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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:04:22 UTC

Update Date

2022-03-07 02:51:27 UTC

HMDB ID

HMDB0012633

Secondary Accession Numbers

HMDB12633

Metabolite Identification

Common Name

20-COOH-10,11-dihydro-LTB4

Description

20-COOH-10,11-dihydro-LTB4 is formed when leukotriene B4 (LTB4) is metabolized by beta-oxidation. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 8632343 , 9667737 ). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02251208092D          

 26 25  0  0  1  0            999 V2000
    9.6093  -14.2413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0218  -13.5268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8468  -13.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2593  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0843  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4968  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343  -11.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218  -10.6689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4968  -10.6689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -9.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -8.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218   -7.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -7.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4968   -7.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6093  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843  -11.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718  -10.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -9.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -8.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6093   -8.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718   -7.8110    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 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  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

HMDB0012633
     RDKit          3D
20-COOH-10,11-dihydro-LTB4
 58 57  0  0  0  0  0  0  0  0999 V2000
    6.7763   -1.2023   -2.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0336   -2.2936   -1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3724   -2.6440   -1.2952 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0161   -3.2242   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -2.6773   -1.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5228   -1.4448   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597   -0.7785   -0.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993    0.3710    0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973    1.5914    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7055    2.0426   -1.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992    2.7052   -0.9823 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3460    3.7230   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3652    1.5876   -0.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0761    2.0534   -0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271    2.8707    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0191    2.6096    1.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567    2.3338    2.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851    1.2684    2.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326    0.4548    1.2694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1138    1.3296    0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7543   -0.6146    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6653   -1.4199    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7727   -2.4666    0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0754   -1.8194    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2206   -0.5835   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2664   -2.5608    0.1585 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1009   -2.3077   -1.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2601   -3.3217    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1207   -4.2142   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524   -2.4374   -2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578   -3.4902   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3379   -0.7544   -0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -1.7707    0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -0.6176   -1.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580   -1.5416    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    0.2057    1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0450    2.4014    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    2.8327   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022    1.2746   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0795    3.1220   -2.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200    4.3148   -0.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3955    0.9093   -1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541    0.9570    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    1.1631   -0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2699    2.6656   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.8305    0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962    3.4817    2.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885    2.9034    3.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3363    1.0556    3.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187   -0.0518    1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9976    0.9281   -0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7124   -0.1041    1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5259   -1.2951    2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6723   -1.9102   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8329   -0.7886   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6515   -3.0626   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6263   -3.1115    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7648   -2.4777    1.0408 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  1  0
 11 13  1  0
 13 14  1  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
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  6
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 26 58  1  0
M  END


  Mrv0541 02251208092D          

 26 25  0  0  1  0            999 V2000
    9.6093  -14.2413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0218  -13.5268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8468  -13.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2593  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0843  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4968  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343  -11.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218  -10.6689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4968  -10.6689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -9.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -8.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3218   -7.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7343   -7.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4968   -7.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6093  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843  -12.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718  -12.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843  -11.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718  -10.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -9.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -8.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6093   -8.5255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3718   -7.8110    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 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  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>
HMDB0012633

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O6/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/h2,4-6,8,13,17-18,21-22H,1,3,7,9-12,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,13-8-/t17-,18-/m0/s1

> <INCHI_KEY>
BCZGHMCTSJAJRR-NSBXBVANSA-N

> <FORMULA>
C20H32O6

> <MOLECULAR_WEIGHT>
368.4645

> <EXACT_MASS>
368.219888756

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
41.85245400766139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic acid

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.0113211086666665

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.8699831562007905

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.267376576220767

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0842016937541343

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
103.6878

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012633
     RDKit          3D
20-COOH-10,11-dihydro-LTB4
 58 57  0  0  0  0  0  0  0  0999 V2000
    6.7763   -1.2023   -2.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0336   -2.2936   -1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3724   -2.6440   -1.2952 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0161   -3.2242   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -2.6773   -1.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5228   -1.4448   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597   -0.7785   -0.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993    0.3710    0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973    1.5914    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7055    2.0426   -1.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992    2.7052   -0.9823 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3460    3.7230   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3652    1.5876   -0.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0761    2.0534   -0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271    2.8707    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0191    2.6096    1.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567    2.3338    2.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851    1.2684    2.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326    0.4548    1.2694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1138    1.3296    0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7543   -0.6146    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6653   -1.4199    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7727   -2.4666    0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0754   -1.8194    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2206   -0.5835   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2664   -2.5608    0.1585 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1009   -2.3077   -1.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2601   -3.3217    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1207   -4.2142   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524   -2.4374   -2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578   -3.4902   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3379   -0.7544   -0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -1.7707    0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -0.6176   -1.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580   -1.5416    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    0.2057    1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0450    2.4014    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    2.8327   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022    1.2746   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0795    3.1220   -2.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200    4.3148   -0.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3955    0.9093   -1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541    0.9570    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    1.1631   -0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2699    2.6656   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.8305    0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962    3.4817    2.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885    2.9034    3.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3363    1.0556    3.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187   -0.0518    1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9976    0.9281   -0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7124   -0.1041    1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5259   -1.2951    2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6723   -1.9102   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8329   -0.7886   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6515   -3.0626   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6263   -3.1115    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7648   -2.4777    1.0408 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  1  0
 11 13  1  0
 13 14  1  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
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  6
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 26 58  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      17.937 -26.584   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      18.707 -25.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.247 -25.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.017 -23.916   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.557 -23.916   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.327 -22.583   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.867 -22.583   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.637 -21.249   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.867 -19.915   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      23.327 -19.915   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      25.637 -18.582   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.867 -17.248   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.637 -15.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.867 -14.581   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      25.637 -13.247   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      23.327 -14.581   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      17.937 -23.916   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.397 -23.916   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.627 -22.583   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.397 -21.249   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.627 -19.915   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.397 -18.582   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.627 -17.248   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.397 -15.914   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      17.937 -15.914   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      15.627 -14.581   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    2   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    HMDB0012633
HETATM    1  O1  UNL     1       6.776  -1.202  -2.041  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.034  -2.294  -1.451  1.00  0.00           C  
HETATM    3  O2  UNL     1       8.372  -2.644  -1.295  1.00  0.00           O  
HETATM    4  C2  UNL     1       6.016  -3.224  -0.915  1.00  0.00           C  
HETATM    5  C3  UNL     1       4.608  -2.677  -1.018  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.523  -1.445  -0.182  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.160  -0.779  -0.214  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.199   0.371   0.685  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.997   1.591   0.283  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.705   2.043  -1.089  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.299   2.705  -0.982  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.346   3.723  -0.059  1.00  0.00           O  
HETATM   13  C10 UNL     1       0.365   1.588  -0.747  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.076   2.053  -0.612  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.227   2.871   0.582  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.019   2.610   1.551  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.857   2.334   2.575  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.685   1.268   2.500  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.633   0.455   1.269  1.00  0.00           C  
HETATM   20  O4  UNL     1      -4.114   1.330   0.256  1.00  0.00           O  
HETATM   21  C17 UNL     1      -4.754  -0.615   1.332  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.665  -1.420   0.073  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.773  -2.467   0.064  1.00  0.00           C  
HETATM   24  C20 UNL     1      -7.075  -1.819   0.047  1.00  0.00           C  
HETATM   25  O5  UNL     1      -7.221  -0.583  -0.068  1.00  0.00           O  
HETATM   26  O6  UNL     1      -8.266  -2.561   0.159  1.00  0.00           O  
HETATM   27  H1  UNL     1       9.101  -2.308  -1.900  1.00  0.00           H  
HETATM   28  H2  UNL     1       6.260  -3.322   0.182  1.00  0.00           H  
HETATM   29  H3  UNL     1       6.121  -4.214  -1.428  1.00  0.00           H  
HETATM   30  H4  UNL     1       4.352  -2.437  -2.065  1.00  0.00           H  
HETATM   31  H5  UNL     1       3.958  -3.490  -0.587  1.00  0.00           H  
HETATM   32  H6  UNL     1       5.338  -0.754  -0.357  1.00  0.00           H  
HETATM   33  H7  UNL     1       4.640  -1.771   0.898  1.00  0.00           H  
HETATM   34  H8  UNL     1       2.766  -0.618  -1.212  1.00  0.00           H  
HETATM   35  H9  UNL     1       2.458  -1.542   0.249  1.00  0.00           H  
HETATM   36  H10 UNL     1       3.418   0.206   1.761  1.00  0.00           H  
HETATM   37  H11 UNL     1       3.045   2.401   1.037  1.00  0.00           H  
HETATM   38  H12 UNL     1       3.442   2.833  -1.377  1.00  0.00           H  
HETATM   39  H13 UNL     1       2.602   1.275  -1.844  1.00  0.00           H  
HETATM   40  H14 UNL     1       1.080   3.122  -2.019  1.00  0.00           H  
HETATM   41  H15 UNL     1       2.120   4.315  -0.251  1.00  0.00           H  
HETATM   42  H16 UNL     1       0.396   0.909  -1.607  1.00  0.00           H  
HETATM   43  H17 UNL     1       0.654   0.957   0.136  1.00  0.00           H  
HETATM   44  H18 UNL     1      -1.678   1.163  -0.729  1.00  0.00           H  
HETATM   45  H19 UNL     1      -1.270   2.666  -1.534  1.00  0.00           H  
HETATM   46  H20 UNL     1      -0.715   3.831   0.650  1.00  0.00           H  
HETATM   47  H21 UNL     1      -1.296   3.482   2.340  1.00  0.00           H  
HETATM   48  H22 UNL     1      -2.989   2.903   3.532  1.00  0.00           H  
HETATM   49  H23 UNL     1      -4.336   1.056   3.319  1.00  0.00           H  
HETATM   50  H24 UNL     1      -2.719  -0.052   1.045  1.00  0.00           H  
HETATM   51  H25 UNL     1      -3.998   0.928  -0.627  1.00  0.00           H  
HETATM   52  H26 UNL     1      -5.712  -0.104   1.453  1.00  0.00           H  
HETATM   53  H27 UNL     1      -4.526  -1.295   2.189  1.00  0.00           H  
HETATM   54  H28 UNL     1      -3.672  -1.910  -0.018  1.00  0.00           H  
HETATM   55  H29 UNL     1      -4.833  -0.789  -0.847  1.00  0.00           H  
HETATM   56  H30 UNL     1      -5.652  -3.063  -0.888  1.00  0.00           H  
HETATM   57  H31 UNL     1      -5.626  -3.111   0.950  1.00  0.00           H  
HETATM   58  H32 UNL     1      -8.765  -2.478   1.041  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   13   40
CONECT   12   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16   16   46
CONECT   16   17   47
CONECT   17   18   18   48
CONECT   18   19   49
CONECT   19   20   21   50
CONECT   20   51
CONECT   21   22   52   53
CONECT   22   23   54   55
CONECT   23   24   56   57
CONECT   24   25   25   26
CONECT   26   58
END

HMDB0012633
     RDKit          3D
20-COOH-10,11-dihydro-LTB4
 58 57  0  0  0  0  0  0  0  0999 V2000
    6.7763   -1.2023   -2.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0336   -2.2936   -1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3724   -2.6440   -1.2952 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0161   -3.2242   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -2.6773   -1.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5228   -1.4448   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597   -0.7785   -0.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993    0.3710    0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973    1.5914    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7055    2.0426   -1.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992    2.7052   -0.9823 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3460    3.7230   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3652    1.5876   -0.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0761    2.0534   -0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271    2.8707    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0191    2.6096    1.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567    2.3338    2.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851    1.2684    2.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6326    0.4548    1.2694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1138    1.3296    0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7543   -0.6146    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6653   -1.4199    0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7727   -2.4666    0.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0754   -1.8194    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2206   -0.5835   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2664   -2.5608    0.1585 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1009   -2.3077   -1.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2601   -3.3217    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1207   -4.2142   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524   -2.4374   -2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9578   -3.4902   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3379   -0.7544   -0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -1.7707    0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -0.6176   -1.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580   -1.5416    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    0.2057    1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0450    2.4014    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    2.8327   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022    1.2746   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0795    3.1220   -2.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200    4.3148   -0.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3955    0.9093   -1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541    0.9570    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    1.1631   -0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2699    2.6656   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.8305    0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962    3.4817    2.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885    2.9034    3.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3363    1.0556    3.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7187   -0.0518    1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9976    0.9281   -0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7124   -0.1041    1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5259   -1.2951    2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6723   -1.9102   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8329   -0.7886   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6515   -3.0626   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6263   -3.1115    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7648   -2.4777    1.0408 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  1  0
 11 13  1  0
 13 14  1  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
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 19 50  1  6
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 26 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5S,12R)-Dihydroxy-(6Z,8E,14Z)-eicosatrien-1,20-dicarboxylic acid anion	HMDB
10,11-dihydro-20-COOH-Leukotriene b(,4)	HMDB
20-Carboxy-10,11-dihydro-LTB(,4)	HMDB

Chemical Formula

C₂₀H₃₂O₆

Average Molecular Weight

368.4645

Monoisotopic Molecular Weight

368.219888756

IUPAC Name

(5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic acid

Traditional Name

(5R,6Z,8E,12R,14Z)-5,12-dihydroxyicosa-6,8,14-trienedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O6/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/h2,4-6,8,13,17-18,21-22H,1,3,7,9-12,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,13-8-/t17-,18-/m0/s1

InChI Key

BCZGHMCTSJAJRR-NSBXBVANSA-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
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0012633)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012633)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012633)

Source

Endogenous

Endogenous (HMDB: HMDB0012633)

Animal

Animal (HMDB: HMDB0012633)

Exogenous

Food

Food (HMDB: HMDB0012633)

Exogenous (HMDB: HMDB0012633)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012633)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012633)

Lipid metabolism pathway (HMDB: HMDB0012633)

Cellular process

Cell signaling (HMDB: HMDB0012633)

Biochemical process

Lipid transport (HMDB: HMDB0012633)

Role

Biological role

Energy source (HMDB: HMDB0012633)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012633)

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	0.04 g/L	ALOGPS
logP	3.17	ALOGPS
logP	3.01	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	103.69 m³·mol⁻¹	ChemAxon
Polarizability	41.85 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]+	193.078	31661259
DarkChem	[M-H]-	190.99	31661259
DeepCCS	[M+H]+	194.475	30932474
DeepCCS	[M-H]-	192.117	30932474
DeepCCS	[M-2H]-	226.39	30932474
DeepCCS	[M+Na]+	201.617	30932474
AllCCS	[M+H]+	194.2	32859911
AllCCS	[M+H-H2O]+	191.7	32859911
AllCCS	[M+NH4]+	196.5	32859911
AllCCS	[M+Na]+	197.2	32859911
AllCCS	[M-H]-	192.8	32859911
AllCCS	[M+Na-2H]-	194.8	32859911
AllCCS	[M+HCOO]-	197.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.49 minutes	32390414
Predicted by Siyang on May 30, 2022	13.7689 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.23 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	87.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2528.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	213.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	270.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	551.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	426.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	180.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1229.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	502.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1260.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	364.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	510.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	195.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
20-COOH-10,11-dihydro-LTB4	O[C@H](CC\C=C\C=C/[C@H](O)CCCC(O)=O)C\C=C/CCCCC(O)=O	5078.7	Standard polar	33892256
20-COOH-10,11-dihydro-LTB4	O[C@H](CC\C=C\C=C/[C@H](O)CCCC(O)=O)C\C=C/CCCCC(O)=O	2755.0	Standard non polar	33892256
20-COOH-10,11-dihydro-LTB4	O[C@H](CC\C=C\C=C/[C@H](O)CCCC(O)=O)C\C=C/CCCCC(O)=O	3153.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
20-COOH-10,11-dihydro-LTB4,1TMS,isomer #1	C[Si](C)(C)O[C@@H](C/C=C\CCCCC(=O)O)CC/C=C/C=C\[C@H](O)CCCC(=O)O	3294.4	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,1TMS,isomer #2	C[Si](C)(C)O[C@@H](/C=C\C=C\CC[C@@H](O)C/C=C\CCCCC(=O)O)CCCC(=O)O	3327.7	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,1TMS,isomer #3	C[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\CC[C@@H](O)C/C=C\CCCCC(=O)O	3247.0	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,1TMS,isomer #4	C[Si](C)(C)OC(=O)CCCC/C=C\C[C@H](O)CC/C=C/C=C\[C@H](O)CCCC(=O)O	3249.6	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC/C=C\C[C@@H](CC/C=C/C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C	3278.0	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TMS,isomer #2	C[Si](C)(C)O[C@@H](/C=C\C=C\CC[C@H](C/C=C\CCCCC(=O)O)O[Si](C)(C)C)CCCC(=O)O	3329.6	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TMS,isomer #3	C[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\CC[C@H](C/C=C\CCCCC(=O)O)O[Si](C)(C)C	3269.3	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TMS,isomer #4	C[Si](C)(C)OC(=O)CCCC/C=C\C[C@H](O)CC/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C	3284.5	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TMS,isomer #5	C[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\CC[C@@H](O)C/C=C\CCCCC(=O)O)O[Si](C)(C)C	3283.8	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TMS,isomer #6	C[Si](C)(C)OC(=O)CCCC/C=C\C[C@H](O)CC/C=C/C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C	3230.2	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC/C=C\C[C@@H](CC/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3265.7	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,3TMS,isomer #2	C[Si](C)(C)OC(=O)CCCC/C=C\C[C@@H](CC/C=C/C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3217.8	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,3TMS,isomer #3	C[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\CC[C@H](C/C=C\CCCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3264.2	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,3TMS,isomer #4	C[Si](C)(C)OC(=O)CCCC/C=C\C[C@H](O)CC/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3240.9	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC/C=C\C[C@@H](CC/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3222.5	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H](C/C=C\CCCCC(=O)O)CC/C=C/C=C\[C@H](O)CCCC(=O)O	3540.3	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H](/C=C\C=C\CC[C@@H](O)C/C=C\CCCCC(=O)O)CCCC(=O)O	3578.1	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\CC[C@@H](O)C/C=C\CCCCC(=O)O	3509.7	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\C[C@H](O)CC/C=C/C=C\[C@H](O)CCCC(=O)O	3515.0	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\C[C@@H](CC/C=C/C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3759.0	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H](/C=C\C=C\CC[C@H](C/C=C\CCCCC(=O)O)O[Si](C)(C)C(C)(C)C)CCCC(=O)O	3806.8	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\CC[C@H](C/C=C\CCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3751.5	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\C[C@H](O)CC/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3775.6	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\CC[C@@H](O)C/C=C\CCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3773.8	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\C[C@H](O)CC/C=C/C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3714.0	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\C[C@@H](CC/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	4010.3	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\C[C@@H](CC/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	3958.0	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\CC[C@H](C/C=C\CCCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4008.5	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\C[C@H](O)CC/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3973.2	Semi standard non polar	33892256
20-COOH-10,11-dihydro-LTB4,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C\C[C@@H](CC/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	4166.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 20-COOH-10,11-dihydro-LTB4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-4889000000-0a4f17f36e62072ae21d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-COOH-10,11-dihydro-LTB4 GC-MS (4 TMS) - 70eV, Positive	splash10-0006-5225978000-f1db1f862df91cbb40af	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20-COOH-10,11-dihydro-LTB4 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-COOH-10,11-dihydro-LTB4 10V, Positive-QTOF	splash10-0f89-0009000000-d74896386373a1dbe944	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 20V, Positive-QTOF	splash10-0pc0-0149000000-83e1daac8c24e0221837	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 40V, Positive-QTOF	splash10-06rf-4393000000-39afb365256d68419980	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 10V, Negative-QTOF	splash10-014j-0009000000-feb029926b28e7c9919c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 20V, Negative-QTOF	splash10-052b-0009000000-7b3856c8ffa4342ac9da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 40V, Negative-QTOF	splash10-0a4i-9233000000-9552f0ef691bec8e5319	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 10V, Negative-QTOF	splash10-000t-0009000000-a46691ffc8aa2920cf13	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 20V, Negative-QTOF	splash10-0a4i-4119000000-7a20b974ecb973a84b40	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 40V, Negative-QTOF	splash10-0a4m-6195000000-02eb968528b4b5dceae8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 10V, Positive-QTOF	splash10-0zgi-0039000000-32a96f33763e32061ee2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 20V, Positive-QTOF	splash10-001i-0095000000-82183d31ed2467145c47	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20-COOH-10,11-dihydro-LTB4 40V, Positive-QTOF	splash10-00m0-3290000000-9b5e834eb946d1c1bf1b	2021-09-24	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

FDB029158

KNApSAcK ID

Not Available

Chemspider ID

30776642

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481507

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)

Not Available

General References

Powell WS, Rokach J, Khanapure SP, Manna S, Hashefi M, Gravel S, Macleod RJ, Falck JR, Bhatt RK: Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels. J Pharmacol Exp Ther. 1996 Feb;276(2):728-36. [PubMed:8632343 ]
Primiano T, Li Y, Kensler TW, Trush MA, Sutter TR: Identification of dithiolethione-inducible gene-1 as a leukotriene B4 12-hydroxydehydrogenase: implications for chemoprevention. Carcinogenesis. 1998 Jun;19(6):999-1005. [PubMed:9667737 ]
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-COOH-10,11-dihydro-LTB4 (HMDB0012633)

MOL for HMDB0012633 (20-COOH-10,11-dihydro-LTB4)

3D MOL for HMDB0012633 (20-COOH-10,11-dihydro-LTB4)

3D SDF for HMDB0012633 (20-COOH-10,11-dihydro-LTB4)

3D-SDF for HMDB0012633 (20-COOH-10,11-dihydro-LTB4)

PDB for HMDB0012633 (20-COOH-10,11-dihydro-LTB4)

3D PDB for HMDB0012633 (20-COOH-10,11-dihydro-LTB4)

SMILES for HMDB0012633 (20-COOH-10,11-dihydro-LTB4)

INCHI for HMDB0012633 (20-COOH-10,11-dihydro-LTB4)

Structure for HMDB0012633 (20-COOH-10,11-dihydro-LTB4)

3D Structure for HMDB0012633 (20-COOH-10,11-dihydro-LTB4)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra