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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-25 08:58:52 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005073

Secondary Accession Numbers

HMDB05073

Metabolite Identification

Common Name

Leukotriene B5

Description

Leukotriene B5 (LTB5) is a 5-lipoxygenase metabolite of arachidonic (AA) and eicosapentaenoic acid (EPA), involved in numerous inflammatory diseases and possesses a substantially less potent inflammatory effect than LTB4. Binding of LTB5 to human neutrophil LTB4 high affinity binding sites is lower than that of LTB4. Polymorphonuclear leukocytes isolated from volunteers who ingested eicosapentaenoic acid (EPA) form LTB5. Enrichment of human neutrophils with EPA, by dietary supplementation for at least 3 weeks, reduces their formation of LTB4 ex vivo. LTB5 is catabolized to 20-OH-LTB5, which in turn is metabolized to 20-COOH-LTB5. Presumably the same enzyme systems are involved in the catabolism of LTB5 that are responsible for catabolism of LTB4. Fish oil supplementation has a protective effect on exercise-induced bronchoconstriction (EIB) in elite athletes, which may be attributed to its antiinflammatory properties due to a significant reduction in LTB4 and a significant increase in LTB5 generation from activated polymorphonuclear leukocytes (PMNLs). (PMID: 1964169 , 15866528 , 2538061 , 16424411 ). 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

HMDB0005073
     RDKit          3D
Leukotriene B5
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.3394    1.1093    3.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4108    0.6395    2.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0593   -0.7609    2.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0554   -1.2877    1.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1411   -0.5015    0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1286   -0.9926   -0.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0928   -1.4939   -1.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7572   -1.7310   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2032   -1.5016    0.5807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8491   -2.2415    1.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616   -1.9650    0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713   -1.2313    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -1.6431    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193   -0.9202   -0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -1.3749   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9063   -0.7088   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6446    0.5528   -1.5561 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1328    1.5242   -0.7088 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448    1.0025   -2.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0669    1.2720   -1.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9358    2.3893   -0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6641    3.6847   -1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5546    4.0135   -1.6641 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7122    4.6343   -1.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2598    1.1184    3.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8180    2.0887    3.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8914    0.3196    4.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5138    0.7629    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8792    1.3674    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7356   -1.4081    2.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9195   -2.3931    1.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2096   -0.1758    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6723    0.5520    0.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1150   -0.9037   -1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3279   -1.8029   -2.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858   -1.3125   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5763   -2.8673   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125   -0.4419    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136   -3.0952    1.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902   -2.8792    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479   -0.3319   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426   -2.5507    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886    0.0154   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1085   -2.3076    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9014   -1.1013   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897    0.3088   -2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302    1.1322    0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0501    0.2418   -3.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5532    1.9637   -2.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4320    0.3770   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8642    1.6006   -2.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9297    2.4410   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2026    2.1580    0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1512    4.6563   -2.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  1
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END


  Mrv0541 02231220202D          

 24 23  0  0  1  0            999 V2000
   23.1534  -17.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5809  -17.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0114  -14.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5824  -14.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5824  -17.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5824  -16.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8679  -17.8734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.2968  -16.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8679  -18.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5809  -18.6985    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.8665  -19.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2968  -15.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1534  -19.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1520  -18.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2955  -19.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4375  -19.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4389  -18.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4375  -19.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0099  -18.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7244  -19.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7230  -20.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7230  -21.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4375  -21.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4375  -22.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
 10  2  1  1  0  0  0
  3 12  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 18  1  0  0  0  0
 16 21  1  0  0  0  0
 17 20  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005073

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3-,8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1

> <INCHI_KEY>
BISQPGCQOHLHQK-HDNPQISLSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.4498

> <EXACT_MASS>
334.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.28348735814384

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6Z,8E,10E,12R,14Z,17Z)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
3.7636270203333324

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720813880416213

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6463449725912485

> <JCHEM_PKA_STRONGEST_BASIC>
-1.274938646611163

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
104.10160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
leukotriene B5

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005073
     RDKit          3D
Leukotriene B5
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.3394    1.1093    3.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4108    0.6395    2.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0593   -0.7609    2.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0554   -1.2877    1.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1411   -0.5015    0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1286   -0.9926   -0.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0928   -1.4939   -1.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7572   -1.7310   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2032   -1.5016    0.5807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8491   -2.2415    1.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616   -1.9650    0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713   -1.2313    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -1.6431    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193   -0.9202   -0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -1.3749   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9063   -0.7088   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6446    0.5528   -1.5561 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1328    1.5242   -0.7088 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448    1.0025   -2.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0669    1.2720   -1.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9358    2.3893   -0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6641    3.6847   -1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5546    4.0135   -1.6641 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7122    4.6343   -1.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2598    1.1184    3.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8180    2.0887    3.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8914    0.3196    4.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5138    0.7629    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8792    1.3674    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7356   -1.4081    2.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9195   -2.3931    1.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2096   -0.1758    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6723    0.5520    0.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1150   -0.9037   -1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3279   -1.8029   -2.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858   -1.3125   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5763   -2.8673   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125   -0.4419    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136   -3.0952    1.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902   -2.8792    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479   -0.3319   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426   -2.5507    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886    0.0154   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1085   -2.3076    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9014   -1.1013   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897    0.3088   -2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302    1.1322    0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0501    0.2418   -3.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5532    1.9637   -2.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4320    0.3770   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8642    1.6006   -2.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9297    2.4410   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2026    2.1580    0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1512    4.6563   -2.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  1
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      43.220 -32.594   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      36.551 -33.364   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      48.555 -27.974   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      45.887 -27.974   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      45.887 -32.594   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      45.887 -31.054   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      44.553 -33.364   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.221 -30.284   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.553 -34.904   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.551 -34.904   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      35.217 -35.674   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      47.221 -28.744   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      43.220 -35.674   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.884 -34.904   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.885 -35.674   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.550 -37.214   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      41.886 -34.904   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.550 -35.674   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      39.218 -34.904   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      40.552 -35.674   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.216 -37.984   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.216 -39.524   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.550 -40.294   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      32.550 -41.834   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   10                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    1    5    9                                                  
CONECT    8    6   12                                                       
CONECT    9    7   13                                                       
CONECT   10    2   11   15                                                  
CONECT   11   10   14                                                       
CONECT   12    3    4    8                                                  
CONECT   13    9   17                                                       
CONECT   14   11   18                                                       
CONECT   15   10   19                                                       
CONECT   16   18   21                                                       
CONECT   17   13   20                                                       
CONECT   18   14   16                                                       
CONECT   19   15   20                                                       
CONECT   20   17   19                                                       
CONECT   21   16   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0005073
HETATM    1  C1  UNL     1      -7.339   1.109   3.721  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.411   0.639   2.239  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.059  -0.761   2.256  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.055  -1.288   1.617  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.141  -0.502   0.781  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.129  -0.993  -0.616  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.093  -1.494  -1.191  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.757  -1.731  -0.737  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.203  -1.502   0.581  1.00  0.00           C  
HETATM   10  O1  UNL     1      -2.849  -2.241   1.577  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.762  -1.965   0.674  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.171  -1.231   0.112  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.571  -1.643   0.180  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.519  -0.920  -0.380  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.900  -1.375  -0.284  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.906  -0.709  -0.821  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.645   0.553  -1.556  1.00  0.00           C  
HETATM   18  O2  UNL     1       4.133   1.524  -0.709  1.00  0.00           O  
HETATM   19  C17 UNL     1       5.845   1.002  -2.346  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.067   1.272  -1.549  1.00  0.00           C  
HETATM   21  C19 UNL     1       6.936   2.389  -0.552  1.00  0.00           C  
HETATM   22  C20 UNL     1       6.664   3.685  -1.181  1.00  0.00           C  
HETATM   23  O3  UNL     1       5.555   4.014  -1.664  1.00  0.00           O  
HETATM   24  O4  UNL     1       7.712   4.634  -1.255  1.00  0.00           O  
HETATM   25  H1  UNL     1      -6.260   1.118   3.960  1.00  0.00           H  
HETATM   26  H2  UNL     1      -7.818   2.089   3.836  1.00  0.00           H  
HETATM   27  H3  UNL     1      -7.891   0.320   4.287  1.00  0.00           H  
HETATM   28  H4  UNL     1      -8.514   0.763   1.994  1.00  0.00           H  
HETATM   29  H5  UNL     1      -6.879   1.367   1.673  1.00  0.00           H  
HETATM   30  H6  UNL     1      -7.736  -1.408   2.884  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.919  -2.393   1.737  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.210  -0.176   1.218  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.672   0.552   0.675  1.00  0.00           H  
HETATM   34  H10 UNL     1      -6.115  -0.904  -1.179  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.328  -1.803  -2.297  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.986  -1.312  -1.503  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.576  -2.867  -0.966  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.112  -0.442   0.894  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.214  -3.095   1.224  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.590  -2.879   1.196  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.148  -0.332  -0.388  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.843  -2.551   0.693  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.289   0.015  -0.917  1.00  0.00           H  
HETATM   44  H20 UNL     1       4.109  -2.308   0.263  1.00  0.00           H  
HETATM   45  H21 UNL     1       5.901  -1.101  -0.712  1.00  0.00           H  
HETATM   46  H22 UNL     1       3.790   0.309  -2.261  1.00  0.00           H  
HETATM   47  H23 UNL     1       4.030   1.132   0.196  1.00  0.00           H  
HETATM   48  H24 UNL     1       6.050   0.242  -3.134  1.00  0.00           H  
HETATM   49  H25 UNL     1       5.553   1.964  -2.841  1.00  0.00           H  
HETATM   50  H26 UNL     1       7.432   0.377  -0.987  1.00  0.00           H  
HETATM   51  H27 UNL     1       7.864   1.601  -2.286  1.00  0.00           H  
HETATM   52  H28 UNL     1       7.930   2.441  -0.023  1.00  0.00           H  
HETATM   53  H29 UNL     1       6.203   2.158   0.250  1.00  0.00           H  
HETATM   54  H30 UNL     1       8.151   4.656  -2.190  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4    4   30
CONECT    4    5   31
CONECT    5    6   32   33
CONECT    6    7    7   34
CONECT    7    8   35
CONECT    8    9   36   37
CONECT    9   10   11   38
CONECT   10   39
CONECT   11   12   12   40
CONECT   12   13   41
CONECT   13   14   14   42
CONECT   14   15   43
CONECT   15   16   16   44
CONECT   16   17   45
CONECT   17   18   19   46
CONECT   18   47
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22   52   53
CONECT   22   23   23   24
CONECT   24   54
END

HMDB0005073
     RDKit          3D
Leukotriene B5
 54 53  0  0  0  0  0  0  0  0999 V2000
   -7.3394    1.1093    3.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4108    0.6395    2.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0593   -0.7609    2.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0554   -1.2877    1.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1411   -0.5015    0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1286   -0.9926   -0.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0928   -1.4939   -1.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7572   -1.7310   -0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2032   -1.5016    0.5807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8491   -2.2415    1.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616   -1.9650    0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713   -1.2313    0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -1.6431    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193   -0.9202   -0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -1.3749   -0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9063   -0.7088   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6446    0.5528   -1.5561 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1328    1.5242   -0.7088 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8448    1.0025   -2.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0669    1.2720   -1.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9358    2.3893   -0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6641    3.6847   -1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5546    4.0135   -1.6641 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7122    4.6343   -1.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2598    1.1184    3.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8180    2.0887    3.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8914    0.3196    4.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5138    0.7629    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8792    1.3674    1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7356   -1.4081    2.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9195   -2.3931    1.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2096   -0.1758    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6723    0.5520    0.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1150   -0.9037   -1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3279   -1.8029   -2.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858   -1.3125   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5763   -2.8673   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1125   -0.4419    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136   -3.0952    1.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5902   -2.8792    1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479   -0.3319   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426   -2.5507    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886    0.0154   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1085   -2.3076    0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9014   -1.1013   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897    0.3088   -2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302    1.1322    0.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0501    0.2418   -3.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5532    1.9637   -2.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4320    0.3770   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8642    1.6006   -2.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9297    2.4410   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2026    2.1580    0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1512    4.6563   -2.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  1
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoic acid	ChEBI
5,12-DiHEPE	ChEBI
LTB5	ChEBI
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoate	Generator
5,12-Dihydroxy-6-trans-leukotriene b(5)	HMDB
5,12-Dihydroxy-6E-LTB5	HMDB
5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoic acid	HMDB
LTB 5	HMDB
Leukotriene b5	MeSH

Chemical Formula

C₂₀H₃₀O₄

Average Molecular Weight

334.4498

Monoisotopic Molecular Weight

334.214409448

IUPAC Name

(5S,6Z,8E,10E,12R,14Z,17Z)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid

Traditional Name

leukotriene B5

CAS Registry Number

80445-66-5

SMILES

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

InChI Identifier

InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3-,8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1

InChI Key

BISQPGCQOHLHQK-HDNPQISLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosapentaenoic acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Leukotrienes (LMFA03020010 )

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	2.895	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	4.68	ALOGPS
logP	3.76	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	104.1 m³·mol⁻¹	ChemAxon
Polarizability	38.28 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]+	186.647	31661259
DarkChem	[M-H]-	183.872	31661259
DeepCCS	[M+H]+	189.944	30932474
DeepCCS	[M-H]-	187.586	30932474
DeepCCS	[M-2H]-	221.864	30932474
DeepCCS	[M+Na]+	197.093	30932474
AllCCS	[M+H]+	189.6	32859911
AllCCS	[M+H-H2O]+	186.7	32859911
AllCCS	[M+NH4]+	192.3	32859911
AllCCS	[M+Na]+	193.0	32859911
AllCCS	[M-H]-	186.0	32859911
AllCCS	[M+Na-2H]-	187.8	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.	5.03 minutes	32390414
Predicted by Siyang on May 30, 2022	16.6995 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.15 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2883.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	295.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	214.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	726.9 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	464.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1601.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	592.6 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	1447.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	527.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	440.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	334.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	305.5 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 B5	CC\C=C/C\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	4749.1	Standard polar	33892256
Leukotriene B5	CC\C=C/C\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	2654.0	Standard non polar	33892256
Leukotriene B5	CC\C=C/C\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	2884.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leukotriene B5,1TMS,isomer #1	CC/C=C\C/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C	3013.7	Semi standard non polar	33892256
Leukotriene B5,1TMS,isomer #2	CC/C=C\C/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C	3005.5	Semi standard non polar	33892256
Leukotriene B5,1TMS,isomer #3	CC/C=C\C/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C	2897.3	Semi standard non polar	33892256
Leukotriene B5,2TMS,isomer #1	CC/C=C\C/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	3059.3	Semi standard non polar	33892256
Leukotriene B5,2TMS,isomer #2	CC/C=C\C/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	2963.6	Semi standard non polar	33892256
Leukotriene B5,2TMS,isomer #3	CC/C=C\C/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	2960.2	Semi standard non polar	33892256
Leukotriene B5,3TMS,isomer #1	CC/C=C\C/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	2994.0	Semi standard non polar	33892256
Leukotriene B5,1TBDMS,isomer #1	CC/C=C\C/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	3254.8	Semi standard non polar	33892256
Leukotriene B5,1TBDMS,isomer #2	CC/C=C\C/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	3251.5	Semi standard non polar	33892256
Leukotriene B5,1TBDMS,isomer #3	CC/C=C\C/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	3140.2	Semi standard non polar	33892256
Leukotriene B5,2TBDMS,isomer #1	CC/C=C\C/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	3508.7	Semi standard non polar	33892256
Leukotriene B5,2TBDMS,isomer #2	CC/C=C\C/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	3438.0	Semi standard non polar	33892256
Leukotriene B5,2TBDMS,isomer #3	CC/C=C\C/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	3434.3	Semi standard non polar	33892256
Leukotriene B5,3TBDMS,isomer #1	CC/C=C\C/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	3734.6	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 B5 GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-5976000000-1308051082500b532d7b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene B5 GC-MS (3 TMS) - 70eV, Positive	splash10-002u-9114550000-fb98f8ad419bf0e2f1eb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene B5 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 - Leukotriene B5 LC-ESI-QIT , negative-QTOF	splash10-001i-0009000000-9449fd58f9fde9620481	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF	splash10-001i-0009000000-a9ad07c18d3c052b63ac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF	splash10-001i-0209000000-a818cc05c0ef95e2ad4d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF	splash10-001j-0829000000-0a8e49082c2592c2e26d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF	splash10-0002-0912000000-00b3332ca1c15daab105	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF	splash10-0gwb-0911000000-58f74003122760d3bd4d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF	splash10-0ir0-0900000000-d4d5e65bf183ee1dd84a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF	splash10-0dpi-2900000000-87002df340696b338906	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF	splash10-0abc-9800000000-487240d905b7a6f046a4	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 10V, Positive-QTOF	splash10-014j-0089000000-945a81862277ca8ffccd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 20V, Positive-QTOF	splash10-00kk-3492000000-1307f5bf34685a04ff67	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 40V, Positive-QTOF	splash10-0a4u-9550000000-dd3a21bd0ec9a9c3281b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 10V, Negative-QTOF	splash10-00lr-0029000000-aea24fc310a30c0083f4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 20V, Negative-QTOF	splash10-0159-2359000000-2767c62677c595b5c621	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 40V, Negative-QTOF	splash10-0a4l-9440000000-c5ad6a89519cdea928ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 10V, Negative-QTOF	splash10-001i-0009000000-1274a6f8c3d97ed0286e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 20V, Negative-QTOF	splash10-00lr-2749000000-7d9e79b3bd2b6189e4d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 40V, Negative-QTOF	splash10-052u-5291000000-b78f6f5274e60d632da2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 10V, Positive-QTOF	splash10-014k-0297000000-fc321826f71b083a009b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 20V, Positive-QTOF	splash10-0002-2592000000-7c86093f3b19ba95ffbe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B5 40V, Positive-QTOF	splash10-05r0-9410000000-35baf3784e923e732e21	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000079 +/- 0.000006 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.000079 +/- 0.0000056 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	<0.0001 uM	Adult (>18 years old)	Both	Normal	21359215	details

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

FDB023616

KNApSAcK ID

Not Available

Chemspider ID

4446249

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283125

PDB ID

Not Available

ChEBI ID

88493

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

von Schacky C, Fahrer C, Fischer S: Catabolism of leukotriene B5 in humans. J Lipid Res. 1990 Oct;31(10):1831-8. [PubMed:1964169 ]
Panchaud A, Avois L, Roulet M, Pilet M, Hug C, Saugy M, Decosterd LA: A validated liquid chromatography-mass spectrometry method for the determination of leukotrienes B4 and B5 produced by stimulated human polymorphonuclear leukocytes. Anal Biochem. 2005 Jun 1;341(1):58-68. [PubMed:15866528 ]
Heidel JR, Taylor SM, Laegreid WW, Silflow RM, Liggitt HD, Leid RW: In vivo chemotaxis of bovine neutrophils induced by 5-lipoxygenase metabolites of arachidonic and eicosapentaenoic acid. Am J Pathol. 1989 Mar;134(3):671-6. [PubMed:2538061 ]
Mickleborough TD, Lindley MR, Ionescu AA, Fly AD: Protective effect of fish oil supplementation on exercise-induced bronchoconstriction in asthma. Chest. 2006 Jan;129(1):39-49. [PubMed:16424411 ]
Lipid Maps (LMFA03020010) [Link]

Showing metabocard for Leukotriene B5 (HMDB0005073)

MOL for HMDB0005073 (Leukotriene B5)

3D MOL for HMDB0005073 (Leukotriene B5)

3D SDF for HMDB0005073 (Leukotriene B5)

3D-SDF for HMDB0005073 (Leukotriene B5)

PDB for HMDB0005073 (Leukotriene B5)

3D PDB for HMDB0005073 (Leukotriene B5)

SMILES for HMDB0005073 (Leukotriene B5)

INCHI for HMDB0005073 (Leukotriene B5)

Structure for HMDB0005073 (Leukotriene B5)

3D Structure for HMDB0005073 (Leukotriene B5)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra