NP-MRD: Showing NP-Card for (S)-N-tetradecanoyl-HSL (NP0010498)

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Record Information

Version

2.0

Created at

2021-01-05 19:59:54 UTC

Updated at

2021-07-15 17:06:16 UTC

NP-MRD ID

NP0010498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-N-tetradecanoyl-HSL

Provided By

NPAtlas

Description

N-tetradecanoyl-homoserine lactone belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Thus, N-tetradecanoyl-homoserine lactone is considered to be a fatty amide. (S)-N-tetradecanoyl-HSL is found in Cronobacter sakazakii and Enterobacter. (S)-N-tetradecanoyl-HSL was first documented in 2008 (PMID: 18603795). Based on a literature review very few articles have been published on N-tetradecanoyl-homoserine lactone (PMID: 22132860) (PMID: 31344938).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306242107383D          

 55 55  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652306242107383D          

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   -1.2686   -0.1626    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4767    0.6626    2.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549   -1.0062    2.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427    0.3799    2.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7007    0.5030    1.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857   -2.2192    2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093   -1.8931    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054   -0.9583    2.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0435   -2.3712    1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997    0.5897    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104   -0.7781   -0.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148    1.0086   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0937   -0.0656    0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1136   -0.0355   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4400   -0.7231   -2.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6705    1.3169   -3.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4264    1.6286   -3.3508 H   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  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 17  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  2 26  1  0  0  0  0
  2 27  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  6 34  1  0  0  0  0
  6 35  1  0  0  0  0
  7 36  1  0  0  0  0
  7 37  1  0  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
  9 40  1  0  0  0  0
  9 41  1  0  0  0  0
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
 11 44  1  0  0  0  0
 11 45  1  0  0  0  0
 12 46  1  0  0  0  0
 12 47  1  0  0  0  0
 13 48  1  0  0  0  0
 13 49  1  0  0  0  0
 16 50  1  0  0  0  0
 17 51  1  1  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
 19 54  1  0  0  0  0
 19 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010498

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N(C(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@]1([H])C(=O)OC([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)/t16-/m0/s1

> <INCHI_KEY>
ZQAYHOXXVBVXPZ-INIZCTEOSA-N

> <FORMULA>
C18H33NO3

> <MOLECULAR_WEIGHT>
311.466

> <EXACT_MASS>
311.246043927

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.55336135380411

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(3S)-2-oxooxolan-3-yl]tetradecanamide

> <ALOGPS_LOGP>
5.02

> <JCHEM_LOGP>
4.508447347333333

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.613445975272043

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3357020593671747

> <JCHEM_POLAR_SURFACE_AREA>
55.4

> <JCHEM_REFRACTIVITY>
88.09589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(3S)-2-oxooxolan-3-yl]tetradecanamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 55  0  0  0  0  0  0  0  0999 V2000
   -5.8422    2.4042    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1289    1.8148   -1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3387    0.5303   -1.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7208   -0.4742   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9525   -1.7460   -0.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612   -1.5496   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5160   -0.1336    2.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1342   -1.4720    1.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6322   -1.3470    1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0444   -0.4259    0.6392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5237   -0.3542    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925   -1.0008    1.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1580    0.4552   -0.3463 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6124    0.5435   -0.3918 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0251    0.1565   -1.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6702    1.4161   -2.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7037    2.4752   -1.6110 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0401    1.9762   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5839    2.5507    0.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7442    2.6164    0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1952    1.8138    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3532    3.4089    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1994    1.5335   -1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8272    2.5459   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5581    0.0747   -2.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2796    0.8001   -1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7958   -0.7098   -0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5652   -0.1037    0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2604   -2.5030    0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1647   -2.1228   -1.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -2.5563   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477   -0.9201   -1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3588   -1.6085    1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086    0.0116    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494   -1.8716    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686   -0.1626    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4767    0.6626    2.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549   -1.0062    2.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427    0.3799    2.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7007    0.5030    1.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857   -2.2192    2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093   -1.8931    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054   -0.9583    2.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0435   -2.3712    1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997    0.5897    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104   -0.7781   -0.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148    1.0086   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0937   -0.0656    0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1136   -0.0355   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4400   -0.7231   -2.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6705    1.3169   -3.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4264    1.6286   -3.3508 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  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 16 50  1  0
 17 51  1  1
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.842   2.404   0.123  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.129   1.815  -1.220  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.339   0.530  -1.414  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.721  -0.474  -0.348  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.952  -1.746  -0.523  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.461  -1.550  -0.431  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.040  -0.985   0.903  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.522  -0.837   0.864  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.984  -0.283   2.137  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.516  -0.134   2.037  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.134  -1.472   1.790  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.632  -1.347   1.746  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.044  -0.426   0.639  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.524  -0.354   0.615  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.192  -1.001   1.433  0.00  0.00           O+0
HETATM   16  N   UNK     0       5.158   0.455  -0.346  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.612   0.544  -0.392  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.025   0.157  -1.807  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.670   1.416  -2.570  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.704   2.475  -1.611  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.040   1.976  -0.362  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.584   2.551   0.616  0.00  0.00           O+0
HETATM   23  H   UNK     0      -4.744   2.616   0.195  0.00  0.00           H+0
HETATM   24  H   UNK     0      -6.195   1.814   0.972  0.00  0.00           H+0
HETATM   25  H   UNK     0      -6.353   3.409   0.152  0.00  0.00           H+0
HETATM   26  H   UNK     0      -7.199   1.534  -1.292  0.00  0.00           H+0
HETATM   27  H   UNK     0      -5.827   2.546  -1.987  0.00  0.00           H+0
HETATM   28  H   UNK     0      -5.558   0.075  -2.395  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.280   0.800  -1.389  0.00  0.00           H+0
HETATM   30  H   UNK     0      -6.796  -0.710  -0.483  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.565  -0.104   0.675  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.260  -2.503   0.205  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.165  -2.123  -1.551  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.995  -2.556  -0.537  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.048  -0.920  -1.217  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.359  -1.609   1.752  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.509   0.012   1.037  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.149  -1.872   0.701  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.269  -0.163   0.033  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.477   0.663   2.443  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.155  -1.006   2.989  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.943   0.380   2.925  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.701   0.503   1.129  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.886  -2.219   2.572  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.809  -1.893   0.801  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.005  -0.958   2.722  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.043  -2.371   1.622  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.600   0.590   0.756  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.710  -0.778  -0.359  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.615   1.009  -1.045  0.00  0.00           H+0
HETATM   51  H   UNK     0       7.094  -0.066   0.373  0.00  0.00           H+0
HETATM   52  H   UNK     0       8.114  -0.036  -1.806  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.440  -0.723  -2.146  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.670   1.317  -3.037  0.00  0.00           H+0
HETATM   55  H   UNK     0       7.426   1.629  -3.351  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3   26   27                                             
CONECT    3    2    4   28   29                                             
CONECT    4    3    5   30   31                                             
CONECT    5    4    6   32   33                                             
CONECT    6    5    7   34   35                                             
CONECT    7    6    8   36   37                                             
CONECT    8    7    9   38   39                                             
CONECT    9    8   10   40   41                                             
CONECT   10    9   11   42   43                                             
CONECT   11   10   12   44   45                                             
CONECT   12   11   13   46   47                                             
CONECT   13   12   14   48   49                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   50                                                  
CONECT   17   16   18   21   51                                             
CONECT   18   17   19   52   53                                             
CONECT   19   18   20   54   55                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   17                                                  
CONECT   22   21                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    2                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   13                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   19                                                            
CONECT   55   19                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  110    0
END

RDKit          3D

55 55  0  0  0  0  0  0  0  0999 V2000
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   -5.8272    2.5459   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5581    0.0747   -2.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2796    0.8001   -1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7958   -0.7098   -0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5652   -0.1037    0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1647   -2.1228   -1.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -2.5563   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477   -0.9201   -1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3588   -1.6085    1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086    0.0116    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494   -1.8716    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686   -0.1626    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4767    0.6626    2.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549   -1.0062    2.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427    0.3799    2.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7007    0.5030    1.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857   -2.2192    2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093   -1.8931    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054   -0.9583    2.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0435   -2.3712    1.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997    0.5897    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104   -0.7781   -0.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6148    1.0086   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0937   -0.0656    0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1136   -0.0355   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4400   -0.7231   -2.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6705    1.3169   -3.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4264    1.6286   -3.3508 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
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  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
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  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
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 11 44  1  0
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 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 16 50  1  0
 17 51  1  1
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₈H₃₃NO₃

Average Mass

311.4660 Da

Monoisotopic Mass

311.24604 Da

IUPAC Name

N-[(3S)-2-oxooxolan-3-yl]tetradecanamide

Traditional Name

N-[(3S)-2-oxooxolan-3-yl]tetradecanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)N[C@H]1CCOC1=O

InChI Identifier

InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)/t16-/m0/s1

InChI Key

ZQAYHOXXVBVXPZ-INIZCTEOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cronobacter sakazakii	LOTUS Database	35616633
Enterobacter	NPAtlas	22132860

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) 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 and derivatives

Alternative Parents

Substituents

Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Acyl-homoserine lactone
Acyl-l-homoserine lactone
Fatty amide
Gamma butyrolactone
N-acyl-amine
Fatty acyl
Oxolane
Secondary carboxylic acid amide
Lactone
Carboxylic acid ester
Carboxamide group
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

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
logP	5.02	ALOGPS
logP	4.51	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	12.61	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.4 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	88.1 m³·mol⁻¹	ChemAxon
Polarizability	37.55 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA005825

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21467810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

58122267

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Araujo FD, Esper LM, Kuaye AY, Sircili MP, Marsaioli AJ: N-acyl-homoserine lactones from Enterobacter sakazakii (Cronobacter spp.) and their degradation by Bacillus cereus enzymes. J Agric Food Chem. 2012 Jan 18;60(2):585-92. doi: 10.1021/jf203846f. Epub 2012 Jan 4. [PubMed:22132860 ]
Liu LP, Huang LH, Ding XT, Yan L, Jia SR, Dai YJ, Xie YY, Zhong C: Identification of Quorum-Sensing Molecules of N-Acyl-Homoserine Lactone in Gluconacetobacter Strains by Liquid Chromatography-Tandem Mass Spectrometry. Molecules. 2019 Jul 24;24(15). pii: molecules24152694. doi: 10.3390/molecules24152694. [PubMed:31344938 ]
Wang Y, Ikawa A, Okaue S, Taniguchi S, Osaka I, Yoshimoto A, Kishida Y, Arakawa R, Enomoto K: Quorum sensing signaling molecules involved in the production of violacein by Pseudoalteromonas. Biosci Biotechnol Biochem. 2008 Jul;72(7):1958-61. doi: 10.1271/bbb.80090. Epub 2008 Jul 7. [PubMed:18603795 ]

Showing NP-Card for (S)-N-tetradecanoyl-HSL (NP0010498)

MOL for NP0010498 ((S)-N-tetradecanoyl-HSL)

3D MOL for NP0010498 ((S)-N-tetradecanoyl-HSL)

3D SDF for NP0010498 ((S)-N-tetradecanoyl-HSL)

3D-SDF for NP0010498 ((S)-N-tetradecanoyl-HSL)

PDB for NP0010498 ((S)-N-tetradecanoyl-HSL)

3D PDB for NP0010498 ((S)-N-tetradecanoyl-HSL)

SMILES for NP0010498 ((S)-N-tetradecanoyl-HSL)

INCHI for NP0010498 ((S)-N-tetradecanoyl-HSL)

Structure for NP0010498 ((S)-N-tetradecanoyl-HSL)

3D Structure for NP0010498 ((S)-N-tetradecanoyl-HSL)