]+	158.712	31661259
DarkChem	[M-H]-	155.318	31661259
DeepCCS	[M+H]+	157.905	30932474
DeepCCS	[M-H]-	153.882	30932474
DeepCCS	[M-2H]-	191.503	30932474
DeepCCS	[M+Na]+	167.168	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	153.4	32859911
AllCCS	[M+NH4]+	159.9	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	158.6	32859911
AllCCS	[M+Na-2H]-	159.5	32859911
AllCCS	[M+HCOO]-	160.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Decanoylglycine	CCCCCCCCCC(=O)NCC(O)=O	2934.1	Standard polar	33892256
N-Decanoylglycine	CCCCCCCCCC(=O)NCC(O)=O	1809.3	Standard non polar	33892256
N-Decanoylglycine	CCCCCCCCCC(=O)NCC(O)=O	2001.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Decanoylglycine,1TMS,isomer #1	CCCCCCCCCC(=O)NCC(=O)O[Si](C)(C)C	2000.4	Semi standard non polar	33892256
N-Decanoylglycine,1TMS,isomer #2	CCCCCCCCCC(=O)N(CC(=O)O)[Si](C)(C)C	1995.2	Semi standard non polar	33892256
N-Decanoylglycine,2TMS,isomer #1	CCCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2033.2	Semi standard non polar	33892256
N-Decanoylglycine,2TMS,isomer #1	CCCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2059.1	Standard non polar	33892256
N-Decanoylglycine,2TMS,isomer #1	CCCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	2164.2	Standard polar	33892256
N-Decanoylglycine,1TBDMS,isomer #1	CCCCCCCCCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	2232.8	Semi standard non polar	33892256
N-Decanoylglycine,1TBDMS,isomer #2	CCCCCCCCCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	2232.9	Semi standard non polar	33892256
N-Decanoylglycine,2TBDMS,isomer #1	CCCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2504.4	Semi standard non polar	33892256
N-Decanoylglycine,2TBDMS,isomer #1	CCCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2435.8	Standard non polar	33892256
N-Decanoylglycine,2TBDMS,isomer #1	CCCCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2421.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Decanoylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdo-9500000000-b07c6e82796c07b65569	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Decanoylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9210000000-9a70957afbb0428240cd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Decanoylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Decanoylglycine 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 - N-Decanoylglycine 10V, Negative-QTOF	splash10-004i-0190000000-7a10ce30c3f1ac2ffe1b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 20V, Negative-QTOF	splash10-00b9-6890000000-2f26a758a1b13799c8b4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 40V, Negative-QTOF	splash10-05fu-9200000000-43236079671c9f34b61f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 10V, Negative-QTOF	splash10-004i-1090000000-07fdd726c9923a121f69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 20V, Negative-QTOF	splash10-00di-9020000000-667a7f00834c702170fd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 40V, Negative-QTOF	splash10-00di-9000000000-89be1e4e4c180a69cc26	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 10V, Positive-QTOF	splash10-053r-5590000000-ed17e2f67be5045a1200	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 20V, Positive-QTOF	splash10-0a6r-9410000000-6a95148ffb4074110f2c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 40V, Positive-QTOF	splash10-056u-9100000000-8b843a81471a27ad78e3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 10V, Positive-QTOF	splash10-003r-9260000000-364fd80d9a3ef0ea874f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 20V, Positive-QTOF	splash10-0a6r-9000000000-b6c5bff210fa9ff35d5b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Decanoylglycine 40V, Positive-QTOF	splash10-0aou-9000000000-9f21b194527b253b016e	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

FDB029360

KNApSAcK ID

Not Available

Chemspider ID

1361783

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1712391

PDB ID

Not Available

ChEBI ID

74430

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

Gregersen N, Kolvraa S, Rasmussen K, Christensen E, Brandt NJ, Ebbesen F, Hansen FH: Biochemical studies in a patient with defects in the metabolism of acyl-CoA and sarcosine: another possible case of glutaric aciduria type II. J Inherit Metab Dis. 1980;3(3):67-72. [PubMed:6158623 ]
Gregersen N, Rosleff F, Kolvraa S, Hobolth N, Rasmussen K, Lauritzen R: Non-ketotic C6-C10-dicarboxylic aciduria: biochemical investigations of two cases. Clin Chim Acta. 1980 Mar 28;102(2-3):179-89. [PubMed:6892795 ]
Gregersen N, Wintzensen H, Christensen SK, Christensen MF, Brandt NJ, Rasmussen K: C6-C10-dicarboxylic aciduria: investigations of a patient with riboflavin responsive multiple acyl-CoA dehydrogenation defects. Pediatr Res. 1982 Oct;16(10):861-8. [PubMed:7145508 ]

Showing metabocard for N-Decanoylglycine (HMDB0013267)

MOL for HMDB0013267 (N-Decanoylglycine)

3D MOL for HMDB0013267 (N-Decanoylglycine)

3D SDF for HMDB0013267 (N-Decanoylglycine)

3D-SDF for HMDB0013267 (N-Decanoylglycine)

PDB for HMDB0013267 (N-Decanoylglycine)

3D PDB for HMDB0013267 (N-Decanoylglycine)

SMILES for HMDB0013267 (N-Decanoylglycine)

INCHI for HMDB0013267 (N-Decanoylglycine)

Structure for HMDB0013267 (N-Decanoylglycine)

3D Structure for HMDB0013267 (N-Decanoylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra