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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:02:44 UTC

Update Date

2022-03-07 02:51:26 UTC

HMDB ID

HMDB0012550

Secondary Accession Numbers

HMDB12550

Metabolite Identification

Common Name

12-Oxo-20-carboxy-leukotriene B4

Description

12-oxo-20-carboxy-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


  Mrv0541 02251208062D          

 26 25  0  0  1  0            999 V2000
   16.6612  -18.2876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0737  -19.0021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8987  -19.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3112  -19.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1362  -19.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5487  -20.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1362  -21.1456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3737  -20.4311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6612  -19.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8362  -19.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4237  -19.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5987  -19.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1862  -18.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3612  -18.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9487  -17.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3612  -16.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1237  -17.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7112  -18.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8862  -18.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4737  -17.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6487  -17.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2362  -16.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4112  -16.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9987  -16.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4112  -15.4298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1737  -16.1443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  2  0  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  1  0  0  0  0
 24 26  2  0  0  0  0
M  END

HMDB0012550
     RDKit          3D
12-Oxo-20-carboxy-leukotriene B4
 54 53  0  0  0  0  0  0  0  0999 V2000
   10.3188    0.9890   -1.4442 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1541    1.0619   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1464    1.4271   -1.8594 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9330    0.7643    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5165    0.7785    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6415   -0.2288    0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2331   -0.1348    0.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6275    1.1815    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5239    1.3740   -0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7278    0.3250   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622    0.2809   -0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434    1.0713    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3946   -0.6732   -0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311   -0.7527   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205   -1.7033   -0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378   -1.6935   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -2.6394   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2172   -2.6892   -0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6006   -1.7615    0.9174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6815   -2.2631    1.6594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1858   -0.5058    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6035    0.4942    1.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1651    1.7461    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3633    1.5182   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4198    0.7354   -1.1025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5411    2.2153    0.1672 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0925    2.3997   -2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3957   -0.2177    0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4776    1.5269    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0636    1.7817    0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5203    0.4508    1.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0361   -1.2517    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5829   -0.0582   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695   -0.9303    0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3412   -0.3377    1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    2.0996    0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1419    2.4184   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1911   -0.6510   -0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5772    0.6507   -1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802   -1.3495   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0657   -0.0494    0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6209   -2.4156   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2040   -0.9649    0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7606   -3.3256   -1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9682   -3.4217   -0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -1.4773    1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5264   -3.1774    1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0514   -0.8655   -0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4433   -0.1073   -0.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6973    0.7305    1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3301    0.0006    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3702    2.2605    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4127    2.4601    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6197    2.9043    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  1
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 26 54  1  0
M  END


  Mrv0541 02251208062D          

 26 25  0  0  1  0            999 V2000
   16.6612  -18.2876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0737  -19.0021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8987  -19.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3112  -19.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1362  -19.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5487  -20.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1362  -21.1456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3737  -20.4311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6612  -19.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8362  -19.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4237  -19.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5987  -19.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1862  -18.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3612  -18.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9487  -17.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3612  -16.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1237  -17.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7112  -18.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8862  -18.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4737  -17.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6487  -17.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2362  -16.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4112  -16.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9987  -16.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4112  -15.4298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1737  -16.1443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  2  0  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  1  0  0  0  0
 24 26  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012550

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,18,22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t18-/m0/s1

> <INCHI_KEY>
VLMCDTMNMDDMLC-NZXMSVEXSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.4327

> <EXACT_MASS>
364.188588628

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
39.68127231480402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.2166454

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.901835489476183

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.294435224190563

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5452464844125013

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
103.753

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012550
     RDKit          3D
12-Oxo-20-carboxy-leukotriene B4
 54 53  0  0  0  0  0  0  0  0999 V2000
   10.3188    0.9890   -1.4442 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1541    1.0619   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1464    1.4271   -1.8594 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9330    0.7643    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5165    0.7785    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6415   -0.2288    0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2331   -0.1348    0.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6275    1.1815    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5239    1.3740   -0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7278    0.3250   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622    0.2809   -0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434    1.0713    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3946   -0.6732   -0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311   -0.7527   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205   -1.7033   -0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378   -1.6935   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -2.6394   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2172   -2.6892   -0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6006   -1.7615    0.9174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6815   -2.2631    1.6594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1858   -0.5058    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6035    0.4942    1.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1651    1.7461    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3633    1.5182   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4198    0.7354   -1.1025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5411    2.2153    0.1672 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0925    2.3997   -2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3957   -0.2177    0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4776    1.5269    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0636    1.7817    0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5203    0.4508    1.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0361   -1.2517    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5829   -0.0582   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695   -0.9303    0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3412   -0.3377    1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    2.0996    0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1419    2.4184   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1911   -0.6510   -0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5772    0.6507   -1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802   -1.3495   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0657   -0.0494    0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6209   -2.4156   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2040   -0.9649    0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7606   -3.3256   -1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9682   -3.4217   -0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -1.4773    1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5264   -3.1774    1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0514   -0.8655   -0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4433   -0.1073   -0.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6973    0.7305    1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3301    0.0006    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3702    2.2605    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4127    2.4601    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6197    2.9043    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  1
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 26 54  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      31.101 -34.137   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      31.871 -35.471   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.411 -35.471   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.181 -36.804   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      35.721 -36.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      36.491 -38.138   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      35.721 -39.472   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      38.031 -38.138   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      31.101 -36.804   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.561 -36.804   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.791 -35.471   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.251 -35.471   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.481 -34.137   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.941 -34.137   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.171 -32.803   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      24.941 -31.470   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      22.631 -32.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.861 -34.137   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.321 -34.137   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.551 -32.803   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.011 -32.803   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.241 -31.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.701 -31.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.931 -30.136   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      15.701 -28.802   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.391 -30.136   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   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0012550
HETATM    1  O1  UNL     1      10.319   0.989  -1.444  1.00  0.00           O  
HETATM    2  C1  UNL     1       9.154   1.062  -0.981  1.00  0.00           C  
HETATM    3  O2  UNL     1       8.146   1.427  -1.859  1.00  0.00           O  
HETATM    4  C2  UNL     1       8.933   0.764   0.428  1.00  0.00           C  
HETATM    5  C3  UNL     1       7.516   0.778   0.883  1.00  0.00           C  
HETATM    6  C4  UNL     1       6.641  -0.229   0.169  1.00  0.00           C  
HETATM    7  C5  UNL     1       5.233  -0.135   0.716  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.628   1.181   0.526  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.524   1.374  -0.162  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.728   0.325  -0.842  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.362   0.281  -0.271  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.043   1.071   0.639  1.00  0.00           O  
HETATM   13  C10 UNL     1       0.395  -0.673  -0.762  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.831  -0.753  -0.284  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.820  -1.703  -0.761  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.038  -1.694  -0.197  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.013  -2.639  -0.674  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.217  -2.689  -0.168  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.601  -1.762   0.917  1.00  0.00           C  
HETATM   20  O4  UNL     1      -6.682  -2.263   1.659  1.00  0.00           O  
HETATM   21  C17 UNL     1      -6.186  -0.506   0.226  1.00  0.00           C  
HETATM   22  C18 UNL     1      -6.603   0.494   1.247  1.00  0.00           C  
HETATM   23  C19 UNL     1      -7.165   1.746   0.679  1.00  0.00           C  
HETATM   24  C20 UNL     1      -8.363   1.518  -0.138  1.00  0.00           C  
HETATM   25  O5  UNL     1      -8.420   0.735  -1.102  1.00  0.00           O  
HETATM   26  O6  UNL     1      -9.541   2.215   0.167  1.00  0.00           O  
HETATM   27  H1  UNL     1       8.093   2.400  -2.185  1.00  0.00           H  
HETATM   28  H2  UNL     1       9.396  -0.218   0.680  1.00  0.00           H  
HETATM   29  H3  UNL     1       9.478   1.527   1.035  1.00  0.00           H  
HETATM   30  H4  UNL     1       7.064   1.782   0.757  1.00  0.00           H  
HETATM   31  H5  UNL     1       7.520   0.451   1.964  1.00  0.00           H  
HETATM   32  H6  UNL     1       7.036  -1.252   0.334  1.00  0.00           H  
HETATM   33  H7  UNL     1       6.583  -0.058  -0.916  1.00  0.00           H  
HETATM   34  H8  UNL     1       4.570  -0.930   0.378  1.00  0.00           H  
HETATM   35  H9  UNL     1       5.341  -0.338   1.838  1.00  0.00           H  
HETATM   36  H10 UNL     1       5.071   2.100   0.958  1.00  0.00           H  
HETATM   37  H11 UNL     1       3.142   2.418  -0.247  1.00  0.00           H  
HETATM   38  H12 UNL     1       3.191  -0.651  -0.888  1.00  0.00           H  
HETATM   39  H13 UNL     1       2.577   0.651  -1.912  1.00  0.00           H  
HETATM   40  H14 UNL     1       0.680  -1.349  -1.550  1.00  0.00           H  
HETATM   41  H15 UNL     1      -1.066  -0.049   0.507  1.00  0.00           H  
HETATM   42  H16 UNL     1      -1.621  -2.416  -1.542  1.00  0.00           H  
HETATM   43  H17 UNL     1      -3.204  -0.965   0.579  1.00  0.00           H  
HETATM   44  H18 UNL     1      -3.761  -3.326  -1.457  1.00  0.00           H  
HETATM   45  H19 UNL     1      -5.968  -3.422  -0.538  1.00  0.00           H  
HETATM   46  H20 UNL     1      -4.813  -1.477   1.604  1.00  0.00           H  
HETATM   47  H21 UNL     1      -6.526  -3.177   1.959  1.00  0.00           H  
HETATM   48  H22 UNL     1      -7.051  -0.865  -0.381  1.00  0.00           H  
HETATM   49  H23 UNL     1      -5.443  -0.107  -0.490  1.00  0.00           H  
HETATM   50  H24 UNL     1      -5.697   0.730   1.867  1.00  0.00           H  
HETATM   51  H25 UNL     1      -7.330   0.001   1.932  1.00  0.00           H  
HETATM   52  H26 UNL     1      -6.370   2.261   0.055  1.00  0.00           H  
HETATM   53  H27 UNL     1      -7.413   2.460   1.508  1.00  0.00           H  
HETATM   54  H28 UNL     1      -9.620   2.904   0.884  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9    9   36
CONECT    9   10   37
CONECT   10   11   38   39
CONECT   11   12   12   13
CONECT   13   14   14   40
CONECT   14   15   41
CONECT   15   16   16   42
CONECT   16   17   43
CONECT   17   18   18   44
CONECT   18   19   45
CONECT   19   20   21   46
CONECT   20   47
CONECT   21   22   48   49
CONECT   22   23   50   51
CONECT   23   24   52   53
CONECT   24   25   25   26
CONECT   26   54
END

HMDB0012550
     RDKit          3D
12-Oxo-20-carboxy-leukotriene B4
 54 53  0  0  0  0  0  0  0  0999 V2000
   10.3188    0.9890   -1.4442 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1541    1.0619   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1464    1.4271   -1.8594 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9330    0.7643    0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5165    0.7785    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6415   -0.2288    0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2331   -0.1348    0.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6275    1.1815    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5239    1.3740   -0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7278    0.3250   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622    0.2809   -0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434    1.0713    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3946   -0.6732   -0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311   -0.7527   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205   -1.7033   -0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378   -1.6935   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -2.6394   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2172   -2.6892   -0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6006   -1.7615    0.9174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6815   -2.2631    1.6594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1858   -0.5058    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6035    0.4942    1.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1651    1.7461    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3633    1.5182   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4198    0.7354   -1.1025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5411    2.2153    0.1672 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0925    2.3997   -2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3957   -0.2177    0.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4776    1.5269    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0636    1.7817    0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5203    0.4508    1.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0361   -1.2517    0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5829   -0.0582   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695   -0.9303    0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3412   -0.3377    1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714    2.0996    0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1419    2.4184   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1911   -0.6510   -0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5772    0.6507   -1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802   -1.3495   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0657   -0.0494    0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6209   -2.4156   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2040   -0.9649    0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7606   -3.3256   -1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9682   -3.4217   -0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -1.4773    1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5264   -3.1774    1.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0514   -0.8655   -0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4433   -0.1073   -0.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6973    0.7305    1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3301    0.0006    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3702    2.2605    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4127    2.4601    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6197    2.9043    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  1
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 26 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6Z,8E,10E,14Z)-(5S,12R)-12-oxo-5-Hydroxyeicosa-6,8,10,14-tetraen-1,20-dioate	HMDB
(6Z,8E,10E,14Z)-(5S,12R)-12-oxo-5-Hydroxyeicosa-6,8,10,14-tetraen-1,20-dioic acid	HMDB
12-oxo-20-Carboxy-LTB(,4)	HMDB
12-oxo-20-COOH-Leukotriene b(,4)	HMDB
12-oxo-20-COOH-LTB(,4)	HMDB

Chemical Formula

C₂₀H₂₈O₆

Average Molecular Weight

364.4327

Monoisotopic Molecular Weight

364.188588628

IUPAC Name

(5R,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenedioic acid

Traditional Name

(5R,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H28O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,18,22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t18-/m0/s1

InChI Key

VLMCDTMNMDDMLC-NZXMSVEXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Keto fatty acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0012550)

Cellular substructure

Extracellular (HMDB: HMDB0012550)
Membrane (HMDB: HMDB0012550)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012550)

Source

Endogenous

Endogenous (HMDB: HMDB0012550)

Animal

Animal (HMDB: HMDB0012550)

Exogenous

Food

Food (HMDB: HMDB0012550)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0012550)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0012550)

Cellular process

Cell signaling (HMDB: HMDB0012550)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0012550)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012550)

Nutrient

Nutrient (HMDB: HMDB0012550)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012550)

Emulsifier (HMDB: HMDB0012550)

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	0.024 g/L	ALOGPS
logP	3.2	ALOGPS
logP	3.22	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	103.75 m³·mol⁻¹	ChemAxon
Polarizability	39.68 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]+	192.247	30932474
DeepCCS	[M-H]-	189.889	30932474
DeepCCS	[M-2H]-	223.701	30932474
DeepCCS	[M+Na]+	198.928	30932474
AllCCS	[M+H]+	191.2	32859911
AllCCS	[M+H-H2O]+	188.6	32859911
AllCCS	[M+NH4]+	193.7	32859911
AllCCS	[M+Na]+	194.4	32859911
AllCCS	[M-H]-	190.7	32859911
AllCCS	[M+Na-2H]-	192.4	32859911
AllCCS	[M+HCOO]-	194.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12-Oxo-20-carboxy-leukotriene B4	O[C@H](CCCC(O)=O)\C=C/C=C/C=C/C(=O)C\C=C/CCCCC(O)=O	5278.3	Standard polar	33892256
12-Oxo-20-carboxy-leukotriene B4	O[C@H](CCCC(O)=O)\C=C/C=C/C=C/C(=O)C\C=C/CCCCC(O)=O	2650.9	Standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4	O[C@H](CCCC(O)=O)\C=C/C=C/C=C/C(=O)C\C=C/CCCCC(O)=O	3332.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12-Oxo-20-carboxy-leukotriene B4,1TMS,isomer #1	C[Si](C)(C)O[C@@H](/C=C\C=C\C=C\C(=O)C/C=C\CCCCC(=O)O)CCCC(=O)O	3394.5	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\C=C\C(=O)C/C=C\CCCCC(=O)O	3337.3	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,1TMS,isomer #3	C[Si](C)(C)OC(=O)CCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](O)CCCC(=O)O	3345.6	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,1TMS,isomer #4	C[Si](C)(C)OC(/C=C/C=C/C=C\[C@H](O)CCCC(=O)O)=C/C=C\CCCCC(=O)O	3542.4	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C	3383.7	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\C=C\C(=O)C/C=C\CCCCC(=O)O)O[Si](C)(C)C	3383.3	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TMS,isomer #3	C[Si](C)(C)OC(/C=C/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C)=C/C=C\CCCCC(=O)O	3570.4	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TMS,isomer #4	C[Si](C)(C)OC(=O)CCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C	3305.7	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TMS,isomer #5	C[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\C=C\C(=C/C=C\CCCCC(=O)O)O[Si](C)(C)C	3479.7	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TMS,isomer #6	C[Si](C)(C)OC(=O)CCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C	3491.7	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3328.8	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,3TMS,isomer #2	C[Si](C)(C)OC(=O)CCCC/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	3502.2	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,3TMS,isomer #3	C[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\C=C\C(=C/C=C\CCCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3503.2	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,3TMS,isomer #4	C[Si](C)(C)OC(=O)CCCC/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	3443.1	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC/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	3465.6	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC/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	3138.6	Standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC/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	3382.2	Standard polar	33892256
12-Oxo-20-carboxy-leukotriene B4,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H](/C=C\C=C\C=C\C(=O)C/C=C\CCCCC(=O)O)CCCC(=O)O	3645.4	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\C=C\C(=O)C/C=C\CCCCC(=O)O	3594.5	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](O)CCCC(=O)O	3604.4	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(/C=C/C=C/C=C\[C@H](O)CCCC(=O)O)=C/C=C\CCCCC(=O)O	3777.0	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3877.0	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\C=C\C(=O)C/C=C\CCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3876.6	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(/C=C/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)=C/C=C\CCCCC(=O)O	4056.3	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3817.4	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\C=C\C(=C/C=C\CCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3998.7	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	4009.1	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC/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	4099.7	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCC/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	4284.1	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\C=C\C(=C/C=C\CCCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4282.7	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCCC/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	4233.4	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC/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	4483.7	Semi standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC/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	3863.8	Standard non polar	33892256
12-Oxo-20-carboxy-leukotriene B4,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC/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	3551.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-2396000000-049d0ed2532a83603e8d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 GC-MS (3 TMS) - 70eV, Positive	splash10-014l-8010790000-265a8699f23e33d936ff	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Oxo-20-carboxy-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-Oxo-20-carboxy-leukotriene B4 10V, Positive-QTOF	splash10-002b-0009000000-c9b641335e028ab02f65	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 20V, Positive-QTOF	splash10-0zia-1259000000-c5f79e5a59adbe1b2ddb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 40V, Positive-QTOF	splash10-0pbm-4592000000-d6ffb3a9622ddd0ffdfe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 10V, Negative-QTOF	splash10-03dj-0009000000-ba6ca094d637d1032cc8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 20V, Negative-QTOF	splash10-0fr2-1229000000-539e5a486759c7051393	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 40V, Negative-QTOF	splash10-0a4i-9342000000-82415e2908492354304f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 10V, Positive-QTOF	splash10-002b-0029000000-eec0a904af5a35cc0da1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 20V, Positive-QTOF	splash10-056s-1295000000-9841c3f62a5e34a031ff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 40V, Positive-QTOF	splash10-05ce-9780000000-7eae0c377d53fefffc5d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 10V, Negative-QTOF	splash10-03dj-0009000000-90e6198f422e904c0f08	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 20V, Negative-QTOF	splash10-052b-4139000000-272cc775df127d6b6a7d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Oxo-20-carboxy-leukotriene B4 40V, Negative-QTOF	splash10-05tf-9861000000-58adbbe7a8b76a28a9d0	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029117

KNApSAcK ID

Not Available

Chemspider ID

30776624

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481457

PDB ID

Not Available

ChEBI ID

Not Available

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)

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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 ]
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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 12-Oxo-20-carboxy-leukotriene B4 (HMDB0012550)

MOL for HMDB0012550 (12-Oxo-20-carboxy-leukotriene B4)

3D MOL for HMDB0012550 (12-Oxo-20-carboxy-leukotriene B4)

3D SDF for HMDB0012550 (12-Oxo-20-carboxy-leukotriene B4)

3D-SDF for HMDB0012550 (12-Oxo-20-carboxy-leukotriene B4)

PDB for HMDB0012550 (12-Oxo-20-carboxy-leukotriene B4)

3D PDB for HMDB0012550 (12-Oxo-20-carboxy-leukotriene B4)

SMILES for HMDB0012550 (12-Oxo-20-carboxy-leukotriene B4)

INCHI for HMDB0012550 (12-Oxo-20-carboxy-leukotriene B4)

Structure for HMDB0012550 (12-Oxo-20-carboxy-leukotriene B4)

3D Structure for HMDB0012550 (12-Oxo-20-carboxy-leukotriene B4)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra