NP-MRD: Showing NP-Card for Capryloylglycine (NP0000206)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-16 18:04:18 UTC

NP-MRD ID

NP0000206

Secondary Accession Numbers

None

Natural Product 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’s 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>
NP0000206

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

201.2628 Da

Monoisotopic Mass

201.13649 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000832

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1358991

References

General References

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 ]

Showing NP-Card for Capryloylglycine (NP0000206)

MOL for NP0000206 (Capryloylglycine)

3D MOL for NP0000206 (Capryloylglycine)

3D SDF for NP0000206 (Capryloylglycine)

3D-SDF for NP0000206 (Capryloylglycine)

PDB for NP0000206 (Capryloylglycine)

3D PDB for NP0000206 (Capryloylglycine)

SMILES for NP0000206 (Capryloylglycine)

INCHI for NP0000206 (Capryloylglycine)

Structure for NP0000206 (Capryloylglycine)

3D Structure for NP0000206 (Capryloylglycine)