NP-MRD: Showing NP-Card for 9-hydroxy-octadeca-10,12,15-trienoic acid (NP0031148)

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Record Information

Version

1.0

Created at

2021-06-19 22:18:43 UTC

Updated at

2021-06-29 23:59:33 UTC

NP-MRD ID

NP0031148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxy-octadeca-10,12,15-trienoic acid

Provided By

JEOL Database JEOL Logo

Description

9S-hotre belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, 9S-hotre is considered to be an octadecanoid. 9-hydroxy-octadeca-10,12,15-trienoic acid is found in Apis cerana and Artocarpus communis. It was first documented in 2000 (PMID: 10830513). Based on a literature review a significant number of articles have been published on 9s-hotre (PMID: 12882150) (PMID: 21481031) (PMID: 23370715) (PMID: 23479199).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100183D          

 51 50  0  0  0  0            999 V2000
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   -0.5268    1.8449    2.8003 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.6995   -1.5562    3.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -2.3203    2.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 51 50  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202100183D          

 51 50  0  0  0  0            999 V2000
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   -1.2173    1.0876   -3.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -0.2455   -2.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    1.3887   -3.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079    2.6932   -2.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831    0.1602    0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 12  1  0  0  0  0
  4  5  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4  3  2  0  0  0  0
 14 15  1  0  0  0  0
  6  7  2  0  0  0  0
 15 16  1  0  0  0  0
  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
  6  5  1  0  0  0  0
 17 18  1  0  0  0  0
  2  1  1  0  0  0  0
 18 19  1  0  0  0  0
  7  8  1  0  0  0  0
 19 21  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8  9  2  0  0  0  0
 19 20  2  0  0  0  0
  6 31  1  0  0  0  0
  7 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  0  0  0  0
  4 28  1  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
  3 27  1  0  0  0  0
  2 25  1  0  0  0  0
  2 26  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
 10 35  1  6  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 13 39  1  0  0  0  0
 13 40  1  0  0  0  0
 14 41  1  0  0  0  0
 14 42  1  0  0  0  0
 15 43  1  0  0  0  0
 15 44  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 21 51  1  0  0  0  0
 11 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(O[H])C(\[H])=C(/[H])\C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14,17,19H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3-,8-6-,14-11+/t17-/m1/s1

> <INCHI_KEY>
RIGGEAZDTKMXSI-MEBVTJQTSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.435

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.1306331849712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid

> <ALOGPS_LOGP>
5.31

> <JCHEM_LOGP>
4.829144070666667

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.795677819372834

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676745528848416

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5759708673155046

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
91.1509

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9(S)-HOTrE

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 50  0  0  0  0  0  0  0  0999 V2000
   -1.1632    2.8808    3.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5268    1.8449    2.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9696    1.8559    2.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7643    0.8855    3.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -0.4384    3.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995   -1.5562    3.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -2.3203    2.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5699   -2.2299    2.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3190   -2.9207    1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8189   -2.8567    1.2883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3963   -2.5822    2.5623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117   -1.7865    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -1.9281   -1.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372   -0.9867   -2.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951    0.5089   -1.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9256    1.0903   -1.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381    0.8226   -2.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4399    1.6242   -2.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0910    1.3954   -0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7223    2.2364   -0.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9749    0.1394   -0.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2511    2.8741    3.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9389    2.6716    4.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042    3.8893    3.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7919    2.0675    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500    0.8622    3.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4522    2.7584    2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8385    1.0715    3.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961   -0.5940    4.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2951   -0.4448    4.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7672   -1.7539    2.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3208   -3.0758    1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0639   -1.5575    2.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326   -3.5672    0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895   -3.8402    0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0249   -3.2328    3.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0895   -0.7932    0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4070   -1.8401    0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6356   -1.7636   -1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621   -2.9583   -1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8385   -1.1570   -3.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858   -1.2723   -2.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9890    0.7169   -0.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6883    1.0565   -2.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6137    0.6978   -0.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0434    2.1735   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2173    1.0876   -3.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -0.2455   -2.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    1.3887   -3.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079    2.6932   -2.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831    0.1602    0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 12  1  0
  4  5  1  0
 12 13  1  0
 13 14  1  0
  4  3  2  0
 14 15  1  0
  6  7  2  0
 15 16  1  0
  3  2  1  0
 16 17  1  0
  6  5  1  0
 17 18  1  0
  2  1  1  0
 18 19  1  0
  7  8  1  0
 19 21  1  0
  9 10  1  0
 10 11  1  0
  8  9  2  0
 19 20  2  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  3 27  1  0
  2 25  1  0
  2 26  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 10 35  1  6
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
 11 36  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.163   2.881   3.713  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.527   1.845   2.800  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.970   1.856   2.922  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.764   0.886   3.403  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.351  -0.438   3.977  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.700  -1.556   3.036  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.871  -2.320   2.307  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.570  -2.230   2.276  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.319  -2.921   1.402  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.819  -2.857   1.288  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.396  -2.582   2.562  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.312  -1.787   0.305  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.718  -1.928  -1.098  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.337  -0.987  -2.134  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.295   0.509  -1.806  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.926   1.090  -1.441  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.838   0.823  -2.486  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.440   1.624  -2.232  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.091   1.395  -0.894  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.722   2.236  -0.273  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.975   0.139  -0.430  0.00  0.00           O+0
HETATM   22  H   UNK     0      -2.251   2.874   3.591  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.939   2.672   4.765  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.804   3.889   3.481  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.792   2.067   1.760  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.950   0.862   3.022  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.452   2.758   2.543  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.838   1.071   3.394  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.896  -0.594   4.916  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.295  -0.445   4.258  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.767  -1.754   2.942  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.321  -3.076   1.662  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.064  -1.558   2.972  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.833  -3.567   0.674  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.189  -3.840   0.977  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.025  -3.233   3.183  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.090  -0.793   0.714  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.407  -1.840   0.251  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.636  -1.764  -1.062  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.862  -2.958  -1.447  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.838  -1.157  -3.096  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.386  -1.272  -2.287  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.989   0.717  -0.982  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.688   1.056  -2.672  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.614   0.698  -0.468  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.043   2.174  -1.311  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.217   1.088  -3.480  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.597  -0.246  -2.515  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.180   1.389  -3.005  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.208   2.693  -2.307  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.383   0.160   0.464  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3    1   25   26                                             
CONECT    3    4    2   27                                                  
CONECT    4    5    3   28                                                  
CONECT    5    4    6   29   30                                             
CONECT    6    7    5   31                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7    9   33                                                  
CONECT    9   10    8   34                                                  
CONECT   10   12    9   11   35                                             
CONECT   11   10   36                                                       
CONECT   12   10   13   37   38                                             
CONECT   13   12   14   39   40                                             
CONECT   14   13   15   41   42                                             
CONECT   15   14   16   43   44                                             
CONECT   16   15   17   45   46                                             
CONECT   17   16   18   47   48                                             
CONECT   18   17   19   49   50                                             
CONECT   19   18   21   20                                                  
CONECT   20   19                                                            
CONECT   21   19   51                                                       
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    2                                                            
CONECT   26    2                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   21                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  100    0
END

RDKit          3D

51 50  0  0  0  0  0  0  0  0999 V2000
   -1.1632    2.8808    3.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5268    1.8449    2.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9696    1.8559    2.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7643    0.8855    3.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -0.4384    3.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995   -1.5562    3.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -2.3203    2.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5699   -2.2299    2.2759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3190   -2.9207    1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8189   -2.8567    1.2883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3963   -2.5822    2.5623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117   -1.7865    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -1.9281   -1.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372   -0.9867   -2.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951    0.5089   -1.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9256    1.0903   -1.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8381    0.8226   -2.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4399    1.6242   -2.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0910    1.3954   -0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7223    2.2364   -0.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9749    0.1394   -0.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2511    2.8741    3.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9389    2.6716    4.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042    3.8893    3.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7919    2.0675    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500    0.8622    3.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4522    2.7584    2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8385    1.0715    3.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961   -0.5940    4.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2951   -0.4448    4.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7672   -1.7539    2.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3208   -3.0758    1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0639   -1.5575    2.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8326   -3.5672    0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895   -3.8402    0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0249   -3.2328    3.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0895   -0.7932    0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4070   -1.8401    0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6356   -1.7636   -1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8621   -2.9583   -1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8385   -1.1570   -3.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858   -1.2723   -2.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9890    0.7169   -0.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6883    1.0565   -2.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6137    0.6978   -0.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0434    2.1735   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2173    1.0876   -3.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -0.2455   -2.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    1.3887   -3.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079    2.6932   -2.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831    0.1602    0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 12  1  0
  4  5  1  0
 12 13  1  0
 13 14  1  0
  4  3  2  0
 14 15  1  0
  6  7  2  0
 15 16  1  0
  3  2  1  0
 16 17  1  0
  6  5  1  0
 17 18  1  0
  2  1  1  0
 18 19  1  0
  7  8  1  0
 19 21  1  0
  9 10  1  0
 10 11  1  0
  8  9  2  0
 19 20  2  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  3 27  1  0
  2 25  1  0
  2 26  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 10 35  1  6
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
 11 36  1  0
M  END

View in JSmol

Synonyms

Value	Source
(9S)-(10E,12Z,15Z)-9-Hydroxyoctadecatri-10,12,15-enoic acid	ChEBI
(9S,10E,12Z,15Z)-9-Hydroxyoctadecatrienoic acid	ChEBI
9(S)-HOT	ChEBI
9-Hydroxy-10,12,15-octadecatrienoic acid	ChEBI
9(S)-HOTrE	Kegg
(9S)-(10E,12Z,15Z)-9-Hydroxyoctadecatri-10,12,15-enoate	Generator
(9S,10E,12Z,15Z)-9-Hydroxyoctadecatrienoate	Generator
9-Hydroxy-10,12,15-octadecatrienoate	Generator
(10E,12Z,15Z)-9-OH-10,12,15-ODTA	MeSH
9-OH-10,12,15-ODTA	MeSH
9S-HOTrE	ChEBI

Chemical Formula

C₁₈H₃₀O₃

Average Mass

294.4350 Da

Monoisotopic Mass

294.21949 Da

IUPAC Name

(9S,10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid

Traditional Name

9(S)-HOTrE

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(O[H])C(\[H])=C(/[H])\C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14,17,19H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3-,8-6-,14-11+/t17-/m1/s1

InChI Key

RIGGEAZDTKMXSI-MEBVTJQTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	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
Apis cerana	LOTUS Database	35616633
Artocarpus altilis	JEOL database	McLean, S., et al, Magn. Reson. Chem. 34, 719 (1996)
Isatis tinctoria	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

lipid (CHEBI:80447 )
Other Octadecanoids (C16326 )
Other Octadecanoids (LMFA02000024 )

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	5.31	ALOGPS
logP	4.83	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	91.15 m³·mol⁻¹	ChemAxon
Polarizability	34.13 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048303

Chemspider ID

4944252

KEGG Compound ID

C16326

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

80447

Good Scents ID

Not Available

References

General References

Dong M, Oda Y, Hirota M: (10E,12Z,15Z)-9-hydroxy-10,12,15-octadecatrienoic acid methyl ester as an anti-inflammatory compound from Ehretia dicksonii. Biosci Biotechnol Biochem. 2000 Apr;64(4):882-6. doi: 10.1271/bbb.64.882. [PubMed:10830513 ]
Komaraiah P, Reddy GV, Reddy PS, Raghavendra AS, Ramakrishna SV, Reddanna P: Enhanced production of antimicrobial sesquiterpenes and lipoxygenase metabolites in elicitor-treated hairy root cultures of Solanum tuberosum. Biotechnol Lett. 2003 Apr;25(8):593-7. doi: 10.1023/a:1023038804556. [PubMed:12882150 ]
Lopez MA, Vicente J, Kulasekaran S, Vellosillo T, Martinez M, Irigoyen ML, Cascon T, Bannenberg G, Hamberg M, Castresana C: Antagonistic role of 9-lipoxygenase-derived oxylipins and ethylene in the control of oxidative stress, lipid peroxidation and plant defence. Plant J. 2011 Aug;67(3):447-58. doi: 10.1111/j.1365-313X.2011.04608.x. Epub 2011 Jun 6. [PubMed:21481031 ]
Vellosillo T, Aguilera V, Marcos R, Bartsch M, Vicente J, Cascon T, Hamberg M, Castresana C: Defense activated by 9-lipoxygenase-derived oxylipins requires specific mitochondrial proteins. Plant Physiol. 2013 Feb;161(2):617-27. doi: 10.1104/pp.112.207514. Epub 2012 Dec 12. [PubMed:23370715 ]
Saubeau G, Goulitquer S, Barloy D, Potin P, Andrivon D, Val F: Differential induction of oxylipin pathway in potato and tobacco cells by bacterial and oomycete elicitors. Plant Cell Rep. 2013 May;32(5):579-89. doi: 10.1007/s00299-012-1377-y. Epub 2013 Mar 12. [PubMed:23479199 ]
McLean, S., et al. (1996). McLean, S., et al, Magn. Reson. Chem. 34, 719 (1996). Mag. Reson. Chem..

Showing NP-Card for 9-hydroxy-octadeca-10,12,15-trienoic acid (NP0031148)

MOL for NP0031148 (9-hydroxy-octadeca-10,12,15-trienoic acid)

3D MOL for NP0031148 (9-hydroxy-octadeca-10,12,15-trienoic acid)

3D SDF for NP0031148 (9-hydroxy-octadeca-10,12,15-trienoic acid)

3D-SDF for NP0031148 (9-hydroxy-octadeca-10,12,15-trienoic acid)

PDB for NP0031148 (9-hydroxy-octadeca-10,12,15-trienoic acid)

3D PDB for NP0031148 (9-hydroxy-octadeca-10,12,15-trienoic acid)

SMILES for NP0031148 (9-hydroxy-octadeca-10,12,15-trienoic acid)

INCHI for NP0031148 (9-hydroxy-octadeca-10,12,15-trienoic acid)

Structure for NP0031148 (9-hydroxy-octadeca-10,12,15-trienoic acid)

3D Structure for NP0031148 (9-hydroxy-octadeca-10,12,15-trienoic acid)