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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:07:39 UTC

Update Date

2021-09-23 20:07:43 UTC

HMDB ID

HMDB0302724

Secondary Accession Numbers

None

Metabolite Identification

Common Name

cis-12-Oxophytodienoic acid

Description

Cis-12-oxophytodienoic acid, also known as 12-oxo-cis-10, cis-15-phytodienoic acid or 12-oxo-pda, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Cis-12-oxophytodienoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cis-12-oxophytodienoic acid can be found in flaxseed, which makes cis-12-oxophytodienoic acid a potential biomarker for the consumption of this food product.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0302724
     RDKit          3D
cis-12-Oxophytodienoic acid
 49 49  0  0  0  0  0  0  0  0999 V2000
   -5.5897    0.9609    2.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7236   -0.2614    2.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243    0.1253    2.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115   -0.4258    1.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276   -1.4779    0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281   -1.1031   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -2.2658   -1.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9218   -3.0801   -1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0124   -2.2991   -2.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0102   -1.4929   -2.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -0.8167   -1.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484    0.6755   -1.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    0.9609   -1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4758    0.4819   -0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8609    0.8584   -1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9479    0.4247   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8386    1.0570    0.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9581    0.5927    1.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2873    0.9373    1.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7323    2.0995    1.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0601   -0.0688    0.7439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4369    0.6014    1.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9970    1.6619    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9531    1.4553    3.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9130   -0.4578    3.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0689   -1.1428    1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9792    0.9283    2.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4743   -0.0435    1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1853   -2.4067    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549   -1.8680    0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625   -0.2312   -1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1062   -2.9233   -3.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1368   -1.3329   -3.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -1.2770   -0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6288    1.0894   -2.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030    1.1724   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169    2.0527   -1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    0.4881   -2.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3590    1.0884    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.5945   -0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    0.2967   -2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101    1.9203   -1.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9405   -0.6693   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9112    0.7556   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949    0.7266    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8360    2.1495    0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8537   -0.5019    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644    1.0688    2.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5211    0.1110   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  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
 11  6  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
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 21 49  1  0
M  END


  Mrv1533007131513432D          

 23 23  0  0  0  0            999 V2000
   -0.0856    0.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2571   -0.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0417   -0.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6548   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2767    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2957    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    0.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9912    2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7638    2.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3159    1.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0101    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9034    1.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2389    0.3847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201    2.5429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7056    1.3054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2132   -1.4081    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394   -0.3040    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 14 13  2  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 21 18  1  0  0  0  0
 22  3  1  0  0  0  0
 23  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302724

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CC)=C(/[H])CC1C(CCCCCCCC(O)=O)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-

> <INCHI_KEY>
PMTMAFAPLCGXGK-CLTKARDFSA-N

> <FORMULA>
C18H28O3

> <MOLECULAR_WEIGHT>
292.419

> <EXACT_MASS>
292.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.70761821366223

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-{4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}octanoic acid

> <ALOGPS_LOGP>
5.09

> <JCHEM_LOGP>
5.079546357333333

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.017647713652938

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.784583565856928

> <JCHEM_PKA_STRONGEST_BASIC>
-4.934463579077429

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
87.25579999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-{4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}octanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302724
     RDKit          3D
cis-12-Oxophytodienoic acid
 49 49  0  0  0  0  0  0  0  0999 V2000
   -5.5897    0.9609    2.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7236   -0.2614    2.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243    0.1253    2.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115   -0.4258    1.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276   -1.4779    0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281   -1.1031   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -2.2658   -1.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9218   -3.0801   -1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0124   -2.2991   -2.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0102   -1.4929   -2.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -0.8167   -1.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484    0.6755   -1.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    0.9609   -1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4758    0.4819   -0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8609    0.8584   -1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9479    0.4247   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8386    1.0570    0.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9581    0.5927    1.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2873    0.9373    1.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7323    2.0995    1.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0601   -0.0688    0.7439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4369    0.6014    1.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9970    1.6619    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9531    1.4553    3.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9130   -0.4578    3.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0689   -1.1428    1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9792    0.9283    2.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4743   -0.0435    1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1853   -2.4067    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549   -1.8680    0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625   -0.2312   -1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1062   -2.9233   -3.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1368   -1.3329   -3.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -1.2770   -0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6288    1.0894   -2.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030    1.1724   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169    2.0527   -1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    0.4881   -2.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3590    1.0884    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.5945   -0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    0.2967   -2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101    1.9203   -1.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9405   -0.6693   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9112    0.7556   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949    0.7266    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8360    2.1495    0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8537   -0.5019    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644    1.0688    2.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5211    0.1110   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  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
 11  6  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
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 21 49  1  0
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -0.160   0.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.480  -0.646   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.945  -1.122   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.582   3.977   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.249   4.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.916   4.747   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.089  -0.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.085   3.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.250   3.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.419   4.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.769   1.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.583   4.747   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.159   4.603   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.190   3.459   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.752   3.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.913   2.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.420   2.125   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.917   3.977   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.046   0.718   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.251   4.747   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.917   2.437   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -2.265  -2.628   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.554  -0.568   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    7   22                                                  
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    4    9                                                       
CONECT    7    3   11   23                                                  
CONECT    8    5   10                                                       
CONECT    9    6   12                                                       
CONECT   10    8   15                                                       
CONECT   11    7   16                                                       
CONECT   12    9   18                                                       
CONECT   13   14   15                                                       
CONECT   14   13   17                                                       
CONECT   15   10   13   16                                                  
CONECT   16   11   15   17                                                  
CONECT   17   14   16   19                                                  
CONECT   18   12   20   21                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22    3                                                            
CONECT   23    7                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0302724
HETATM    1  C1  UNL     1      -5.590   0.961   2.142  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.724  -0.261   2.442  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.324   0.125   2.313  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.511  -0.426   1.462  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.828  -1.478   0.526  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.628  -1.103  -0.935  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.983  -2.266  -1.770  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.922  -3.080  -1.619  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.012  -2.299  -2.840  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.010  -1.493  -2.597  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.211  -0.817  -1.304  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.948   0.676  -1.457  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.472   0.961  -1.826  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.476   0.482  -0.832  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.861   0.858  -1.377  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.948   0.425  -0.452  1.00  0.00           C  
HETATM   17  C16 UNL     1       3.839   1.057   0.919  1.00  0.00           C  
HETATM   18  C17 UNL     1       4.958   0.593   1.830  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.287   0.937   1.298  1.00  0.00           C  
HETATM   20  O2  UNL     1       6.732   2.100   1.331  1.00  0.00           O  
HETATM   21  O3  UNL     1       7.060  -0.069   0.744  1.00  0.00           O  
HETATM   22  H1  UNL     1      -6.437   0.601   1.493  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.997   1.662   1.514  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.953   1.455   3.045  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.913  -0.458   3.545  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.069  -1.143   1.925  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.979   0.928   2.990  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.474  -0.043   1.476  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.185  -2.407   0.668  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.855  -1.868   0.597  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.262  -0.231  -1.213  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.106  -2.923  -3.740  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.137  -1.333  -3.256  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.491  -1.277  -0.595  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.629   1.089  -2.229  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.203   1.172  -0.519  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.617   2.053  -1.996  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.719   0.488  -2.815  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.359   1.088   0.101  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.423  -0.594  -0.672  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.001   0.297  -2.337  1.00  0.00           H  
HETATM   42  H21 UNL     1       2.910   1.920  -1.632  1.00  0.00           H  
HETATM   43  H22 UNL     1       3.941  -0.669  -0.389  1.00  0.00           H  
HETATM   44  H23 UNL     1       4.911   0.756  -0.886  1.00  0.00           H  
HETATM   45  H24 UNL     1       2.895   0.727   1.385  1.00  0.00           H  
HETATM   46  H25 UNL     1       3.836   2.150   0.868  1.00  0.00           H  
HETATM   47  H26 UNL     1       4.854  -0.502   1.996  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.764   1.069   2.822  1.00  0.00           H  
HETATM   49  H28 UNL     1       7.521   0.111  -0.143  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4    4   27
CONECT    4    5   28
CONECT    5    6   29   30
CONECT    6    7   11   31
CONECT    7    8    8    9
CONECT    9   10   10   32
CONECT   10   11   33
CONECT   11   12   34
CONECT   12   13   35   36
CONECT   13   14   37   38
CONECT   14   15   39   40
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   45   46
CONECT   18   19   47   48
CONECT   19   20   20   21
CONECT   21   49
END

HMDB0302724
     RDKit          3D
cis-12-Oxophytodienoic acid
 49 49  0  0  0  0  0  0  0  0999 V2000
   -5.5897    0.9609    2.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7236   -0.2614    2.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243    0.1253    2.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115   -0.4258    1.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276   -1.4779    0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281   -1.1031   -0.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832   -2.2658   -1.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9218   -3.0801   -1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0124   -2.2991   -2.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0102   -1.4929   -2.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -0.8167   -1.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484    0.6755   -1.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723    0.9609   -1.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4758    0.4819   -0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8609    0.8584   -1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9479    0.4247   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8386    1.0570    0.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9581    0.5927    1.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2873    0.9373    1.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7323    2.0995    1.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0601   -0.0688    0.7439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4369    0.6014    1.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9970    1.6619    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9531    1.4553    3.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9130   -0.4578    3.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0689   -1.1428    1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9792    0.9283    2.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4743   -0.0435    1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1853   -2.4067    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549   -1.8680    0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625   -0.2312   -1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1062   -2.9233   -3.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1368   -1.3329   -3.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -1.2770   -0.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6288    1.0894   -2.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030    1.1724   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169    2.0527   -1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    0.4881   -2.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3590    1.0884    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.5945   -0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    0.2967   -2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101    1.9203   -1.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9405   -0.6693   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9112    0.7556   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949    0.7266    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8360    2.1495    0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8537   -0.5019    1.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644    1.0688    2.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5211    0.1110   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  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
 11  6  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
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 21 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-{4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}octanoate	Generator
cis-12-Oxophytodienoic acid	ChEMBL
cis-12-Oxophytodienoate	Generator
12-oxo-PDA	MeSH
12-oxo-cis-10, cis-15-Phytodienoic acid	MeSH
8-(2-(cis-2'-Pentenyl)-3-oxo-cis-4-cyclopentenyl)octanoic acid	MeSH
OPDA acid	MeSH
12-oxo-Phytodienoic acid	MeSH
12-Oxophytodienoate	MeSH

Chemical Formula

C₁₈H₂₈O₃

Average Molecular Weight

292.419

Monoisotopic Molecular Weight

292.203844762

IUPAC Name

8-{4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}octanoic acid

Traditional Name

8-{4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}octanoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CC)=C(/[H])CC1C(CCCCCCCC(O)=O)C=CC1=O

InChI Identifier

InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-

InChI Key

PMTMAFAPLCGXGK-CLTKARDFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Medium-chain fatty acid
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Flaxseed (FooDB: FOOD00101)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.09	ALOGPS
logP	5.08	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.78	ChemAxon
pKa (Strongest Basic)	-4.9	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	11	ChemAxon
Refractivity	87.26 m³·mol⁻¹	ChemAxon
Polarizability	34.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	176.24	32859911
AllCCS	[M+H-H2O]+	173.133	32859911
AllCCS	[M+Na]+	179.944	32859911
AllCCS	[M+NH4]+	179.118	32859911
AllCCS	[M-H]-	179.05	32859911
AllCCS	[M+Na-2H]-	179.972	32859911
AllCCS	[M+HCOO]-	181.13	32859911
DeepCCS	[M+H]+	179.842	30932474
DeepCCS	[M-H]-	177.484	30932474
DeepCCS	[M-2H]-	210.371	30932474
DeepCCS	[M+Na]+	185.935	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-12-Oxophytodienoic acid,2TMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C)C=CC1CCCCCCCC(=O)O[Si](C)(C)C	2553.5	Semi standard non polar	33892256
cis-12-Oxophytodienoic acid,2TMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C)C=CC1CCCCCCCC(=O)O[Si](C)(C)C	2465.2	Standard non polar	33892256
cis-12-Oxophytodienoic acid,2TMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C)C=CC1CCCCCCCC(=O)O[Si](C)(C)C	2696.3	Standard polar	33892256
cis-12-Oxophytodienoic acid,2TBDMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)C=CC1CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3028.8	Semi standard non polar	33892256
cis-12-Oxophytodienoic acid,2TBDMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)C=CC1CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2829.2	Standard non polar	33892256
cis-12-Oxophytodienoic acid,2TBDMS,isomer #1	CC/C=C\CC1=C(O[Si](C)(C)C(C)(C)C)C=CC1CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2856.7	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 10V, Positive-QTOF	splash10-002f-0090000000-9e001b387642892b2e29	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 20V, Positive-QTOF	splash10-003r-9670000000-2542263ca019f7436aa5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 40V, Positive-QTOF	splash10-0f9x-9110000000-fd1ef2bcb07783aa0e38	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 10V, Negative-QTOF	splash10-0006-0090000000-abdf8cebd8c34aacba6d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 20V, Negative-QTOF	splash10-0007-1090000000-87a6bfb759bfc815f3d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 40V, Negative-QTOF	splash10-0a4i-9330000000-b99bb0a622dfcba347b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 10V, Positive-QTOF	splash10-056u-0190000000-68e8b867fefe884ea9cc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 20V, Positive-QTOF	splash10-0aba-9830000000-b4c83647bdb72a8cd067	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 40V, Positive-QTOF	splash10-0a4i-9500000000-60e70370d3fbe907dea8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 10V, Negative-QTOF	splash10-0006-0090000000-31a006636e02cb6df785	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 20V, Negative-QTOF	splash10-0596-0190000000-e5bf2c38064c63beab36	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-12-Oxophytodienoic acid 40V, Negative-QTOF	splash10-05g0-3930000000-0c263a96ab0c4ec583fd	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005939

KNApSAcK ID

Not Available

Chemspider ID

8510000

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for cis-12-Oxophytodienoic acid (HMDB0302724)

MOL for HMDB0302724 (cis-12-Oxophytodienoic acid)

3D MOL for HMDB0302724 (cis-12-Oxophytodienoic acid)

3D SDF for HMDB0302724 (cis-12-Oxophytodienoic acid)

3D-SDF for HMDB0302724 (cis-12-Oxophytodienoic acid)

PDB for HMDB0302724 (cis-12-Oxophytodienoic acid)

3D PDB for HMDB0302724 (cis-12-Oxophytodienoic acid)

SMILES for HMDB0302724 (cis-12-Oxophytodienoic acid)

INCHI for HMDB0302724 (cis-12-Oxophytodienoic acid)

Structure for HMDB0302724 (cis-12-Oxophytodienoic acid)

3D Structure for HMDB0302724 (cis-12-Oxophytodienoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra