NP-MRD: Showing NP-Card for (8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid (NP0034357)

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Record Information

Version

2.0

Created at

2021-06-20 18:06:36 UTC

Updated at

2021-06-30 00:04:41 UTC

NP-MRD ID

NP0034357

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid

Provided By

JEOL Database JEOL Logo

Description

CHEMBL562102 belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, CHEMBL562102 is considered to be an octadecanoid lipid molecule. CHEMBL562102 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid is found in Dracontium loretense. (8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid was first documented in 2009 (Benavides, A., et al.). Based on a literature review very few articles have been published on CHEMBL562102.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306202120063D          

 57 56  0  0  0  0            999 V2000
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   -4.4650    0.7703    2.5904 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.2973    2.3966    0.3393 C   0  0  2  0  0  0  0  0  0  0  0  0
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  7  6  1  0  0  0  0
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M  END

     RDKit          3D

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M  END

  Mrv1652306202120063D          

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   -1.1548    3.0151    1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227    1.7641   -0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2304    0.5117    0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518    2.1707    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484    3.4645    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516    2.8482   -0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557    2.4633   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542    0.0469   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    0.8248    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062    1.0351   -3.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5106    0.9644   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951   -1.3780   -1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4874   -1.7717   -3.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8702   -1.4941   -4.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5023   -3.1745   -3.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0621   -3.1816   -0.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4381   -2.1787   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4575   -5.1317   -1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9470   -4.2049   -1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393   -5.6464    0.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -4.1945    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0781   -4.2239    2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0563   -4.4840    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057   -0.8851    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0  0  0  0
  4  3  1  0  0  0  0
 11  9  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
 13 14  1  0  0  0  0
 15 13  1  0  0  0  0
  9 10  1  0  0  0  0
  8  7  1  0  0  0  0
 16 17  1  0  0  0  0
 11 12  1  0  0  0  0
  7  6  1  0  0  0  0
 18 19  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
  6  5  1  0  0  0  0
 20 21  1  0  0  0  0
 11 13  1  0  0  0  0
 21 22  2  0  0  0  0
  5  4  1  0  0  0  0
 21 23  1  0  0  0  0
 15 47  1  0  0  0  0
 16 48  1  0  0  0  0
 17 49  1  0  0  0  0
 17 50  1  0  0  0  0
 11 43  1  6  0  0  0
 13 45  1  1  0  0  0
  9 41  1  6  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  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
 14 46  1  0  0  0  0
 10 42  1  0  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
 12 44  1  0  0  0  0
 19 53  1  0  0  0  0
 19 54  1  0  0  0  0
 20 55  1  0  0  0  0
 20 56  1  0  0  0  0
 23 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034357

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O5/c1-2-3-4-5-6-9-12-15(19)18(23)16(20)13-10-7-8-11-14-17(21)22/h10,13,15-16,18-20,23H,2-9,11-12,14H2,1H3,(H,21,22)/b13-10-/t15-,16+,18+/m0/s1

> <INCHI_KEY>
XADHJHFFBMPQOS-OVXXOIRXSA-N

> <FORMULA>
C18H34O5

> <MOLECULAR_WEIGHT>
330.465

> <EXACT_MASS>
330.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
37.94080177728953

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6Z,8R,9R,10S)-8,9,10-trihydroxyoctadec-6-enoic acid

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
3.4031801699999997

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.0390684015001

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.363775331959443

> <JCHEM_PKA_STRONGEST_BASIC>
-3.185135317785541

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
91.64069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6Z,8R,9R,10S)-8,9,10-trihydroxyoctadec-6-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 56  0  0  0  0  0  0  0  0999 V2000
   -4.3575   -0.7369    2.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4650    0.7703    2.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139    1.4876    2.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    1.1255    1.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119    1.9463    1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0022    1.5824    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973    2.3966    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1962    2.1681   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7044    0.7259   -1.0351 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4251    0.3729    0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471    0.5781   -2.2477 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8557    1.3152   -1.9527 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0359   -0.8895   -2.5433 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1623   -0.8542   -3.4402 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744   -1.6928   -3.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1935   -2.6481   -2.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1173   -3.0221   -1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9212   -4.2773   -0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -4.5585    0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1458   -3.9960    1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3282   -2.5126    1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012   -1.9733    0.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -1.8061    1.6404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3568   -1.1795    2.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8432   -1.2024    1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8164   -0.9898    3.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9811    0.9936    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0913    1.1692    3.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6046    1.2644    3.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    2.5687    2.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7324    1.3042    0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511    0.0597    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3843    1.7705    2.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1548    3.0151    1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227    1.7641   -0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2304    0.5117    0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518    2.1707    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484    3.4645    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516    2.8482   -0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557    2.4633   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542    0.0469   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    0.8248    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062    1.0351   -3.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5106    0.9644   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951   -1.3780   -1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4874   -1.7717   -3.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8702   -1.4941   -4.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5023   -3.1745   -3.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0621   -3.1816   -0.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4381   -2.1787   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4575   -5.1317   -1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9470   -4.2049   -1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393   -5.6464    0.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -4.1945    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0781   -4.2239    2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0563   -4.4840    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057   -0.8851    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
  4  3  1  0
 11  9  1  0
  3  2  1  0
  2  1  1  0
  9  8  1  0
 13 14  1  0
 15 13  1  0
  9 10  1  0
  8  7  1  0
 16 17  1  0
 11 12  1  0
  7  6  1  0
 18 19  1  0
 17 18  1  0
 19 20  1  0
  6  5  1  0
 20 21  1  0
 11 13  1  0
 21 22  2  0
  5  4  1  0
 21 23  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 11 43  1  6
 13 45  1  1
  9 41  1  6
  8 39  1  0
  8 40  1  0
  7 37  1  0
  7 38  1  0
  6 35  1  0
  6 36  1  0
  5 33  1  0
  5 34  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  2 27  1  0
  2 28  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 14 46  1  0
 10 42  1  0
 18 51  1  0
 18 52  1  0
 12 44  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  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      -4.357  -0.737   2.763  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.465   0.770   2.590  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.114   1.488   2.627  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.203   1.125   1.452  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.912   1.946   1.478  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.002   1.582   0.306  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.297   2.397   0.339  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.196   2.168  -0.884  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.704   0.726  -1.035  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.425   0.373   0.162  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.647   0.578  -2.248  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.856   1.315  -1.953  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.036  -0.890  -2.543  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.162  -0.854  -3.440  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.974  -1.693  -3.241  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.193  -2.648  -2.707  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.117  -3.022  -1.256  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.921  -4.277  -0.909  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.930  -4.559   0.603  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.146  -3.996   1.345  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.328  -2.513   1.193  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.301  -1.973   0.690  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.274  -1.806   1.640  0.00  0.00           O+0
HETATM   24  H   UNK     0      -5.357  -1.180   2.827  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.843  -1.202   1.918  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.816  -0.990   3.681  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.981   0.994   1.649  0.00  0.00           H+0
HETATM   28  H   UNK     0      -5.091   1.169   3.397  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.605   1.264   3.572  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.300   2.569   2.616  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.732   1.304   0.508  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.951   0.060   1.487  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.384   1.771   2.423  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.155   3.015   1.436  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.523   1.764  -0.640  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.230   0.512   0.352  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.852   2.171   1.258  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.048   3.465   0.381  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.052   2.848  -0.784  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.656   2.463  -1.791  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.854   0.047  -1.136  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.294   0.825   0.048  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.206   1.035  -3.142  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.511   0.964  -2.594  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.395  -1.378  -1.635  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.487  -1.772  -3.492  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.870  -1.494  -4.308  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.502  -3.175  -3.365  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.062  -3.182  -1.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.438  -2.179  -0.647  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.458  -5.132  -1.418  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.947  -4.205  -1.290  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.939  -5.646   0.748  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.004  -4.194   1.064  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.078  -4.224   2.415  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.056  -4.484   0.977  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.406  -0.885   1.289  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    3    1   27   28                                             
CONECT    3    4    2   29   30                                             
CONECT    4    3    5   31   32                                             
CONECT    5    6    4   33   34                                             
CONECT    6    7    5   35   36                                             
CONECT    7    8    6   37   38                                             
CONECT    8    9    7   39   40                                             
CONECT    9   11    8   10   41                                             
CONECT   10    9   42                                                       
CONECT   11    9   12   13   43                                             
CONECT   12   11   44                                                       
CONECT   13   14   15   11   45                                             
CONECT   14   13   46                                                       
CONECT   15   16   13   47                                                  
CONECT   16   15   17   48                                                  
CONECT   17   16   18   49   50                                             
CONECT   18   19   17   51   52                                             
CONECT   19   18   20   53   54                                             
CONECT   20   19   21   55   56                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   57                                                       
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    2                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   20                                                            
CONECT   56   20                                                            
CONECT   57   23                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  112    0
END

RDKit          3D

57 56  0  0  0  0  0  0  0  0999 V2000
   -4.3575   -0.7369    2.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4650    0.7703    2.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139    1.4876    2.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    1.1255    1.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119    1.9463    1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0022    1.5824    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973    2.3966    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1962    2.1681   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7044    0.7259   -1.0351 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4251    0.3729    0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471    0.5781   -2.2477 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8557    1.3152   -1.9527 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0359   -0.8895   -2.5433 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1623   -0.8542   -3.4402 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744   -1.6928   -3.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1935   -2.6481   -2.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1173   -3.0221   -1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9212   -4.2773   -0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1458   -3.9960    1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3282   -2.5126    1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3012   -1.9733    0.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2740   -1.8061    1.6404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3568   -1.1795    2.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8432   -1.2024    1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8164   -0.9898    3.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9811    0.9936    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0913    1.1692    3.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6046    1.2644    3.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    2.5687    2.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7324    1.3042    0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511    0.0597    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3843    1.7705    2.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1548    3.0151    1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227    1.7641   -0.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2304    0.5117    0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518    2.1707    1.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484    3.4645    0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0516    2.8482   -0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557    2.4633   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542    0.0469   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    0.8248    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2062    1.0351   -3.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5106    0.9644   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951   -1.3780   -1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4874   -1.7717   -3.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8702   -1.4941   -4.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5023   -3.1745   -3.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0621   -3.1816   -0.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4381   -2.1787   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4575   -5.1317   -1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9470   -4.2049   -1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393   -5.6464    0.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -4.1945    1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0781   -4.2239    2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0563   -4.4840    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057   -0.8851    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
  4  3  1  0
 11  9  1  0
  3  2  1  0
  2  1  1  0
  9  8  1  0
 13 14  1  0
 15 13  1  0
  9 10  1  0
  8  7  1  0
 16 17  1  0
 11 12  1  0
  7  6  1  0
 18 19  1  0
 17 18  1  0
 19 20  1  0
  6  5  1  0
 20 21  1  0
 11 13  1  0
 21 22  2  0
  5  4  1  0
 21 23  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 11 43  1  6
 13 45  1  1
  9 41  1  6
  8 39  1  0
  8 40  1  0
  7 37  1  0
  7 38  1  0
  6 35  1  0
  6 36  1  0
  5 33  1  0
  5 34  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  2 27  1  0
  2 28  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 14 46  1  0
 10 42  1  0
 18 51  1  0
 18 52  1  0
 12 44  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 23 57  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₄O₅

Average Mass

330.4650 Da

Monoisotopic Mass

330.24062 Da

IUPAC Name

(6Z,8R,9R,10S)-8,9,10-trihydroxyoctadec-6-enoic acid

Traditional Name

(6Z,8R,9R,10S)-8,9,10-trihydroxyoctadec-6-enoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H34O5/c1-2-3-4-5-6-9-12-15(19)18(23)16(20)13-10-7-8-11-14-17(21)22/h10,13,15-16,18-20,23H,2-9,11-12,14H2,1H3,(H,21,22)/b13-10-/t15-,16+,18+/m0/s1

InChI Key

XADHJHFFBMPQOS-OVXXOIRXSA-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 long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic 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	3.93	ALOGPS
logP	3.4	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.36	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	15	ChemAxon
Refractivity	91.64 m³·mol⁻¹	ChemAxon
Polarizability	37.94 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

24626308

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44139365

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Benavides, A., et al. (2009). Benavides, A., et al, J. Nat. Prod. 72, 813 (2009). J. Nat. Prod..

Showing NP-Card for (8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid (NP0034357)

MOL for NP0034357 ((8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

3D MOL for NP0034357 ((8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

3D SDF for NP0034357 ((8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

3D-SDF for NP0034357 ((8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

PDB for NP0034357 ((8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

3D PDB for NP0034357 ((8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

SMILES for NP0034357 ((8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

INCHI for NP0034357 ((8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

Structure for NP0034357 ((8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

3D Structure for NP0034357 ((8R*,9R*,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

Showing NP-Card for (8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid (NP0034357)

MOL for NP0034357 ((8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

3D MOL for NP0034357 ((8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

3D SDF for NP0034357 ((8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

3D-SDF for NP0034357 ((8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

PDB for NP0034357 ((8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

3D PDB for NP0034357 ((8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

SMILES for NP0034357 ((8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

INCHI for NP0034357 ((8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

Structure for NP0034357 ((8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid)

3D Structure for NP0034357 ((8R,9R,10S*,6Z)-trihydroxyoctadec-6-enoic acid)