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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:10 UTC

HMDB ID

HMDB0001452

Secondary Accession Numbers

HMDB01452

Metabolite Identification

Common Name

Thromboxane A2

Description

Thromboxane A2 is an unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).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

HMDB0001452
     RDKit          3D
Thromboxane A2
 57 58  0  0  0  0  0  0  0  0999 V2000
    7.6938    0.7626    0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2279   -0.4358   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484   -1.1376    0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138   -0.2838    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4183    0.2002   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874    1.0571   -0.7823 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3224    2.1979   -0.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9502    0.3300   -0.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0997   -0.1335   -1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.8595   -1.0453 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1513   -2.2007   -0.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -2.8636   -0.2767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1116   -2.5134    1.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8918   -1.3726    0.5570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1479   -2.1940   -0.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9864   -0.2617    0.0756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8788    0.7860   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7545    1.4522    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0624    1.5066    0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8821    0.8572   -0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8152   -0.1829   -0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8031    0.2877    0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7163    1.2869    0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5543    1.8244    1.1873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7465    1.7036   -0.9144 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1846    1.6532    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7879    0.9597    0.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4913    0.6985    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0788   -0.1899   -1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0723   -1.1752   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8133   -2.0112   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3508   -1.4729    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0708    0.5736    1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9927   -0.9011    0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3568   -0.6592   -1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2889    0.8283   -1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678    1.4437   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4200    2.4489    0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6880    0.1460    0.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859    0.0623   -2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7520   -0.8751   -1.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0560   -3.9237   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571   -2.2376    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7579   -3.2045    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815   -1.0406    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.1528    0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4493    0.2342   -1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2660    1.5213   -1.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596    1.9918    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6022    2.0638    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3091    0.4057   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4922    1.6633   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2273   -1.0615    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4077   -0.5703   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4332   -0.6178    1.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3447    0.5661    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8282    2.7143   -1.0699 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  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
 15 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 12 42  1  1
 13 43  1  0
 13 44  1  0
 14 45  1  1
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END


  Mrv0541 02231219092D          

 25 26  0  0  1  0            999 V2000
   -2.9150    0.8813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1994    0.4707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6268    0.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9187    0.0565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994   -0.3578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4801    0.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6268   -0.3578    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9150   -0.7758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763   -0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7570    0.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7533   -0.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0603    0.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0377   -0.7419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7871    0.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6628   -0.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263   -1.5592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -0.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    0.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9187    0.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601   -0.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268    0.9340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9301   -0.2523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8114   -0.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  3  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  1  0  0  0
  6 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  6  0  0  0
 14 17  1  0  0  0  0
 15 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
 22 25  1  0  0  0  0
  7  4  1  6  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001452

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-20(24-17)25-18)10-7-4-5-8-11-19(22)23/h4,7,12-13,15-18,20-21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,20+/m0/s1

> <INCHI_KEY>
DSNBHJFQCNUKMA-SCKDECHMSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.986578730875166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,6-dioxabicyclo[3.1.1]heptan-4-yl]hept-5-enoic acid

> <ALOGPS_LOGP>
4.31

> <JCHEM_LOGP>
4.084688313999998

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.890087909070239

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.273003012940413

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8468755485772634

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
97.67429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thromboxane

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001452
     RDKit          3D
Thromboxane A2
 57 58  0  0  0  0  0  0  0  0999 V2000
    7.6938    0.7626    0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2279   -0.4358   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484   -1.1376    0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138   -0.2838    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4183    0.2002   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874    1.0571   -0.7823 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3224    2.1979   -0.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9502    0.3300   -0.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0997   -0.1335   -1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.8595   -1.0453 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1513   -2.2007   -0.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -2.8636   -0.2767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1116   -2.5134    1.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8918   -1.3726    0.5570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1479   -2.1940   -0.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9864   -0.2617    0.0756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8788    0.7860   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7545    1.4522    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0624    1.5066    0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8821    0.8572   -0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8152   -0.1829   -0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8031    0.2877    0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7163    1.2869    0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5543    1.8244    1.1873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7465    1.7036   -0.9144 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1846    1.6532    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7879    0.9597    0.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4913    0.6985    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0788   -0.1899   -1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0723   -1.1752   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8133   -2.0112   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3508   -1.4729    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0708    0.5736    1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9927   -0.9011    0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3568   -0.6592   -1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2889    0.8283   -1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678    1.4437   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4200    2.4489    0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6880    0.1460    0.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859    0.0623   -2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7520   -0.8751   -1.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0560   -3.9237   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571   -2.2376    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7579   -3.2045    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815   -1.0406    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.1528    0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4493    0.2342   -1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2660    1.5213   -1.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596    1.9918    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6022    2.0638    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3091    0.4057   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4922    1.6633   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2273   -1.0615    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4077   -0.5703   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4332   -0.6178    1.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3447    0.5661    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8282    2.7143   -1.0699 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  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
 15 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 12 42  1  1
 13 43  1  0
 13 44  1  0
 14 45  1  1
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  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      -5.441   1.645   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.106   0.879   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.770   0.879   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.448   0.105   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.106  -0.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.763   1.666   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.770  -0.668   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.441  -1.448   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.756  -1.441   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.413   0.893   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.406  -0.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.113   0.900   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.070  -1.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.469   1.701   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.237  -0.598   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.049  -2.911   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.805   0.942   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.573  -1.343   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.120   1.722   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.888  -0.555   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.448   0.963   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.526  -1.385   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.770   1.743   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.470  -0.471   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.115  -0.534   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8    9                                                  
CONECT    6    2   10                                                       
CONECT    7    3    4    8                                                  
CONECT    8    5    7                                                       
CONECT    9    5   11                                                       
CONECT   10    6   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15   16                                                  
CONECT   14   12   17                                                       
CONECT   15   13   18                                                       
CONECT   16   13                                                            
CONECT   17   14   19                                                       
CONECT   18   15   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23   24                                                  
CONECT   22   20   25                                                       
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0001452
HETATM    1  C1  UNL     1       7.694   0.763   0.639  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.228  -0.436  -0.119  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.048  -1.138   0.469  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.814  -0.284   0.586  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.418   0.200  -0.791  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.187   1.057  -0.782  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.322   2.198  -0.005  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.950   0.330  -0.392  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.100  -0.133  -1.308  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.144  -0.860  -1.045  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.151  -2.201  -0.778  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.968  -2.864  -0.277  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.112  -2.513   1.167  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.892  -1.373   0.557  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.148  -2.194  -0.558  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.986  -0.262   0.076  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.879   0.786  -0.583  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.755   1.452   0.372  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.062   1.507   0.385  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.882   0.857  -0.637  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.815  -0.183  -0.086  1.00  0.00           C  
HETATM   22  C19 UNL     1      -6.803   0.288   0.913  1.00  0.00           C  
HETATM   23  C20 UNL     1      -7.716   1.287   0.394  1.00  0.00           C  
HETATM   24  O4  UNL     1      -8.554   1.824   1.187  1.00  0.00           O  
HETATM   25  O5  UNL     1      -7.747   1.704  -0.914  1.00  0.00           O  
HETATM   26  H1  UNL     1       7.185   1.653   0.178  1.00  0.00           H  
HETATM   27  H2  UNL     1       8.788   0.960   0.473  1.00  0.00           H  
HETATM   28  H3  UNL     1       7.491   0.698   1.722  1.00  0.00           H  
HETATM   29  H4  UNL     1       7.079  -0.190  -1.196  1.00  0.00           H  
HETATM   30  H5  UNL     1       8.072  -1.175  -0.113  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.813  -2.011  -0.174  1.00  0.00           H  
HETATM   32  H7  UNL     1       6.351  -1.473   1.499  1.00  0.00           H  
HETATM   33  H8  UNL     1       5.071   0.574   1.260  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.993  -0.901   1.000  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.357  -0.659  -1.454  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.289   0.828  -1.138  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.068   1.444  -1.840  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.420   2.449   0.318  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.688   0.146   0.643  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.386   0.062  -2.347  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.752  -0.875  -1.992  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.056  -3.924  -0.565  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.157  -2.238   1.654  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.758  -3.205   1.705  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.781  -1.041   1.102  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.377   0.153   0.890  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.449   0.234  -1.339  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.266   1.521  -1.154  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.260   1.992   1.210  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.602   2.064   1.195  1.00  0.00           H  
HETATM   51  H26 UNL     1      -4.309   0.406  -1.461  1.00  0.00           H  
HETATM   52  H27 UNL     1      -5.492   1.663  -1.156  1.00  0.00           H  
HETATM   53  H28 UNL     1      -5.227  -1.062   0.252  1.00  0.00           H  
HETATM   54  H29 UNL     1      -6.408  -0.570  -0.966  1.00  0.00           H  
HETATM   55  H30 UNL     1      -7.433  -0.618   1.179  1.00  0.00           H  
HETATM   56  H31 UNL     1      -6.345   0.566   1.893  1.00  0.00           H  
HETATM   57  H32 UNL     1      -7.828   2.714  -1.070  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9    9   39
CONECT    9   10   40
CONECT   10   11   16   41
CONECT   11   12
CONECT   12   13   15   42
CONECT   13   14   43   44
CONECT   14   15   16   45
CONECT   16   17   46
CONECT   17   18   47   48
CONECT   18   19   19   49
CONECT   19   20   50
CONECT   20   21   51   52
CONECT   21   22   53   54
CONECT   22   23   55   56
CONECT   23   24   24   25
CONECT   25   57
END

HMDB0001452
     RDKit          3D
Thromboxane A2
 57 58  0  0  0  0  0  0  0  0999 V2000
    7.6938    0.7626    0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2279   -0.4358   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484   -1.1376    0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8138   -0.2838    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4183    0.2002   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874    1.0571   -0.7823 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3224    2.1979   -0.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9502    0.3300   -0.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0997   -0.1335   -1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.8595   -1.0453 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1513   -2.2007   -0.7783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -2.8636   -0.2767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1116   -2.5134    1.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8918   -1.3726    0.5570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1479   -2.1940   -0.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9864   -0.2617    0.0756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8788    0.7860   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7545    1.4522    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0624    1.5066    0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8821    0.8572   -0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8152   -0.1829   -0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8031    0.2877    0.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7163    1.2869    0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5543    1.8244    1.1873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7465    1.7036   -0.9144 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1846    1.6532    0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7879    0.9597    0.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4913    0.6985    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0788   -0.1899   -1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0723   -1.1752   -0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8133   -2.0112   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3508   -1.4729    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0708    0.5736    1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9927   -0.9011    0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3568   -0.6592   -1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2889    0.8283   -1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678    1.4437   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4200    2.4489    0.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6880    0.1460    0.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3859    0.0623   -2.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7520   -0.8751   -1.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0560   -3.9237   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571   -2.2376    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7579   -3.2045    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7815   -1.0406    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    0.1528    0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4493    0.2342   -1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2660    1.5213   -1.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596    1.9918    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6022    2.0638    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3091    0.4057   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4922    1.6633   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2273   -1.0615    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4077   -0.5703   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4332   -0.6178    1.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3447    0.5661    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8282    2.7143   -1.0699 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  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 10  1  0
 15 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 12 42  1  1
 13 43  1  0
 13 44  1  0
 14 45  1  1
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,13E)-(15S)-9alpha,11alpha-Epoxy-15-hydroxythromboxa-5,13-dienoate	ChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acid	ChEBI
9S,11S-Epoxy,15S-hydroxy-thromboxa-5Z,13E-dien-1-Oic acid	ChEBI
TXA-2	ChEBI
TXA2	ChEBI
(5Z,13E)-(15S)-9a,11a-Epoxy-15-hydroxythromboxa-5,13-dienoate	Generator
(5Z,13E)-(15S)-9a,11a-Epoxy-15-hydroxythromboxa-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-9alpha,11alpha-Epoxy-15-hydroxythromboxa-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-9Α,11α-epoxy-15-hydroxythromboxa-5,13-dienoate	Generator
(5Z,13E)-(15S)-9Α,11α-epoxy-15-hydroxythromboxa-5,13-dienoic acid	Generator
(5Z,9a,11a,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oate	Generator
(5Z,9a,11a,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acid	Generator
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oate	Generator
(5Z,9Α,11α,13E,15S)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-Oate	Generator
(5Z,9Α,11α,13E,15S)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acid	Generator
9S,11S-Epoxy,15S-hydroxy-thromboxa-5Z,13E-dien-1-Oate	Generator
(1S-(1alpha,3alpha,3R*),4beta(Z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-heptenoate	HMDB
(1S-(1alpha,3alpha,3R*),4beta(Z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-heptenoic acid	HMDB
(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-Hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-heptenoate	HMDB
(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-Hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-heptenoic acid	HMDB
(5Z,13E)-(15S)-9,11-Epoxy-15-hydroxythromba-5,13-dienoate	HMDB
(5Z,13E)-(15S)-9,11-Epoxy-15-hydroxythromba-5,13-dienoic acid	HMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epoxy-15-hydroxythromboxa-5,13-dienoate	HMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epoxy-15-hydroxythromboxa-5,13-dienoic acid	HMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxy-thromboxa-5,13-dien-1-Oate	HMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxy-thromboxa-5,13-dien-1-Oic acid	HMDB
7-[3-(3-Hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1S-[1alpha,3alpha(1E,3R*),4beta(Z),5alpha]]-5-heptenoate	HMDB
7-[3-(3-Hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1S-[1alpha,3alpha(1E,3R*),4beta(Z),5alpha]]-5-heptenoic acid	HMDB
Cid	HMDB
Rabbit aorta contracting substance	HMDB, MeSH
RCS	HMDB
a2, Thromboxane	MeSH, HMDB

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,6-dioxabicyclo[3.1.1]heptan-4-yl]hept-5-enoic acid

Traditional Name

thromboxane

CAS Registry Number

57576-52-0

SMILES

CCCCC[C@H](O)\C=C\[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-20(24-17)25-18)10-7-4-5-8-11-19(22)23/h4,7,12-13,15-18,20-21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,20+/m0/s1

InChI Key

DSNBHJFQCNUKMA-SCKDECHMSA-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
Heterocyclic fatty acid
Hydroxy fatty acid
Meta-dioxane
Fatty acid
Oxane
Unsaturated fatty acid
Secondary alcohol
Oxetane
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxy monocarboxylic acid (CHEBI:15627 )
thromboxanes A (CHEBI:15627 )
thromboxane (C02198 )
Thromboxanes (C02198 )
Thromboxanes (LMFA03030001 )

Ontology

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	0.047 g/L	ALOGPS
logP	4.31	ALOGPS
logP	4.08	ChemAxon
logS	-3.9	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	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	97.67 m³·mol⁻¹	ChemAxon
Polarizability	39.99 Å³	ChemAxon
Number of Rings	2	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]+	187.696	31661259
DarkChem	[M-H]-	190.682	31661259
AllCCS	[M+H]+	193.237	32859911
AllCCS	[M-H]-	192.513	32859911
DeepCCS	[M+H]+	196.005	30932474
DeepCCS	[M-H]-	193.61	30932474
DeepCCS	[M-2H]-	226.939	30932474
DeepCCS	[M+Na]+	201.882	30932474
AllCCS	[M+H]+	193.2	32859911
AllCCS	[M+H-H2O]+	190.6	32859911
AllCCS	[M+NH4]+	195.7	32859911
AllCCS	[M+Na]+	196.4	32859911
AllCCS	[M-H]-	192.5	32859911
AllCCS	[M+Na-2H]-	193.7	32859911
AllCCS	[M+HCOO]-	195.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thromboxane A2	CCCCC[C@H](O)\C=C\[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C\C=C/CCCC(O)=O	3878.0	Standard polar	33892256
Thromboxane A2	CCCCC[C@H](O)\C=C\[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C\C=C/CCCC(O)=O	2570.9	Standard non polar	33892256
Thromboxane A2	CCCCC[C@H](O)\C=C\[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C\C=C/CCCC(O)=O	2704.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thromboxane A2,1TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C	2804.1	Semi standard non polar	33892256
Thromboxane A2,1TMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C	2728.7	Semi standard non polar	33892256
Thromboxane A2,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2760.8	Semi standard non polar	33892256
Thromboxane A2,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3019.6	Semi standard non polar	33892256
Thromboxane A2,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2974.0	Semi standard non polar	33892256
Thromboxane A2,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3244.2	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 - Thromboxane A2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5c-8092000000-447fd05a27e321c2cde4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thromboxane A2 GC-MS (2 TMS) - 70eV, Positive	splash10-05d0-9412500000-8ee6a6da7d17d4a312ad	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thromboxane 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 - Thromboxane A2 10V, Positive-QTOF	splash10-0f79-0019000000-0d4465c059cecdc63423	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 20V, Positive-QTOF	splash10-052r-9377000000-bbdaa5d2f847ef4ce9ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 40V, Positive-QTOF	splash10-0aou-9230000000-95f4e70640a0a301ed86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 10V, Negative-QTOF	splash10-0udi-0019000000-c75e176e0b60712ef7c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 20V, Negative-QTOF	splash10-0zfr-2149000000-030f294fbd453ce195d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 40V, Negative-QTOF	splash10-0a4i-9231000000-e7bad0956de1ed773d0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 10V, Negative-QTOF	splash10-0udi-0009000000-380bcdac41775c30cac2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 20V, Negative-QTOF	splash10-0udi-0009000000-99b3f8cff0edf57c5c84	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 40V, Negative-QTOF	splash10-0ki2-4490000000-4417bbfe96ca092158b2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 10V, Positive-QTOF	splash10-000i-0009000000-69a34801f1522c7965b8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 20V, Positive-QTOF	splash10-000i-3229000000-1ee59a8ff7e44516dba5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thromboxane A2 40V, Positive-QTOF	splash10-05rr-9500000000-fc766f27d3958eb30b52	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Platelet
Smooth Muscle

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	0.00024 +/- 0.000036 uM	Adult (>18 years old)	Both	Normal	7858766	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00045 +/- 0.000047 uM	Children (1-13 years old)	Both	Coronary heart disease	7858766	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0029 (0.00021-0.0136) uM	Not Specified	Not Specified	Acute lymphoblastic leukemia	18996865	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00346 uM	Not Specified	Not Specified	Bronchopulmonary dysplasia	18996865	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00062 uM	Not Specified	Not Specified	Burkitt's lymphoma	18996865	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00237 uM	Not Specified	Not Specified	Head injury	18996865	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00057 (0.0005-0.00063) uM	Not Specified	Not Specified	Lymphoblastic lymphoma	18996865	details
Urine	Detected and Quantified	0.00078 +/- 0.00035 umol/mmol creatinine	Adult (>18 years old)	Both	Hepatocellular carcinoma	9222688	details

Associated Disorders and Diseases

Disease References

Coronary heart disease
Akimova EV: Prostacyclin and thromboxane A2 levels in children and adolescents with an inherited predisposition to coronary heart disease: a family study. Coron Artery Dis. 1994 Sep;5(9):761-5. [PubMed:7858766 ]
Acute Lymphoblastic Leukemia
Bogusiewicz A, Stratton SL, Ellison DA, Mock DM: Biotin accounts for less than half of all biotin and biotin metabolites in the cerebrospinal fluid of children. Am J Clin Nutr. 2008 Nov;88(5):1291-6. [PubMed:18996865 ]
Head injury
Bogusiewicz A, Stratton SL, Ellison DA, Mock DM: Biotin accounts for less than half of all biotin and biotin metabolites in the cerebrospinal fluid of children. Am J Clin Nutr. 2008 Nov;88(5):1291-6. [PubMed:18996865 ]
Hepatocellular carcinoma
Matsumata T, Yamamoto K, Shirabe K, Shimada M, Sugimachi K, Takesue F, Muto Y, Ikeda T: Urinary excretion of prostaglandins and renal function after hepatic resection. Hepatogastroenterology. 1997 May-Jun;44(15):774-8. [PubMed:9222688 ]

Associated OMIM IDs

114550 (Hepatocellular carcinoma)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444137

KEGG Compound ID

C02198

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thromboxane A2

METLIN ID

Not Available

PubChem Compound

5280497

PDB ID

Not Available

ChEBI ID

15627

Food Biomarker Ontology

Not Available

VMH ID

TXA2

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Wu X, Dev A, Leong AB: Zileuton, a 5-lipoxygenase inhibitor, increases production of thromboxane A2 and platelet aggregation in patients with asthma. Am J Hematol. 2003 Sep;74(1):23-5. [PubMed:12949886 ]
Feldman M, Cryer B, Rushin K, Betancourt J: A comparison of every-third-day versus daily low-dose aspirin therapy on serum thromboxane concentrations in healthy men and women. Clin Appl Thromb Hemost. 2001 Jan;7(1):53-7. [PubMed:11190906 ]
Kobayashi T, Suzuki J, Watanabe M, Suzuki S, Yoshida K, Kume K, Suzuki H: Changes in platelet calcium concentration by thromboxane A2 stimulation in patients with nephrotic syndrome of childhood. Nephron. 1997;77(3):309-14. [PubMed:9375825 ]
Amari T, Kubo K, Kobayashi T, Sekiguchi M: Effects of recombinant human superoxide dismutase on tumor necrosis factor-induced lung injury in awake sheep. J Appl Physiol (1985). 1993 Jun;74(6):2641-8. [PubMed:8396104 ]
Hada S, Hashizume M, Yoshioka F, Nishii S, Yasunaga K: [Measurement of platelet thromboxane A2/prostaglandin H2 receptor in asthmatic patients]. Arerugi. 1993 May;42(5):609-16. [PubMed:8323459 ]
Cattaneo M, Lombardi R, Zighetti ML, Gachet C, Ohlmann P, Cazenave JP, Mannucci PM: Deficiency of (33P)2MeS-ADP binding sites on platelets with secretion defect, normal granule stores and normal thromboxane A2 production. Evidence that ADP potentiates platelet secretion independently of the formation of large platelet aggregates and thromboxane A2 production. Thromb Haemost. 1997 May;77(5):986-90. [PubMed:9184415 ]
Schror K: The effect of prostaglandins and thromboxane A2 on coronary vessel tone--mechanisms of action and therapeutic implications. Eur Heart J. 1993 Nov;14 Suppl I:34-41. [PubMed:7507439 ]
Marttunen MB, Pyrhonen S, Tiitinen AE, Viinikka LU, Ylikorkala O: Effect of antiestrogen regimen on prostacyclin and thromboxane A2 in postmenopausal patients with breast cancer: evidence of significance of hypertension, smoking or previous use of estrogen therapy. Prostaglandins. 1996 Oct;52(4):317-26. [PubMed:8936586 ]
Tanaka K, Roberts MH, Yamamoto N, Sugiura H, Uehara M, Mao XQ, Shirakawa T, Hopkin JM: Genetic variants of the receptors for thromboxane A2 and IL-4 in atopic dermatitis. Biochem Biophys Res Commun. 2002 Apr 5;292(3):776-80. [PubMed:11922633 ]
Leonhardt A, Bernert S, Watzer B, Schmitz-Ziegler G, Seyberth HW: Low-dose aspirin in pregnancy: maternal and neonatal aspirin concentrations and neonatal prostanoid formation. Pediatrics. 2003 Jan;111(1):e77-81. [PubMed:12509599 ]
Sheu JR, Hsiao G, Shen MY, Lin WY, Tzeng CR: The hyperaggregability of platelets from normal pregnancy is mediated through thromboxane A2 and cyclic AMP pathways. Clin Lab Haematol. 2002 Apr;24(2):121-9. [PubMed:11985559 ]
Djellas Y, Manganello JM, Antonakis K, Le Breton GC: Identification of Galpha13 as one of the G-proteins that couple to human platelet thromboxane A2 receptors. J Biol Chem. 1999 May 14;274(20):14325-30. [PubMed:10318854 ]
Rocca B, Ranelletti FO, Maggiano N, Ciabattoni G, De Cristofaro R, Landolfi R: Inherited macrothrombocytopenia with distinctive platelet ultrastructural and functional features. Thromb Haemost. 2000 Jan;83(1):35-41. [PubMed:10669151 ]
Liel N, Nathan I, Yermiyahu T, Zolotov Z, Lieberman JR, Dvilansky A, Halushka PV: Increased platelet thromboxane A2/prostaglandin H2 receptors in patients with pregnancy induced hypertension. Thromb Res. 1993 May 1;70(3):205-10. [PubMed:8327985 ]
Modesti PA, Colella A, Cecioni I, Costoli A, Biagini D, Migliorini A, Neri Serneri GG: Increased number of thromboxane A2-prostaglandin H2 platelet receptors in active unstable angina and causative role of enhanced thrombin formation. Am Heart J. 1995 May;129(5):873-9. [PubMed:7732975 ]
Storlien LH, Kriketos AD, Calvert GD, Baur LA, Jenkins AB: Fatty acids, triglycerides and syndromes of insulin resistance. Prostaglandins Leukot Essent Fatty Acids. 1997 Oct;57(4-5):379-85. [PubMed:9430382 ]
Wennmalm A, Benthin G, Granstrom EF, Persson L, Winell S: Maintained hyperexcretion of thromboxane A2 metabolite in healthy young cigarette smokers: results from a prospective study in randomly sampled males with stable smoking habits. Clin Physiol. 1993 May;13(3):257-64. [PubMed:8519161 ]
Ogawa S, Takeuchi K, Sugimura K, Sato C, Fukuda M, Lee R, Ito S, Sato T: The 5-HT2 receptor antagonist sarpogrelate reduces urinary and plasma levels of thromboxane A2 and urinary albumin excretion in non-insulin-dependent diabetes mellitus patients. Clin Exp Pharmacol Physiol. 1999 May-Jun;26(5-6):461-4. [PubMed:10386239 ]
Michelson AD, Wencel-Drake JD, Kestin AS, Barnard MR: Platelet activation results in a redistribution of glycoprotein IV (CD36). Arterioscler Thromb. 1994 Jul;14(7):1193-201. [PubMed:7517184 ]
Komiotis D, Wencel-Drake JD, Dieter JP, Lim CT, Le Breton GC: Labeling of human platelet plasma membrane thromboxane A2/prostaglandin H2 receptors using SQB, a novel biotinylated receptor probe. Biochem Pharmacol. 1996 Sep 13;52(5):763-70. [PubMed:8765474 ]

Enzymes

Enzyme Details

1. Thromboxane-A synthase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: TBXAS1
Uniprot ID:: P24557
Molecular weight:: 60648.885

Reactions

Prostaglandin H2 → Thromboxane A2	details

Enzyme Details

2. Thromboxane A2 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for thromboxane A2 (TXA2), a potent stimulator of platelet aggregation. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol-calcium second messenger system. In the kidney, the binding of TXA2 to glomerular TP receptors causes intense vasoconstriction. Activates phospholipase C. Isoform 1 activates adenylyl cyclase. Isoform 2 inhibits adenylyl cyclase
Gene Name:: TBXA2R
Uniprot ID:: P21731
Molecular weight:: 37430.7

Enzyme Details

3. HCG14925, isoform CRA_a

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: Q53F23
Molecular weight:: 60648.9

Showing metabocard for Thromboxane A2 (HMDB0001452)

MOL for HMDB0001452 (Thromboxane A2)

3D MOL for HMDB0001452 (Thromboxane A2)

3D SDF for HMDB0001452 (Thromboxane A2)

3D-SDF for HMDB0001452 (Thromboxane A2)

PDB for HMDB0001452 (Thromboxane A2)

3D PDB for HMDB0001452 (Thromboxane A2)

SMILES for HMDB0001452 (Thromboxane A2)

INCHI for HMDB0001452 (Thromboxane A2)

Structure for HMDB0001452 (Thromboxane A2)

3D Structure for HMDB0001452 (Thromboxane A2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions