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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

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:09 UTC

HMDB ID

HMDB0001337

Secondary Accession Numbers

HMDB01337

Metabolite Identification

Common Name

Leukotriene A4

Description

Leukotriene A4 (LTA4) is the first metabolite in the series of reactions leading to the synthesis of all leukotrienes. 5-Lipoxygenase (5-LO) catalyzes the two-step conversion of arachidonic acid to LTA4.The first step consists of the oxidation of arachidonic acid to the unstable intermediate 5-hydroperoxyeicosatetraenoic acid (5-HPETE), and the second step is the dehydration of 5-HPETE to form LTA4. Leukotriene A4, an unstable epoxide, is hydrolyzed to leukotriene B4 or conjugated with glutathione to yield leukotriene C4 and its metabolites, leukotriene D4 and leukotriene E4. The leukotrienes participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. Recent studies also suggest a neuroendocrine role for leukotriene C4 in luteinizing hormone secretion. (PMID: 10591081 , 2820055 ). 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

HMDB0001337
     RDKit          3D
Leukotriene A4
 53 53  0  0  0  0  0  0  0  0999 V2000
   -8.3590    0.6116    0.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0756    0.5084    1.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8981    0.2617    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1769   -1.0197   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0489   -1.3314   -1.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9385   -0.0979   -1.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8059    0.4156   -2.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4518   -0.0412   -2.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350   -1.2726   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059   -1.3196   -0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810   -0.1771   -0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8227   -0.2776    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    0.9974    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959    0.9712    1.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602    0.9601    1.7964 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9108    1.9336    1.9461 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1143    0.9392    0.8902 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2395    0.0031    0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2291    0.2862   -0.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3868   -0.6494   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3362   -0.2708   -1.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9846    0.5683   -2.0308 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5603   -0.8717   -1.2272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0120    1.3990    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8723   -0.3666    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1295    0.8862   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1212   -0.2791    2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9009    1.4951    2.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8157    1.0922   -0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9526    0.1546    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2005   -1.9171    0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1301   -0.9483   -0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1686   -1.4286   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3068   -2.2338   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8844    0.4124   -2.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9413    1.3964   -2.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0119    0.8276   -1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477    0.1055   -3.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7089   -2.1626   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437   -2.2611   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482    0.7948   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029   -1.1608    0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114    1.8513    0.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5749    2.3404    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793    0.2200    2.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9627    1.4509   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -1.1120    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8146    0.0887    1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6702    0.0605   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5103    1.3316   -0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9731   -1.6585   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8363   -0.8168    0.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3333   -0.6894   -0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 17 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  1
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 23 53  1  0
M  END

5280383
  Mrv0541 02231219042D          

 23 23  0  0  1  0            999 V2000
    7.5069   -1.2986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4918   -2.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7774   -1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9194   -2.0130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0944   -2.0130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6339   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3484   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0629   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7774   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  1  0  0  0
  5  8  1  6  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 17  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 20 23  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001337

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1

> <INCHI_KEY>
UFPQIRYSPUYQHK-WAQVJNLQSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.95354796119527

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid

> <ALOGPS_LOGP>
6.04

> <JCHEM_LOGP>
5.443159709333332

> <ALOGPS_LOGS>
-5.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.491353902247431

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2325255672362525

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
99.32090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.24e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
leukotriene A4

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001337
     RDKit          3D
Leukotriene A4
 53 53  0  0  0  0  0  0  0  0999 V2000
   -8.3590    0.6116    0.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0756    0.5084    1.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8981    0.2617    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1769   -1.0197   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0489   -1.3314   -1.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9385   -0.0979   -1.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8059    0.4156   -2.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4518   -0.0412   -2.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350   -1.2726   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059   -1.3196   -0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810   -0.1771   -0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8227   -0.2776    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    0.9974    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959    0.9712    1.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602    0.9601    1.7964 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9108    1.9336    1.9461 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1143    0.9392    0.8902 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2395    0.0031    0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2291    0.2862   -0.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3868   -0.6494   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3362   -0.2708   -1.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9846    0.5683   -2.0308 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5603   -0.8717   -1.2272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0120    1.3990    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8723   -0.3666    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1295    0.8862   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1212   -0.2791    2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9009    1.4951    2.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8157    1.0922   -0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9526    0.1546    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2005   -1.9171    0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1301   -0.9483   -0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1686   -1.4286   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3068   -2.2338   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8844    0.4124   -2.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9413    1.3964   -2.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0119    0.8276   -1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477    0.1055   -3.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7089   -2.1626   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437   -2.2611   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482    0.7948   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029   -1.1608    0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114    1.8513    0.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5749    2.3404    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793    0.2200    2.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9627    1.4509   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -1.1120    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8146    0.0887    1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6702    0.0605   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5103    1.3316   -0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9731   -1.6585   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8363   -0.8168    0.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3333   -0.6894   -0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 17 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  1
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 23 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5280383                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      14.013  -2.424   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      21.451  -4.528   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      20.118  -2.218   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      14.783  -3.758   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.243  -3.758   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.117  -4.528   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.450  -3.758   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.909  -4.528   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.784  -4.528   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.576  -3.758   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.118  -3.758   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.242  -4.528   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.241   2.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574   3.172   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.241   0.862   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574   4.713   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.908  -3.758   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.907   0.092   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.908   5.483   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.574  -4.528   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.907  -1.448   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.241  -2.218   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.241  -3.758   0.000  0.00  0.00           C+0
CONECT    1    4    5                                                       
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    1    5    6                                                  
CONECT    5    1    4    8                                                  
CONECT    6    4    7                                                       
CONECT    7    6    9                                                       
CONECT    8    5   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    2    3    9                                                  
CONECT   12   10   17                                                       
CONECT   13   14   15                                                       
CONECT   14   13   16                                                       
CONECT   15   13   18                                                       
CONECT   16   14   19                                                       
CONECT   17   12   20                                                       
CONECT   18   15   21                                                       
CONECT   19   16                                                            
CONECT   20   17   23                                                       
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   20   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0001337
HETATM    1  C1  UNL     1      -8.359   0.612   0.837  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.076   0.508   1.661  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.898   0.262   0.693  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.177  -1.020  -0.022  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.049  -1.331  -1.060  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.938  -0.098  -1.876  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.806   0.416  -2.305  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.452  -0.041  -2.146  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.135  -1.273  -1.430  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.106  -1.320  -0.587  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.281  -0.177  -0.387  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.823  -0.278   0.405  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.594   0.997   0.524  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.696   0.971   1.118  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.960   0.960   1.796  1.00  0.00           C  
HETATM   16  O1  UNL     1       4.911   1.934   1.946  1.00  0.00           O  
HETATM   17  C16 UNL     1       5.114   0.939   0.890  1.00  0.00           C  
HETATM   18  C17 UNL     1       6.240   0.003   0.994  1.00  0.00           C  
HETATM   19  C18 UNL     1       7.229   0.286  -0.126  1.00  0.00           C  
HETATM   20  C19 UNL     1       8.387  -0.649  -0.121  1.00  0.00           C  
HETATM   21  C20 UNL     1       9.336  -0.271  -1.192  1.00  0.00           C  
HETATM   22  O2  UNL     1       8.985   0.568  -2.031  1.00  0.00           O  
HETATM   23  O3  UNL     1      10.560  -0.872  -1.227  1.00  0.00           O  
HETATM   24  H1  UNL     1      -9.012   1.399   1.260  1.00  0.00           H  
HETATM   25  H2  UNL     1      -8.872  -0.367   0.859  1.00  0.00           H  
HETATM   26  H3  UNL     1      -8.129   0.886  -0.220  1.00  0.00           H  
HETATM   27  H4  UNL     1      -7.121  -0.279   2.396  1.00  0.00           H  
HETATM   28  H5  UNL     1      -6.901   1.495   2.121  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.816   1.092  -0.014  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.953   0.155   1.244  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.200  -1.917   0.623  1.00  0.00           H  
HETATM   32  H9  UNL     1      -7.130  -0.948  -0.613  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.169  -1.429  -0.340  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.307  -2.234  -1.587  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.884   0.412  -2.169  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.941   1.396  -2.905  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.012   0.828  -1.432  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.848   0.106  -3.100  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.709  -2.163  -1.647  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.944  -2.261  -0.067  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.448   0.795  -0.812  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.003  -1.161   0.858  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.211   1.851   0.079  1.00  0.00           H  
HETATM   44  H21 UNL     1       2.575   2.340   1.193  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.979   0.220   2.659  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.963   1.451  -0.101  1.00  0.00           H  
HETATM   47  H24 UNL     1       5.969  -1.112   0.960  1.00  0.00           H  
HETATM   48  H25 UNL     1       6.815   0.089   1.971  1.00  0.00           H  
HETATM   49  H26 UNL     1       6.670   0.061  -1.071  1.00  0.00           H  
HETATM   50  H27 UNL     1       7.510   1.332  -0.080  1.00  0.00           H  
HETATM   51  H28 UNL     1       7.973  -1.659  -0.424  1.00  0.00           H  
HETATM   52  H29 UNL     1       8.836  -0.817   0.880  1.00  0.00           H  
HETATM   53  H30 UNL     1      11.333  -0.689  -0.581  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   35
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   10   39
CONECT   10   11   40
CONECT   11   12   12   41
CONECT   12   13   42
CONECT   13   14   14   43
CONECT   14   15   44
CONECT   15   16   17   45
CONECT   16   17
CONECT   17   18   46
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21   51   52
CONECT   21   22   22   23
CONECT   23   53
END

HMDB0001337
     RDKit          3D
Leukotriene A4
 53 53  0  0  0  0  0  0  0  0999 V2000
   -8.3590    0.6116    0.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0756    0.5084    1.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8981    0.2617    0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1769   -1.0197   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0489   -1.3314   -1.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9385   -0.0979   -1.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8059    0.4156   -2.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4518   -0.0412   -2.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350   -1.2726   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059   -1.3196   -0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810   -0.1771   -0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8227   -0.2776    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    0.9974    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959    0.9712    1.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602    0.9601    1.7964 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9108    1.9336    1.9461 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1143    0.9392    0.8902 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2395    0.0031    0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2291    0.2862   -0.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3868   -0.6494   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3362   -0.2708   -1.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9846    0.5683   -2.0308 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5603   -0.8717   -1.2272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0120    1.3990    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8723   -0.3666    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1295    0.8862   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1212   -0.2791    2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9009    1.4951    2.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8157    1.0922   -0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9526    0.1546    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2005   -1.9171    0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1301   -0.9483   -0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1686   -1.4286   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3068   -2.2338   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8844    0.4124   -2.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9413    1.3964   -2.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0119    0.8276   -1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477    0.1055   -3.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7089   -2.1626   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437   -2.2611   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482    0.7948   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029   -1.1608    0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2114    1.8513    0.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5749    2.3404    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793    0.2200    2.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9627    1.4509   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693   -1.1120    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8146    0.0887    1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6702    0.0605   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5103    1.3316   -0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9731   -1.6585   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8363   -0.8168    0.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3333   -0.6894   -0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  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
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 17 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  1
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 23 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoate	ChEBI
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoate	ChEBI
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoic acid	ChEBI
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoate	ChEBI
5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoic acid	ChEBI
5S,6S-Epoxy-7E,9E,11Z,14Z-eicosatetraenoic acid	ChEBI
5S,6S-Leukotriene a4	ChEBI
LTA4	ChEBI
(5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acid	Generator
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acid	Generator
5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoate	Generator
5S,6S-Epoxy-7E,9E,11Z,14Z-eicosatetraenoate	Generator
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoate	HMDB
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoic acid	HMDB
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetrenoioc acid	HMDB
Leukotriene a	HMDB
Leukotriene a 4	HMDB
Leukotrienes a	HMDB
Leukotriene a-4	HMDB

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid

Traditional Name

leukotriene A4

CAS Registry Number

72059-45-1

SMILES

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

InChI Identifier

InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1

InChI Key

UFPQIRYSPUYQHK-WAQVJNLQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Epoxy fatty acids

Alternative Parents

Substituents

Epoxy fatty acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:15651 )
leukotriene (CHEBI:15651 )
polyunsaturated fatty acid (CHEBI:15651 )
oxylipin (CHEBI:15651 )
epoxy fatty acid (CHEBI:15651 )
Epoxy fatty acids (C00909 )
Leukotrienes (C00909 )
Leukotrienes (LMFA03020023 )

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	0.00042 g/L	ALOGPS
logP	6.04	ALOGPS
logP	5.44	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	99.32 m³·mol⁻¹	ChemAxon
Polarizability	37.95 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.491	31661259
DarkChem	[M-H]-	185.88	31661259
AllCCS	[M+H]+	187.067	32859911
AllCCS	[M-H]-	186.573	32859911
DeepCCS	[M+H]+	193.81	30932474
DeepCCS	[M-H]-	191.452	30932474
DeepCCS	[M-2H]-	225.045	30932474
DeepCCS	[M+Na]+	200.272	30932474
AllCCS	[M+H]+	187.1	32859911
AllCCS	[M+H-H2O]+	184.1	32859911
AllCCS	[M+NH4]+	189.8	32859911
AllCCS	[M+Na]+	190.6	32859911
AllCCS	[M-H]-	186.6	32859911
AllCCS	[M+Na-2H]-	188.1	32859911
AllCCS	[M+HCOO]-	189.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.33 minutes	32390414
Predicted by Siyang on May 30, 2022	24.0095 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.89 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3133.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	606.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	240.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	394.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	660.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1110.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	574.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2262.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	714.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1778.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	841.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	534.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	391.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	601.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Leukotriene A4	CCCCC\C=C/C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=O	4134.3	Standard polar	33892256
Leukotriene A4	CCCCC\C=C/C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=O	2436.9	Standard non polar	33892256
Leukotriene A4	CCCCC\C=C/C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=O	2656.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leukotriene A4,1TMS,isomer #1	CCCCC/C=C\C/C=C\C=C\C=C\[C@@H]1O[C@H]1CCCC(=O)O[Si](C)(C)C	2675.9	Semi standard non polar	33892256
Leukotriene A4,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C=C\C=C\[C@@H]1O[C@H]1CCCC(=O)O[Si](C)(C)C(C)(C)C	2909.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene A4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uec-8290000000-c9cb5a94725e337cb3e0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene A4 GC-MS (1 TMS) - 70eV, Positive	splash10-00gr-9143000000-62d8773d6e2e97f53892	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene A4 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 - Leukotriene A4 10V, Positive-QTOF	splash10-0gb9-1129000000-fffe04743dab285e2ca8	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 20V, Positive-QTOF	splash10-052g-9421000000-f30ef9628caae676c4c0	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 40V, Positive-QTOF	splash10-0006-9610000000-5d083c3562218df21b53	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 10V, Negative-QTOF	splash10-014i-0139000000-39394fbcd6b959bb3bf7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 20V, Negative-QTOF	splash10-01b9-4396000000-97fa16078ceabe3f07db	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 40V, Negative-QTOF	splash10-052f-9230000000-62723f520381db54d71c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 10V, Positive-QTOF	splash10-0uxr-3529000000-0fbbeee57f59de11f177	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 20V, Positive-QTOF	splash10-0fyn-9533000000-d9537938ec7f6d247757	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 40V, Positive-QTOF	splash10-052f-9100000000-e99fd57f045ac7fdae48	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 10V, Negative-QTOF	splash10-014i-0009000000-144e64ffbb4253ee3d97	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 20V, Negative-QTOF	splash10-014i-6339000000-eb15f4eeced3dd8bfaed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene A4 40V, Negative-QTOF	splash10-052f-9320000000-a3755453c278384f23ba	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Not Available

Tissue Locations

Epidermis

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

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022561

KNApSAcK ID

Not Available

Chemspider ID

4444074

KEGG Compound ID

C00909

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15651

Food Biomarker Ontology

Not Available

VMH ID

LEUKTRA4

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Iversen L, Fogh K, Ziboh VA, Kristensen P, Schmedes A, Kragballe K: Leukotriene B4 formation during human neutrophil keratinocyte interactions: evidence for transformation of leukotriene A4 by putative keratinocyte leukotriene A4 hydrolase. J Invest Dermatol. 1993 Mar;100(3):293-8. [PubMed:8382716 ]
Luscinskas FW, Nicolaou KC, Webber SE, Veale CA, Gimbrone MA Jr, Serhan CN: Ca2+ mobilization with leukotriene A4 and epoxytetraenes in human neutrophils. Biochem Pharmacol. 1990 Jan 15;39(2):355-65. [PubMed:2154229 ]
MacMillan DK, Hill E, Sala A, Sigal E, Shuman T, Henson PM, Murphy RC: Eosinophil 15-lipoxygenase is a leukotriene A4 synthase. J Biol Chem. 1994 Oct 28;269(43):26663-8. [PubMed:7929400 ]
Iversen L, Ziboh VA, Shimizu T, Ohishi N, Radmark O, Wetterholm A, Kragballe K: Identification and subcellular localization of leukotriene A4-hydrolase activity in human epidermis. J Dermatol Sci. 1994 Jun;7(3):191-201. [PubMed:7918238 ]
Nicholson DW, Klemba MW, Rasper DM, Metters KM, Zamboni RJ, Ford-Hutchinson AW: Purification of human leukotriene C4 synthase from dimethylsulfoxide-differentiated U937 cells. Eur J Biochem. 1992 Oct 15;209(2):725-34. [PubMed:1425677 ]
Silverman ES, Drazen JM: The biology of 5-lipoxygenase: function, structure, and regulatory mechanisms. Proc Assoc Am Physicians. 1999 Nov-Dec;111(6):525-36. [PubMed:10591081 ]
Samuelsson B, Dahlen SE, Lindgren JA, Rouzer CA, Serhan CN: Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science. 1987 Sep 4;237(4819):1171-6. [PubMed:2820055 ]

Enzymes

Enzyme Details

1. Leukotriene C4 synthase

General function:: Involved in enzyme activator activity
Specific function:: Catalyzes the conjugation of leukotriene A4 with reduced glutathione to form leukotriene C4.
Gene Name:: LTC4S
Uniprot ID:: Q16873
Molecular weight:: 16566.465

Reactions

Leukotriene A4 + Glutathione → Leukotriene C4	details

Enzyme Details

2. Arachidonate 5-lipoxygenase

General function:: Involved in metal ion binding
Specific function:: Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:: ALOX5
Uniprot ID:: P09917
Molecular weight:: 77982.595

Reactions

5(S)-Hydroperoxyeicosatetraenoic acid → Leukotriene A4 + Water	details
Arachidonic acid + Oxygen → Leukotriene A4 + Water	details

Enzyme Details

3. Leukotriene A-4 hydrolase

General function:: Involved in binding
Specific function:: Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity.
Gene Name:: LTA4H
Uniprot ID:: P09960
Molecular weight:: 69284.64

Reactions

Leukotriene A4 + Water → Leukotriene B4	details

Showing metabocard for Leukotriene A4 (HMDB0001337)

MOL for HMDB0001337 (Leukotriene A4)

3D MOL for HMDB0001337 (Leukotriene A4)

3D SDF for HMDB0001337 (Leukotriene A4)

3D-SDF for HMDB0001337 (Leukotriene A4)

PDB for HMDB0001337 (Leukotriene A4)

3D PDB for HMDB0001337 (Leukotriene A4)

SMILES for HMDB0001337 (Leukotriene A4)

INCHI for HMDB0001337 (Leukotriene A4)

Structure for HMDB0001337 (Leukotriene A4)

3D Structure for HMDB0001337 (Leukotriene A4)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions