MiMeDB: Showing metabocard for leukotriene A4 (MMDBc0032952)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:28:38 UTC

Update Date

2024-04-30 19:55:58 UTC

Metabolite ID

MMDBc0032952

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>
MMDBc0032952

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₂₀H₃₀O₃

Average Mass

318.4504

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uec-8290000000-c9cb5a94725e337cb3e0	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00gr-9143000000-62d8773d6e2e97f53892	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-1129000000-fffe04743dab285e2ca8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052g-9421000000-f30ef9628caae676c4c0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9610000000-5d083c3562218df21b53	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0139000000-39394fbcd6b959bb3bf7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-4396000000-97fa16078ceabe3f07db	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9230000000-62723f520381db54d71c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-3529000000-0fbbeee57f59de11f177	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fyn-9533000000-d9537938ec7f6d247757	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-e99fd57f045ac7fdae48	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-144e64ffbb4253ee3d97	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-6339000000-eb15f4eeced3dd8bfaed	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9320000000-a3755453c278384f23ba	2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Epidermis
Feces

Tissue Locations

Epidermis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192427	Leukotriene C4 synthase	Enzyme	Q16873	Homo sapiens
MMDBp0192584	Arachidonate 5-lipoxygenase	Unknown	P09917	Homo sapiens
MMDBp0192627	Leukotriene A-4 hydrolase	Unknown	P09960	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000293	5(S)-Hydroperoxyeicosatetraenoic acid	leukotriene A4	arachidonate 5-lipoxygenase	VMH	11160764
MMDBr0001593	leukotriene A4	Leukotriene B4	leukotriene A4 hydrolase	VMH	7918238
MMDBr0001595	Glutathione	Leukotriene C4	leukotriene C4 synthase	VMH; KEGG	30371894
MMDBr0004476	leukotriene A4	5(S),6(S)-Epoxy-15(S)-Hydroxy-7E,9E,11Z,13E-Eicosatetraenoic Acid Anion	arachidonate 12-lipoxygenase	VMH	10224163 11323741 9870464
MMDBr0004477	leukotriene A4	5(S),6(S)-Epoxy-15(S)-Hydroxy-7E,9E,11Z,13E-Eicosatetraenoic Acid Anion	arachidonate 5-lipoxygenase	VMH	10224163 11323741 9870464
MMDBr0009436	Glutathione	Leukotriene C4	leukotriene C4 synthase	VMH	30371894
MMDBr0009440	leukotriene A4	5S,12S-Dihydroxy-6Z,8E,10E,14Z-Eicosatetraenoic Acid	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001337

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1111/j.1432-1033.1992.tb17341.x. [PubMed:1425677 ]
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. doi: 10.1016/0006-2952(90)90035-j. [PubMed:2154229 ]
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. doi: 10.1126/science.2820055. [PubMed:2820055 ]
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. doi: 10.1016/0923-1811(94)90095-7. [PubMed:7918238 ]
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, 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. doi: 10.1111/1523-1747.ep12469865. [PubMed:8382716 ]
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. doi: 10.1046/j.1525-1381.1999.t01-1-99231.x. [PubMed:10591081 ]

Showing metabocard for leukotriene A4 (MMDBc0032952)

MOL for #<Metabolite:0x00007fdad882eed8>

3D MOL for #<Metabolite:0x00007fdad882eed8>

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3D-SDF for #<Metabolite:0x00007fdad882eed8>

PDB for #<Metabolite:0x00007fdad882eed8>

3D PDB for #<Metabolite:0x00007fdad882eed8>

SMILES for #<Metabolite:0x00007fdad882eed8>

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Structure for #<Metabolite:0x00007fdad882eed8>

3D Structure for #<Metabolite:0x00007fdad882eed8>