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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 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

HMDB0001509

Secondary Accession Numbers

HMDB0005092
HMDB01509
HMDB05092

Metabolite Identification

Common Name

20-Hydroxy-leukotriene B4

Description

20-hydroxy- Leukotriene B4 (20-OH-LTB4) is an omega-hydroxylated metabolite of leukotriene B4 in human neutrophils. Elevated urinary concentrations of 20-OH-LTB4 and LTB4 are found in patients with Sjogren-Larsson syndrome (SLS, OMIM 270220 ), an autosomal recessively inherited neurocutaneous disorder caused by a deficiency of the microsomal enzyme fatty aldehyde dehydrogenase (FALDH), which as an essential role in LTB4 metabolism. Preterm birth seems to be one of the features of the syndrome. The reason for the preterm birth is unclear. It is hypothesized that it relates to the defective LTB4 degradation in SLS. The pathological urinary excretion of LTB4 and 20-OH-LTB4 is a biochemical marker for SLS. Surprisingly, 20-OH-LTB4 concentrations are normal in CSF. Leukotriene B4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. (PMID: 12709426 , 9799565 , 11408337 , 17623009 ). Leukotrienes 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

HMDB0001509
     RDKit          3D
20-Hydroxy-leukotriene B4
 57 56  0  0  0  0  0  0  0  0999 V2000
    7.9125    1.2002   -0.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6345    2.2332   -1.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6538    3.1115   -1.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2391    2.4062   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410    2.9664   -0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3276    2.0401    0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    2.6234    1.6105 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9747    3.8794    1.9502 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3769    1.7532    2.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5924    0.6995    2.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    0.3506    1.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274   -0.6905    1.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767   -1.0158    0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -2.0477    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6063   -2.3258   -0.5478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8947   -1.1803   -1.2428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720   -3.0814   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791   -2.3346    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -1.9651    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5845   -2.2685   -0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9604   -0.9114   -1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8608   -0.1038   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1729   -0.7902   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9202   -1.0647   -1.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1948    0.1101   -2.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0861    3.0575   -2.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2178    3.0312   -2.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8274    1.4049   -2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6561    3.9927   -0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253    3.0160   -1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3427    1.9073    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9941    1.0434    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024    2.7872    1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6753    3.7044    2.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9933    1.9458    3.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5607    0.0680    3.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    0.9352    0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069   -1.3054    2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0995   -0.3818   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2291   -2.6702    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443   -3.0103   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -0.6434   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387   -3.9520    0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3500   -3.5713   -0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2444   -2.0629    1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5053   -1.3984    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0559   -2.7933   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5636   -2.8027   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3047   -1.0182   -2.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772   -0.3573   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3790    0.2333    0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1228    0.8158   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0552   -1.7404    0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7549   -0.1121    0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8641   -1.5583   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3283   -1.7336   -2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2079   -0.0204   -3.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 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  1  0
 24 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  6
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
M  END


  Mrv0541 02231219112D          

 25 24  0  0  0  0            999 V2000
    4.8255  -12.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0106  -12.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5290  -11.7210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2796  -11.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2387  -12.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5256  -10.9061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5623  -12.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9423  -11.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8416  -11.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6527  -12.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243  -12.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3555  -11.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112  -11.7525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0659  -12.1074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3487  -10.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958  -12.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112  -10.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958  -12.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112  -13.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243  -12.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8450  -13.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5657  -12.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2967  -13.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210  -12.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7414  -13.3953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  1  0  0  0
  4  7  2  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  2  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001509

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1

> <INCHI_KEY>
PTJFJXLGRSTECQ-PSPARDEHSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.46273183675189

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6Z,8E,10E,12R,14Z)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
2.688870060333332

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.843936486031904

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.646345072403522

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1987619626600479

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
104.91369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-hydroxy-LTB4

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001509
     RDKit          3D
20-Hydroxy-leukotriene B4
 57 56  0  0  0  0  0  0  0  0999 V2000
    7.9125    1.2002   -0.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6345    2.2332   -1.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6538    3.1115   -1.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2391    2.4062   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410    2.9664   -0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3276    2.0401    0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    2.6234    1.6105 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9747    3.8794    1.9502 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3769    1.7532    2.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5924    0.6995    2.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    0.3506    1.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274   -0.6905    1.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767   -1.0158    0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -2.0477    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6063   -2.3258   -0.5478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8947   -1.1803   -1.2428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720   -3.0814   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791   -2.3346    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -1.9651    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5845   -2.2685   -0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9604   -0.9114   -1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8608   -0.1038   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1729   -0.7902   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9202   -1.0647   -1.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1948    0.1101   -2.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0861    3.0575   -2.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2178    3.0312   -2.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8274    1.4049   -2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6561    3.9927   -0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253    3.0160   -1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3427    1.9073    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9941    1.0434    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024    2.7872    1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6753    3.7044    2.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9933    1.9458    3.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5607    0.0680    3.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    0.9352    0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069   -1.3054    2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0995   -0.3818   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2291   -2.6702    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443   -3.0103   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -0.6434   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387   -3.9520    0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3500   -3.5713   -0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2444   -2.0629    1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5053   -1.3984    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0559   -2.7933   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5636   -2.8027   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3047   -1.0182   -2.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772   -0.3573   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3790    0.2333    0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1228    0.8158   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0552   -1.7404    0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7549   -0.1121    0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8641   -1.5583   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3283   -1.7336   -2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2079   -0.0204   -3.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 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  1  0
 24 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  6
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 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       9.008 -22.645   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.486 -22.652   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.321 -21.879   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.122 -21.886   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.646 -22.632   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.314 -20.358   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.783 -22.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.959 -21.866   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.438 -21.911   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.285 -22.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.099 -22.692   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.597 -21.839   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.768 -21.938   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.923 -22.600   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      15.584 -20.320   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.552 -22.692   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.768 -20.411   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.552 -24.232   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.768 -25.012   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.099 -24.232   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.444 -25.012   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.789 -24.238   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.154 -25.012   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.506 -24.225   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.851 -25.005   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    7                                                       
CONECT    5    3    8                                                       
CONECT    6    3                                                            
CONECT    7    4    9                                                       
CONECT    8    5   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14   15                                                  
CONECT   13   11   16   17                                                  
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   13   18                                                       
CONECT   17   13                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0001509
HETATM    1  O1  UNL     1       7.912   1.200  -0.623  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.635   2.233  -1.306  1.00  0.00           C  
HETATM    3  O2  UNL     1       8.654   3.111  -1.580  1.00  0.00           O  
HETATM    4  C2  UNL     1       6.239   2.406  -1.750  1.00  0.00           C  
HETATM    5  C3  UNL     1       5.341   2.966  -0.644  1.00  0.00           C  
HETATM    6  C4  UNL     1       5.328   2.040   0.544  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.430   2.623   1.611  1.00  0.00           C  
HETATM    8  O3  UNL     1       4.975   3.879   1.950  1.00  0.00           O  
HETATM    9  C6  UNL     1       4.377   1.753   2.802  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.592   0.699   2.886  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.726   0.351   1.770  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.927  -0.690   1.807  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.077  -1.016   0.685  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.249  -2.048   0.653  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.606  -2.326  -0.548  1.00  0.00           C  
HETATM   16  O4  UNL     1      -0.895  -1.180  -1.243  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.872  -3.081  -0.134  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.679  -2.335   0.815  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.906  -1.965   0.576  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.584  -2.269  -0.675  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.960  -0.911  -1.297  1.00  0.00           C  
HETATM   22  C18 UNL     1      -5.861  -0.104  -0.424  1.00  0.00           C  
HETATM   23  C19 UNL     1      -7.173  -0.790  -0.121  1.00  0.00           C  
HETATM   24  C20 UNL     1      -7.920  -1.065  -1.409  1.00  0.00           C  
HETATM   25  O5  UNL     1      -8.195   0.110  -2.104  1.00  0.00           O  
HETATM   26  H1  UNL     1       9.086   3.058  -2.508  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.218   3.031  -2.643  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.827   1.405  -2.040  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.656   3.993  -0.367  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.325   3.016  -1.085  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.343   1.907   0.971  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.994   1.043   0.205  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.402   2.787   1.237  1.00  0.00           H  
HETATM   34  H9  UNL     1       5.675   3.704   2.618  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.993   1.946   3.680  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.561   0.068   3.764  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.697   0.935   0.849  1.00  0.00           H  
HETATM   38  H13 UNL     1       1.907  -1.305   2.680  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.100  -0.382  -0.213  1.00  0.00           H  
HETATM   40  H15 UNL     1       0.229  -2.670   1.537  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.044  -3.010  -1.214  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.628  -0.643  -0.894  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.439  -3.952   0.474  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.350  -3.571  -0.968  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.244  -2.063   1.784  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.505  -1.398   1.317  1.00  0.00           H  
HETATM   47  H22 UNL     1      -4.056  -2.793  -1.452  1.00  0.00           H  
HETATM   48  H23 UNL     1      -5.564  -2.803  -0.464  1.00  0.00           H  
HETATM   49  H24 UNL     1      -5.305  -1.018  -2.324  1.00  0.00           H  
HETATM   50  H25 UNL     1      -3.977  -0.357  -1.342  1.00  0.00           H  
HETATM   51  H26 UNL     1      -5.379   0.233   0.494  1.00  0.00           H  
HETATM   52  H27 UNL     1      -6.123   0.816  -0.991  1.00  0.00           H  
HETATM   53  H28 UNL     1      -7.055  -1.740   0.425  1.00  0.00           H  
HETATM   54  H29 UNL     1      -7.755  -0.112   0.523  1.00  0.00           H  
HETATM   55  H30 UNL     1      -8.864  -1.558  -1.165  1.00  0.00           H  
HETATM   56  H31 UNL     1      -7.328  -1.734  -2.058  1.00  0.00           H  
HETATM   57  H32 UNL     1      -8.208  -0.020  -3.070  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8    9   33
CONECT    8   34
CONECT    9   10   10   35
CONECT   10   11   36
CONECT   11   12   12   37
CONECT   12   13   38
CONECT   13   14   14   39
CONECT   14   15   40
CONECT   15   16   17   41
CONECT   16   42
CONECT   17   18   43   44
CONECT   18   19   19   45
CONECT   19   20   46
CONECT   20   21   47   48
CONECT   21   22   49   50
CONECT   22   23   51   52
CONECT   23   24   53   54
CONECT   24   25   55   56
CONECT   25   57
END

HMDB0001509
     RDKit          3D
20-Hydroxy-leukotriene B4
 57 56  0  0  0  0  0  0  0  0999 V2000
    7.9125    1.2002   -0.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6345    2.2332   -1.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6538    3.1115   -1.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2391    2.4062   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410    2.9664   -0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3276    2.0401    0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    2.6234    1.6105 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9747    3.8794    1.9502 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3769    1.7532    2.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5924    0.6995    2.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264    0.3506    1.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274   -0.6905    1.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767   -1.0158    0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -2.0477    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6063   -2.3258   -0.5478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8947   -1.1803   -1.2428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720   -3.0814   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791   -2.3346    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9060   -1.9651    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5845   -2.2685   -0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9604   -0.9114   -1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8608   -0.1038   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1729   -0.7902   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9202   -1.0647   -1.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1948    0.1101   -2.1039 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0861    3.0575   -2.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2178    3.0312   -2.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8274    1.4049   -2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6561    3.9927   -0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253    3.0160   -1.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3427    1.9073    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9941    1.0434    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024    2.7872    1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6753    3.7044    2.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9933    1.9458    3.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5607    0.0680    3.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974    0.9352    0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069   -1.3054    2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0995   -0.3818   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2291   -2.6702    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443   -3.0103   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -0.6434   -0.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387   -3.9520    0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3500   -3.5713   -0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2444   -2.0629    1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5053   -1.3984    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0559   -2.7933   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5636   -2.8027   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3047   -1.0182   -2.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772   -0.3573   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3790    0.2333    0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1228    0.8158   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0552   -1.7404    0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7549   -0.1121    0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8641   -1.5583   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3283   -1.7336   -2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2079   -0.0204   -3.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 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  1  0
 24 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  6
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyeicosa-6,8,10,14-tetraenoate	ChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoate	ChEBI
20-Hydroxy-LTB4	ChEBI
20-OH-Leukotriene b4	ChEBI
20-OH-LTB4	ChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyeicosa-6,8,10,14-tetraenoic acid	Generator
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoic acid	Generator
(5S,12R)-5,12,20-Trihydroxy-(6Z,8E,10E,14Z)-eicosatetraenoate	HMDB
(5S,12R)-5,12,20-Trihydroxy-(6Z,8E,10E,14Z)-eicosatetraenoic acid	HMDB
(5S,6Z,8E,10E,12R,14Z)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoate	HMDB
(5S,6Z,8E,10E,12R,14Z)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoic acid	HMDB
20-Hydroxy LTB4	HMDB
20-Hydroxyleukotriene b4	HMDB
20-OH-5S,12S-Dihydroxy-6,10-trans-8,14-cis-eicosatetraenoate	HMDB
20-OH-5S,12S-Dihydroxy-6,10-trans-8,14-cis-eicosatetraenoic acid	HMDB
5,12,20-THETE	HMDB
5,12,20-TriHETE	HMDB
5S,12R,20-Trihydroxy-6Z,8E,10E,14Z-eicosatetraenoate	HMDB
5S,12R,20-Trihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid	HMDB
Omega-hydroxy-LTB4	HMDB
W-Hydroxy-LTB4	HMDB
[S-[R,s-(e,Z,e,Z)]]-5,12,20-trihydroxy-6,8,10,14-eicosatetraenoate	HMDB
[S-[R,s-(e,Z,e,Z)]]-5,12,20-trihydroxy-6,8,10,14-eicosatetraenoic acid	HMDB
20-Hydroxy-leukotriene b	HMDB
5,12,20-Trihydroxy-6,8,10,14-eicosatetraenoic acid	HMDB
5,12,20-Trihydroxy-6,8,10,14-eicosatetraenoic acid, (S-(r,s-(e,Z,e,Z)))-isomer	HMDB

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

(5S,6Z,8E,10E,12R,14Z)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid

Traditional Name

20-hydroxy-LTB4

CAS Registry Number

79516-82-8

SMILES

OCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1

InChI Key

PTJFJXLGRSTECQ-PSPARDEHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Leukotrienes

Alternative Parents

Substituents

Leukotriene
Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:15646 )
Leukotrienes (C04853 )
Leukotrienes (LMFA03020018 )

Ontology

Not Available

Physical Properties

State

Liquid

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	0.033 g/L	ALOGPS
logP	4.22	ALOGPS
logP	2.69	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	104.91 m³·mol⁻¹	ChemAxon
Polarizability	40.46 Å³	ChemAxon
Number of Rings	0	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]+	192.313	31661259
DarkChem	[M-H]-	189.224	31661259
AllCCS	[M+H]+	190.807	32859911
AllCCS	[M-H]-	189.651	32859911
DeepCCS	[M+H]+	201.55	30932474
DeepCCS	[M-H]-	198.683	30932474
DeepCCS	[M-2H]-	233.483	30932474
DeepCCS	[M+Na]+	209.264	30932474
AllCCS	[M+H]+	190.8	32859911
AllCCS	[M+H-H2O]+	188.1	32859911
AllCCS	[M+NH4]+	193.3	32859911
AllCCS	[M+Na]+	194.0	32859911
AllCCS	[M-H]-	189.7	32859911
AllCCS	[M+Na-2H]-	191.6	32859911
AllCCS	[M+HCOO]-	193.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
20-Hydroxy-leukotriene B4	OCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	4853.3	Standard polar	33892256
20-Hydroxy-leukotriene B4	OCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	2787.7	Standard non polar	33892256
20-Hydroxy-leukotriene B4	OCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	3165.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
20-Hydroxy-leukotriene B4,1TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O	3269.3	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,1TMS,isomer #2	C[Si](C)(C)O[C@@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)C/C=C\CCCCCO	3260.7	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,1TMS,isomer #3	C[Si](C)(C)O[C@H](/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCCO)CCCC(=O)O	3254.2	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,1TMS,isomer #4	C[Si](C)(C)OC(=O)CCC[C@H](O)/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCCO	3171.5	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C	3329.8	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TMS,isomer #2	C[Si](C)(C)OCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C	3316.7	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TMS,isomer #3	C[Si](C)(C)OCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C	3225.1	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TMS,isomer #4	C[Si](C)(C)O[C@H](/C=C\C=C\C=C\[C@@H](C/C=C\CCCCCO)O[Si](C)(C)C)CCCC(=O)O	3314.8	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TMS,isomer #5	C[Si](C)(C)OC(=O)CCC[C@H](O)/C=C\C=C\C=C\[C@@H](C/C=C\CCCCCO)O[Si](C)(C)C	3234.1	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TMS,isomer #6	C[Si](C)(C)OC(=O)CCC[C@@H](/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCCO)O[Si](C)(C)C	3220.9	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,3TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3323.9	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,3TMS,isomer #2	C[Si](C)(C)OCCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3237.5	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,3TMS,isomer #3	C[Si](C)(C)OCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3223.2	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,3TMS,isomer #4	C[Si](C)(C)OC(=O)CCC[C@@H](/C=C\C=C\C=C\[C@@H](C/C=C\CCCCCO)O[Si](C)(C)C)O[Si](C)(C)C	3256.0	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,4TMS,isomer #1	C[Si](C)(C)OCCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3244.9	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O	3518.4	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)C/C=C\CCCCCO	3497.3	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H](/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCCO)CCCC(=O)O	3491.7	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](O)/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCCO	3418.7	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3803.9	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3792.6	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3713.9	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H](/C=C\C=C\C=C\[C@@H](C/C=C\CCCCCO)O[Si](C)(C)C(C)(C)C)CCCC(=O)O	3776.8	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](O)/C=C\C=C\C=C\[C@@H](C/C=C\CCCCCO)O[Si](C)(C)C(C)(C)C	3713.9	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCCO)O[Si](C)(C)C(C)(C)C	3705.3	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4059.2	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3999.6	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3987.5	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](/C=C\C=C\C=C\[C@@H](C/C=C\CCCCCO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3992.2	Semi standard non polar	33892256
20-Hydroxy-leukotriene B4,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4241.5	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 - 20-Hydroxy-leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lj-3798000000-5bb085b2304969403378	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-Hydroxy-leukotriene B4 GC-MS (4 TMS) - 70eV, Positive	splash10-004i-7400967000-a9f5c76728347ea2738b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-Hydroxy-leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-Hydroxy-leukotriene B4 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0udi-0009000000-2b98c651c0cd0833ccef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0udi-0009000000-a681c9193735a4386b49	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0udi-0009000000-8db36dce15edb0d7b2f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0udi-0109000000-e01ef44cb36e9df489f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0uea-0709000000-d7a7994b98cf3bfbe072	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0f8b-0924000000-bb49aa4e02bfea5085c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0il1-0910000000-8f7913074625390c6208	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0di9-0900000000-a87a75ca80ddc1745a1f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 LC-ESI-QIT , negative-QTOF	splash10-0a4i-1900000000-972b13fd5c8b54c14aa2	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 10V, Positive-QTOF	splash10-00kr-0019000000-fed023a2c990a5c6753f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 20V, Positive-QTOF	splash10-014r-1269000000-22fedd5f102230a634a7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 40V, Positive-QTOF	splash10-00tp-6491000000-bfc9e7fd9147e861f375	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 10V, Negative-QTOF	splash10-0udi-0009000000-e84044e33fbc237fabfc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 20V, Negative-QTOF	splash10-0uei-1129000000-f307e44b0f4e538946e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 40V, Negative-QTOF	splash10-0a4l-9341000000-49f0ced38039afa26a80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 10V, Positive-QTOF	splash10-014r-0019000000-f4220ba5e589bf99a9ea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 20V, Positive-QTOF	splash10-014i-1139000000-9334bf38981381cc7a00	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 40V, Positive-QTOF	splash10-002g-9532000000-8d635fd79d5a07bfbaa8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 10V, Negative-QTOF	splash10-0udi-0009000000-9b61e666ea58e89197b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 20V, Negative-QTOF	splash10-0udi-1229000000-f6625299fa9cf1f41bbf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-Hydroxy-leukotriene B4 40V, Negative-QTOF	splash10-0a6u-6298000000-f0b013babab01e4ad7b8	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Not Available

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	<0.0001 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0000075 (0.0 - 0.000015) uM	Children (1-13 years old)	Both	Normal	11166796	details
Urine	Detected and Quantified	0.0000025 (0.0 - 0.000005) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	11166796	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0003 +/- 0.00014 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Sjögren-Larsson syndrome	11166796	details

Associated Disorders and Diseases

Disease References

Sjögren-Larsson syndrome
Willemsen MA, Rotteveel JJ, de Jong JG, Wanders RJ, IJlst L, Hoffmann GF, Mayatepek E: Defective metabolism of leukotriene B4 in the Sjogren-Larsson syndrome. J Neurol Sci. 2001 Jan 15;183(1):61-7. [PubMed:11166796 ]

Associated OMIM IDs

270200 (Sjögren-Larsson syndrome)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022663

KNApSAcK ID

Not Available

Chemspider ID

4444320

KEGG Compound ID

C04853

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6287

PubChem Compound

5280745

PDB ID

Not Available

ChEBI ID

15646

Food Biomarker Ontology

Not Available

VMH ID

LEUKTRB4WOH

MarkerDB ID

MDB00000334

Good Scents ID

Not Available

References

Synthesis Reference

Zamboni, Robert; Rokach, Joshua. Stereospecific synthesis of two metabolites of LTB4. Tetrahedron Letters (1982), 23(46), 4751-4.

Material Safety Data Sheet (MSDS)

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General References

Berry KA, Borgeat P, Gosselin J, Flamand L, Murphy RC: Urinary metabolites of leukotriene B4 in the human subject. J Biol Chem. 2003 Jul 4;278(27):24449-60. Epub 2003 Apr 22. [PubMed:12709426 ]
Willemsen MA, Rotteveel JJ, de Jong JG, Wanders RJ, IJlst L, Hoffmann GF, Mayatepek E: Defective metabolism of leukotriene B4 in the Sjogren-Larsson syndrome. J Neurol Sci. 2001 Jan 15;183(1):61-7. [PubMed:11166796 ]
Goldman DW, Olson DM, Payan DG, Gifford LA, Goetzl EJ: Development of receptors for leukotriene B4 on HL-60 cells induced to differentiate by 1 alpha,25-dihydroxyvitamin D3. J Immunol. 1986 Jun 15;136(12):4631-6. [PubMed:3011899 ]
Willemsen MA, IJlst L, Steijlen PM, Rotteveel JJ, de Jong JG, van Domburg PH, Mayatepek E, Gabreels FJ, Wanders RJ: Clinical, biochemical and molecular genetic characteristics of 19 patients with the Sjogren-Larsson syndrome. Brain. 2001 Jul;124(Pt 7):1426-37. [PubMed:11408337 ]
Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]
Jin R, Koop DR, Raucy JL, Lasker JM: Role of human CYP4F2 in hepatic catabolism of the proinflammatory agent leukotriene B4. Arch Biochem Biophys. 1998 Nov 1;359(1):89-98. [PubMed:9799565 ]

Enzymes

Enzyme Details

1. Leukotriene-B(4) omega-hydroxylase 1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP4F2
Uniprot ID:: P78329
Molecular weight:: 59852.825

Reactions

Leukotriene B4 + NADPH + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details
Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details

Enzyme Details

2. Leukotriene-B(4) omega-hydroxylase 2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. This enzyme requires molecular oxygen and NADPH for the omega-hydroxylation of LTB4, a potent chemoattractant for polymorphonuclear leukocytes.
Gene Name:: CYP4F3
Uniprot ID:: Q08477
Molecular weight:: 59846.085

Reactions

Leukotriene B4 + NADPH + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details
Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details

Enzyme Details

3. Cytochrome P450 4F11

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Not Available
Gene Name:: CYP4F11
Uniprot ID:: Q9HBI6
Molecular weight:: 60145.165

Reactions

Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details

Enzyme Details

4. Cytochrome P450 4F8

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Hydroxylates arachidonic acid (20:4n-6) to (18R)-hydroxyarachidonate. Shows little activity against prostaglandin (PG) D2, PGE1, PGE2, PGF2alpha, and leukotriene B4. Catalyzes omega-2 and omega-3-hydroxylation of PGH1 and PGH2. Catalyzes epoxidation of 4,7,10,13,16,19-(Z)-docosahexaenoic acid (22:6n-3) and 7,10,13,16,19-(Z)-docosapentaenoic acid (22:5n-3) and omega-3-hydroxylation of 4,7,10,13,16-(Z)-docosapentaenoic acid (22:5n-6). Catalyzes hydroxylation of PGI2 and carbaprostacyclin.
Gene Name:: CYP4F8
Uniprot ID:: P98187
Molecular weight:: 59993.995

Reactions

Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details

Enzyme Details

5. Cytochrome P450 4F22

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP4F22
Uniprot ID:: Q6NT55
Molecular weight:: Not Available

Reactions

Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Water	details

Showing metabocard for 20-Hydroxy-leukotriene B4 (HMDB0001509)

MOL for HMDB0001509 (20-Hydroxy-leukotriene B4)

3D MOL for HMDB0001509 (20-Hydroxy-leukotriene B4)

3D SDF for HMDB0001509 (20-Hydroxy-leukotriene B4)

3D-SDF for HMDB0001509 (20-Hydroxy-leukotriene B4)

PDB for HMDB0001509 (20-Hydroxy-leukotriene B4)

3D PDB for HMDB0001509 (20-Hydroxy-leukotriene B4)

SMILES for HMDB0001509 (20-Hydroxy-leukotriene B4)

INCHI for HMDB0001509 (20-Hydroxy-leukotriene B4)

Structure for HMDB0001509 (20-Hydroxy-leukotriene B4)

3D Structure for HMDB0001509 (20-Hydroxy-leukotriene B4)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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