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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 14:56:58 UTC

Update Date

2022-03-07 02:49:20 UTC

HMDB ID

HMDB0004234

Secondary Accession Numbers

HMDB0005086
HMDB04234
HMDB05086

Metabolite Identification

Common Name

12-Keto-leukotriene B4

Description

12-Keto-leukotriene B4 is formed when leukotriene B4 (LTB4) is metabolized by beta-oxidation. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 8632343 , 9667737 )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

HMDB0004234
     RDKit          3D
12-Keto-leukotriene B4
 54 53  0  0  0  0  0  0  0  0999 V2000
    6.7205    0.6088    2.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3184   -0.2096    1.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7616   -0.2203    0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3892   -0.7272   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    0.0626    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    1.4473    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854    1.9634   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071    1.3162   -0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    1.2255   -2.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4776    1.6652   -3.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345    0.6312   -2.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243    0.1631   -1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892   -0.4443   -2.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4891   -0.8863   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571   -1.5014   -1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -1.9319   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2223   -1.8181    0.9796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9623   -2.3747    1.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130   -0.4858    1.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7941    0.0730    1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4101    0.3505    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7960    0.9393    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2042    1.1005    1.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5723    1.2826   -0.6714 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5662    0.9809    3.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0880    0.0349    3.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2093    1.5295    2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117    0.1009    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4126   -1.2787    1.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7609    0.8424   -0.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4375   -0.8032   -0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -1.7888    0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1263   -0.7204   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4803    0.1080    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3178   -0.4397    0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2353    2.0685    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4220    3.0162   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283    1.9654   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559    0.3167   -0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389    0.5356   -3.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    0.2571   -0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193   -0.5598   -3.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1297   -0.7743   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0932   -1.6257   -2.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5193   -2.4463   -0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9418   -2.5096    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589   -2.4971    2.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7917    0.2963    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -0.4031    2.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4650   -0.6961    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8489    1.0053    2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5113   -0.4937   -0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7935    1.1082   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2093    0.6408   -1.1221 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
  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
 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  1
 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 02231219542D          

 24 23  0  0  1  0            999 V2000
   38.9978  -25.1472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1398  -27.6222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5689  -27.6222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.5702  -24.7347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.4281  -21.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4281  -22.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5689  -25.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5689  -25.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1427  -21.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7137  -22.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2833  -24.7347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   36.8543  -26.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1427  -20.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7137  -23.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2833  -23.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9992  -23.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8543  -27.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2847  -23.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9978  -23.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5702  -23.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7122  -23.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8557  -23.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4268  -23.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1413  -23.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  1  0  0  0
  2 17  1  0  0  0  0
  3 17  2  0  0  0  0
  4 20  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 17  1  0  0  0  0
 14 16  2  0  0  0  0
 15 19  2  0  0  0  0
 16 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004234

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/CC(=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/h6-11,14-15,19,22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t19-/m1/s1

> <INCHI_KEY>
SJVWVCVZWMJXOK-NOJHDUNKSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.4498

> <EXACT_MASS>
334.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.22862404671311

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.67

> <JCHEM_LOGP>
4.5368871649999996

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.576950530711784

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.646344731373186

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5452461358017588

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
102.0876

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-oxo-LTB4

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004234
     RDKit          3D
12-Keto-leukotriene B4
 54 53  0  0  0  0  0  0  0  0999 V2000
    6.7205    0.6088    2.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3184   -0.2096    1.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7616   -0.2203    0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3892   -0.7272   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    0.0626    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    1.4473    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854    1.9634   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071    1.3162   -0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    1.2255   -2.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4776    1.6652   -3.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345    0.6312   -2.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243    0.1631   -1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892   -0.4443   -2.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4891   -0.8863   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571   -1.5014   -1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -1.9319   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2223   -1.8181    0.9796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9623   -2.3747    1.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130   -0.4858    1.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7941    0.0730    1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4101    0.3505    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7960    0.9393    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2042    1.1005    1.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5723    1.2826   -0.6714 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5662    0.9809    3.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0880    0.0349    3.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2093    1.5295    2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117    0.1009    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4126   -1.2787    1.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7609    0.8424   -0.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4375   -0.8032   -0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -1.7888    0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1263   -0.7204   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4803    0.1080    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3178   -0.4397    0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2353    2.0685    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4220    3.0162   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283    1.9654   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559    0.3167   -0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389    0.5356   -3.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    0.2571   -0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193   -0.5598   -3.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1297   -0.7743   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0932   -1.6257   -2.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5193   -2.4463   -0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9418   -2.5096    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589   -2.4971    2.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7917    0.2963    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -0.4031    2.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4650   -0.6961    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8489    1.0053    2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5113   -0.4937   -0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7935    1.1082   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2093    0.6408   -1.1221 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
  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
 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  1
 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      72.796 -46.941   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      67.461 -51.561   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      70.129 -51.561   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      79.464 -46.171   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      84.799 -40.011   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      84.799 -41.551   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      70.129 -46.941   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      70.129 -48.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      86.133 -39.241   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      83.466 -42.321   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      71.462 -46.171   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      68.795 -49.251   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      86.133 -37.701   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      83.466 -43.861   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      71.462 -44.631   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      82.132 -44.631   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      68.795 -50.791   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      80.798 -43.861   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      72.796 -43.861   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      79.464 -44.631   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      74.129 -44.631   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      78.131 -43.861   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      75.463 -43.861   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      76.797 -44.631   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4   20                                                            
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   14                                                       
CONECT   11    1    7   15                                                  
CONECT   12    8   17                                                       
CONECT   13    9                                                            
CONECT   14   10   16                                                       
CONECT   15   11   19                                                       
CONECT   16   14   18                                                       
CONECT   17    2    3   12                                                  
CONECT   18   16   20                                                       
CONECT   19   15   21                                                       
CONECT   20    4   18   22                                                  
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0004234
HETATM    1  C1  UNL     1       6.720   0.609   2.599  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.318  -0.210   1.527  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.762  -0.220   0.170  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.389  -0.727  -0.024  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.319   0.063   0.637  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.319   1.447   0.108  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.285   1.963  -0.489  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.007   1.316  -0.735  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.676   1.226  -2.186  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.478   1.665  -3.026  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.434   0.631  -2.596  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.424   0.163  -1.692  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.689  -0.444  -2.077  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.489  -0.886  -1.109  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.757  -1.501  -1.364  1.00  0.00           C  
HETATM   16  C15 UNL     1      -4.555  -1.932  -0.435  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.222  -1.818   0.980  1.00  0.00           C  
HETATM   18  O2  UNL     1      -2.962  -2.375   1.277  1.00  0.00           O  
HETATM   19  C17 UNL     1      -4.413  -0.486   1.560  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.794   0.073   1.538  1.00  0.00           C  
HETATM   21  C19 UNL     1      -6.410   0.351   0.209  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.796   0.939   0.416  1.00  0.00           C  
HETATM   23  O3  UNL     1      -8.204   1.101   1.578  1.00  0.00           O  
HETATM   24  O4  UNL     1      -8.572   1.283  -0.671  1.00  0.00           O  
HETATM   25  H1  UNL     1       7.566   0.981   3.296  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.088   0.035   3.342  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.209   1.530   2.282  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.412   0.101   1.420  1.00  0.00           H  
HETATM   29  H5  UNL     1       7.413  -1.279   1.937  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.761   0.842  -0.259  1.00  0.00           H  
HETATM   31  H7  UNL     1       7.438  -0.803  -0.546  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.277  -1.789   0.347  1.00  0.00           H  
HETATM   33  H9  UNL     1       5.126  -0.720  -1.136  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.480   0.108   1.732  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.318  -0.440   0.513  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.235   2.068   0.221  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.422   3.016  -0.838  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.228   1.965  -0.217  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.856   0.317  -0.320  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.139   0.536  -3.652  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.138   0.257  -0.655  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.019  -0.560  -3.078  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.130  -0.774  -0.103  1.00  0.00           H  
HETATM   44  H20 UNL     1      -4.093  -1.626  -2.408  1.00  0.00           H  
HETATM   45  H21 UNL     1      -5.519  -2.446  -0.734  1.00  0.00           H  
HETATM   46  H22 UNL     1      -4.942  -2.510   1.570  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.959  -2.497   2.260  1.00  0.00           H  
HETATM   48  H24 UNL     1      -3.792   0.296   0.996  1.00  0.00           H  
HETATM   49  H25 UNL     1      -3.968  -0.403   2.603  1.00  0.00           H  
HETATM   50  H26 UNL     1      -6.465  -0.696   2.052  1.00  0.00           H  
HETATM   51  H27 UNL     1      -5.849   1.005   2.195  1.00  0.00           H  
HETATM   52  H28 UNL     1      -6.511  -0.494  -0.476  1.00  0.00           H  
HETATM   53  H29 UNL     1      -5.794   1.108  -0.331  1.00  0.00           H  
HETATM   54  H30 UNL     1      -9.209   0.641  -1.122  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   10   11
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

HMDB0004234
     RDKit          3D
12-Keto-leukotriene B4
 54 53  0  0  0  0  0  0  0  0999 V2000
    6.7205    0.6088    2.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3184   -0.2096    1.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7616   -0.2203    0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3892   -0.7272   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    0.0626    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    1.4473    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854    1.9634   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071    1.3162   -0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    1.2255   -2.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4776    1.6652   -3.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345    0.6312   -2.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243    0.1631   -1.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892   -0.4443   -2.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4891   -0.8863   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571   -1.5014   -1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -1.9319   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2223   -1.8181    0.9796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9623   -2.3747    1.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130   -0.4858    1.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7941    0.0730    1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4101    0.3505    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7960    0.9393    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2042    1.1005    1.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5723    1.2826   -0.6714 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5662    0.9809    3.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0880    0.0349    3.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2093    1.5295    2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117    0.1009    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4126   -1.2787    1.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7609    0.8424   -0.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4375   -0.8032   -0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -1.7888    0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1263   -0.7204   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4803    0.1080    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3178   -0.4397    0.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2353    2.0685    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4220    3.0162   -0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283    1.9654   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559    0.3167   -0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389    0.5356   -3.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    0.2571   -0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193   -0.5598   -3.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1297   -0.7743   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0932   -1.6257   -2.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5193   -2.4463   -0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9418   -2.5096    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589   -2.4971    2.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7917    0.2963    0.9962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -0.4031    2.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4650   -0.6961    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8489    1.0053    2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5113   -0.4937   -0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7935    1.1082   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2093    0.6408   -1.1221 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
  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
 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  1
 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,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoic acid	ChEBI
12-Keto-LTB4	ChEBI
12-oxo-LTB4	ChEBI
12-Oxoleukotriene b4	ChEBI
5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acid	ChEBI
5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoic acid	ChEBI
5S-Hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoic acid	ChEBI
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoate	Generator
5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoate	Generator
5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoate	Generator
5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoate	Generator
5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoic acid	Generator
5S-Hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoate	Generator
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoicosa-6,8,10,14-tetraenoate	HMDB
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid	HMDB
12-Dehydro-leukotriene b4	HMDB

Chemical Formula

C₂₀H₃₀O₄

Average Molecular Weight

334.4498

Monoisotopic Molecular Weight

334.214409448

IUPAC Name

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

Traditional Name

12-oxo-LTB4

CAS Registry Number

136696-10-1

SMILES

CCCCC\C=C/CC(=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/h6-11,14-15,19,22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t19-/m1/s1

InChI Key

SJVWVCVZWMJXOK-NOJHDUNKSA-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
Keto fatty acid
Fatty acid
Unsaturated fatty acid
Alpha,beta-unsaturated ketone
Acryloyl-group
Enone
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:27814 )
polyunsaturated fatty acid (CHEBI:27814 )
oxo fatty acid (CHEBI:27814 )
hydroxy fatty acid (CHEBI:27814 )
Leukotrienes (C05949 )
Leukotrienes (LMFA03020024 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0004234)
Membrane (HMDB: HMDB0004234)

Source

Exogenous

Exogenous (HMDB: HMDB0004234)

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: HMDB0004234)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0120510)

Metabolic pathway

Arachidonic Acid Metabolism (PathBank: SMP0087315)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

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	3.884	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0077 g/L	ALOGPS
logP	4.67	ALOGPS
logP	4.54	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	102.09 m³·mol⁻¹	ChemAxon
Polarizability	38.23 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
DeepCCS	[M+H]+	193.987	30932474
DeepCCS	[M-H]-	191.629	30932474
DeepCCS	[M-2H]-	225.148	30932474
DeepCCS	[M+Na]+	200.375	30932474
AllCCS	[M+H]+	189.0	32859911
AllCCS	[M+H-H2O]+	186.1	32859911
AllCCS	[M+NH4]+	191.6	32859911
AllCCS	[M+Na]+	192.4	32859911
AllCCS	[M-H]-	187.2	32859911
AllCCS	[M+Na-2H]-	189.0	32859911
AllCCS	[M+HCOO]-	191.0	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.	6.88 minutes	32390414
Predicted by Siyang on May 30, 2022	17.5238 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.92 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2834.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	324.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	186.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	208.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	414.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	758.5 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	510.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	107.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1773.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	586.9 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	1453.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	565.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	292.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	387.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12-Keto-leukotriene B4	CCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	4647.0	Standard polar	33892256
12-Keto-leukotriene B4	CCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	2586.7	Standard non polar	33892256
12-Keto-leukotriene B4	CCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O	2924.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12-Keto-leukotriene B4,1TMS,isomer #1	CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C	3020.3	Semi standard non polar	33892256
12-Keto-leukotriene B4,1TMS,isomer #2	CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C	2935.0	Semi standard non polar	33892256
12-Keto-leukotriene B4,1TMS,isomer #3	CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C	3125.1	Semi standard non polar	33892256
12-Keto-leukotriene B4,2TMS,isomer #1	CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2979.0	Semi standard non polar	33892256
12-Keto-leukotriene B4,2TMS,isomer #2	CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3159.7	Semi standard non polar	33892256
12-Keto-leukotriene B4,2TMS,isomer #3	CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3060.8	Semi standard non polar	33892256
12-Keto-leukotriene B4,3TMS,isomer #1	CCCCC/C=C\C=C(/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	3118.4	Semi standard non polar	33892256
12-Keto-leukotriene B4,3TMS,isomer #1	CCCCC/C=C\C=C(/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	2925.1	Standard non polar	33892256
12-Keto-leukotriene B4,3TMS,isomer #1	CCCCC/C=C\C=C(/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	3023.1	Standard polar	33892256
12-Keto-leukotriene B4,1TBDMS,isomer #1	CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3256.6	Semi standard non polar	33892256
12-Keto-leukotriene B4,1TBDMS,isomer #2	CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3176.9	Semi standard non polar	33892256
12-Keto-leukotriene B4,1TBDMS,isomer #3	CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3361.7	Semi standard non polar	33892256
12-Keto-leukotriene B4,2TBDMS,isomer #1	CCCCC/C=C\CC(=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	3466.5	Semi standard non polar	33892256
12-Keto-leukotriene B4,2TBDMS,isomer #2	CCCCC/C=C\C=C(/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	3631.1	Semi standard non polar	33892256
12-Keto-leukotriene B4,2TBDMS,isomer #3	CCCCC/C=C\C=C(/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	3570.0	Semi standard non polar	33892256
12-Keto-leukotriene B4,3TBDMS,isomer #1	CCCCC/C=C\C=C(/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	3845.0	Semi standard non polar	33892256
12-Keto-leukotriene B4,3TBDMS,isomer #1	CCCCC/C=C\C=C(/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	3526.6	Standard non polar	33892256
12-Keto-leukotriene B4,3TBDMS,isomer #1	CCCCC/C=C\C=C(/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	3192.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Keto-leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-066s-8693000000-270563be8dfdc24e992a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Keto-leukotriene B4 GC-MS (2 TMS) - 70eV, Positive	splash10-03di-9144800000-4b327172349a2e771070	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Keto-leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Keto-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-Keto-leukotriene B4 10V, Positive-QTOF	splash10-014j-0159000000-e48b7199180a29e45efb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 20V, Positive-QTOF	splash10-0fr2-4492000000-f4f3d525c56b7199ffe5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 40V, Positive-QTOF	splash10-052f-9550000000-602ab114fa3ef4af9e01	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 10V, Negative-QTOF	splash10-001i-0019000000-2b71bf068687ac05eecf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 20V, Negative-QTOF	splash10-0159-2679000000-f1fac0f3be2948f287f4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 40V, Negative-QTOF	splash10-0a4l-9530000000-10303e21f4d2373a1b9d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 10V, Positive-QTOF	splash10-014j-0189000000-09dd2ea98a8fc120f55c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 20V, Positive-QTOF	splash10-00kb-3393000000-6fcc70d755077df7da3e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 40V, Positive-QTOF	splash10-0aor-9310000000-0661b8fef37b0dbab8c6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 10V, Negative-QTOF	splash10-001i-0009000000-b749c60e47a942be0e50	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 20V, Negative-QTOF	splash10-05o0-3749000000-c3ef7aedfd2291dc938a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 40V, Negative-QTOF	splash10-059l-5190000000-2e5d3124c6c577abd53b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

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

FDB023341

KNApSAcK ID

Not Available

Chemspider ID

4444399

KEGG Compound ID

C05949

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280876

PDB ID

Not Available

ChEBI ID

27814

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

Powell WS, Rokach J, Khanapure SP, Manna S, Hashefi M, Gravel S, Macleod RJ, Falck JR, Bhatt RK: Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels. J Pharmacol Exp Ther. 1996 Feb;276(2):728-36. [PubMed:8632343 ]
Primiano T, Li Y, Kensler TW, Trush MA, Sutter TR: Identification of dithiolethione-inducible gene-1 as a leukotriene B4 12-hydroxydehydrogenase: implications for chemoprevention. Carcinogenesis. 1998 Jun;19(6):999-1005. [PubMed:9667737 ]
Lipid Maps (LMFA03020024) [Link]

Showing metabocard for 12-Keto-leukotriene B4 (HMDB0004234)

MOL for HMDB0004234 (12-Keto-leukotriene B4)

3D MOL for HMDB0004234 (12-Keto-leukotriene B4)

3D SDF for HMDB0004234 (12-Keto-leukotriene B4)

3D-SDF for HMDB0004234 (12-Keto-leukotriene B4)

PDB for HMDB0004234 (12-Keto-leukotriene B4)

3D PDB for HMDB0004234 (12-Keto-leukotriene B4)

SMILES for HMDB0004234 (12-Keto-leukotriene B4)

INCHI for HMDB0004234 (12-Keto-leukotriene B4)

Structure for HMDB0004234 (12-Keto-leukotriene B4)

3D Structure for HMDB0004234 (12-Keto-leukotriene B4)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra