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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-25 13:16:40 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005089

Secondary Accession Numbers

HMDB05089

Metabolite Identification

Common Name

12(S)-Leukotriene B4

Description

12(S)-Leukotriene B4 is an agonist of G-protein-coupled receptors for leukotriene B4 (LTB4), BLT1, and BLT2. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region, and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation (PMID: 7649996 , 17623009 , 2866160 , 15866883 ). 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

HMDB0005089
     RDKit          3D
12(S)-Leukotriene B4
 56 55  0  0  0  0  0  0  0  0999 V2000
    7.6246    1.0348   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7123    1.0733    1.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4989    0.8552    1.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8635   -0.4539    1.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2839   -0.8349    0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2120    0.0565    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9761   -0.2598   -0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4617   -1.6212   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9459   -2.1964   -1.4130 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0046   -2.2195   -2.3288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8796   -1.3427   -1.9939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -1.0357   -1.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2668   -0.1929   -1.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007    0.1283   -1.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4052    0.9725   -1.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5071    1.2604   -1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7360    0.7294    0.0199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9100    1.3265    0.9575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2034    0.9097    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4103    0.3678    1.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8200    0.4770    2.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8083   -0.2425    1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5306   -0.9099    0.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1372   -0.1739    1.8107 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6741    1.2371   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3660    1.8081   -0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0538    0.0838   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5717    0.4214    1.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0815    2.1222    1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7179    1.6594    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7416    1.0058    3.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258   -1.2560    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1198   -0.5742    2.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0705   -0.9054   -0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9300   -1.9002    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4680    1.1241   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2824    0.5395   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -2.3327    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108   -1.5132    0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5632   -3.2069   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769   -2.0477   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736   -0.9159   -2.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3729   -1.4371   -0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1359    0.2105   -2.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5150   -0.2813   -0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2415    1.3570   -2.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2838    1.9001   -1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4925   -0.3724    0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0146    2.3044    1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7636    0.3622   -0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4207    1.9941    0.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0868   -0.6869    1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7687    0.9798    2.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8497    0.0684    3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1159    1.5546    2.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7153   -1.0109    1.8958 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  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
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  1
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  6
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

  Mrv1652306171918282D          

 24 23  0  0  0  0            999 V2000
10001.736610004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.561910004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.277010004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.991810004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.706610004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.422410004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.135910004.4998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10006.851710004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.565210004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.392310004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.105910004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.821610004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.537210004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.250810004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.968610004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.135910005.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.021710004.4998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.306710004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.591810004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.877010004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.162210004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.445010004.0882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.162210005.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.021710005.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 17 18  1  0  0  0  0
 17 24  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005089

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19+/m0/s1

> <INCHI_KEY>
VNYSSYRCGWBHLG-CBBLYLIKSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.61153583247407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
4.125548676999999

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720820347637158

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6463449725928205

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2749373349576958

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
102.985

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-Hydroxy-LTB4

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005089
     RDKit          3D
12(S)-Leukotriene B4
 56 55  0  0  0  0  0  0  0  0999 V2000
    7.6246    1.0348   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7123    1.0733    1.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4989    0.8552    1.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8635   -0.4539    1.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2839   -0.8349    0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2120    0.0565    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9761   -0.2598   -0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4617   -1.6212   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9459   -2.1964   -1.4130 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0046   -2.2195   -2.3288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8796   -1.3427   -1.9939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -1.0357   -1.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2668   -0.1929   -1.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007    0.1283   -1.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4052    0.9725   -1.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5071    1.2604   -1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7360    0.7294    0.0199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9100    1.3265    0.9575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2034    0.9097    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4103    0.3678    1.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8200    0.4770    2.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8083   -0.2425    1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5306   -0.9099    0.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1372   -0.1739    1.8107 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6741    1.2371   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3660    1.8081   -0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0538    0.0838   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5717    0.4214    1.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0815    2.1222    1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7179    1.6594    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7416    1.0058    3.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258   -1.2560    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1198   -0.5742    2.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0705   -0.9054   -0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9300   -1.9002    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4680    1.1241   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2824    0.5395   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -2.3327    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108   -1.5132    0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5632   -3.2069   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769   -2.0477   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736   -0.9159   -2.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3729   -1.4371   -0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1359    0.2105   -2.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5150   -0.2813   -0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2415    1.3570   -2.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2838    1.9001   -1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4925   -0.3724    0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0146    2.3044    1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7636    0.3622   -0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4207    1.9941    0.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0868   -0.6869    1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7687    0.9798    2.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8497    0.0684    3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1159    1.5546    2.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7153   -1.0109    1.8958 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  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
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  1
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  6
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 17-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-19         0                                  
HETATM    1  C   UNK     0    8669.9088674.298   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8671.4498674.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8672.7848675.066   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8674.1188674.298   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8675.4528675.066   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8676.7888674.298   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8678.1208675.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8679.4568674.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8680.7888675.066   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8682.3328675.066   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8683.6648674.298   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8685.0008675.066   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8686.3368674.298   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8687.6688675.066   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8689.0088674.298   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8678.1208676.607   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8668.5748675.066   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.2398674.298   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.9058675.066   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.5708674.298   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8663.2368675.066   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8661.8978674.298   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8663.2368676.607   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8668.5748676.607   0.000  0.00  0.00           O+0
CONECT    1    2   17                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    7                                                            
CONECT   17    1   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0005089
HETATM    1  C1  UNL     1       7.625   1.035  -0.393  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.712   1.073   1.080  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.499   0.855   1.895  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.864  -0.454   1.789  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.284  -0.835   0.483  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.212   0.057   0.013  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.976  -0.260  -0.251  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.462  -1.621  -0.105  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.946  -2.196  -1.413  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.005  -2.219  -2.329  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.880  -1.343  -1.994  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.240  -1.036  -1.368  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.267  -0.193  -1.971  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.401   0.128  -1.357  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.405   0.972  -1.988  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.507   1.260  -1.348  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.736   0.729   0.020  1.00  0.00           C  
HETATM   18  O2  UNL     1      -3.910   1.326   0.958  1.00  0.00           O  
HETATM   19  C17 UNL     1      -6.203   0.910   0.368  1.00  0.00           C  
HETATM   20  C18 UNL     1      -6.410   0.368   1.757  1.00  0.00           C  
HETATM   21  C19 UNL     1      -7.820   0.477   2.244  1.00  0.00           C  
HETATM   22  C20 UNL     1      -8.808  -0.243   1.421  1.00  0.00           C  
HETATM   23  O3  UNL     1      -8.531  -0.910   0.398  1.00  0.00           O  
HETATM   24  O4  UNL     1     -10.137  -0.174   1.811  1.00  0.00           O  
HETATM   25  H1  UNL     1       6.674   1.237  -0.864  1.00  0.00           H  
HETATM   26  H2  UNL     1       8.366   1.808  -0.846  1.00  0.00           H  
HETATM   27  H3  UNL     1       8.054   0.084  -0.820  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.572   0.421   1.434  1.00  0.00           H  
HETATM   29  H5  UNL     1       8.081   2.122   1.356  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.718   1.659   1.675  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.742   1.006   3.008  1.00  0.00           H  
HETATM   32  H8  UNL     1       6.626  -1.256   2.038  1.00  0.00           H  
HETATM   33  H9  UNL     1       5.120  -0.574   2.635  1.00  0.00           H  
HETATM   34  H10 UNL     1       6.071  -0.905  -0.282  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.930  -1.900   0.588  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.468   1.124  -0.131  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.282   0.540  -0.601  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.061  -2.333   0.460  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.511  -1.513   0.523  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.563  -3.207  -1.195  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.877  -2.048  -1.922  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.974  -0.916  -2.996  1.00  0.00           H  
HETATM   43  H19 UNL     1      -0.373  -1.437  -0.375  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.136   0.211  -2.966  1.00  0.00           H  
HETATM   45  H21 UNL     1      -2.515  -0.281  -0.363  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.241   1.357  -2.979  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.284   1.900  -1.808  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.492  -0.372   0.042  1.00  0.00           H  
HETATM   49  H25 UNL     1      -4.015   2.304   1.002  1.00  0.00           H  
HETATM   50  H26 UNL     1      -6.764   0.362  -0.418  1.00  0.00           H  
HETATM   51  H27 UNL     1      -6.421   1.994   0.313  1.00  0.00           H  
HETATM   52  H28 UNL     1      -6.087  -0.687   1.848  1.00  0.00           H  
HETATM   53  H29 UNL     1      -5.769   0.980   2.428  1.00  0.00           H  
HETATM   54  H30 UNL     1      -7.850   0.068   3.275  1.00  0.00           H  
HETATM   55  H31 UNL     1      -8.116   1.555   2.286  1.00  0.00           H  
HETATM   56  H32 UNL     1     -10.715  -1.011   1.896  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7   36
CONECT    7    8   37
CONECT    8    9   38   39
CONECT    9   10   11   40
CONECT   10   41
CONECT   11   12   12   42
CONECT   12   13   43
CONECT   13   14   14   44
CONECT   14   15   45
CONECT   15   16   16   46
CONECT   16   17   47
CONECT   17   18   19   48
CONECT   18   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   23   23   24
CONECT   24   56
END

HMDB0005089
     RDKit          3D
12(S)-Leukotriene B4
 56 55  0  0  0  0  0  0  0  0999 V2000
    7.6246    1.0348   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7123    1.0733    1.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4989    0.8552    1.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8635   -0.4539    1.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2839   -0.8349    0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2120    0.0565    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9761   -0.2598   -0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4617   -1.6212   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9459   -2.1964   -1.4130 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0046   -2.2195   -2.3288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8796   -1.3427   -1.9939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -1.0357   -1.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2668   -0.1929   -1.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007    0.1283   -1.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4052    0.9725   -1.9883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5071    1.2604   -1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7360    0.7294    0.0199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9100    1.3265    0.9575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2034    0.9097    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4103    0.3678    1.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8200    0.4770    2.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8083   -0.2425    1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5306   -0.9099    0.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1372   -0.1739    1.8107 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6741    1.2371   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3660    1.8081   -0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0538    0.0838   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5717    0.4214    1.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0815    2.1222    1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7179    1.6594    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7416    1.0058    3.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258   -1.2560    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1198   -0.5742    2.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0705   -0.9054   -0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9300   -1.9002    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4680    1.1241   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2824    0.5395   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609   -2.3327    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108   -1.5132    0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5632   -3.2069   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769   -2.0477   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736   -0.9159   -2.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3729   -1.4371   -0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1359    0.2105   -2.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5150   -0.2813   -0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2415    1.3570   -2.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2838    1.9001   -1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4925   -0.3724    0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0146    2.3044    1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7636    0.3622   -0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4207    1.9941    0.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0868   -0.6869    1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7687    0.9798    2.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8497    0.0684    3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1159    1.5546    2.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7153   -1.0109    1.8958 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  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
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  1
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  6
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12-Epi-LTB4	ChEBI
12S-LTB4	ChEBI
5S,12S-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid	ChEBI
5S,12S-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoate	Generator
2-Epi-LTB4	HMDB
5(S),12(S)-Dihydroxyeicosatetraenoate	HMDB
5(S),12(S)-Dihydroxyeicosatetraenoic acid	HMDB
5S,12S-Dihydroxy-6Z,8E,10E,14Z-eicsatetraenoate	HMDB
5S,12S-Dihydroxy-6Z,8E,10E,14Z-eicsatetraenoic acid	HMDB
[S-[R,r-(e,Z,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoate	HMDB
[S-[R,r-(e,Z,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid	HMDB
(5S,6Z,8E,10E,12S,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acid	HMDB
12-Epi-leukotriene b4	HMDB
12(S)-Leukotriene b4	ChEBI
12(S)-Leukotriene B4	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(5S,6Z,8E,10E,12S,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid

Traditional Name

20-Hydroxy-LTB4

CAS Registry Number

83709-73-3

SMILES

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

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19+/m0/s1

InChI Key

VNYSSYRCGWBHLG-CBBLYLIKSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Leukotrienes

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:72795 )
leukotriene (CHEBI:72795 )
dihydroxy monocarboxylic acid (CHEBI:72795 )
polyunsaturated fatty acid (CHEBI:72795 )
hydroxy fatty acid (CHEBI:72795 )
Leukotrienes (LMFA03020015 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0005089)
Membrane (HMDB: HMDB0005089)

Source

Exogenous

Exogenous (HMDB: HMDB0005089)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0005089)

Process

Not Available

Role

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	0.015 g/L	ALOGPS
logP	5.46	ALOGPS
logP	4.13	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	14	ChemAxon
Refractivity	102.98 m³·mol⁻¹	ChemAxon
Polarizability	39.61 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]+	191.037	31661259
DarkChem	[M-H]-	187.259	31661259
DeepCCS	[M+H]+	197.761	30932474
DeepCCS	[M-H]-	195.096	30932474
DeepCCS	[M-2H]-	229.695	30932474
DeepCCS	[M+Na]+	205.247	30932474
AllCCS	[M+H]+	190.8	32859911
AllCCS	[M+H-H2O]+	188.0	32859911
AllCCS	[M+NH4]+	193.4	32859911
AllCCS	[M+Na]+	194.1	32859911
AllCCS	[M-H]-	187.9	32859911
AllCCS	[M+Na-2H]-	189.7	32859911
AllCCS	[M+HCOO]-	191.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12(S)-Leukotriene B4	CCCCC\C=C/C[C@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	4605.7	Standard polar	33892256
12(S)-Leukotriene B4	CCCCC\C=C/C[C@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	2645.4	Standard non polar	33892256
12(S)-Leukotriene B4	CCCCC\C=C/C[C@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	2873.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12(S)-Leukotriene B4,1TMS,isomer #1	CCCCC/C=C\C[C@@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C	3003.9	Semi standard non polar	33892256
12(S)-Leukotriene B4,1TMS,isomer #2	CCCCC/C=C\C[C@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C	2997.2	Semi standard non polar	33892256
12(S)-Leukotriene B4,1TMS,isomer #3	CCCCC/C=C\C[C@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C	2902.7	Semi standard non polar	33892256
12(S)-Leukotriene B4,2TMS,isomer #1	CCCCC/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	3062.5	Semi standard non polar	33892256
12(S)-Leukotriene B4,2TMS,isomer #2	CCCCC/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	2960.7	Semi standard non polar	33892256
12(S)-Leukotriene B4,2TMS,isomer #3	CCCCC/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	2958.3	Semi standard non polar	33892256
12(S)-Leukotriene B4,3TMS,isomer #1	CCCCC/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	3003.4	Semi standard non polar	33892256
12(S)-Leukotriene B4,1TBDMS,isomer #1	CCCCC/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	3251.3	Semi standard non polar	33892256
12(S)-Leukotriene B4,1TBDMS,isomer #2	CCCCC/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	3244.7	Semi standard non polar	33892256
12(S)-Leukotriene B4,1TBDMS,isomer #3	CCCCC/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	3148.3	Semi standard non polar	33892256
12(S)-Leukotriene B4,2TBDMS,isomer #1	CCCCC/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	3518.0	Semi standard non polar	33892256
12(S)-Leukotriene B4,2TBDMS,isomer #2	CCCCC/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	3449.6	Semi standard non polar	33892256
12(S)-Leukotriene B4,2TBDMS,isomer #3	CCCCC/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	3444.0	Semi standard non polar	33892256
12(S)-Leukotriene B4,3TBDMS,isomer #1	CCCCC/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	3735.9	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 - 12(S)-Leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-7896000000-782d01776a33cc451555	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12(S)-Leukotriene B4 GC-MS (3 TMS) - 70eV, Positive	splash10-01rl-9113530000-205b0d713aeb42a9afc2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12(S)-Leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 10V, Positive-QTOF	splash10-0gb9-0019000000-69c64ad7b55da6a633e1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 20V, Positive-QTOF	splash10-0v4i-5598000000-0a1483f60114546ce2c7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 40V, Positive-QTOF	splash10-052f-9550000000-0ad5f1d400a5ff275f25	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 10V, Negative-QTOF	splash10-00kr-0029000000-0164a507a03180713a2e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 20V, Negative-QTOF	splash10-014r-2269000000-52f6b9d4ecc4e26ff1fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 40V, Negative-QTOF	splash10-0a4l-9340000000-c2e72464c072384447e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 10V, Negative-QTOF	splash10-000i-0009000000-74962f74765b30de04ac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 20V, Negative-QTOF	splash10-00kr-3659000000-98607094f1fa036e16e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 40V, Negative-QTOF	splash10-052f-5191000000-91a6c7d4dfff9bd70967	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 10V, Positive-QTOF	splash10-0uxr-0019000000-bbfb0bde6a04ea9b05bc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 20V, Positive-QTOF	splash10-0udi-3439000000-d8140c418a63ad2159a3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 40V, Positive-QTOF	splash10-0ar0-9320000000-afb563cb7a2b51e02836	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB023627

KNApSAcK ID

Not Available

Chemspider ID

4446254

KEGG Compound ID

C04853

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283130

PDB ID

Not Available

ChEBI ID

72795

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

Wheelan P, Murphy RC: Metabolism of 6-trans-isomers of leukotriene B4 in cultured hepatoma cells and in human polymorphonuclear leukocytes. Identification of a delta 6-reductase metabolic pathway. J Biol Chem. 1995 Aug 25;270(34):19845-52. [PubMed:7649996 ]
Bremm KD, Konig W, Pfeiffer P, Rauschen I, Theobald K, Thelestam M, Alouf JE: Effect of thiol-activated toxins (streptolysin O, alveolysin, and theta toxin) on the generation of leukotrienes and leukotriene-inducing and -metabolizing enzymes from human polymorphonuclear granulocytes. Infect Immun. 1985 Dec;50(3):844-51. [PubMed:2866160 ]
Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]
Iizuka Y, Yokomizo T, Terawaki K, Komine M, Tamaki K, Shimizu T: Characterization of a mouse second leukotriene B4 receptor, mBLT2: BLT2-dependent ERK activation and cell migration of primary mouse keratinocytes. J Biol Chem. 2005 Jul 1;280(26):24816-23. Epub 2005 May 2. [PubMed:15866883 ]
Lipid Maps (LMFA03020015) [Link]

Enzymes

Enzyme Details

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

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

Enzyme Details

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

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

Showing metabocard for 12(S)-Leukotriene B4 (HMDB0005089)

MOL for HMDB0005089 (12(S)-Leukotriene B4)

3D MOL for HMDB0005089 (12(S)-Leukotriene B4)

3D SDF for HMDB0005089 (12(S)-Leukotriene B4)

3D-SDF for HMDB0005089 (12(S)-Leukotriene B4)

PDB for HMDB0005089 (12(S)-Leukotriene B4)

3D PDB for HMDB0005089 (12(S)-Leukotriene B4)

SMILES for HMDB0005089 (12(S)-Leukotriene B4)

INCHI for HMDB0005089 (12(S)-Leukotriene B4)

Structure for HMDB0005089 (12(S)-Leukotriene B4)

3D Structure for HMDB0005089 (12(S)-Leukotriene B4)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes