NP-MRD: Showing NP-Card for 11-Keto-9(E),12(E)-octadecadienoic acid (NP0001632)

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Record Information

Version

1.0

Created at

2020-09-23 01:59:27 UTC

Updated at

2021-08-10 02:55:51 UTC

NP-MRD ID

NP0001632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Keto-9(E),12(E)-octadecadienoic acid

Provided By

NPAtlas

Description

(9E,12E)-11-oxooctadeca-9,12-dienoic 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. 11-Keto-9(E),12(E)-octadecadienoic acid is found in Lithothamnion corallioides and Trichoderma. It was first documented in 1999 (PMID: 10344571). Based on a literature review very few articles have been published on (9E,12E)-11-oxooctadeca-9,12-dienoic acid (PMID: 34380192) (PMID: 34380191) (PMID: 34380190) (PMID: 34380189).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117443D          

 51 50  0  0  0  0            999 V2000
   -7.6420   -0.8134   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7603    0.1084    0.7529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5158    0.6732    1.3044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7112    1.5423    0.4209 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0724    0.9333   -0.7745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0859   -0.1311   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042   -0.0428   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302   -1.0750   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167   -2.0818    0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4532   -0.8844   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.7689   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8776   -1.5377   -1.1278 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8778   -1.4954    0.0085 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2358   -1.2521   -0.6166 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3320   -1.1879    0.4173 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1392   -0.1020    1.4180 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0858    1.2695    0.8436 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3181    1.6802    0.1004 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5369    1.6745    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1039    0.5949    1.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1484    2.8557    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8447   -0.2769   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6389   -1.2513   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4029   -1.6689   -0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3907   -0.3503    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4524    0.9542    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7679    1.3281    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8661   -0.1682    1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4121    2.3605    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9636    2.1477    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795    1.7740   -1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7831    0.6407   -1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3558   -1.0148    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    0.8614   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1408    0.0040   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -2.6713   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -0.5280   -1.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233   -2.2619   -1.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587   -2.4837    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183   -0.7459    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4523   -2.1246   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3406   -2.1582    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9771   -0.1443    2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2181    1.4451    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651    1.9858    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5013    1.1154   -0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1530    2.7478   -0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7327    3.2644    2.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
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  8 10  1  0  0  0  0
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  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
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  4 30  1  0  0  0  0
  5 31  1  0  0  0  0
  5 32  1  0  0  0  0
  6 33  1  0  0  0  0
  7 34  1  0  0  0  0
 10 35  1  0  0  0  0
 11 36  1  0  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
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 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
M  END

     RDKit          3D

 51 50  0  0  0  0  0  0  0  0999 V2000
   -7.6420   -0.8134   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7603    0.1084    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5158    0.6732    1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7112    1.5423    0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0724    0.9333   -0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8302   -1.0750   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4532   -0.8844   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.7689   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2358   -1.2521   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3320   -1.1879    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392   -0.1020    1.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0858    1.2695    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3181    1.6802    0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5369    1.6745    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1039    0.5949    1.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1484    2.8557    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8447   -0.2769   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6389   -1.2513   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4029   -1.6689   -0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3907   -0.3503    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4524    0.9542    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9636    2.1477    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795    1.7740   -1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9651    1.9858    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7327    3.2644    2.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
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 21 51  1  0
M  END


  Mrv1652306242117443D          

 51 50  0  0  0  0            999 V2000
   -7.6420   -0.8134   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7603    0.1084    0.7529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5158    0.6732    1.3044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7112    1.5423    0.4209 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0724    0.9333   -0.7745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0859   -0.1311   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042   -0.0428   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302   -1.0750   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167   -2.0818    0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4532   -0.8844   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.7689   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8776   -1.5377   -1.1278 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8778   -1.4954    0.0085 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2358   -1.2521   -0.6166 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3320   -1.1879    0.4173 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1392   -0.1020    1.4180 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0858    1.2695    0.8436 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3181    1.6802    0.1004 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5369    1.6745    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1484    2.8557    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2233   -2.2619   -1.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587   -2.4837    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1965   -0.3704   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9771   -0.1443    2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166   -0.2791    1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    1.4451    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651    1.9858    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5013    1.1154   -0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1530    2.7478   -0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7327    3.2644    2.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  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
  2 25  1  0  0  0  0
  2 26  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  5 31  1  0  0  0  0
  5 32  1  0  0  0  0
  6 33  1  0  0  0  0
  7 34  1  0  0  0  0
 10 35  1  0  0  0  0
 11 36  1  0  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
M  END
> <DATABASE_ID>
NP0001632

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O3/c1-2-3-4-8-11-14-17(19)15-12-9-6-5-7-10-13-16-18(20)21/h11-12,14-15H,2-10,13,16H2,1H3,(H,20,21)/b14-11+,15-12+

> <INCHI_KEY>
PQDJTTDGUJFDQI-LCPPQYOVSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.435

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.003526704848724

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9E,12E)-11-oxooctadeca-9,12-dienoic acid

> <ALOGPS_LOGP>
5.69

> <JCHEM_LOGP>
5.9621493616666665

> <ALOGPS_LOGS>
-5.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.98816728416319

> <JCHEM_PKA_STRONGEST_BASIC>
-4.23567620477451

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
89.11359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9E,12E)-11-oxooctadeca-9,12-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 50  0  0  0  0  0  0  0  0999 V2000
   -7.6420   -0.8134   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7603    0.1084    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5158    0.6732    1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7112    1.5423    0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0724    0.9333   -0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0859   -0.1311   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042   -0.0428   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302   -1.0750   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167   -2.0818    0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4532   -0.8844   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.7689   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8776   -1.5377   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8778   -1.4954    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2358   -1.2521   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3320   -1.1879    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392   -0.1020    1.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0858    1.2695    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3181    1.6802    0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5369    1.6745    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1039    0.5949    1.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1484    2.8557    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8447   -0.2769   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6389   -1.2513   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4029   -1.6689   -0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3907   -0.3503    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4524    0.9542    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7679    1.3281    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8661   -0.1682    1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4121    2.3605    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9636    2.1477    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795    1.7740   -1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7831    0.6407   -1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3558   -1.0148    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    0.8614   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1408    0.0040   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -2.6713   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -0.5280   -1.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233   -2.2619   -1.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587   -2.4837    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183   -0.7459    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4523   -2.1246   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1965   -0.3704   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2884   -1.0905   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3406   -2.1582    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9771   -0.1443    2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166   -0.2791    1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    1.4451    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651    1.9858    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5013    1.1154   -0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1530    2.7478   -0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7327    3.2644    2.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 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
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -7.642  -0.813  -0.403  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.760   0.108   0.753  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.516   0.673   1.304  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.711   1.542   0.421  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.072   0.933  -0.775  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.086  -0.131  -0.441  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.804  -0.043  -0.799  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.830  -1.075  -0.480  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.217  -2.082   0.155  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.453  -0.884  -0.915  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.500  -1.769  -0.671  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.878  -1.538  -1.128  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.878  -1.495   0.009  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.236  -1.252  -0.617  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.332  -1.188   0.417  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.139  -0.102   1.418  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.086   1.270   0.844  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.318   1.680   0.100  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.537   1.675   0.928  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.104   0.595   1.277  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.148   2.856   1.383  0.00  0.00           O+0
HETATM   22  H   UNK     0      -7.845  -0.277  -1.356  0.00  0.00           H+0
HETATM   23  H   UNK     0      -6.639  -1.251  -0.443  0.00  0.00           H+0
HETATM   24  H   UNK     0      -8.403  -1.669  -0.313  0.00  0.00           H+0
HETATM   25  H   UNK     0      -8.391  -0.350   1.582  0.00  0.00           H+0
HETATM   26  H   UNK     0      -8.452   0.954   0.392  0.00  0.00           H+0
HETATM   27  H   UNK     0      -6.768   1.328   2.217  0.00  0.00           H+0
HETATM   28  H   UNK     0      -5.866  -0.168   1.707  0.00  0.00           H+0
HETATM   29  H   UNK     0      -6.412   2.361   0.020  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.964   2.148   1.024  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.479   1.774  -1.263  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.783   0.641  -1.536  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.356  -1.015   0.104  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.528   0.861  -1.351  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.141   0.004  -1.467  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.274  -2.671  -0.132  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.947  -0.528  -1.628  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.223  -2.262  -1.875  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.859  -2.484   0.519  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.618  -0.746   0.771  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.452  -2.125  -1.268  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.197  -0.370  -1.268  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.288  -1.091  -0.131  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.341  -2.158   0.954  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.977  -0.144   2.137  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.217  -0.279   1.993  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.218   1.445   0.177  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.965   1.986   1.697  0.00  0.00           H+0
HETATM   49  H   UNK     0       6.501   1.115  -0.819  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.153   2.748  -0.224  0.00  0.00           H+0
HETATM   51  H   UNK     0       7.733   3.264   2.209  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3   25   26                                             
CONECT    3    2    4   27   28                                             
CONECT    4    3    5   29   30                                             
CONECT    5    4    6   31   32                                             
CONECT    6    5    7   33                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   35                                                  
CONECT   11   10   12   36                                                  
CONECT   12   11   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   20   21                                                  
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    3                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
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
   -7.6420   -0.8134   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7603    0.1084    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5158    0.6732    1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7112    1.5423    0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0724    0.9333   -0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0859   -0.1311   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042   -0.0428   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302   -1.0750   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167   -2.0818    0.1548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4532   -0.8844   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.7689   -0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8776   -1.5377   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8778   -1.4954    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2358   -1.2521   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3320   -1.1879    0.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392   -0.1020    1.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0858    1.2695    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3181    1.6802    0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5369    1.6745    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1039    0.5949    1.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1484    2.8557    1.3830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8447   -0.2769   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6389   -1.2513   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4029   -1.6689   -0.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3907   -0.3503    1.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4524    0.9542    0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7679    1.3281    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8661   -0.1682    1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4121    2.3605    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9636    2.1477    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4795    1.7740   -1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7831    0.6407   -1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3558   -1.0148    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    0.8614   -1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1408    0.0040   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -2.6713   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -0.5280   -1.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2233   -2.2619   -1.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587   -2.4837    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183   -0.7459    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4523   -2.1246   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1965   -0.3704   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2884   -1.0905   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3406   -2.1582    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9771   -0.1443    2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166   -0.2791    1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    1.4451    0.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651    1.9858    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5013    1.1154   -0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1530    2.7478   -0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7327    3.2644    2.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 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
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(9E,12E)-11-Oxooctadeca-9,12-dienoate	Generator
11-Keto-9(e),12(e)-octadecadienoate	Generator
11-Keto-9,12(e)-octadecadienoic acid	MeSH
KOD	MeSH

Chemical Formula

C₁₈H₃₀O₃

Average Mass

294.4350 Da

Monoisotopic Mass

294.21949 Da

IUPAC Name

(9E,12E)-11-oxooctadeca-9,12-dienoic acid

Traditional Name

(9E,12E)-11-oxooctadeca-9,12-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])=C(/[H])C(=O)C(\[H])=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C18H30O3/c1-2-3-4-8-11-14-17(19)15-12-9-6-5-7-10-13-16-18(20)21/h11-12,14-15H,2-10,13,16H2,1H3,(H,20,21)/b14-11+,15-12+

InChI Key

PQDJTTDGUJFDQI-LCPPQYOVSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lithothamnion corallioides	--	KNApSAcK
Trichoderma	NPAtlas	10344571

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
Unsaturated fatty acid
Fatty acid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	5.69	ALOGPS
logP	5.96	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	89.11 m³·mol⁻¹	ChemAxon
Polarizability	36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020018

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8058275

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9882600

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shinohara C, Hasumi K, Chikanishi T, Kikuchi T, Endo A: 11-Keto-9(E),12(E)-octadecadienoic acid, a novel fatty acid that enhances fibrinolytic activity of endothelial cells. J Antibiot (Tokyo). 1999 Feb;52(2):171-4. doi: 10.7164/antibiotics.52.171. [PubMed:10344571 ]
Kim S, Park KY, Chung J, Kim YB, Lee JW, Huh SK: Comparative Analysis of Feasibility of the Retrograde Suction Decompression Technique for Microsurgical Treatment of Large and Giant Internal Carotid Artery Aneurysms. J Korean Neurosurg Soc. 2021 Aug 12. pii: jkns.2021.0066. doi: 10.3340/jkns.2021.0066. [PubMed:34380192 ]
Bahloul M, Kharrat S, Chtara K, Hafdhi M, Turki O, Baccouche N, Ammar R, Kallel N, Hsairi M, Chakroun-Walha O, Hamida CB, Chelly H, Mahfoudh KB, Karoui A, Karray H, Rekik N, Bouaziz M: Clinical characteristics and outcomes of critically ill COVID-19 patients in Sfax, Tunisia. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00129. doi: 10.4266/acc.2021.00129. [PubMed:34380191 ]
Yi J, Kim KH: Identification and infection control of carbapenem-resistant Enterobacterales in intensive care units. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00409. doi: 10.4266/acc.2021.00409. [PubMed:34380190 ]
Lee Y, Kim SH, Hwang HY, Sohn SH, Choi JW, Kim KH: Perfusion parameters during cardiopulmonary bypass as a predictor of acute kidney injury after aortic valve replacement. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00094. doi: 10.4266/acc.2021.00094. [PubMed:34380189 ]

Showing NP-Card for 11-Keto-9(E),12(E)-octadecadienoic acid (NP0001632)

MOL for NP0001632 (11-Keto-9(E),12(E)-octadecadienoic acid)

3D MOL for NP0001632 (11-Keto-9(E),12(E)-octadecadienoic acid)

3D SDF for NP0001632 (11-Keto-9(E),12(E)-octadecadienoic acid)

3D-SDF for NP0001632 (11-Keto-9(E),12(E)-octadecadienoic acid)

PDB for NP0001632 (11-Keto-9(E),12(E)-octadecadienoic acid)

3D PDB for NP0001632 (11-Keto-9(E),12(E)-octadecadienoic acid)

SMILES for NP0001632 (11-Keto-9(E),12(E)-octadecadienoic acid)

INCHI for NP0001632 (11-Keto-9(E),12(E)-octadecadienoic acid)

Structure for NP0001632 (11-Keto-9(E),12(E)-octadecadienoic acid)

3D Structure for NP0001632 (11-Keto-9(E),12(E)-octadecadienoic acid)