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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001244

Secondary Accession Numbers

HMDB01244

Metabolite Identification

Common Name

15-Keto-13,14-dihydroprostaglandin A2

Description

13,14-dihydro-15-keto PGA2 is produced via non-enzymatic dehydration of 13,14-dihydro-15-keto PGE2. PGE2 is the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). (PMID: 16978535 , 7384561 , 7384560 )Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

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

HMDB0001244
     RDKit          3D
15-Keto-13,14-dihydroprostaglandin A2
 54 54  0  0  0  0  0  0  0  0999 V2000
   -7.0142    1.4485    0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2596    0.5858   -0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8025   -0.6302    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0387   -1.6236   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7716   -1.1441   -1.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211   -0.6589   -0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610    0.5342    0.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -1.6771    0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -1.0949    1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733   -0.5513    0.3804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1769    0.4912   -0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065    1.6833   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392    1.5512    1.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    2.4601    1.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2457    0.0996    1.2646 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5893   -0.3173    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976    0.1569   -0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5981    0.9877   -1.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6745    1.5991   -0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0308    1.2825   -0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4369   -0.1330   -0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4938   -0.8896    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5276   -1.5805    0.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6282   -0.8684    1.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2587    2.4419    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4004    1.5003    1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9356    0.8716    0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4544    1.1730   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9985    0.3490   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7462   -1.1555    0.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2794   -0.3811    1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567   -2.4524    0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6960   -2.1300   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9051   -0.3080   -1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2786   -1.9962   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246   -2.2797    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7028   -2.4454   -0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176   -1.8954    1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277   -0.2631    1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260   -1.4424   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7453    0.3736   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1656    2.6022   -0.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207   -0.1979    2.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721   -1.4634    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4011   -0.0060    1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.2114   -1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478    1.2528   -2.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5300    1.3775    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4957    2.7274   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204    1.7401   -1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7730    1.8972   -0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7694   -0.6736   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4373   -0.1492   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5438   -0.5669    0.7978 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 12 42  1  0
 15 43  1  1
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END


  Mrv0541 02231219002D          

 24 24  0  0  1  0            999 V2000
   17.6523   -9.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8677   -9.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6962   -8.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9116   -8.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7401   -7.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9554   -7.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3424   -7.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7840   -6.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3971   -5.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2255   -4.9147    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4718   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5581   -3.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3650   -3.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7005   -2.8335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7775   -4.3015    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5980   -4.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0829   -3.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9033   -3.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2388   -4.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0593   -4.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3949   -5.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2153   -5.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7002   -4.8189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5508   -6.2401    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 16  1  0  0  0  0
 17 18  2  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  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001244

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,13,15-16,18H,2-3,5-6,8-12,14H2,1H3,(H,23,24)/b7-4-/t16-,18+/m0/s1

> <INCHI_KEY>
FMKLAIBZMCURLI-BFVRRIQPSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.4498

> <EXACT_MASS>
334.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.63884678784078

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,5S)-2-oxo-5-(3-oxooctyl)cyclopent-3-en-1-yl]hept-5-enoic acid

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
4.7894659619999995

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.199903044826442

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.352559727615073

> <JCHEM_PKA_STRONGEST_BASIC>
-4.935905732087984

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
97.0992

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13,14-dihydro-15-keto-PGA2

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001244
     RDKit          3D
15-Keto-13,14-dihydroprostaglandin A2
 54 54  0  0  0  0  0  0  0  0999 V2000
   -7.0142    1.4485    0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2596    0.5858   -0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8025   -0.6302    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0387   -1.6236   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7716   -1.1441   -1.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211   -0.6589   -0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610    0.5342    0.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -1.6771    0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -1.0949    1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733   -0.5513    0.3804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1769    0.4912   -0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065    1.6833   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392    1.5512    1.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    2.4601    1.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2457    0.0996    1.2646 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5893   -0.3173    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976    0.1569   -0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5981    0.9877   -1.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6745    1.5991   -0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0308    1.2825   -0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4369   -0.1330   -0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4938   -0.8896    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5276   -1.5805    0.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6282   -0.8684    1.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2587    2.4419    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4004    1.5003    1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9356    0.8716    0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4544    1.1730   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9985    0.3490   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7462   -1.1555    0.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2794   -0.3811    1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567   -2.4524    0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6960   -2.1300   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9051   -0.3080   -1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2786   -1.9962   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246   -2.2797    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7028   -2.4454   -0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176   -1.8954    1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277   -0.2631    1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260   -1.4424   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7453    0.3736   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1656    2.6022   -0.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207   -0.1979    2.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721   -1.4634    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4011   -0.0060    1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.2114   -1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478    1.2528   -2.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5300    1.3775    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4957    2.7274   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204    1.7401   -1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7730    1.8972   -0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7694   -0.6736   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4373   -0.1492   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5438   -0.5669    0.7978 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 12 42  1  0
 15 43  1  1
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      32.951 -17.657   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.486 -17.181   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.166 -15.675   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.702 -15.199   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.382 -13.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.917 -13.217   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      26.772 -14.248   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      27.597 -11.711   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.741 -10.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.421  -9.174   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.014  -8.548   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.175  -7.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.681  -6.696   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      29.308  -5.289   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      29.451  -8.030   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.983  -8.191   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.888  -6.945   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.419  -7.106   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.046  -8.513   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.577  -8.674   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      36.204 -10.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.735 -10.241   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      38.640  -8.995   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      38.362 -11.648   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    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   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                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0001244
HETATM    1  C1  UNL     1      -7.014   1.448   0.535  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.260   0.586  -0.483  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.803  -0.630   0.266  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.039  -1.624  -0.529  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.772  -1.144  -1.152  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.821  -0.659  -0.087  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.761   0.534   0.156  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.024  -1.677   0.594  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.858  -1.095   1.312  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.173  -0.551   0.380  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.177   0.491  -0.549  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.306   1.683  -0.166  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.039   1.551   1.073  1.00  0.00           C  
HETATM   14  O2  UNL     1       1.442   2.460   1.863  1.00  0.00           O  
HETATM   15  C13 UNL     1       1.246   0.100   1.265  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.589  -0.317   0.720  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.698   0.157  -0.679  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.598   0.988  -1.135  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.674   1.599  -0.320  1.00  0.00           C  
HETATM   20  C18 UNL     1       6.031   1.283  -0.850  1.00  0.00           C  
HETATM   21  C19 UNL     1       6.437  -0.133  -0.929  1.00  0.00           C  
HETATM   22  C20 UNL     1       6.494  -0.890   0.312  1.00  0.00           C  
HETATM   23  O3  UNL     1       5.528  -1.580   0.701  1.00  0.00           O  
HETATM   24  O4  UNL     1       7.628  -0.868   1.108  1.00  0.00           O  
HETATM   25  H1  UNL     1      -7.259   2.442   0.152  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.400   1.500   1.470  1.00  0.00           H  
HETATM   27  H3  UNL     1      -7.936   0.872   0.833  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.454   1.173  -0.942  1.00  0.00           H  
HETATM   29  H5  UNL     1      -6.999   0.349  -1.275  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.746  -1.156   0.603  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.279  -0.381   1.207  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.757  -2.452   0.186  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.696  -2.130  -1.278  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.905  -0.308  -1.859  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.279  -1.996  -1.652  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.625  -2.280   1.325  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.703  -2.445  -0.166  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.418  -1.895   1.961  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.228  -0.263   1.990  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.626  -1.442  -0.138  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.745   0.374  -1.486  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.166   2.602  -0.709  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.121  -0.198   2.330  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.572  -1.463   0.728  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.401  -0.006   1.367  1.00  0.00           H  
HETATM   46  H22 UNL     1       1.969  -0.211  -1.438  1.00  0.00           H  
HETATM   47  H23 UNL     1       3.548   1.253  -2.218  1.00  0.00           H  
HETATM   48  H24 UNL     1       4.530   1.378   0.730  1.00  0.00           H  
HETATM   49  H25 UNL     1       4.496   2.727  -0.427  1.00  0.00           H  
HETATM   50  H26 UNL     1       6.120   1.740  -1.884  1.00  0.00           H  
HETATM   51  H27 UNL     1       6.773   1.897  -0.256  1.00  0.00           H  
HETATM   52  H28 UNL     1       5.769  -0.674  -1.671  1.00  0.00           H  
HETATM   53  H29 UNL     1       7.437  -0.149  -1.469  1.00  0.00           H  
HETATM   54  H30 UNL     1       8.544  -0.567   0.798  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7    8
CONECT    8    9   36   37
CONECT    9   10   38   39
CONECT   10   11   15   40
CONECT   11   12   12   41
CONECT   12   13   42
CONECT   13   14   14   15
CONECT   15   16   43
CONECT   16   17   44   45
CONECT   17   18   18   46
CONECT   18   19   47
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22   52   53
CONECT   22   23   23   24
CONECT   24   54
END

HMDB0001244
     RDKit          3D
15-Keto-13,14-dihydroprostaglandin A2
 54 54  0  0  0  0  0  0  0  0999 V2000
   -7.0142    1.4485    0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2596    0.5858   -0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8025   -0.6302    0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0387   -1.6236   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7716   -1.1441   -1.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211   -0.6589   -0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610    0.5342    0.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -1.6771    0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -1.0949    1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733   -0.5513    0.3804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1769    0.4912   -0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065    1.6833   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392    1.5512    1.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421    2.4601    1.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2457    0.0996    1.2646 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5893   -0.3173    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976    0.1569   -0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5981    0.9877   -1.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6745    1.5991   -0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0308    1.2825   -0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4369   -0.1330   -0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4938   -0.8896    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5276   -1.5805    0.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6282   -0.8684    1.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2587    2.4419    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4004    1.5003    1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9356    0.8716    0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4544    1.1730   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9985    0.3490   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7462   -1.1555    0.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2794   -0.3811    1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567   -2.4524    0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6960   -2.1300   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9051   -0.3080   -1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2786   -1.9962   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246   -2.2797    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7028   -2.4454   -0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176   -1.8954    1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277   -0.2631    1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260   -1.4424   -0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7453    0.3736   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1656    2.6022   -0.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207   -0.1979    2.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721   -1.4634    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4011   -0.0060    1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.2114   -1.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478    1.2528   -2.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5300    1.3775    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4957    2.7274   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204    1.7401   -1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7730    1.8972   -0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7694   -0.6736   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4373   -0.1492   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5438   -0.5669    0.7978 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 15 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  6
 11 41  1  0
 12 42  1  0
 15 43  1  1
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z)-9,15-Dioxo-prosta-5,10-dien-1-Oate	HMDB
(5Z)-9,15-Dioxo-prosta-5,10-dien-1-Oic acid	HMDB
15-Keto-13,14-dihydro-pga2	HMDB
9,15-Dioxo-5Z,10-prostadienoate	HMDB
9,15-Dioxo-5Z,10-prostadienoic acid	HMDB
DHK-PGA2	HMDB
15-Keto-13,14-dihydroprostaglandin a2	MeSH

Chemical Formula

C₂₀H₃₀O₄

Average Molecular Weight

334.4498

Monoisotopic Molecular Weight

334.214409448

IUPAC Name

(5Z)-7-[(1R,5S)-2-oxo-5-(3-oxooctyl)cyclopent-3-en-1-yl]hept-5-enoic acid

Traditional Name

13,14-dihydro-15-keto-PGA2

CAS Registry Number

74872-89-2

SMILES

CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,13,15-16,18H,2-3,5-6,8-12,14H2,1H3,(H,23,24)/b7-4-/t16-,18+/m0/s1

InChI Key

FMKLAIBZMCURLI-BFVRRIQPSA-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

Prostaglandins (LMFA03010033 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Cellular substructure

Extracellular (HMDB: HMDB0001244)
Membrane (HMDB: HMDB0001244)

Source

Exogenous

Exogenous (HMDB: HMDB0001244)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0001244)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	0.012 g/L	ALOGPS
logP	4.13	ALOGPS
logP	4.79	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	97.1 m³·mol⁻¹	ChemAxon
Polarizability	38.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DarkChem	[M+H]+	184.31	31661259
DarkChem	[M-H]-	182.431	31661259
AllCCS	[M+H]+	187.585	32859911
AllCCS	[M-H]-	188.674	32859911
DeepCCS	[M+H]+	193.965	30932474
DeepCCS	[M-H]-	191.607	30932474
DeepCCS	[M-2H]-	225.612	30932474
DeepCCS	[M+Na]+	200.839	30932474
AllCCS	[M+H]+	187.6	32859911
AllCCS	[M+H-H2O]+	184.8	32859911
AllCCS	[M+NH4]+	190.2	32859911
AllCCS	[M+Na]+	190.9	32859911
AllCCS	[M-H]-	188.7	32859911
AllCCS	[M+Na-2H]-	190.0	32859911
AllCCS	[M+HCOO]-	191.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	8.4 minutes	32390414
Predicted by Siyang on May 30, 2022	17.5146 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.96 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2818.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	350.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	203.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	199.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	757.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	561.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1666.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	549.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1547.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	453.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	444.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	310.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	343.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
15-Keto-13,14-dihydroprostaglandin A2	CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O	4283.2	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2	CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O	2534.9	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2	CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O	2668.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
15-Keto-13,14-dihydroprostaglandin A2,1TMS,isomer #1	CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2742.4	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,1TMS,isomer #2	CCCCCC(=O)CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O	2843.7	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,1TMS,isomer #3	CCCCCC(=CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2845.8	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,1TMS,isomer #4	CCCCC=C(CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2875.5	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #1	CCCCCC(=O)CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C	2806.3	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #1	CCCCCC(=O)CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C	2706.4	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #1	CCCCCC(=O)CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C	3024.3	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #2	CCCCCC(=CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2815.9	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #2	CCCCCC(=CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2772.0	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #2	CCCCCC(=CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3210.1	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #3	CCCCC=C(CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2821.6	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #3	CCCCC=C(CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2770.0	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #3	CCCCC=C(CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3149.4	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #4	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2929.9	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #4	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2702.7	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #4	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C	3265.5	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #5	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2939.6	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #5	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2712.5	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TMS,isomer #5	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C	3222.9	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TMS,isomer #1	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2919.6	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TMS,isomer #1	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2763.3	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TMS,isomer #1	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2974.9	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TMS,isomer #2	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2912.5	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TMS,isomer #2	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2765.8	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TMS,isomer #2	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2911.5	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,1TBDMS,isomer #1	CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2988.8	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,1TBDMS,isomer #2	CCCCCC(=O)CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O	3075.9	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,1TBDMS,isomer #3	CCCCCC(=CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3088.1	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,1TBDMS,isomer #4	CCCCC=C(CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3107.2	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #1	CCCCCC(=O)CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3286.7	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #1	CCCCCC(=O)CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3048.4	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #1	CCCCCC(=O)CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3169.2	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #2	CCCCCC(=CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3294.5	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #2	CCCCCC(=CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3129.6	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #2	CCCCCC(=CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3298.7	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #3	CCCCC=C(CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3290.2	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #3	CCCCC=C(CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3124.4	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #3	CCCCC=C(CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3244.7	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #4	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3372.9	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #4	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3041.9	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #4	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3386.9	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #5	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3363.7	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #5	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3050.0	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,2TBDMS,isomer #5	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3342.5	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TBDMS,isomer #1	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3600.0	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TBDMS,isomer #1	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3239.2	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TBDMS,isomer #1	CCCCCC(=CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3167.2	Standard polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TBDMS,isomer #2	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3576.3	Semi standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TBDMS,isomer #2	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3237.0	Standard non polar	33892256
15-Keto-13,14-dihydroprostaglandin A2,3TBDMS,isomer #2	CCCCC=C(CC[C@H]1C=CC(O[Si](C)(C)C(C)(C)C)=C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3117.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bti-5290000000-24254cd7666bb88650bd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 GC-MS (1 TMS) - 70eV, Positive	splash10-005c-9077000000-1d776bc4aeae04880455	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 15-Keto-13,14-dihydroprostaglandin A2 10V, Positive-QTOF	splash10-014r-0059000000-cd839316fe5c8de8c7ab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 20V, Positive-QTOF	splash10-01bj-5492000000-9aa476ddaf4afa586e70	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 40V, Positive-QTOF	splash10-0fld-9220000000-6da9eac652a9a4ea517a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 10V, Negative-QTOF	splash10-001i-0019000000-8160ad86f6fc73dd6159	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 20V, Negative-QTOF	splash10-02ar-3389000000-6cb0f8955f9e692128e7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 40V, Negative-QTOF	splash10-0bt9-9530000000-5fe451a36aa6da7d6982	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 10V, Positive-QTOF	splash10-00kb-1096000000-eacb9c1ff50ad4852882	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 20V, Positive-QTOF	splash10-01c1-9872000000-8c21341c86a39e4e5d15	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 40V, Positive-QTOF	splash10-00pl-9310000000-d513eb33cb41aabbbfb8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 10V, Negative-QTOF	splash10-001i-0009000000-fdef3b9ecd8b738341ea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 20V, Negative-QTOF	splash10-01po-7934000000-eb3c7c6b54ab436cf1d9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Keto-13,14-dihydroprostaglandin A2 40V, Negative-QTOF	splash10-0a4i-9620000000-fd6316281d8ae18eec63	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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 and Quantified	0.000130 +/- 0.000059 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	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

FDB022509

KNApSAcK ID

Not Available

Chemspider ID

4446169

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283042

PDB ID

Not Available

ChEBI ID

89315

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

Harizi H, Gualde N: Pivotal role of PGE2 and IL-10 in the cross-regulation of dendritic cell-derived inflammatory mediators. Cell Mol Immunol. 2006 Aug;3(4):271-7. [PubMed:16978535 ]
Granstrom E, Hamberg M, Hansson G, Kindahl H: Chemical instability of 15-keto-13,14-dihydro-PGE2: the reason for low assay reliability. Prostaglandins. 1980 Jun;19(6):933-57. [PubMed:7384561 ]
Fitzpatrick FA, Aguirre R, Pike JE, Lincoln FH: The stability of 13,14-dihydro-15 keto-PGE2. Prostaglandins. 1980 Jun;19(6):917-31. [PubMed:7384560 ]

Showing metabocard for 15-Keto-13,14-dihydroprostaglandin A2 (HMDB0001244)

MOL for HMDB0001244 (15-Keto-13,14-dihydroprostaglandin A2)

3D MOL for HMDB0001244 (15-Keto-13,14-dihydroprostaglandin A2)

3D SDF for HMDB0001244 (15-Keto-13,14-dihydroprostaglandin A2)

3D-SDF for HMDB0001244 (15-Keto-13,14-dihydroprostaglandin A2)

PDB for HMDB0001244 (15-Keto-13,14-dihydroprostaglandin A2)

3D PDB for HMDB0001244 (15-Keto-13,14-dihydroprostaglandin A2)

SMILES for HMDB0001244 (15-Keto-13,14-dihydroprostaglandin A2)

INCHI for HMDB0001244 (15-Keto-13,14-dihydroprostaglandin A2)

Structure for HMDB0001244 (15-Keto-13,14-dihydroprostaglandin A2)

3D Structure for HMDB0001244 (15-Keto-13,14-dihydroprostaglandin A2)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra