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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:33:28 UTC

Update Date

2021-09-26 22:57:18 UTC

HMDB ID

HMDB0247553

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid

Description

(5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid, also known as 15D-PGJ2;15-deoxy-δ12,14-PGJ2, 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. Based on a literature review a significant number of articles have been published on (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (5z)-11-oxoprosta-5,9,12,14-tetraene-1-oic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0247553
     RDKit          3D
(5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    6.8948   -0.0179    1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9102    0.5396    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1329   -0.1708   -0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -0.2762   -0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0910   -0.9553    0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139   -0.9816    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9871   -0.4475   -0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5411   -0.4904   -0.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615    0.0201   -1.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3381    0.7047   -2.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126    1.0052   -3.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028    0.9999   -3.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840    0.5884   -3.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.0367   -1.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    0.8584   -0.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0438    0.5757    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8832    0.1945    1.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3075   -0.0118    1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1913    0.8855    2.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6343    0.6286    1.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0973   -0.7265    2.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3725   -1.5535    2.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3820   -1.0985    1.7256 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9374    0.0280    2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2636    0.5686    2.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6148   -1.0789    1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5875    1.6216    0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9944    0.6286   -0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6030   -1.1860   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197    0.3595   -1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2579    0.7700   -0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076   -0.8105   -1.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4172   -2.0200    0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3802   -0.5040    1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -1.4454    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204    0.0254   -1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -1.0015    0.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7641    1.4910   -4.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.6484   -3.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263   -1.0376   -1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817    0.9108   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547    1.9254   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    0.7542    0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621    0.0322    2.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5210   -1.0753    1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5528    0.2179    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    0.5771    3.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9142    1.9418    2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2987    1.4170    2.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8189    0.7604    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6761   -1.0930    0.7406 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  3
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 14  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 23 51  1  0
M  END

  Mrv1652309112102332D          

 23 23  0  0  0  0            999 V2000
   -3.7222    3.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5506    2.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1637    2.2143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9922    1.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6053    0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4338    0.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0469   -0.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8753   -1.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4884   -1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022   -2.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1559   -3.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7079   -2.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2954   -1.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6310   -0.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6877   -3.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9733   -2.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2588   -3.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5443   -2.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8298   -3.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1154   -2.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4009   -3.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136   -2.6832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4009   -3.9207    0.0000 O   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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 10 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247553

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC=CC=C1C(CC=CCCCC(O)=O)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)

> <INCHI_KEY>
VHRUMKCAEVRUBK-UHFFFAOYSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.90441655833231

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[5-(oct-2-en-1-ylidene)-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid

> <ALOGPS_LOGP>
5.39

> <JCHEM_LOGP>
5.457149731333333

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.786482545828832

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.658500253952263

> <JCHEM_PKA_STRONGEST_BASIC>
-5.001707861342161

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
98.4503

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-[5-(oct-2-en-1-ylidene)-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247553
     RDKit          3D
(5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    6.8948   -0.0179    1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9102    0.5396    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1329   -0.1708   -0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -0.2762   -0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0910   -0.9553    0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139   -0.9816    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9871   -0.4475   -0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5411   -0.4904   -0.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615    0.0201   -1.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3381    0.7047   -2.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126    1.0052   -3.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028    0.9999   -3.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840    0.5884   -3.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.0367   -1.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    0.8584   -0.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0438    0.5757    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8832    0.1945    1.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3075   -0.0118    1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1913    0.8855    2.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6343    0.6286    1.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0973   -0.7265    2.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3725   -1.5535    2.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3820   -1.0985    1.7256 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9374    0.0280    2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2636    0.5686    2.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6148   -1.0789    1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5875    1.6216    0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9944    0.6286   -0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6030   -1.1860   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197    0.3595   -1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2579    0.7700   -0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076   -0.8105   -1.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4172   -2.0200    0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3802   -0.5040    1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -1.4454    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204    0.0254   -1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -1.0015    0.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7641    1.4910   -4.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.6484   -3.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263   -1.0376   -1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817    0.9108   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547    1.9254   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    0.7542    0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621    0.0322    2.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5210   -1.0753    1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5528    0.2179    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    0.5771    3.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9142    1.9418    2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2987    1.4170    2.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8189    0.7604    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6761   -1.0930    0.7406 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  3
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 14  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 23 51  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -6.948   6.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.628   5.164   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.772   4.133   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.452   2.627   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.597   1.596   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.276   0.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.421  -0.940   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.101  -2.447   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.245  -3.477   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.084  -5.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -11.491  -5.635   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.521  -4.491   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.751  -3.157   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -12.378  -1.750   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -8.750  -5.779   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.417  -5.009   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.083  -5.779   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.749  -5.009   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.416  -5.779   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.082  -5.009   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.748  -5.779   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.585  -5.009   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.748  -7.319   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0247553
HETATM    1  C1  UNL     1       6.895  -0.018   1.561  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.910   0.540   0.173  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.133  -0.171  -0.859  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.667  -0.276  -0.729  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.091  -0.955   0.445  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.614  -0.982   0.356  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.987  -0.447  -0.667  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.541  -0.490  -0.724  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.161   0.020  -1.712  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.338   0.705  -2.913  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.513   1.005  -3.209  1.00  0.00           O  
HETATM   12  C11 UNL     1      -0.803   1.000  -3.759  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.884   0.588  -3.185  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.628  -0.037  -1.835  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.320   0.858  -0.810  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.044   0.576   0.596  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.883   0.195   1.535  1.00  0.00           C  
HETATM   18  C17 UNL     1      -4.307  -0.012   1.275  1.00  0.00           C  
HETATM   19  C18 UNL     1      -5.191   0.885   2.107  1.00  0.00           C  
HETATM   20  C19 UNL     1      -6.634   0.629   1.779  1.00  0.00           C  
HETATM   21  C20 UNL     1      -7.097  -0.727   2.084  1.00  0.00           C  
HETATM   22  O2  UNL     1      -6.373  -1.553   2.656  1.00  0.00           O  
HETATM   23  O3  UNL     1      -8.382  -1.098   1.726  1.00  0.00           O  
HETATM   24  H1  UNL     1       7.937   0.028   2.008  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.264   0.569   2.243  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.615  -1.079   1.617  1.00  0.00           H  
HETATM   27  H4  UNL     1       6.588   1.622   0.217  1.00  0.00           H  
HETATM   28  H5  UNL     1       7.994   0.629  -0.153  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.603  -1.186  -1.004  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.320   0.360  -1.853  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.258   0.770  -0.844  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.308  -0.810  -1.665  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.417  -2.020   0.520  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.380  -0.504   1.424  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.038  -1.445   1.140  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.520   0.025  -1.471  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.031  -1.002   0.071  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.764   1.491  -4.727  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.902   0.648  -3.564  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.026  -1.038  -1.735  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.382   0.911  -1.105  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.955   1.925  -1.055  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.974   0.754   0.911  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.462   0.032   2.550  1.00  0.00           H  
HETATM   45  H22 UNL     1      -4.521  -1.075   1.526  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.553   0.218   0.226  1.00  0.00           H  
HETATM   47  H24 UNL     1      -5.007   0.577   3.171  1.00  0.00           H  
HETATM   48  H25 UNL     1      -4.914   1.942   2.040  1.00  0.00           H  
HETATM   49  H26 UNL     1      -7.299   1.417   2.220  1.00  0.00           H  
HETATM   50  H27 UNL     1      -6.819   0.760   0.663  1.00  0.00           H  
HETATM   51  H28 UNL     1      -8.676  -1.093   0.741  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   35
CONECT    7    8   36
CONECT    8    9    9   37
CONECT    9   10   14
CONECT   10   11   11   12
CONECT   12   13   13   38
CONECT   13   14   39
CONECT   14   15   40
CONECT   15   16   41   42
CONECT   16   17   17   43
CONECT   17   18   44
CONECT   18   19   45   46
CONECT   19   20   47   48
CONECT   20   21   49   50
CONECT   21   22   22   23
CONECT   23   51
END

HMDB0247553
     RDKit          3D
(5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    6.8948   -0.0179    1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9102    0.5396    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1329   -0.1708   -0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -0.2762   -0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0910   -0.9553    0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139   -0.9816    0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9871   -0.4475   -0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5411   -0.4904   -0.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615    0.0201   -1.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3381    0.7047   -2.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126    1.0052   -3.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028    0.9999   -3.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840    0.5884   -3.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.0367   -1.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    0.8584   -0.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0438    0.5757    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8832    0.1945    1.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3075   -0.0118    1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1913    0.8855    2.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6343    0.6286    1.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0973   -0.7265    2.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3725   -1.5535    2.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3820   -1.0985    1.7256 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9374    0.0280    2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2636    0.5686    2.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6148   -1.0789    1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5875    1.6216    0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9944    0.6286   -0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6030   -1.1860   -1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197    0.3595   -1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2579    0.7700   -0.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076   -0.8105   -1.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4172   -2.0200    0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3802   -0.5040    1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -1.4454    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204    0.0254   -1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -1.0015    0.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7641    1.4910   -4.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    0.6484   -3.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263   -1.0376   -1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817    0.9108   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547    1.9254   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    0.7542    0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621    0.0322    2.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5210   -1.0753    1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5528    0.2179    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    0.5771    3.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9142    1.9418    2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2987    1.4170    2.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8189    0.7604    0.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6761   -1.0930    0.7406 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  3
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 14  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-Oate	Generator
15D-PGJ2;15-deoxy-δ12,14-PGJ2	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.441

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

7-[5-(oct-2-en-1-ylidene)-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid

Traditional Name

7-[5-(oct-2-en-1-ylidene)-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC=CC=C1C(CC=CCCCC(O)=O)C=CC1=O

InChI Identifier

InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)

InChI Key

VHRUMKCAEVRUBK-UHFFFAOYSA-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
Long-chain fatty acid
Fatty acid
Unsaturated 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

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	5.39	ALOGPS
logP	5.46	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	-5	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	98.45 m³·mol⁻¹	ChemAxon
Polarizability	37.9 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
DeepCCS	[M+H]+	183.692	30932474
DeepCCS	[M-H]-	181.291	30932474
DeepCCS	[M-2H]-	214.344	30932474
DeepCCS	[M+Na]+	190.034	30932474
AllCCS	[M+H]+	183.5	32859911
AllCCS	[M+H-H2O]+	180.5	32859911
AllCCS	[M+NH4]+	186.3	32859911
AllCCS	[M+Na]+	187.1	32859911
AllCCS	[M-H]-	184.7	32859911
AllCCS	[M+Na-2H]-	185.9	32859911
AllCCS	[M+HCOO]-	187.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid	CCCCCC=CC=C1C(CC=CCCCC(O)=O)C=CC1=O	4216.0	Standard polar	33892256
(5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid	CCCCCC=CC=C1C(CC=CCCCC(O)=O)C=CC1=O	2545.1	Standard non polar	33892256
(5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid	CCCCCC=CC=C1C(CC=CCCCC(O)=O)C=CC1=O	2743.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6290000000-3dc60f4b59ef5f20d684	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid 10V, Positive-QTOF	splash10-000t-1292000000-9881f6499ef2d60f0d0f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid 20V, Positive-QTOF	splash10-001i-9730000000-e86765cb72eecd2feb8c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid 40V, Positive-QTOF	splash10-05rr-9500000000-43060ace2e2f26804b0f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid 10V, Negative-QTOF	splash10-014i-0029000000-c1967ca10292a13ad947	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid 20V, Negative-QTOF	splash10-066r-0294000000-ecdf0c0084d7f716f9a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid 40V, Negative-QTOF	splash10-053r-1930000000-dd5d68b51f67954b6ba6	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1400

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1444

PDB ID

Not Available

ChEBI ID

95176

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid (HMDB0247553)

MOL for HMDB0247553 ((5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid)

3D MOL for HMDB0247553 ((5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid)

3D SDF for HMDB0247553 ((5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid)

3D-SDF for HMDB0247553 ((5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid)

PDB for HMDB0247553 ((5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid)

3D PDB for HMDB0247553 ((5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid)

SMILES for HMDB0247553 ((5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid)

INCHI for HMDB0247553 ((5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid)

Structure for HMDB0247553 ((5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid)

3D Structure for HMDB0247553 ((5Z)-11-Oxoprosta-5,9,12,14-tetraene-1-oic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra