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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 15:03:00 UTC

Update Date

2022-03-07 02:49:20 UTC

HMDB ID

HMDB0004242

Secondary Accession Numbers

HMDB04242

Metabolite Identification

Common Name

11-Dehydro-thromboxane B2

Description

11-Dehydro-thromboxane B2, a stable thromboxane metabolite, is a full agonist of chemoattractant receptor-homologous molecule expressed on TH2 cells (CRTH2) in human eosinophils and basophils. Given its production in the allergic lung, antagonism of the 11-dehydro- thromboxane B2/CRTH2axis may be of therapeutic relevance. (PMID 14668348 )Thromboxanes 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


  Mrv0541 02231219542D          

 26 26  0  0  1  0            999 V2000
   27.2914  -12.3903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5784  -13.2153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0073   -8.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4349  -14.4528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5784   -8.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1494  -15.6903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2914  -13.2153    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.5770  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8625  -13.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1481  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5784   -9.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4335  -13.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2929   -9.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5784  -10.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1494  -12.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7190  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8639  -13.6278    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.1494  -13.2153    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.4349  -13.6278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.8639  -14.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2929   -8.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8639  -11.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8639  -11.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0060  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7205  -13.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1494  -14.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  6  0  0  0
 17  2  1  1  0  0  0
  3 21  1  0  0  0  0
  4 19  1  0  0  0  0
  4 26  1  0  0  0  0
  5 21  2  0  0  0  0
  6 26  2  0  0  0  0
  7  8  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 16  1  0  0  0  0
 13 21  1  0  0  0  0
 14 22  1  0  0  0  0
 18 15  1  1  0  0  0
 15 23  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 25  1  6  0  0  0
 20 26  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  2  0  0  0  0
M  END

HMDB0004242
     RDKit          3D
11-Dehydro-thromboxane B2
 58 58  0  0  0  0  0  0  0  0999 V2000
    7.2615    1.0988   -1.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5504    0.7830   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4340    0.7864    0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3331   -0.1963    0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821   -0.0912   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4226   -1.0920   -0.9118 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8152   -0.8759   -2.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -0.8343    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676   -0.2241   -0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758    0.0217    0.9152 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6223    1.1756    1.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157    1.7078    2.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3391    2.8995    2.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5747    0.8370    2.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563    0.0431    1.6029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9932   -1.3125    1.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    0.2505    0.4296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5147   -0.5700   -0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9406   -0.1897   -1.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235   -1.0791   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3422   -0.6824   -1.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1630   -1.0050   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6127   -0.6916   -0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8454    0.7306   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0344    1.1097   -0.6899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8404    1.6529   -0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3062    0.1756   -2.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0577    1.8191   -2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2836    1.5912   -1.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3613    1.4929   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0742   -0.2305   -0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0012    1.8547    0.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8434    0.7782    1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6818   -0.1046    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7939   -1.2215    0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978    0.8936   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2486   -0.4464   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8422   -2.1166   -0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2428   -1.4446   -2.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -1.1296    1.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    0.1007   -1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993   -0.8261    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269    1.4348    3.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2440    0.1922    3.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1066    0.2927    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5406   -1.8797    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2163    1.3276    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8954   -0.2414   -1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438   -1.6447   -0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1818    0.8422   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6693   -2.1030   -0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3909    0.3486   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6610   -1.3874   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9596   -2.0538    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7346   -0.3878    0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1324   -1.3443   -1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0612   -0.9520    0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4275    2.1176    0.2633 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  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 17 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  6
  7 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  1
 14 43  1  0
 14 44  1  0
 15 45  1  6
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 26 58  1  0
M  END


  Mrv0541 02231219542D          

 26 26  0  0  1  0            999 V2000
   27.2914  -12.3903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5784  -13.2153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0073   -8.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4349  -14.4528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5784   -8.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1494  -15.6903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2914  -13.2153    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.5770  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8625  -13.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1481  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5784   -9.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4335  -13.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2929   -9.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5784  -10.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1494  -12.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7190  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8639  -13.6278    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.1494  -13.2153    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.4349  -13.6278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.8639  -14.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2929   -8.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8639  -11.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8639  -11.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0060  -13.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7205  -13.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1494  -14.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  6  0  0  0
 17  2  1  1  0  0  0
  3 21  1  0  0  0  0
  4 19  1  0  0  0  0
  4 26  1  0  0  0  0
  5 21  2  0  0  0  0
  6 26  2  0  0  0  0
  7  8  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 16  1  0  0  0  0
 13 21  1  0  0  0  0
 14 22  1  0  0  0  0
 18 15  1  1  0  0  0
 15 23  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 25  1  6  0  0  0
 20 26  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004242

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1OC(=O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,23,24)/b7-4+,13-12+/t15-,16-,17-,18+/m0/s1

> <INCHI_KEY>
KJYIVXDPWBUJBQ-SOGWKEBJSA-N

> <FORMULA>
C20H32O6

> <MOLECULAR_WEIGHT>
368.4645

> <EXACT_MASS>
368.219888756

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.70300195639902

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-7-[(2R,3S,4S)-4-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-6-oxooxan-3-yl]hept-5-enoic acid

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
2.924771171333332

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.407726559505786

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2730030102327685

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8469665790769447

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
100.21229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-7-[(2R,3S,4S)-4-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-6-oxooxan-3-yl]hept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004242
     RDKit          3D
11-Dehydro-thromboxane B2
 58 58  0  0  0  0  0  0  0  0999 V2000
    7.2615    1.0988   -1.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5504    0.7830   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4340    0.7864    0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3331   -0.1963    0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821   -0.0912   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4226   -1.0920   -0.9118 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8152   -0.8759   -2.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -0.8343    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676   -0.2241   -0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758    0.0217    0.9152 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6223    1.1756    1.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157    1.7078    2.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3391    2.8995    2.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5747    0.8370    2.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563    0.0431    1.6029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9932   -1.3125    1.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    0.2505    0.4296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5147   -0.5700   -0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9406   -0.1897   -1.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235   -1.0791   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3422   -0.6824   -1.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1630   -1.0050   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6127   -0.6916   -0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8454    0.7306   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0344    1.1097   -0.6899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8404    1.6529   -0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3062    0.1756   -2.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0577    1.8191   -2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2836    1.5912   -1.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3613    1.4929   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0742   -0.2305   -0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0012    1.8547    0.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8434    0.7782    1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6818   -0.1046    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7939   -1.2215    0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978    0.8936   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2486   -0.4464   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8422   -2.1166   -0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2428   -1.4446   -2.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -1.1296    1.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    0.1007   -1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993   -0.8261    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269    1.4348    3.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2440    0.1922    3.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1066    0.2927    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5406   -1.8797    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2163    1.3276    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8954   -0.2414   -1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438   -1.6447   -0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1818    0.8422   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6693   -2.1030   -0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3909    0.3486   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6610   -1.3874   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9596   -2.0538    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7346   -0.3878    0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1324   -1.3443   -1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0612   -0.9520    0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4275    2.1176    0.2633 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  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 17 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  6
  7 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  1
 14 43  1  0
 14 44  1  0
 15 45  1  6
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 26 58  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  O   UNK     0      50.944 -23.129   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      58.946 -24.669   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      61.614 -15.428   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      54.945 -26.979   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      58.946 -15.428   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      56.279 -29.289   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      50.944 -24.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.610 -25.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.277 -24.669   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      46.943 -25.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      58.946 -18.508   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.609 -24.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      60.280 -17.738   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      58.946 -20.048   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      56.279 -23.129   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      44.275 -25.439   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      57.613 -25.439   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      56.279 -24.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      54.945 -25.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      57.613 -26.979   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      60.280 -16.198   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      57.613 -20.818   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      57.613 -22.359   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      52.278 -25.439   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      53.612 -24.669   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      56.279 -27.749   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   17                                                            
CONECT    3   21                                                            
CONECT    4   19   26                                                       
CONECT    5   21                                                            
CONECT    6   26                                                            
CONECT    7    1    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   12                                                       
CONECT   11   13   14                                                       
CONECT   12   10   16                                                       
CONECT   13   11   21                                                       
CONECT   14   11   22                                                       
CONECT   15   18   23                                                       
CONECT   16   12                                                            
CONECT   17    2   18   20                                                  
CONECT   18   15   17   19                                                  
CONECT   19    4   18   25                                                  
CONECT   20   17   26                                                       
CONECT   21    3    5   13                                                  
CONECT   22   14   23                                                       
CONECT   23   15   22                                                       
CONECT   24    7   25                                                       
CONECT   25   19   24                                                       
CONECT   26    4    6   20                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

COMPND    HMDB0004242
HETATM    1  C1  UNL     1       7.262   1.099  -1.826  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.550   0.783  -0.411  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.434   0.786   0.559  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.333  -0.196   0.419  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.582  -0.091  -0.845  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.423  -1.092  -0.912  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.815  -0.876  -2.148  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.410  -0.834   0.138  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.268  -0.224  -0.143  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.276   0.022   0.915  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.622   1.176   1.700  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.416   1.708   2.450  1.00  0.00           C  
HETATM   13  O3  UNL     1      -0.339   2.899   2.828  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.575   0.837   2.772  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.056   0.043   1.603  1.00  0.00           C  
HETATM   16  O4  UNL     1      -1.993  -1.313   1.953  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.122   0.250   0.430  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.515  -0.570  -0.766  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.941  -0.190  -1.085  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.923  -1.079  -1.075  1.00  0.00           C  
HETATM   21  C17 UNL     1      -5.342  -0.682  -1.396  1.00  0.00           C  
HETATM   22  C18 UNL     1      -6.163  -1.005  -0.187  1.00  0.00           C  
HETATM   23  C19 UNL     1      -7.613  -0.692  -0.288  1.00  0.00           C  
HETATM   24  C20 UNL     1      -7.845   0.731  -0.507  1.00  0.00           C  
HETATM   25  O5  UNL     1      -9.034   1.110  -0.690  1.00  0.00           O  
HETATM   26  O6  UNL     1      -6.840   1.653  -0.522  1.00  0.00           O  
HETATM   27  H1  UNL     1       7.306   0.176  -2.439  1.00  0.00           H  
HETATM   28  H2  UNL     1       8.058   1.819  -2.235  1.00  0.00           H  
HETATM   29  H3  UNL     1       6.284   1.591  -1.987  1.00  0.00           H  
HETATM   30  H4  UNL     1       8.361   1.493  -0.050  1.00  0.00           H  
HETATM   31  H5  UNL     1       8.074  -0.231  -0.384  1.00  0.00           H  
HETATM   32  H6  UNL     1       6.001   1.855   0.526  1.00  0.00           H  
HETATM   33  H7  UNL     1       6.843   0.778   1.631  1.00  0.00           H  
HETATM   34  H8  UNL     1       4.682  -0.105   1.330  1.00  0.00           H  
HETATM   35  H9  UNL     1       5.794  -1.222   0.534  1.00  0.00           H  
HETATM   36  H10 UNL     1       4.198   0.894  -1.125  1.00  0.00           H  
HETATM   37  H11 UNL     1       5.249  -0.446  -1.680  1.00  0.00           H  
HETATM   38  H12 UNL     1       3.842  -2.117  -0.854  1.00  0.00           H  
HETATM   39  H13 UNL     1       3.243  -1.445  -2.846  1.00  0.00           H  
HETATM   40  H14 UNL     1       2.552  -1.130   1.183  1.00  0.00           H  
HETATM   41  H15 UNL     1       1.049   0.101  -1.147  1.00  0.00           H  
HETATM   42  H16 UNL     1       0.299  -0.826   1.662  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.427   1.435   3.181  1.00  0.00           H  
HETATM   44  H18 UNL     1      -1.244   0.192   3.633  1.00  0.00           H  
HETATM   45  H19 UNL     1      -3.107   0.293   1.342  1.00  0.00           H  
HETATM   46  H20 UNL     1      -2.541  -1.880   1.350  1.00  0.00           H  
HETATM   47  H21 UNL     1      -1.216   1.328   0.147  1.00  0.00           H  
HETATM   48  H22 UNL     1      -0.895  -0.241  -1.625  1.00  0.00           H  
HETATM   49  H23 UNL     1      -1.444  -1.645  -0.616  1.00  0.00           H  
HETATM   50  H24 UNL     1      -3.182   0.842  -1.332  1.00  0.00           H  
HETATM   51  H25 UNL     1      -3.669  -2.103  -0.827  1.00  0.00           H  
HETATM   52  H26 UNL     1      -5.391   0.349  -1.734  1.00  0.00           H  
HETATM   53  H27 UNL     1      -5.661  -1.387  -2.200  1.00  0.00           H  
HETATM   54  H28 UNL     1      -5.960  -2.054   0.115  1.00  0.00           H  
HETATM   55  H29 UNL     1      -5.735  -0.388   0.657  1.00  0.00           H  
HETATM   56  H30 UNL     1      -8.132  -1.344  -1.037  1.00  0.00           H  
HETATM   57  H31 UNL     1      -8.061  -0.952   0.716  1.00  0.00           H  
HETATM   58  H32 UNL     1      -6.427   2.118   0.263  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7    8   38
CONECT    7   39
CONECT    8    9    9   40
CONECT    9   10   41
CONECT   10   11   17   42
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   43   44
CONECT   15   16   17   45
CONECT   16   46
CONECT   17   18   47
CONECT   18   19   48   49
CONECT   19   20   20   50
CONECT   20   21   51
CONECT   21   22   52   53
CONECT   22   23   54   55
CONECT   23   24   56   57
CONECT   24   25   25   26
CONECT   26   58
END

HMDB0004242
     RDKit          3D
11-Dehydro-thromboxane B2
 58 58  0  0  0  0  0  0  0  0999 V2000
    7.2615    1.0988   -1.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5504    0.7830   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4340    0.7864    0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3331   -0.1963    0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821   -0.0912   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4226   -1.0920   -0.9118 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8152   -0.8759   -2.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -0.8343    0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676   -0.2241   -0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758    0.0217    0.9152 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6223    1.1756    1.6996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157    1.7078    2.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3391    2.8995    2.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5747    0.8370    2.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563    0.0431    1.6029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9932   -1.3125    1.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    0.2505    0.4296 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5147   -0.5700   -0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9406   -0.1897   -1.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235   -1.0791   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3422   -0.6824   -1.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1630   -1.0050   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6127   -0.6916   -0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8454    0.7306   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0344    1.1097   -0.6899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8404    1.6529   -0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3062    0.1756   -2.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0577    1.8191   -2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2836    1.5912   -1.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3613    1.4929   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0742   -0.2305   -0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0012    1.8547    0.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8434    0.7782    1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6818   -0.1046    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7939   -1.2215    0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978    0.8936   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2486   -0.4464   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8422   -2.1166   -0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2428   -1.4446   -2.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -1.1296    1.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    0.1007   -1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993   -0.8261    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4269    1.4348    3.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2440    0.1922    3.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1066    0.2927    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5406   -1.8797    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2163    1.3276    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8954   -0.2414   -1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438   -1.6447   -0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1818    0.8422   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6693   -2.1030   -0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3909    0.3486   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6610   -1.3874   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9596   -2.0538    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7346   -0.3878    0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1324   -1.3443   -1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0612   -0.9520    0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4275    2.1176    0.2633 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  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 17 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  6
  7 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  1
 14 43  1  0
 14 44  1  0
 15 45  1  6
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 26 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11-dehydro-Thromboxane	HMDB
11-dehydro-TXB2	HMDB, MeSH
11-Dehydrothromboxane	HMDB
11-Dehydrothromboxane b2	HMDB, MeSH
11-DehydroTXB2	HMDB
11-keto-Thromboxane	HMDB
11-keto-Thromboxane b2	MeSH, HMDB

Chemical Formula

C₂₀H₃₂O₆

Average Molecular Weight

368.4645

Monoisotopic Molecular Weight

368.219888756

IUPAC Name

(5E)-7-[(2R,3S,4S)-4-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-6-oxooxan-3-yl]hept-5-enoic acid

Traditional Name

(5E)-7-[(2R,3S,4S)-4-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-6-oxooxan-3-yl]hept-5-enoic acid

CAS Registry Number

67910-12-7

SMILES

CCCCC[C@H](O)\C=C\[C@H]1OC(=O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,23,24)/b7-4+,13-12+/t15-,16-,17-,18+/m0/s1

InChI Key

KJYIVXDPWBUJBQ-SOGWKEBJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thromboxanes. These are eicosanoids structurally characterized by the presence of a 6-member ether containing ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Thromboxanes

Alternative Parents

Substituents

Thromboxane
Long-chain fatty acid
Delta valerolactone
Heterocyclic fatty acid
Hydroxy fatty acid
Delta_valerolactone
Unsaturated fatty acid
Oxane
Fatty acid
Dicarboxylic acid or derivatives
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Angina (HMDB: HMDB0004242)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0004242)
Cell membrane (HMDB: HMDB0004242)

Biofluid or Excreta

Blood (HMDB: HMDB0004242)
Urine (HMDB: HMDB0004242)

Cellular element

Platelet (HMDB: HMDB0004242)

Cell

Hematocyte

Platelet (HMDB: HMDB0004242)

Excreta

Biofluid or Excreta

Urine (PMID: 1844445)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 1590375)

Cellular substructure

Membrane (HMDB: HMDB0004242)
Extracellular (HMDB: HMDB0004242)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004242)

Source

Endogenous

Endogenous (HMDB: HMDB0004242)

Animal

Animal (HMDB: HMDB0004242)

Exogenous

Food

Food (HMDB: HMDB0004242)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arachidonic Acid Metabolism (HMDB: HMDB0004242)

Acetaminophen Action Pathway (HMDB: HMDB0004242)

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0000353)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium Salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-Choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-Sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

Chemical reaction

Lipid peroxidation (HMDB: HMDB0004242)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0004242)

Cellular process

Cell signaling (HMDB: HMDB0004242)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0004242)

Nutrient

Nutrient (HMDB: HMDB0004242)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004242)

Emulsifier (HMDB: HMDB0004242)

Pharmaceutical industry

Biomarker

Angina (MarkerDB: MDB00000445)

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	0.1 g/L	ALOGPS
logP	4	ALOGPS
logP	2.92	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	100.21 m³·mol⁻¹	ChemAxon
Polarizability	41.7 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]+	192.787	31661259
DarkChem	[M-H]-	195.807	31661259
DeepCCS	[M+H]+	195.634	30932474
DeepCCS	[M-H]-	193.239	30932474
DeepCCS	[M-2H]-	226.814	30932474
DeepCCS	[M+Na]+	201.709	30932474
AllCCS	[M+H]+	196.1	32859911
AllCCS	[M+H-H2O]+	193.5	32859911
AllCCS	[M+NH4]+	198.5	32859911
AllCCS	[M+Na]+	199.2	32859911
AllCCS	[M-H]-	193.7	32859911
AllCCS	[M+Na-2H]-	195.1	32859911
AllCCS	[M+HCOO]-	196.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11-Dehydro-thromboxane B2	CCCCC[C@H](O)\C=C\[C@H]1OC(=O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O	4491.1	Standard polar	33892256
11-Dehydro-thromboxane B2	CCCCC[C@H](O)\C=C\[C@H]1OC(=O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O	2737.8	Standard non polar	33892256
11-Dehydro-thromboxane B2	CCCCC[C@H](O)\C=C\[C@H]1OC(=O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O	3075.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11-Dehydro-thromboxane B2,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1OC(=O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C	2891.1	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1OC(=O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O	2844.7	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,1TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1OC(=O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C	2859.7	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1OC(=O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C	2827.0	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,2TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1OC(=O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2882.9	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,2TMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1OC(=O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C	2824.0	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,3TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1OC(=O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2815.0	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1OC(=O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3114.7	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1OC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O	3041.5	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1OC(=O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C	3101.9	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1OC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3279.8	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1OC(=O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3357.2	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,2TBDMS,isomer #3	CCCCC[C@H](O)/C=C/[C@H]1OC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C	3275.3	Semi standard non polar	33892256
11-Dehydro-thromboxane B2,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1OC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3502.7	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 - 11-Dehydro-thromboxane B2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-8694000000-b3e1575c156ad43560a4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Dehydro-thromboxane B2 GC-MS (3 TMS) - 70eV, Positive	splash10-01b9-3503590000-33e79e5366d8cf9dd7dd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Dehydro-thromboxane B2 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Dehydro-thromboxane B2 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 - 11-Dehydro-thromboxane B2 10V, Positive-QTOF	splash10-0ue9-0029000000-14e5a0b6b8a0ad2b4202	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 20V, Positive-QTOF	splash10-0kh9-3179000000-f322c721c2db5ce99c1c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 40V, Positive-QTOF	splash10-0l0m-9040000000-cd3172ac0337835ae861	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 10V, Negative-QTOF	splash10-00kb-0069000000-46a20251644a343285c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 20V, Negative-QTOF	splash10-05bb-2197000000-44ea48cdcb64f0e36817	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 40V, Negative-QTOF	splash10-0a4i-9342000000-b6b00743b4251325d4d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 10V, Positive-QTOF	splash10-0ue9-0019000000-a730bfd252e796a9a5eb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 20V, Positive-QTOF	splash10-053u-9314000000-50e0714da1dd551fc405	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 40V, Positive-QTOF	splash10-067i-9300000000-fdf67ce1738087b8440c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 10V, Negative-QTOF	splash10-014i-0009000000-03251a704cebdfe34808	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 20V, Negative-QTOF	splash10-066s-1049000000-afb6c183b0f042652b2f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Dehydro-thromboxane B2 40V, Negative-QTOF	splash10-000l-8692000000-ca867302a7906d2e249f	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00280 +/- 0.00068 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.0027 (0.0021-0.0035) uM	Adult (>18 years old)	Both	Normal	1590375	details
Urine	Detected and Quantified	0.006 +/- 0.00076 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9373880	details
Urine	Detected and Quantified	0.01 +/- 0.0015 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9373880	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0000733 +/- 0.0000266 umol/mmol creatinine	Adult (>18 years old)	Both	Angina	1844445	details
Urine	Detected and Quantified	0.000165 +/- 0.0000544 umol/mmol creatinine	Adult (>18 years old)	Both	Angina	1844445	details

Associated Disorders and Diseases

Disease References

Angina
Koike T, Hattori A, Igarashi Y, Matsubara T, Tamura Y, Yamazoe M, Izumi T, Shibata A: [Elevation of 11-dehydro-thromboxane B2 levels in unstable angina]. J Cardiol. 1991;21(4):899-904. [PubMed:1844445 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023347

KNApSAcK ID

Not Available

Chemspider ID

30776537

KEGG Compound ID

C05964

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7037

PubChem Compound

53477781

PDB ID

Not Available

ChEBI ID

28667

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000445

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Cipollone F, Ganci A, Panara MR, Greco A, Cuccurullo F, Patrono C, Patrignani P: Effects of nabumetone on prostanoid biosynthesis in humans. Clin Pharmacol Ther. 1995 Sep;58(3):335-41. [PubMed:7554708 ]
Clarke MW, Ward NC, Wu JH, Hodgson JM, Puddey IB, Croft KD: Supplementation with mixed tocopherols increases serum and blood cell gamma-tocopherol but does not alter biomarkers of platelet activation in subjects with type 2 diabetes. Am J Clin Nutr. 2006 Jan;83(1):95-102. [PubMed:16400056 ]
De Cristofaro R, Rocca B, Vitacolonna E, Falco A, Marchesani P, Ciabattoni G, Landolfi R, Patrono C, Davi G: Lipid and protein oxidation contribute to a prothrombotic state in patients with type 2 diabetes mellitus. J Thromb Haemost. 2003 Feb;1(2):250-6. [PubMed:12871497 ]
Davi G, Ciabattoni G, Consoli A, Mezzetti A, Falco A, Santarone S, Pennese E, Vitacolonna E, Bucciarelli T, Costantini F, Capani F, Patrono C: In vivo formation of 8-iso-prostaglandin f2alpha and platelet activation in diabetes mellitus: effects of improved metabolic control and vitamin E supplementation. Circulation. 1999 Jan 19;99(2):224-9. [PubMed:9892587 ]
Foulon I, Bachir D, Galacteros F, Maclouf J: Increased in vivo production of thromboxane in patients with sickle cell disease is accompanied by an impairment of platelet functions to the thromboxane A2 agonist U46619. Arterioscler Thromb. 1993 Mar;13(3):421-6. [PubMed:8443146 ]
Koudstaal PJ, Ciabattoni G, van Gijn J, Nieuwenhuis HK, de Groot PG, Sixma JJ, Patrono C: Increased thromboxane biosynthesis in patients with acute cerebral ischemia. Stroke. 1993 Feb;24(2):219-23. [PubMed:8421822 ]
Rebuzzi AG, Natale A, Bianchi C, Albanese S, Lanza GA, Coppola E, Ciabattoni G: Importance of reperfusion on thromboxane A2 metabolite excretion after thrombolysis. Am Heart J. 1992 Mar;123(3):560-6. [PubMed:1539506 ]
Cipollone F, Mezzetti A, Porreca E, Di Febbo C, Nutini M, Fazia M, Falco A, Cuccurullo F, Davi G: Association between enhanced soluble CD40L and prothrombotic state in hypercholesterolemia: effects of statin therapy. Circulation. 2002 Jul 23;106(4):399-402. [PubMed:12135935 ]
Wang Z, Ciabattoni G, Creminon C, Lawson J, Fitzgerald GA, Patrono C, Maclouf J: Immunological characterization of urinary 8-epi-prostaglandin F2 alpha excretion in man. J Pharmacol Exp Ther. 1995 Oct;275(1):94-100. [PubMed:7562601 ]
Morrow JD, Oates JA, Roberts LJ 2nd, Zackert WE, Mitchell TA, Lazarus G, Guzzo C: Increased formation of thromboxane in vivo in humans with mastocytosis. J Invest Dermatol. 1999 Jul;113(1):93-7. [PubMed:10417625 ]
Maclouf J, Lellouche F, Martinuzzo M, Said P, Carreras LO: Increased production of platelet-derived thromboxane in patients with lupus anticoagulant. Agents Actions Suppl. 1992;37:27-33. [PubMed:1632300 ]
Williams PC, Coffey MJ, Coles B, Sanchez S, Morrow JD, Cockcroft JR, Lewis MJ, O'Donnell VB: In vivo aspirin supplementation inhibits nitric oxide consumption by human platelets. Blood. 2005 Oct 15;106(8):2737-43. Epub 2005 Jun 21. [PubMed:15972451 ]
Bohm E, Sturm GJ, Weiglhofer I, Sandig H, Shichijo M, McNamee A, Pease JE, Kollroser M, Peskar BA, Heinemann A: 11-Dehydro-thromboxane B2, a stable thromboxane metabolite, is a full agonist of chemoattractant receptor-homologous molecule expressed on TH2 cells (CRTH2) in human eosinophils and basophils. J Biol Chem. 2004 Feb 27;279(9):7663-70. Epub 2003 Dec 10. [PubMed:14668348 ]

Showing metabocard for 11-Dehydro-thromboxane B2 (HMDB0004242)

MOL for HMDB0004242 (11-Dehydro-thromboxane B2)

3D MOL for HMDB0004242 (11-Dehydro-thromboxane B2)

3D SDF for HMDB0004242 (11-Dehydro-thromboxane B2)

3D-SDF for HMDB0004242 (11-Dehydro-thromboxane B2)

PDB for HMDB0004242 (11-Dehydro-thromboxane B2)

3D PDB for HMDB0004242 (11-Dehydro-thromboxane B2)

SMILES for HMDB0004242 (11-Dehydro-thromboxane B2)

INCHI for HMDB0004242 (11-Dehydro-thromboxane B2)

Structure for HMDB0004242 (11-Dehydro-thromboxane B2)

3D Structure for HMDB0004242 (11-Dehydro-thromboxane B2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra