NP-MRD: Showing NP-Card for 20-Carboxy-leukotriene B4 (NP0136770)

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Record Information

Version

2.0

Created at

2022-05-12 15:23:10 UTC

Updated at

2022-05-12 15:23:10 UTC

NP-MRD ID

NP0136770

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-Carboxy-leukotriene B4

Description

20-Carboxy-leukotriene B4, also known as 20-COOH-LTB4 or 20-carboxy-LTB4, 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. Thus, 20-carboxy-leukotriene B4 is considered to be an eicosanoid lipid molecule. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. This activity has been ascribed to LTB4 omega-hydroxylase (cytochrome P-450LTB omega). 20-Carboxy-leukotriene B4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In humans, 20-carboxy-leukotriene B4 is involved in mefenamic acid action pathway. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). 20-Carboxyleukotriene B4 is an omega-oxidized metabolite of leukotriene B4 (LTB4). 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. All mammalian cells except erythrocytes synthesize eicosanoids. 20-Carboxy-leukotriene B4 was first documented in 1990 (PMID: 2155225). The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304202019592D          

 26 25  0  0  1  0            999 V2000
   20.0281   -5.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4558   -6.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8861   -3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1687  -11.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4571   -3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5979  -11.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5979   -8.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4571   -5.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5979   -9.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4571   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3123   -8.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7427   -6.3250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.1717   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8833  -10.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3123   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7411   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4558   -7.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.0267   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7427   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1702   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1717   -3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8833  -10.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0281   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8846   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3136   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5992   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  1  0  0  0
 17  2  1  1  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 21  2  0  0  0  0
  6 22  2  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 14  1  0  0  0  0
 10 13  1  0  0  0  0
 11 15  1  0  0  0  0
 12 19  1  0  0  0  0
 13 21  1  0  0  0  0
 14 22  1  0  0  0  0
 15 18  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 56 55  0  0  0  0  0  0  0  0999 V2000
   -8.3082   -2.3758    2.8629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5093   -1.7328    2.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1620   -2.0284    2.2544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0741   -0.7672    1.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0471   -0.0261    0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1305    0.7757    1.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0869    1.5303    0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2589    0.6097   -0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9523    0.5043   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1640    1.3080    0.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1435    2.1429   -0.1173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3796    2.9345    0.7170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2242    1.2534   -0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8454    0.7261   -0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7198   -0.1477   -1.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8137   -0.7095   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6762   -1.5669   -1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7650   -2.1199   -0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1880   -1.9044    0.4773 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1311   -2.9168    0.8182 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8392   -0.6158    0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1179   -0.3229    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0162   -0.1912   -1.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1010    0.9028   -1.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8216    1.0725   -2.9747 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116    1.7765   -0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8666   -2.9908    2.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7505   -0.0492    1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7384   -1.3300    0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6152    0.6581   -0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5095   -0.7417   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5844    0.1686    1.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7263    1.5681    1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6797    2.1628   -0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5877    2.1997    1.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8138   -0.0229   -1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4849   -0.2454   -0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5889    0.5547    1.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7136    1.9007    1.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6963    2.8134   -0.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477    3.6845    1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206    1.0165   -1.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417    0.9507    0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5033   -0.3634   -2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9969   -0.4870    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4475   -1.7802   -2.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3692   -2.8044   -1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3337   -2.1184    1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5975   -3.7670    0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1388    0.2727    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0586   -0.6608    1.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9227   -1.0767    0.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5486    0.6317    0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7662   -1.0997   -1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0540    0.1248   -1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8392    2.7191   -0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 26  1  0
 24 25  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 20 49  1  0
 19 48  1  1
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 26 56  1  0
 18 47  1  0
 17 46  1  0
 16 45  1  0
 15 44  1  0
 14 43  1  0
 13 42  1  0
 11 40  1  6
 12 41  1  0
 10 38  1  0
 10 39  1  0
  9 37  1  0
  8 36  1  0
  7 34  1  0
  7 35  1  0
  6 32  1  0
  6 33  1  0
  5 30  1  0
  5 31  1  0
  4 28  1  0
  4 29  1  0
  3 27  1  0
M  END

  Mrv1652304202019592D          

 26 25  0  0  1  0            999 V2000
   20.0281   -5.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4558   -6.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8861   -3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1687  -11.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4571   -3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5979  -11.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5979   -8.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4571   -5.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5979   -9.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4571   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3123   -8.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7427   -6.3250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.1717   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8833  -10.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3123   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7411   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4558   -7.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.0267   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7427   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1702   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1717   -3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8833  -10.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0281   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8846   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3136   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5992   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  1  0  0  0
 17  2  1  1  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 21  2  0  0  0  0
  6 22  2  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 14  1  0  0  0  0
 10 13  1  0  0  0  0
 11 15  1  0  0  0  0
 12 19  1  0  0  0  0
 13 21  1  0  0  0  0
 14 22  1  0  0  0  0
 15 18  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  2  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136770

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O6/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/h2,4-8,12-13,17-18,21-22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t17-,18-/m1/s1

> <INCHI_KEY>
SXWGPVJGNOLNHT-VFLUTPEKSA-N

> <FORMULA>
C20H30O6

> <MOLECULAR_WEIGHT>
366.4486

> <EXACT_MASS>
366.204238692

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.38747068988632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.8053069119999994

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.9319599563623

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.329333179094752

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2749378066483987

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
104.6504

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-cooh-LTB4

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  O   UNK     0      37.386 -11.037   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.717 -11.807   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      42.721  -6.417   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      22.715 -21.047   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      40.053  -6.417   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      25.383 -21.047   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      25.383 -16.427   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      40.053 -11.037   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.383 -17.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      40.053  -9.497   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.716 -15.657   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      38.720 -11.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.387  -8.727   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.049 -18.737   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.716 -14.117   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.383 -14.117   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.717 -13.347   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.050 -13.347   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.720 -13.347   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.051 -14.117   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      41.387  -7.187   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.049 -20.277   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.386 -14.117   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.385 -13.347   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      36.052 -13.347   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      34.719 -14.117   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   17                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   21                                                            
CONECT    6   22                                                            
CONECT    7    9   11                                                       
CONECT    8   10   12                                                       
CONECT    9    7   14                                                       
CONECT   10    8   13                                                       
CONECT   11    7   15                                                       
CONECT   12    1    8   19                                                  
CONECT   13   10   21                                                       
CONECT   14    9   22                                                       
CONECT   15   11   18                                                       
CONECT   16   17   18                                                       
CONECT   17    2   16   20                                                  
CONECT   18   15   16                                                       
CONECT   19   12   23                                                       
CONECT   20   17   24                                                       
CONECT   21    3    5   13                                                  
CONECT   22    4    6   14                                                  
CONECT   23   19   25                                                       
CONECT   24   20   26                                                       
CONECT   25   23   26                                                       
CONECT   26   24   25                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

View in JSmol

Synonyms

Value	Source
20-Carboxy-LTB4	ChEBI
20-COOH-Leukotriene b4	ChEBI
20-COOH-LTB4	ChEBI
5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioic acid	ChEBI
5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioate	Generator
5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioate	Generator
5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioic acid	Generator
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenedioate	HMDB
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenedioic acid	HMDB
(S-(R,s-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenedioate	HMDB
(S-(R,s-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenedioic acid	HMDB
20-Carboxy-leukotriene- b4	HMDB
20-Carboxyleukotriene b4	HMDB
20-Hydroxy-20-oxo-leukotriene b4	HMDB
5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoate	HMDB
5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoic acid	HMDB
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioate	HMDB
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioic acid	HMDB
20-COOH LTB4	HMDB

Chemical Formula

C₂₀H₃₀O₆

Average Mass

366.4486 Da

Monoisotopic Mass

366.20424 Da

IUPAC Name

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

Traditional Name

20-cooh-LTB4

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O6/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/h2,4-8,12-13,17-18,21-22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t17-,18-/m1/s1

InChI Key

SXWGPVJGNOLNHT-VFLUTPEKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

icosatetraenedioic acid (CHEBI:27562 )
Leukotrienes (C05950 )
Leukotrienes (LMFA03020016 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.17	ALOGPS
logP	2.81	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	-1.3	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	15	ChemAxon
Refractivity	104.65 m³·mol⁻¹	ChemAxon
Polarizability	40.39 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

External Links

HMDB ID

HMDB0006059

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023824

KNApSAcK ID

Not Available

Chemspider ID

4444400

KEGG Compound ID

C05950

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280877

PDB ID

Not Available

ChEBI ID

27562

Good Scents ID

Not Available

References

General References

Sumimoto H, Minakami S: Oxidation of 20-hydroxyleukotriene B4 to 20-carboxyleukotriene B4 by human neutrophil microsomes. Role of aldehyde dehydrogenase and leukotriene B4 omega-hydroxylase (cytochrome P-450LTB omega) in leukotriene B4 omega-oxidation. J Biol Chem. 1990 Mar 15;265(8):4348-53. [PubMed:2155225 ]

Showing NP-Card for 20-Carboxy-leukotriene B4 (NP0136770)

MOL for NP0136770 (20-Carboxy-leukotriene B4)

3D MOL for NP0136770 (20-Carboxy-leukotriene B4)

3D SDF for NP0136770 (20-Carboxy-leukotriene B4)

3D-SDF for NP0136770 (20-Carboxy-leukotriene B4)

PDB for NP0136770 (20-Carboxy-leukotriene B4)

3D PDB for NP0136770 (20-Carboxy-leukotriene B4)

SMILES for NP0136770 (20-Carboxy-leukotriene B4)

INCHI for NP0136770 (20-Carboxy-leukotriene B4)

Structure for NP0136770 (20-Carboxy-leukotriene B4)

3D Structure for NP0136770 (20-Carboxy-leukotriene B4)