NP-MRD: Showing NP-Card for (9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid (NP0034354)

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Record Information

Version

2.0

Created at

2021-06-20 18:06:28 UTC

Updated at

2021-06-30 00:04:41 UTC

NP-MRD ID

NP0034354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid

Provided By

JEOL Database JEOL Logo

Description

9S,10s,11r-trihydroxy-12z,15z-octadecadienoic acid 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. (9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid is found in Dracontium loretense. (9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid was first documented in 2017 (PMID: 28489938). Based on a literature review very few articles have been published on 9s,10s,11r-trihydroxy-12z,15z-octadecadienoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306202120063D          

 55 54  0  0  0  0            999 V2000
    0.8301    3.2758   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5264    2.0565    0.5423 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.4693   -0.5402   -2.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7  6  2  0  0  0  0
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M  END

     RDKit          3D

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M  END

  Mrv1652306202120063D          

 55 54  0  0  0  0            999 V2000
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   -0.7930    0.3111   -1.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7974    1.9511   -2.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0912   -0.1653   -2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    0.2174   -4.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815   -2.5745   -2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -2.6233   -3.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278   -3.3907   -0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -2.0161   -0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7576   -1.8974    0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6936   -0.5007   -0.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2453   -1.5935    1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563   -2.8654    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1537   -0.7945    2.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925   -1.5954    3.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5502    0.0835    3.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1357    0.7876    3.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332    2.1834    2.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351    0.9267    1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232    1.1532    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0345    2.5143    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8900    4.5744   -0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 18 19  1  0  0  0  0
 10 12  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 14  1  0  0  0  0
  4  3  2  0  0  0  0
  7  8  1  0  0  0  0
  3  2  1  0  0  0  0
 14 15  1  0  0  0  0
  2  1  1  0  0  0  0
  6  5  1  0  0  0  0
  8  9  1  0  0  0  0
 15 16  1  0  0  0  0
 12 13  1  0  0  0  0
  5  4  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10  8  1  0  0  0  0
 21 22  2  0  0  0  0
 17 18  1  0  0  0  0
 21 23  1  0  0  0  0
  7 34  1  0  0  0  0
  6 33  1  0  0  0  0
  5 31  1  0  0  0  0
  5 32  1  0  0  0  0
 10 37  1  1  0  0  0
  8 35  1  1  0  0  0
 12 39  1  1  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
 19 51  1  0  0  0  0
 19 52  1  0  0  0  0
 20 53  1  0  0  0  0
 20 54  1  0  0  0  0
  3 29  1  0  0  0  0
  2 27  1  0  0  0  0
  2 28  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  9 36  1  0  0  0  0
 13 40  1  0  0  0  0
  4 30  1  0  0  0  0
 11 38  1  0  0  0  0
 23 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034354

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O5/c1-2-3-4-6-9-12-15(19)18(23)16(20)13-10-7-5-8-11-14-17(21)22/h3-4,9,12,15-16,18-20,23H,2,5-8,10-11,13-14H2,1H3,(H,21,22)/b4-3-,12-9-/t15-,16+,18-/m1/s1

> <INCHI_KEY>
KFINXCASWPGHEW-YQFBSDGMSA-N

> <FORMULA>
C18H32O5

> <MOLECULAR_WEIGHT>
328.449

> <EXACT_MASS>
328.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
36.487589965660106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10S,11R,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
3.0412585133333327

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.038719043839944

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615325349527033

> <JCHEM_PKA_STRONGEST_BASIC>
-3.185135414786136

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
92.75729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10S,11R,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 54  0  0  0  0  0  0  0  0999 V2000
    0.8301    3.2758   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5264    2.0565    0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7276    1.6724   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821    0.5843   -1.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8932   -0.5173   -1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4693   -0.5402   -2.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614   -0.2479   -3.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9746    0.1972   -2.5244 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2720    1.5032   -3.0483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2368   -0.6724   -2.7657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5405   -0.6952   -4.1809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1918   -2.1300   -2.2657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2923   -2.9022   -3.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065   -2.3177   -0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7218   -1.5676    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130   -1.8004    1.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1497   -0.9822    2.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4942    0.3271    3.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2006    1.3576    1.9915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4549    1.9320    1.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0778    2.8024    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834    2.4083   -0.9101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1769    4.1148    0.4493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0173    3.5642    0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106    4.1319   -0.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500    3.0696   -1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8081    1.2374    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8564    2.2813    1.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5627    2.3709   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341    0.4726   -1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3759   -1.4747   -1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0360   -0.4559   -0.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469   -0.8394   -3.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533   -0.3213   -4.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7930    0.3111   -1.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7974    1.9511   -2.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0912   -0.1653   -2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    0.2174   -4.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815   -2.5745   -2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -2.6233   -3.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278   -3.3907   -0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -2.0161   -0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7576   -1.8974    0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6936   -0.5007   -0.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2453   -1.5935    1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563   -2.8654    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1537   -0.7945    2.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925   -1.5954    3.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5502    0.0835    3.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1357    0.7876    3.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332    2.1834    2.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351    0.9267    1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232    1.1532    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0345    2.5143    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8900    4.5744   -0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0
 18 19  1  0
 10 12  1  0
 19 20  1  0
 20 21  1  0
 12 14  1  0
  4  3  2  0
  7  8  1  0
  3  2  1  0
 14 15  1  0
  2  1  1  0
  6  5  1  0
  8  9  1  0
 15 16  1  0
 12 13  1  0
  5  4  1  0
 16 17  1  0
 10 11  1  0
 10  8  1  0
 21 22  2  0
 17 18  1  0
 21 23  1  0
  7 34  1  0
  6 33  1  0
  5 31  1  0
  5 32  1  0
 10 37  1  1
  8 35  1  1
 12 39  1  1
 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
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
  3 29  1  0
  2 27  1  0
  2 28  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  9 36  1  0
 13 40  1  0
  4 30  1  0
 11 38  1  0
 23 55  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       0.830   3.276  -0.041  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.526   2.057   0.542  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.728   1.672  -0.271  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.882   0.584  -1.044  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.893  -0.517  -1.297  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.469  -0.540  -2.737  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.261  -0.248  -3.251  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.975   0.197  -2.524  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.272   1.503  -3.048  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.237  -0.672  -2.766  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.541  -0.695  -4.181  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.192  -2.130  -2.266  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.292  -2.902  -3.068  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.807  -2.318  -0.796  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.722  -1.568   0.172  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.313  -1.800   1.629  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.150  -0.982   2.621  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.494   0.327   3.081  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.201   1.358   1.992  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.455   1.932   1.343  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.078   2.802   0.178  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.683   2.408  -0.910  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.177   4.115   0.449  0.00  0.00           O+0
HETATM   24  H   UNK     0      -0.017   3.564   0.589  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.511   4.132  -0.102  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.450   3.070  -1.047  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.808   1.237   0.626  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.856   2.281   1.563  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.563   2.371  -0.217  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.834   0.473  -1.563  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.376  -1.475  -1.065  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.036  -0.456  -0.625  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.247  -0.839  -3.439  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.153  -0.321  -4.332  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.793   0.311  -1.453  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.797   1.951  -2.349  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.091  -0.165  -2.301  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.353   0.217  -4.485  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.182  -2.575  -2.430  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.476  -2.623  -3.988  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.828  -3.391  -0.564  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.765  -2.016  -0.642  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.758  -1.897   0.027  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.694  -0.501  -0.054  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.245  -1.593   1.768  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.456  -2.865   1.853  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.154  -0.795   2.224  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.293  -1.595   3.521  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.550   0.084   3.586  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.136   0.788   3.843  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.633   2.183   2.441  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.535   0.927   1.236  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.123   1.153   0.962  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.035   2.514   2.068  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.890   4.574  -0.368  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    3    1   27   28                                             
CONECT    3    4    2   29                                                  
CONECT    4    3    5   30                                                  
CONECT    5    6    4   31   32                                             
CONECT    6    7    5   33                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9   10   35                                             
CONECT    9    8   36                                                       
CONECT   10   12   11    8   37                                             
CONECT   11   10   38                                                       
CONECT   12   10   14   13   39                                             
CONECT   13   12   40                                                       
CONECT   14   12   15   41   42                                             
CONECT   15   14   16   43   44                                             
CONECT   16   15   17   45   46                                             
CONECT   17   16   18   47   48                                             
CONECT   18   19   17   49   50                                             
CONECT   19   18   20   51   52                                             
CONECT   20   19   21   53   54                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   55                                                       
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    2                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
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   19                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   23                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  108    0
END

RDKit          3D

55 54  0  0  0  0  0  0  0  0999 V2000
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    1.5264    2.0565    0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7276    1.6724   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821    0.5843   -1.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8932   -0.5173   -1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4693   -0.5402   -2.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614   -0.2479   -3.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9746    0.1972   -2.5244 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.2368   -0.6724   -2.7657 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.2923   -2.9022   -3.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8081    1.2374    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8564    2.2813    1.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5627    2.3709   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341    0.4726   -1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3759   -1.4747   -1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0360   -0.4559   -0.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469   -0.8394   -3.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0912   -0.1653   -2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    0.2174   -4.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815   -2.5745   -2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -2.6233   -3.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278   -3.3907   -0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -2.0161   -0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7576   -1.8974    0.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6936   -0.5007   -0.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2453   -1.5935    1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563   -2.8654    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1537   -0.7945    2.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925   -1.5954    3.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5502    0.0835    3.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1357    0.7876    3.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332    2.1834    2.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351    0.9267    1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232    1.1532    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0345    2.5143    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8900    4.5744   -0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0
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 10 12  1  0
 19 20  1  0
 20 21  1  0
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  4  3  2  0
  7  8  1  0
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  2  1  1  0
  6  5  1  0
  8  9  1  0
 15 16  1  0
 12 13  1  0
  5  4  1  0
 16 17  1  0
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 17 18  1  0
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  7 34  1  0
  6 33  1  0
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  5 32  1  0
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  3 29  1  0
  2 27  1  0
  2 28  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  9 36  1  0
 13 40  1  0
  4 30  1  0
 11 38  1  0
 23 55  1  0
M  END

View in JSmol

Synonyms

Value	Source
9S,10S,11R-Trihydroxy-12Z,15Z-octadecadienoate	Generator

Chemical Formula

C₁₈H₃₂O₅

Average Mass

328.4490 Da

Monoisotopic Mass

328.22497 Da

IUPAC Name

(9S,10S,11R,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid

Traditional Name

(9S,10S,11R,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid

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

InChI Identifier

InChI=1S/C18H32O5/c1-2-3-4-6-9-12-15(19)18(23)16(20)13-10-7-5-8-11-14-17(21)22/h3-4,9,12,15-16,18-20,23H,2,5-8,10-11,13-14H2,1H3,(H,21,22)/b4-3-,12-9-/t15-,16+,18-/m1/s1

InChI Key

KFINXCASWPGHEW-YQFBSDGMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Dracontium loretense	JEOL database	Benavides, A., et al, J. Nat. Prod. 72, 813 (2009)

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
1,2-diol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Other Octadecanoids (LMFA02000021 )

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	3.81	ALOGPS
logP	3.04	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	92.76 m³·mol⁻¹	ChemAxon
Polarizability	36.49 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

Not Available

Chemspider ID

17220738

KEGG Compound ID

Not Available

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

Not Available

Good Scents ID

Not Available

References

General References

Hu W, Pan X, Abbas HMK, Li F, Dong W: Metabolites contributing to Rhizoctonia solani AG-1-IA maturation and sclerotial differentiation revealed by UPLC-QTOF-MS metabolomics. PLoS One. 2017 May 10;12(5):e0177464. doi: 10.1371/journal.pone.0177464. eCollection 2017. [PubMed:28489938 ]
Benavides, A., et al. (2009). Benavides, A., et al, J. Nat. Prod. 72, 813 (2009). J. Nat. Prod..

Showing NP-Card for (9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid (NP0034354)

MOL for NP0034354 ((9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

3D MOL for NP0034354 ((9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

3D SDF for NP0034354 ((9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

3D-SDF for NP0034354 ((9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

PDB for NP0034354 ((9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

3D PDB for NP0034354 ((9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

SMILES for NP0034354 ((9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

INCHI for NP0034354 ((9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

Structure for NP0034354 ((9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

3D Structure for NP0034354 ((9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

Showing NP-Card for (9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid (NP0034354)

MOL for NP0034354 ((9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

3D MOL for NP0034354 ((9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

3D SDF for NP0034354 ((9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

3D-SDF for NP0034354 ((9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

PDB for NP0034354 ((9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

3D PDB for NP0034354 ((9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

SMILES for NP0034354 ((9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

INCHI for NP0034354 ((9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

Structure for NP0034354 ((9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)

3D Structure for NP0034354 ((9S,10R,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid)