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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 17:15:13 UTC

HMDB ID

HMDB0000832

Secondary Accession Numbers

HMDB00832

Metabolite Identification

Common Name

Capryloylglycine

Description

Capryloylglycine is an acylglycine consisting of caprylic acid (an 8-carbon medium chain fatty acid) conjugated to glycine. Acylglycines have an aliphatic acyl chain attached to the amino group of glycine through a peptide bond. Capryloylglycine is a solid with moderate solubility in water. Acylglycines are produced through the action of the enzyme glycine N-acyltransferase (EC 2.3.1.13). Acylglycines are normally minor metabolites of fatty acids. However, the excretion of certain acylglycines 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, including medium-chain acyl-coenzyme A (CoA) dehydrogenase (MCAD) deficiency and multiple acyl-CoA dehydrogenation defect (MAD) (PMID: 10708405 ). Capryloylglycine is frequently used as a cosmetic ingredient where it functions as a conditioning agent or a surfactant. It helps protect the skin‚Äôs surface from water loss and can enhance the effectiveness of cosmetic preservatives. Capryloylglycine-containing creams have been shown to inhibit hair growth in individuals suffering from hypertrichosis (PMID: 33934471 ), due to it inhibiting ornithine decarboxylase 1, which is present in hair follicles.

Structure

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

HMDB0000832
     RDKit          3D
Capryloylglycine
 33 32  0  0  0  0  0  0  0  0999 V2000
   -4.2001    1.9141   -0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2898    0.6867   -0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0512    0.2696    0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1662   -0.9352    0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -0.6979   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -1.9584    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948   -1.9293   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -0.9147    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -0.2409    1.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868   -0.6906   -0.2083 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192    0.2993    0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936    1.6261    0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943    1.7290   -0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4285    2.7456    0.8225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2764    2.3272    0.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8129    2.7318   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2468    1.6332   -1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3670    0.8868   -1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531   -0.1229   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794    1.1308    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0351    0.0006    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562   -1.1502    1.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -1.7897    0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    0.1602    0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9161   -0.5439   -1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396   -2.8078   -0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0036   -2.1540    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -1.8303   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -2.9576   -0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401   -1.2675   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4309    0.2824   -0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310    0.0736    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6217    3.4942    0.1588 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  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
M  END


  Mrv1652305271900052D          

 14 13  0  0  0  0            999 V2000
   27.1145  -17.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8291  -19.0198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9724  -16.9573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2580  -18.1948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8303  -17.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1159  -18.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5448  -18.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4013  -17.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2594  -17.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5435  -17.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6870  -18.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9738  -18.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8291  -18.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9724  -17.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2 13  2  0  0  0  0
  3 14  2  0  0  0  0
  4 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000832

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H19NO3/c1-2-3-4-5-6-7-9(12)11-8-10(13)14/h2-8H2,1H3,(H,11,12)(H,13,14)

> <INCHI_KEY>
SAVLIIGUQOSOEP-UHFFFAOYSA-N

> <FORMULA>
C10H19NO3

> <MOLECULAR_WEIGHT>
201.2628

> <EXACT_MASS>
201.136493479

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
22.924265159712697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-octanamidoacetic acid

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
1.5947502179999993

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.121574001873764

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.046618031912552

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6781963754346627

> <JCHEM_POLAR_SURFACE_AREA>
66.39999999999999

> <JCHEM_REFRACTIVITY>
53.0791

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-octanoylglycine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000832
     RDKit          3D
Capryloylglycine
 33 32  0  0  0  0  0  0  0  0999 V2000
   -4.2001    1.9141   -0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2898    0.6867   -0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0512    0.2696    0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1662   -0.9352    0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -0.6979   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -1.9584    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948   -1.9293   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -0.9147    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -0.2409    1.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868   -0.6906   -0.2083 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192    0.2993    0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936    1.6261    0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943    1.7290   -0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4285    2.7456    0.8225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2764    2.3272    0.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8129    2.7318   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2468    1.6332   -1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3670    0.8868   -1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531   -0.1229   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794    1.1308    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0351    0.0006    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562   -1.1502    1.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -1.7897    0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    0.1602    0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9161   -0.5439   -1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396   -2.8078   -0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0036   -2.1540    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -1.8303   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -2.9576   -0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401   -1.2675   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4309    0.2824   -0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310    0.0736    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6217    3.4942    0.1588 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  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      50.614 -33.193   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      51.948 -35.504   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      55.948 -31.654   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      54.615 -33.964   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      61.283 -33.193   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      59.950 -33.964   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      62.617 -33.964   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      58.616 -33.193   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      63.951 -33.193   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      53.281 -33.193   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      57.282 -33.964   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      65.284 -33.964   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.948 -33.964   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      55.948 -33.193   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   10   14                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   11                                                       
CONECT    9    7   12                                                       
CONECT   10    4   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9                                                            
CONECT   13    1    2   10                                                  
CONECT   14    3    4   11                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0000832
HETATM    1  C1  UNL     1      -4.200   1.914  -0.947  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.290   0.687  -0.992  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.051   0.270   0.429  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.166  -0.935   0.558  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.790  -0.698  -0.047  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.010  -1.958   0.135  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.395  -1.929  -0.399  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.252  -0.915   0.238  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.800  -0.241   1.185  1.00  0.00           O  
HETATM   10  N1  UNL     1       3.587  -0.691  -0.208  1.00  0.00           N  
HETATM   11  C9  UNL     1       4.419   0.299   0.415  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.794   1.626   0.284  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.694   1.729  -0.311  1.00  0.00           O  
HETATM   14  O3  UNL     1       4.428   2.746   0.822  1.00  0.00           O  
HETATM   15  H1  UNL     1      -4.276   2.327   0.081  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.813   2.732  -1.590  1.00  0.00           H  
HETATM   17  H3  UNL     1      -5.247   1.633  -1.242  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.367   0.887  -1.547  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.853  -0.123  -1.501  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.679   1.131   1.051  1.00  0.00           H  
HETATM   21  H7  UNL     1      -4.035   0.001   0.865  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.056  -1.150   1.641  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.670  -1.790   0.092  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.290   0.160   0.428  1.00  0.00           H  
HETATM   25  H11 UNL     1      -0.916  -0.544  -1.151  1.00  0.00           H  
HETATM   26  H12 UNL     1      -0.540  -2.808  -0.372  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.004  -2.154   1.249  1.00  0.00           H  
HETATM   28  H14 UNL     1       1.391  -1.830  -1.518  1.00  0.00           H  
HETATM   29  H15 UNL     1       1.841  -2.958  -0.236  1.00  0.00           H  
HETATM   30  H16 UNL     1       3.940  -1.268  -1.001  1.00  0.00           H  
HETATM   31  H17 UNL     1       5.431   0.282  -0.084  1.00  0.00           H  
HETATM   32  H18 UNL     1       4.631   0.074   1.482  1.00  0.00           H  
HETATM   33  H19 UNL     1       4.622   3.494   0.159  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8   28   29
CONECT    8    9    9   10
CONECT   10   11   30
CONECT   11   12   31   32
CONECT   12   13   13   14
CONECT   14   33
END

HMDB0000832
     RDKit          3D
Capryloylglycine
 33 32  0  0  0  0  0  0  0  0999 V2000
   -4.2001    1.9141   -0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2898    0.6867   -0.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0512    0.2696    0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1662   -0.9352    0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -0.6979   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -1.9584    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948   -1.9293   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -0.9147    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -0.2409    1.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868   -0.6906   -0.2083 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192    0.2993    0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936    1.6261    0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943    1.7290   -0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4285    2.7456    0.8225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2764    2.3272    0.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8129    2.7318   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2468    1.6332   -1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3670    0.8868   -1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8531   -0.1229   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794    1.1308    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0351    0.0006    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562   -1.1502    1.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -1.7897    0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2902    0.1602    0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9161   -0.5439   -1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396   -2.8078   -0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0036   -2.1540    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -1.8303   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -2.9576   -0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401   -1.2675   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4309    0.2824   -0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310    0.0736    1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6217    3.4942    0.1588 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  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Octanamidoacetic acid	ChEBI
Caprylylglycine	ChEBI
N-(1-Oxooctyl)glycine	ChEBI
2-Octanamidoacetate	Generator
Capryloyl glycine	HMDB
Lipacide C 8g	HMDB
N-(1-Oxooctyl)-glycine	HMDB
N-Octanoyl-glycine	HMDB
N-Octanoylglycine	HMDB

Chemical Formula

C₁₀H₁₉NO₃

Average Molecular Weight

201.2628

Monoisotopic Molecular Weight

201.136493479

IUPAC Name

2-octanamidoacetic acid

Traditional Name

N-octanoylglycine

CAS Registry Number

14246-53-8

SMILES

CCCCCCCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C10H19NO3/c1-2-3-4-5-6-7-9(12)11-8-10(13)14/h2-8H2,1H3,(H,11,12)(H,13,14)

InChI Key

SAVLIIGUQOSOEP-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:74099 )
N-acylglycine (CHEBI:74099 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	403.00 to 404.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	980.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.065 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1 g/L	ALOGPS
logP	2.07	ALOGPS
logP	1.59	ChemAxon
logS	-2.3	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	8	ChemAxon
Refractivity	53.08 m³·mol⁻¹	ChemAxon
Polarizability	22.92 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]+	149.318	31661259
DarkChem	[M-H]-	145.5	31661259
AllCCS	[M+H]+	148.175	32859911
AllCCS	[M-H]-	149.261	32859911
DeepCCS	[M+H]+	148.783	30932474
DeepCCS	[M-H]-	144.757	30932474
DeepCCS	[M-2H]-	182.255	30932474
DeepCCS	[M+Na]+	157.881	30932474
AllCCS	[M+H]+	148.2	32859911
AllCCS	[M+H-H2O]+	144.6	32859911
AllCCS	[M+NH4]+	151.5	32859911
AllCCS	[M+Na]+	152.5	32859911
AllCCS	[M-H]-	149.3	32859911
AllCCS	[M+Na-2H]-	150.4	32859911
AllCCS	[M+HCOO]-	151.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Capryloylglycine	CCCCCCCC(=O)NCC(O)=O	2723.6	Standard polar	33892256
Capryloylglycine	CCCCCCCC(=O)NCC(O)=O	1628.3	Standard non polar	33892256
Capryloylglycine	CCCCCCCC(=O)NCC(O)=O	1809.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Capryloylglycine,1TMS,isomer #1	CCCCCCCC(=O)NCC(=O)O[Si](C)(C)C	1807.0	Semi standard non polar	33892256
Capryloylglycine,1TMS,isomer #2	CCCCCCCC(=O)N(CC(=O)O)[Si](C)(C)C	1794.8	Semi standard non polar	33892256
Capryloylglycine,2TMS,isomer #1	CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1840.0	Semi standard non polar	33892256
Capryloylglycine,2TMS,isomer #1	CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1869.9	Standard non polar	33892256
Capryloylglycine,2TMS,isomer #1	CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1986.4	Standard polar	33892256
Capryloylglycine,1TBDMS,isomer #1	CCCCCCCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	2035.3	Semi standard non polar	33892256
Capryloylglycine,1TBDMS,isomer #2	CCCCCCCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	2028.7	Semi standard non polar	33892256
Capryloylglycine,2TBDMS,isomer #1	CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2305.3	Semi standard non polar	33892256
Capryloylglycine,2TBDMS,isomer #1	CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2257.6	Standard non polar	33892256
Capryloylglycine,2TBDMS,isomer #1	CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2250.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Capryloylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kfx-9300000000-65a0f0b1f51f64e885b7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capryloylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9110000000-c57e7cf876a1e77e8ae0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capryloylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capryloylglycine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capryloylglycine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capryloylglycine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4i-9000000000-03ca05ec686d1dda5b8a	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-9000000000-62dc4fa9a9a964274ce9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0le9-9410000000-2ee2571efa7db061b49d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine 40V, Negative-QTOF	splash10-00di-9000000000-fc6cc7311141fc5fe717	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine 10V, Negative-QTOF	splash10-00di-9020000000-d03999d949be77b4d8a6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine 20V, Negative-QTOF	splash10-00di-9000000000-70b04aa8b2675c21fa16	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine 20V, Positive-QTOF	splash10-0a4i-9000000000-874f5c3a11de4ee90031	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine 40V, Positive-QTOF	splash10-052f-9000000000-e2229641a6019ff1a56d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine 20V, Positive-QTOF	splash10-0a4i-9000000000-bca784da02e2fac6d0ba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine 10V, Positive-QTOF	splash10-056r-9100000000-8d0322475c5030f907a3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine 10V, Positive-QTOF	splash10-056r-9100000000-0d09d6d23bc8462fa3e4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capryloylglycine 40V, Positive-QTOF	splash10-0a4l-9000000000-2daf8062135b4c7bbfd8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 10V, Positive-QTOF	splash10-0zi0-7890000000-57a37a082260c6fadf12	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 20V, Positive-QTOF	splash10-0a6r-9300000000-ed7dd37f13803abae61c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 40V, Positive-QTOF	splash10-0a6u-9000000000-5b71e57265e05e05caf0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 10V, Negative-QTOF	splash10-0udi-0390000000-1a1e6edc2e6566ff36b0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 20V, Negative-QTOF	splash10-0zmi-7960000000-dbf3a16fa0aa2d14fa42	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 40V, Negative-QTOF	splash10-05fu-9000000000-f6cc9608b6c803996d2b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 10V, Positive-QTOF	splash10-0fb9-9030000000-7f1b4ff2c9242662a6a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 20V, Positive-QTOF	splash10-0a6r-9000000000-4b500c86935ecdb797c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 40V, Positive-QTOF	splash10-0a4i-9000000000-45956863a016267b72c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 10V, Negative-QTOF	splash10-0udi-2090000000-24660e2b635d6ddb6dfd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 20V, Negative-QTOF	splash10-00di-9000000000-67d5d2d94d2b5bccd9dd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capryloylglycine 40V, Negative-QTOF	splash10-00di-9000000000-d0d8d779699b764c9cb0	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, 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
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	<0.0015–0.0347 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	<0.0015–0.0414 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	<0.0015–0.0489 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	<0.2 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	6616873	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.2-1.7 umol/mmol creatinine	Children (1 - 13 years old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	6616873	details

Associated Disorders and Diseases

Disease References

Medium Chain Acyl-CoA Dehydrogenase Deficiency
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 ]

Associated OMIM IDs

201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022273

KNApSAcK ID

Not Available

Chemspider ID

76040

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5795

PubChem Compound

84290

PDB ID

Not Available

ChEBI ID

74099

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029861

Good Scents ID

rw1358991

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Costa CG, Guerand WS, Struys EA, Holwerda U, ten Brink HJ, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of urinary acylglycines for the diagnosis of beta-oxidation defects using GC-NCI-MS. J Pharm Biomed Anal. 2000 Jan;21(6):1215-24. doi: 10.1016/s0731-7085(99)00235-6. [PubMed:10708405 ]
Barbareschi M, Benetti F, Gaio E, Angileri L, Veraldi S: Capryloyl glycine and soy isoflavonoids in hypertrichosis: An experimental and placebo-controlled clinical study. J Cosmet Dermatol. 2021 Apr;20 Suppl 1:18-22. doi: 10.1111/jocd.14096. [PubMed:33934471 ]

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 Capryloylglycine (HMDB0000832)

MOL for HMDB0000832 (Capryloylglycine)

3D MOL for HMDB0000832 (Capryloylglycine)

3D SDF for HMDB0000832 (Capryloylglycine)

3D-SDF for HMDB0000832 (Capryloylglycine)

PDB for HMDB0000832 (Capryloylglycine)

3D PDB for HMDB0000832 (Capryloylglycine)

SMILES for HMDB0000832 (Capryloylglycine)

INCHI for HMDB0000832 (Capryloylglycine)

Structure for HMDB0000832 (Capryloylglycine)

3D Structure for HMDB0000832 (Capryloylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes