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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:44:32 UTC

Update Date

2022-11-23 22:29:17 UTC

HMDB ID

HMDB0255165

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Lauroylsarcosine

Description

Lauroyl sarcosine 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. They may also react to produce N-nitrososarcosine, which is believed to be carcinogenic. Lauroyl sarcosine is an extremely weak basic (essentially neutral) compound (based on its pKa). Once in the body, nitrosamines are metabolized by cytochrome P-450 enzymes, which essentially activates them into carcinogens. Lauroyl sarcosine is a potentially toxic compound. While acyl sarcosines themselves are not toxic, they are nitrosating agents. They are used as hair-conditioning agents and surfactant-cleansing agents in cosmetics, as well as to improve wetting and penetration of topical pharmaceutical products. Acyl sarcosines are considered modifiŽed fatty acids in which the hydrocarbon chains are interrupted by an amidomethyl group in the alpha position. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. Nitrosating agents may decompose and/or react to cause nitrosamine contamination. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-lauroylsarcosine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Lauroylsarcosine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255165
     RDKit          3D
N-LAUROYLSARCOSINE
 48 47  0  0  0  0  0  0  0  0999 V2000
    5.8502   -0.2465   -1.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    0.0277   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142    0.0650   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865    0.3412    1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6360    0.4035    1.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8791    1.4892    1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4638    1.5124    1.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146    0.2034    1.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2308   -0.1328   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216   -1.4472   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -1.4141    0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105   -0.4142   -0.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302    0.1350   -1.6340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4109   -0.0830   -0.1966 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -0.7139    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1813    0.9037   -0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9715    0.2139   -1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7247    0.8497   -2.7771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9080   -1.1616   -2.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7943   -0.7665   -2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7825    0.7426   -2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9843   -0.8631   -2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2088   -0.7341    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1068    1.0464   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8021    0.9513   -0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7400   -0.8811   -0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -0.4628    1.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112    1.2852    1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565   -0.5672    1.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442    0.5484    2.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782    2.4899    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8706    1.3720   -0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264    1.7549    2.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1320    2.2982    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2052   -0.6592    1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931    0.2836    1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    0.7200   -0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -0.2284   -0.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231   -2.1978    0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -1.8092   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4401   -1.2362    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8074   -2.4379   -0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1460   -1.8177    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8871   -0.1913    1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2875   -0.6617    1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8856    1.4454   -0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4626    1.5783   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004   -1.5332   -2.7887 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  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 19 48  1  0
M  END


  Mrv0541 02241205452D          

 19 18  0  0  0  0            999 V2000
    5.9961    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255165

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCC(=O)N(C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H29NO3/c1-3-4-5-6-7-8-9-10-11-12-14(17)16(2)13-15(18)19/h3-13H2,1-2H3,(H,18,19)

> <INCHI_KEY>
BACYUWVYYTXETD-UHFFFAOYSA-N

> <FORMULA>
C15H29NO3

> <MOLECULAR_WEIGHT>
271.3957

> <EXACT_MASS>
271.214743799

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.11615049129472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(N-methyldodecanamido)acetic acid

> <ALOGPS_LOGP>
3.82

> <JCHEM_LOGP>
3.5967009436666677

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.124377820021252

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7584015200535718

> <JCHEM_POLAR_SURFACE_AREA>
57.61000000000001

> <JCHEM_REFRACTIVITY>
76.37979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gardol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255165
     RDKit          3D
N-LAUROYLSARCOSINE
 48 47  0  0  0  0  0  0  0  0999 V2000
    5.8502   -0.2465   -1.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    0.0277   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142    0.0650   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865    0.3412    1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6360    0.4035    1.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8791    1.4892    1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4638    1.5124    1.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146    0.2034    1.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2308   -0.1328   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216   -1.4472   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -1.4141    0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105   -0.4142   -0.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302    0.1350   -1.6340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4109   -0.0830   -0.1966 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -0.7139    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1813    0.9037   -0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9715    0.2139   -1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7247    0.8497   -2.7771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9080   -1.1616   -2.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7943   -0.7665   -2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7825    0.7426   -2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9843   -0.8631   -2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2088   -0.7341    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1068    1.0464   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8021    0.9513   -0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7400   -0.8811   -0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -0.4628    1.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112    1.2852    1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565   -0.5672    1.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442    0.5484    2.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782    2.4899    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8706    1.3720   -0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264    1.7549    2.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1320    2.2982    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2052   -0.6592    1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931    0.2836    1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    0.7200   -0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -0.2284   -0.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231   -2.1978    0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -1.8092   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4401   -1.2362    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8074   -2.4379   -0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1460   -1.8177    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8871   -0.1913    1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2875   -0.6617    1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8856    1.4454   -0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4626    1.5783   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004   -1.5332   -2.7887 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  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 19 48  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      11.193   8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.194   8.772   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      25.863  10.312   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      27.197   8.002   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      27.197   6.462   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.531   8.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.864   8.002   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      31.198   8.772   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      29.864   6.462   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0255165
HETATM    1  C1  UNL     1       5.850  -0.247  -1.939  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.705   0.028  -0.473  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.214   0.065  -0.162  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.087   0.341   1.314  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.636   0.403   1.754  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.879   1.489   1.037  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.464   1.512   1.526  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.215   0.203   1.291  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.231  -0.133  -0.183  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.922  -1.447  -0.372  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.324  -1.414   0.111  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.110  -0.414  -0.629  1.00  0.00           C  
HETATM   13  O1  UNL     1      -2.630   0.135  -1.634  1.00  0.00           O  
HETATM   14  N1  UNL     1      -4.411  -0.083  -0.197  1.00  0.00           N  
HETATM   15  C13 UNL     1      -4.967  -0.714   0.960  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.181   0.904  -0.935  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.972   0.214  -1.997  1.00  0.00           C  
HETATM   18  O2  UNL     1      -6.725   0.850  -2.777  1.00  0.00           O  
HETATM   19  O3  UNL     1      -5.908  -1.162  -2.167  1.00  0.00           O  
HETATM   20  H1  UNL     1       6.794  -0.767  -2.202  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.783   0.743  -2.465  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.984  -0.863  -2.266  1.00  0.00           H  
HETATM   23  H4  UNL     1       6.209  -0.734   0.164  1.00  0.00           H  
HETATM   24  H5  UNL     1       6.107   1.046  -0.209  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.802   0.951  -0.726  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.740  -0.881  -0.471  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.588  -0.463   1.862  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.611   1.285   1.530  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.156  -0.567   1.517  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.644   0.548   2.851  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.378   2.490   1.192  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.871   1.372  -0.062  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.426   1.755   2.627  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.132   2.298   1.007  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.205  -0.659   1.827  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.293   0.284   1.669  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.654   0.720  -0.715  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.847  -0.228  -0.513  1.00  0.00           H  
HETATM   39  H20 UNL     1      -0.323  -2.198   0.216  1.00  0.00           H  
HETATM   40  H21 UNL     1      -0.867  -1.809  -1.424  1.00  0.00           H  
HETATM   41  H22 UNL     1      -2.440  -1.236   1.211  1.00  0.00           H  
HETATM   42  H23 UNL     1      -2.807  -2.438  -0.025  1.00  0.00           H  
HETATM   43  H24 UNL     1      -5.146  -1.818   0.816  1.00  0.00           H  
HETATM   44  H25 UNL     1      -5.887  -0.191   1.258  1.00  0.00           H  
HETATM   45  H26 UNL     1      -4.287  -0.662   1.856  1.00  0.00           H  
HETATM   46  H27 UNL     1      -5.886   1.445  -0.272  1.00  0.00           H  
HETATM   47  H28 UNL     1      -4.463   1.578  -1.432  1.00  0.00           H  
HETATM   48  H29 UNL     1      -5.200  -1.533  -2.789  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   37   38
CONECT   10   11   39   40
CONECT   11   12   41   42
CONECT   12   13   13   14
CONECT   14   15   16
CONECT   15   43   44   45
CONECT   16   17   46   47
CONECT   17   18   18   19
CONECT   19   48
END

HMDB0255165
     RDKit          3D
N-LAUROYLSARCOSINE
 48 47  0  0  0  0  0  0  0  0999 V2000
    5.8502   -0.2465   -1.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    0.0277   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142    0.0650   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865    0.3412    1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6360    0.4035    1.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8791    1.4892    1.0368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4638    1.5124    1.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146    0.2034    1.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2308   -0.1328   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216   -1.4472   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236   -1.4141    0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105   -0.4142   -0.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302    0.1350   -1.6340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4109   -0.0830   -0.1966 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -0.7139    0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1813    0.9037   -0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9715    0.2139   -1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7247    0.8497   -2.7771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9080   -1.1616   -2.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7943   -0.7665   -2.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7825    0.7426   -2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9843   -0.8631   -2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2088   -0.7341    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1068    1.0464   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8021    0.9513   -0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7400   -0.8811   -0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -0.4628    1.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112    1.2852    1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565   -0.5672    1.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442    0.5484    2.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782    2.4899    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8706    1.3720   -0.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264    1.7549    2.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1320    2.2982    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2052   -0.6592    1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931    0.2836    1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    0.7200   -0.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -0.2284   -0.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231   -2.1978    0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -1.8092   -1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4401   -1.2362    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8074   -2.4379   -0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1460   -1.8177    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8871   -0.1913    1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2875   -0.6617    1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8856    1.4454   -0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4626    1.5783   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004   -1.5332   -2.7887 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  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 19 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sarkosyl	MeSH
Sarkosyl L	MeSH
Sarkosyl, ammonium salt	MeSH
4-Isopropylaminoantipyrine	MeSH
Gardol	MeSH
Lauroyl sarcosine	MeSH
Sarkosyl NL 30	MeSH
Sarkosyl, potassium salt	MeSH
Sarkosyl NL	MeSH
Sodium N-laurylsarcosinate	MeSH
N-Lauroyl sarcosine	MeSH
N-Lauroylsarcosinate	MeSH
Sarcosyl NL	MeSH
N-Dodecanoyl-N-methylglycine	MeSH
N-Lauroyl sarcosinate	MeSH
N-Lauroyl-N-methylaminoacetic acid	MeSH
N-Lauroylsarcosine sodium salt	MeSH
N-Methyl-N-(1-oxododecyl)glycine sodium salt (1:1)	MeSH
Sodium N-lauroyl sarcosinate	MeSH
Sodium N-lauroylsarcosinate	MeSH
Sodium lauroyl sarcosinate	MeSH

Chemical Formula

C₁₅H₂₉NO₃

Average Molecular Weight

271.3957

Monoisotopic Molecular Weight

271.214743799

IUPAC Name

2-(N-methyldodecanamido)acetic acid

Traditional Name

gardol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H29NO3/c1-3-4-5-6-7-8-9-10-11-12-14(17)16(2)13-15(18)19/h3-13H2,1-2H3,(H,18,19)

InChI Key

BACYUWVYYTXETD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	3.82	ALOGPS
logP	3.6	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-0.76	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	76.38 m³·mol⁻¹	ChemAxon
Polarizability	33.12 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
DeepCCS	[M+H]+	172.708	30932474
DeepCCS	[M-H]-	168.688	30932474
DeepCCS	[M-2H]-	205.747	30932474
DeepCCS	[M+Na]+	181.629	30932474
AllCCS	[M+H]+	172.4	32859911
AllCCS	[M+H-H2O]+	169.3	32859911
AllCCS	[M+NH4]+	175.2	32859911
AllCCS	[M+Na]+	176.0	32859911
AllCCS	[M-H]-	172.0	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	174.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-LAUROYLSARCOSINE	CCCCCCCCCCCC(=O)N(C)CC(O)=O	3093.0	Standard polar	33892256
N-LAUROYLSARCOSINE	CCCCCCCCCCCC(=O)N(C)CC(O)=O	1963.7	Standard non polar	33892256
N-LAUROYLSARCOSINE	CCCCCCCCCCCC(=O)N(C)CC(O)=O	2178.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lauroylsarcosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-8910000000-9c0aca02bf332b3c35d7	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lauroylsarcosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lauroylsarcosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Lauroylsarcosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 30V, Positive-QTOF	splash10-0006-9000000000-0c21cfcd51fc37fa1d86	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 15V, Positive-QTOF	splash10-0006-9010000000-9efd146a59fcec39bf9b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 45V, Positive-QTOF	splash10-0006-9000000000-d6a868a0fb6fbb42ab99	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 60V, Positive-QTOF	splash10-052f-9000000000-fd56e9d07dfa3f3f9d4e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 30V, Negative-QTOF	splash10-000i-9010000000-db44bd91cc691e9dc14a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 15V, Negative-QTOF	splash10-000i-9050000000-01589d9126eb4d22e3f8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 75V, Positive-QTOF	splash10-0a4i-9000000000-5254fbd1915f04b8f4ee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 90V, Positive-QTOF	splash10-0a4i-9000000000-a1e8067c7e5a5cdd15d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 90V, Positive-QTOF	splash10-0a4i-9000000000-4df8acd1fe6dff4dc3ee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 45V, Negative-QTOF	splash10-000i-9000000000-8f0c95e2acd64d84482a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 60V, Negative-QTOF	splash10-000i-9000000000-b64915fbcae172d66178	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 75V, Negative-QTOF	splash10-000i-9000000000-83875d710aab43e3f3f3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Lauroylsarcosine 45V, Positive-QTOF	splash10-0006-9000000000-999a782c9b43d5f67d29	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lauroylsarcosine 10V, Positive-QTOF	splash10-00di-3190000000-f5691b835c5d230bfb41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lauroylsarcosine 20V, Positive-QTOF	splash10-006x-9320000000-f31dcd8e7a50da48d279	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lauroylsarcosine 40V, Positive-QTOF	splash10-006x-9200000000-d478a6c9401aaf7f8942	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lauroylsarcosine 10V, Negative-QTOF	splash10-00di-0090000000-83fae2d4e0ac59334f5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lauroylsarcosine 20V, Negative-QTOF	splash10-00fr-3290000000-6eb8787123d5468c024c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Lauroylsarcosine 40V, Negative-QTOF	splash10-022l-9310000000-908cffbe1ba38e6745a5	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7348

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for N-Lauroylsarcosine (HMDB0255165)

MOL for HMDB0255165 (N-Lauroylsarcosine)

3D MOL for HMDB0255165 (N-Lauroylsarcosine)

3D SDF for HMDB0255165 (N-Lauroylsarcosine)

3D-SDF for HMDB0255165 (N-Lauroylsarcosine)

PDB for HMDB0255165 (N-Lauroylsarcosine)

3D PDB for HMDB0255165 (N-Lauroylsarcosine)

SMILES for HMDB0255165 (N-Lauroylsarcosine)

INCHI for HMDB0255165 (N-Lauroylsarcosine)

Structure for HMDB0255165 (N-Lauroylsarcosine)

3D Structure for HMDB0255165 (N-Lauroylsarcosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra