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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:04:30 UTC

Update Date

2022-03-07 02:51:27 UTC

HMDB ID

HMDB0012641

Secondary Accession Numbers

HMDB12641

Metabolite Identification

Common Name

20-oxo-leukotriene B4

Description

20-oxo-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human 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 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 , 2853166 , 6088485 ). 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

HMDB0012641
     RDKit          3D
20-oxo-leukotriene B4
 55 54  0  0  0  0  0  0  0  0999 V2000
    5.0544    1.2672    2.9207 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0391    1.6783    2.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2793    1.4009    0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7793   -0.0207    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0411   -0.3784   -0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8222   -0.3599   -1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822   -1.3349   -0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605   -1.0916   -0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074    0.2147   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584    0.1492   -1.5744 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2068   -0.2513   -2.8336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -0.9056   -1.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075   -0.7043   -0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.7514   -0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695   -1.4964    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4697   -2.5332    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6985   -2.2272    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1767   -0.8507    0.8427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4687    0.0885    1.5534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5778   -0.4099   -0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0421    1.0091   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2330    1.2234    0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6072    2.6702    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5961    3.0331    1.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9320    3.6131   -0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7578    2.2565    2.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1222    2.0427    0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    1.5866    0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0069   -0.7392    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7373   -0.1463    1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7727    0.3132   -1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4902   -1.3960   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2695   -0.7028   -2.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4637    0.6422   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638   -2.3906   -0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0611   -1.9496   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    0.6053    0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6894    0.9678   -1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242    1.1473   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705    0.4829   -3.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2056   -1.9183   -1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789    0.3079   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170   -2.7886   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8614   -0.4663    0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421   -3.5881    0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3371   -3.0669    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1841   -0.8662    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5810    0.0689    2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149   -0.5171   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4164   -1.1086   -0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1962    1.6477   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3587    1.2938   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1111    0.6581    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8926    1.0355    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7790    4.5562   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  6
 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  0
 18 47  1  1
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 25 55  1  0
M  END


  Mrv0541 02251208092D          

 25 24  0  0  1  0            999 V2000
    9.1385  -19.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8530  -19.4965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5675  -19.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2819  -19.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9964  -19.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7109  -19.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7109  -20.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4254  -19.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8530  -20.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1385  -20.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4241  -20.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7096  -20.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9951  -20.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2806  -20.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661  -20.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8517  -20.7340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661  -19.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8517  -19.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8517  -18.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661  -17.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5661  -17.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2806  -16.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2806  -15.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9951  -15.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9951  -14.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012641

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,17-19,22-23H,1-2,6,10-12,15-16H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1

> <INCHI_KEY>
LVLQYGYNBVIONY-PSPARDEHSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.4492

> <EXACT_MASS>
350.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.599232303081564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-20-oxoicosa-6,8,10,14-tetraenoic acid

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
2.6466906596666666

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.509166952408247

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.646344972587978

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2749364051123648

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
103.725

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-aldehyde leukotriene B4

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012641
     RDKit          3D
20-oxo-leukotriene B4
 55 54  0  0  0  0  0  0  0  0999 V2000
    5.0544    1.2672    2.9207 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0391    1.6783    2.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2793    1.4009    0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7793   -0.0207    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0411   -0.3784   -0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8222   -0.3599   -1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822   -1.3349   -0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605   -1.0916   -0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074    0.2147   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584    0.1492   -1.5744 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2068   -0.2513   -2.8336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -0.9056   -1.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075   -0.7043   -0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.7514   -0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695   -1.4964    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4697   -2.5332    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6985   -2.2272    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1767   -0.8507    0.8427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4687    0.0885    1.5534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5778   -0.4099   -0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0421    1.0091   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2330    1.2234    0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6072    2.6702    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5961    3.0331    1.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9320    3.6131   -0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7578    2.2565    2.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1222    2.0427    0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    1.5866    0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0069   -0.7392    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7373   -0.1463    1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7727    0.3132   -1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4902   -1.3960   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2695   -0.7028   -2.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4637    0.6422   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638   -2.3906   -0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0611   -1.9496   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    0.6053    0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6894    0.9678   -1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242    1.1473   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705    0.4829   -3.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2056   -1.9183   -1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789    0.3079   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170   -2.7886   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8614   -0.4663    0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421   -3.5881    0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3371   -3.0669    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1841   -0.8662    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5810    0.0689    2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149   -0.5171   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4164   -1.1086   -0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1962    1.6477   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3587    1.2938   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1111    0.6581    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8926    1.0355    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7790    4.5562   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  6
 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  0
 18 47  1  1
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 25 55  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  O   UNK     0      17.059 -35.623   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      18.392 -36.393   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.726 -35.623   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.060 -36.393   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.393 -35.623   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.727 -36.393   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      23.727 -37.933   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      25.061 -35.623   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      18.392 -37.933   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.059 -38.703   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.725 -37.933   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.391 -38.703   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.058 -37.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.724 -38.703   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.390 -37.933   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.057 -38.703   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.390 -36.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.057 -35.623   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.057 -34.083   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.390 -33.313   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.390 -31.773   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.724 -31.003   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.724 -29.463   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.058 -28.693   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.058 -27.153   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0012641
HETATM    1  O1  UNL     1       5.054   1.267   2.921  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.039   1.678   2.359  1.00  0.00           C  
HETATM    3  C2  UNL     1       6.279   1.401   0.923  1.00  0.00           C  
HETATM    4  C3  UNL     1       6.779  -0.021   0.830  1.00  0.00           C  
HETATM    5  C4  UNL     1       7.041  -0.378  -0.577  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.822  -0.360  -1.497  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.882  -1.335  -0.966  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.660  -1.092  -0.611  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.007   0.215  -0.687  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.758   0.149  -1.574  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.207  -0.251  -2.834  1.00  0.00           O  
HETATM   12  C10 UNL     1       0.828  -0.906  -1.096  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.407  -0.704  -0.728  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.314  -1.751  -0.258  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.569  -1.496   0.106  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.470  -2.533   0.573  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.698  -2.227   0.920  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.177  -0.851   0.843  1.00  0.00           C  
HETATM   19  O3  UNL     1      -4.469   0.088   1.553  1.00  0.00           O  
HETATM   20  C17 UNL     1      -5.578  -0.410  -0.549  1.00  0.00           C  
HETATM   21  C18 UNL     1      -6.042   1.009  -0.496  1.00  0.00           C  
HETATM   22  C19 UNL     1      -7.233   1.223   0.411  1.00  0.00           C  
HETATM   23  C20 UNL     1      -7.607   2.670   0.382  1.00  0.00           C  
HETATM   24  O4  UNL     1      -8.596   3.033   1.084  1.00  0.00           O  
HETATM   25  O5  UNL     1      -6.932   3.613  -0.365  1.00  0.00           O  
HETATM   26  H1  UNL     1       6.758   2.256   2.908  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.122   2.043   0.569  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.377   1.587   0.321  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.007  -0.739   1.232  1.00  0.00           H  
HETATM   30  H5  UNL     1       7.737  -0.146   1.397  1.00  0.00           H  
HETATM   31  H6  UNL     1       7.773   0.313  -1.078  1.00  0.00           H  
HETATM   32  H7  UNL     1       7.490  -1.396  -0.709  1.00  0.00           H  
HETATM   33  H8  UNL     1       6.270  -0.703  -2.493  1.00  0.00           H  
HETATM   34  H9  UNL     1       5.464   0.642  -1.679  1.00  0.00           H  
HETATM   35  H10 UNL     1       5.264  -2.391  -0.861  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.061  -1.950  -0.214  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.692   0.605   0.317  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.689   0.968  -1.097  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.324   1.147  -1.574  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.971   0.483  -3.464  1.00  0.00           H  
HETATM   41  H16 UNL     1       1.206  -1.918  -1.049  1.00  0.00           H  
HETATM   42  H17 UNL     1      -0.779   0.308  -0.777  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.017  -2.789  -0.181  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.861  -0.466   0.028  1.00  0.00           H  
HETATM   45  H20 UNL     1      -3.142  -3.588   0.644  1.00  0.00           H  
HETATM   46  H21 UNL     1      -5.337  -3.067   1.268  1.00  0.00           H  
HETATM   47  H22 UNL     1      -6.184  -0.866   1.385  1.00  0.00           H  
HETATM   48  H23 UNL     1      -4.581   0.069   2.510  1.00  0.00           H  
HETATM   49  H24 UNL     1      -4.815  -0.517  -1.311  1.00  0.00           H  
HETATM   50  H25 UNL     1      -6.416  -1.109  -0.843  1.00  0.00           H  
HETATM   51  H26 UNL     1      -5.196   1.648  -0.238  1.00  0.00           H  
HETATM   52  H27 UNL     1      -6.359   1.294  -1.537  1.00  0.00           H  
HETATM   53  H28 UNL     1      -8.111   0.658   0.108  1.00  0.00           H  
HETATM   54  H29 UNL     1      -6.893   1.036   1.455  1.00  0.00           H  
HETATM   55  H30 UNL     1      -6.779   4.556  -0.066  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8    8   35
CONECT    8    9   36
CONECT    9   10   37   38
CONECT   10   11   12   39
CONECT   11   40
CONECT   12   13   13   41
CONECT   13   14   42
CONECT   14   15   15   43
CONECT   15   16   44
CONECT   16   17   17   45
CONECT   17   18   46
CONECT   18   19   20   47
CONECT   19   48
CONECT   20   21   49   50
CONECT   21   22   51   52
CONECT   22   23   53   54
CONECT   23   24   24   25
CONECT   25   55
END

HMDB0012641
     RDKit          3D
20-oxo-leukotriene B4
 55 54  0  0  0  0  0  0  0  0999 V2000
    5.0544    1.2672    2.9207 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0391    1.6783    2.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2793    1.4009    0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7793   -0.0207    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0411   -0.3784   -0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8222   -0.3599   -1.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822   -1.3349   -0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605   -1.0916   -0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074    0.2147   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584    0.1492   -1.5744 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2068   -0.2513   -2.8336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281   -0.9056   -1.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075   -0.7043   -0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.7514   -0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695   -1.4964    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4697   -2.5332    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6985   -2.2272    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1767   -0.8507    0.8427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4687    0.0885    1.5534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5778   -0.4099   -0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0421    1.0091   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2330    1.2234    0.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6072    2.6702    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5961    3.0331    1.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9320    3.6131   -0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7578    2.2565    2.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1222    2.0427    0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    1.5866    0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0069   -0.7392    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7373   -0.1463    1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7727    0.3132   -1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4902   -1.3960   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2695   -0.7028   -2.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4637    0.6422   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638   -2.3906   -0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0611   -1.9496   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    0.6053    0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6894    0.9678   -1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242    1.1473   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705    0.4829   -3.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2056   -1.9183   -1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789    0.3079   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170   -2.7886   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8614   -0.4663    0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421   -3.5881    0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3371   -3.0669    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1841   -0.8662    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5810    0.0689    2.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149   -0.5171   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4164   -1.1086   -0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1962    1.6477   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3587    1.2938   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1111    0.6581    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8926    1.0355    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7790    4.5562   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  6
 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  0
 18 47  1  1
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 25 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
20-Aldehyde leukotriene b4	ChEBI
20-oxo-LTB4	ChEBI
20Cho-LTB4	ChEBI
Leukotriene b4-20-aldehyde	ChEBI
LTB4-20-Aldehyde	ChEBI
20-Carboxyleukotriene b4	HMDB
20-Oxoleukotriene b4	MeSH, HMDB

Chemical Formula

C₂₀H₃₀O₅

Average Molecular Weight

350.4492

Monoisotopic Molecular Weight

350.20932407

IUPAC Name

(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-20-oxoicosa-6,8,10,14-tetraenoic acid

Traditional Name

20-aldehyde leukotriene B4

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,17-19,22-23H,1-2,6,10-12,15-16H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1

InChI Key

LVLQYGYNBVIONY-PSPARDEHSA-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
Alpha-hydrogen aldehyde
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:63979 )
leukotriene (CHEBI:63979 )
dihydroxy monocarboxylic acid (CHEBI:63979 )
hydroxyaldehyde (CHEBI:63979 )
polyunsaturated fatty acid (CHEBI:63979 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0012641)
Cell membrane (HMDB: HMDB0012641)

Biofluid or Excreta

Urine (HMDB: HMDB0012641)

Cellular substructure

Extracellular (HMDB: HMDB0012641)
Membrane (HMDB: HMDB0012641)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012641)

Source

Endogenous

Endogenous (HMDB: HMDB0012641)

Animal

Animal (HMDB: HMDB0012641)

Exogenous

Food

Food (HMDB: HMDB0012641)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0012641)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0012641)

Cellular process

Cell signaling (HMDB: HMDB0012641)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0012641)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012641)

Nutrient

Nutrient (HMDB: HMDB0012641)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012641)

Emulsifier (HMDB: HMDB0012641)

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	0.026 g/L	ALOGPS
logP	3.53	ALOGPS
logP	2.65	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	103.72 m³·mol⁻¹	ChemAxon
Polarizability	39.6 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]+	192.548	31661259
DarkChem	[M-H]-	184.949	31661259
DeepCCS	[M+H]+	187.684	30932474
DeepCCS	[M-H]-	185.326	30932474
DeepCCS	[M-2H]-	219.518	30932474
DeepCCS	[M+Na]+	194.741	30932474
AllCCS	[M+H]+	189.8	32859911
AllCCS	[M+H-H2O]+	187.1	32859911
AllCCS	[M+NH4]+	192.3	32859911
AllCCS	[M+Na]+	193.0	32859911
AllCCS	[M-H]-	188.9	32859911
AllCCS	[M+Na-2H]-	190.8	32859911
AllCCS	[M+HCOO]-	192.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
20-oxo-leukotriene B4	O[C@@H](CCCC(O)=O)\C=C/C=C/C=C/[C@H](O)C\C=C/CCCCC=O	4913.2	Standard polar	33892256
20-oxo-leukotriene B4	O[C@@H](CCCC(O)=O)\C=C/C=C/C=C/[C@H](O)C\C=C/CCCCC=O	2633.4	Standard non polar	33892256
20-oxo-leukotriene B4	O[C@@H](CCCC(O)=O)\C=C/C=C/C=C/[C@H](O)C\C=C/CCCCC=O	3095.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
20-oxo-leukotriene B4,1TMS,isomer #1	C[Si](C)(C)O[C@H](/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCC=O)CCCC(=O)O	3223.5	Semi standard non polar	33892256
20-oxo-leukotriene B4,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCC[C@H](O)/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCC=O	3138.4	Semi standard non polar	33892256
20-oxo-leukotriene B4,1TMS,isomer #3	C[Si](C)(C)O[C@@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)C/C=C\CCCCC=O	3225.7	Semi standard non polar	33892256
20-oxo-leukotriene B4,1TMS,isomer #4	C[Si](C)(C)OC=CCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O	3317.9	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TMS,isomer #1	C[Si](C)(C)O[C@H](/C=C\C=C\C=C\[C@@H](C/C=C\CCCCC=O)O[Si](C)(C)C)CCCC(=O)O	3290.9	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCC[C@@H](/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCC=O)O[Si](C)(C)C	3182.3	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TMS,isomer #3	C[Si](C)(C)OC=CCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C	3351.9	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TMS,isomer #4	C[Si](C)(C)OC(=O)CCC[C@H](O)/C=C\C=C\C=C\[C@@H](C/C=C\CCCCC=O)O[Si](C)(C)C	3181.7	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TMS,isomer #5	C[Si](C)(C)OC=CCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C	3264.5	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TMS,isomer #6	C[Si](C)(C)OC=CCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C	3360.4	Semi standard non polar	33892256
20-oxo-leukotriene B4,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCC[C@@H](/C=C\C=C\C=C\[C@@H](C/C=C\CCCCC=O)O[Si](C)(C)C)O[Si](C)(C)C	3218.1	Semi standard non polar	33892256
20-oxo-leukotriene B4,3TMS,isomer #2	C[Si](C)(C)OC=CCCC/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	3363.9	Semi standard non polar	33892256
20-oxo-leukotriene B4,3TMS,isomer #3	C[Si](C)(C)OC=CCCC/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	3268.9	Semi standard non polar	33892256
20-oxo-leukotriene B4,3TMS,isomer #4	C[Si](C)(C)OC=CCCC/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	3279.8	Semi standard non polar	33892256
20-oxo-leukotriene B4,4TMS,isomer #1	C[Si](C)(C)OC=CCCC/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	3272.0	Semi standard non polar	33892256
20-oxo-leukotriene B4,4TMS,isomer #1	C[Si](C)(C)OC=CCCC/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	2998.2	Standard non polar	33892256
20-oxo-leukotriene B4,4TMS,isomer #1	C[Si](C)(C)OC=CCCC/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	3116.1	Standard polar	33892256
20-oxo-leukotriene B4,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H](/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCC=O)CCCC(=O)O	3464.6	Semi standard non polar	33892256
20-oxo-leukotriene B4,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](O)/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCC=O	3385.1	Semi standard non polar	33892256
20-oxo-leukotriene B4,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)C/C=C\CCCCC=O	3468.5	Semi standard non polar	33892256
20-oxo-leukotriene B4,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=CCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O	3557.1	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H](/C=C\C=C\C=C\[C@@H](C/C=C\CCCCC=O)O[Si](C)(C)C(C)(C)C)CCCC(=O)O	3740.2	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCC=O)O[Si](C)(C)C(C)(C)C	3661.7	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=CCCC/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	3807.9	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](O)/C=C\C=C\C=C\[C@@H](C/C=C\CCCCC=O)O[Si](C)(C)C(C)(C)C	3667.1	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC=CCCC/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	3728.0	Semi standard non polar	33892256
20-oxo-leukotriene B4,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC=CCCC/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	3816.2	Semi standard non polar	33892256
20-oxo-leukotriene B4,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](/C=C\C=C\C=C\[C@@H](C/C=C\CCCCC=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3952.4	Semi standard non polar	33892256
20-oxo-leukotriene B4,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CCCC/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	4063.7	Semi standard non polar	33892256
20-oxo-leukotriene B4,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=CCCC/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	3989.7	Semi standard non polar	33892256
20-oxo-leukotriene B4,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=CCCC/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	4002.3	Semi standard non polar	33892256
20-oxo-leukotriene B4,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCCC/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	4231.9	Semi standard non polar	33892256
20-oxo-leukotriene B4,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCCC/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	3696.0	Standard non polar	33892256
20-oxo-leukotriene B4,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCCC/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	3316.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 20-oxo-leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-4988000000-53e597a21bd896c4a805	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-oxo-leukotriene B4 GC-MS (3 TMS) - 70eV, Positive	splash10-0fb9-5211930000-66a5c8ed75ca098169de	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-oxo-leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-oxo-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 - 20-oxo-leukotriene B4 10V, Positive-QTOF	splash10-00lr-0009000000-71f71f823ff27878d9ec	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 20V, Positive-QTOF	splash10-0159-2469000000-ac965d5f539e60c86898	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 40V, Positive-QTOF	splash10-00g3-8691000000-01e84f4ad6ae6758b338	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 10V, Negative-QTOF	splash10-000t-0009000000-30512f86878821f6b67c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 20V, Negative-QTOF	splash10-001j-2129000000-e45a1d18efbcfb315252	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 40V, Negative-QTOF	splash10-0006-9110000000-83c7268674cfd841cd05	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 10V, Negative-QTOF	splash10-000t-0009000000-42a0d7ed5251c08a184c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 20V, Negative-QTOF	splash10-053r-4159000000-4e55e4ea9073cc0db8d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 40V, Negative-QTOF	splash10-0a4l-9581000000-5c4231804493ffb591d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 10V, Positive-QTOF	splash10-0159-0039000000-4c6247753babc5559eba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 20V, Positive-QTOF	splash10-0api-2196000000-ec888b6cefe1abcbfc83	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-oxo-leukotriene B4 40V, Positive-QTOF	splash10-00g0-6490000000-52483e12abc7de057f68	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	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

FDB029163

KNApSAcK ID

Not Available

Chemspider ID

4952515

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6449839

PDB ID

Not Available

ChEBI ID

63979

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 ]
Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]
Mita H, Yui Y, Yasueda H, Shida T: Isocratic determination of arachidonic acid 5-lipoxygenase products in human neutrophils by high-performance liquid chromatography. J Chromatogr. 1988 Sep 9;430(2):299-308. [PubMed:2853166 ]
Shak S, Goldstein IM: Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. J Biol Chem. 1984 Aug 25;259(16):10181-7. [PubMed:6088485 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 20-oxo-leukotriene B4 (HMDB0012641)

MOL for HMDB0012641 (20-oxo-leukotriene B4)

3D MOL for HMDB0012641 (20-oxo-leukotriene B4)

3D SDF for HMDB0012641 (20-oxo-leukotriene B4)

3D-SDF for HMDB0012641 (20-oxo-leukotriene B4)

PDB for HMDB0012641 (20-oxo-leukotriene B4)

3D PDB for HMDB0012641 (20-oxo-leukotriene B4)

SMILES for HMDB0012641 (20-oxo-leukotriene B4)

INCHI for HMDB0012641 (20-oxo-leukotriene B4)

Structure for HMDB0012641 (20-oxo-leukotriene B4)

3D Structure for HMDB0012641 (20-oxo-leukotriene B4)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra