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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:47 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002304

Secondary Accession Numbers

HMDB02304

Metabolite Identification

Common Name

Leukotriene B4 ethanolamide

Description

Leukotriene B4 ethanolamide is a synthetic agonist of leukotriene B4 (LTB4), that interacts with both leukotriene B4 receptors and Vanilloid TRPV1 receptors. Leukotriene B4 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. 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. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. 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. (PMID 17623009 , 16207832 )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 02231219282D          

 27 26  0  0  1  0            999 V2000
   27.2724  -12.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6999  -12.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7014  -10.0024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8449   -7.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1304  -10.0024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7014  -12.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7014  -11.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8420  -15.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8420  -16.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9869  -12.8899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.4158  -11.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5566  -14.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1275  -16.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5566  -14.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4158  -10.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9869  -13.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9855  -14.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1275  -17.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2710  -13.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6999  -13.7150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.1304   -9.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2724  -14.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4145  -14.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5579  -13.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8449   -8.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1290  -13.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8434  -14.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  1  0  0  0
 20  2  1  1  0  0  0
  3 15  2  0  0  0  0
  4 25  1  0  0  0  0
  5 15  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 16  1  0  0  0  0
 11 15  1  0  0  0  0
 12 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  2  0  0  0  0
 16 22  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 23  1  0  0  0  0
 21 25  1  0  0  0  0
 22 24  1  0  0  0  0
 23 26  2  0  0  0  0
 24 27  2  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0002304
     RDKit          3D
Leukotriene B4 ethanolamide
 64 63  0  0  0  0  0  0  0  0999 V2000
   -9.1582    2.9791    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6582    1.7329   -0.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2275    1.4973   -0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7195    0.2705   -0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2976   -0.1051   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2177   -0.3212    0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9037   -1.4645    1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5902   -2.6941    0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1841   -3.1645    1.0755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0146   -4.3558    0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2099   -2.2168    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953   -2.4647    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088   -1.5563    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234   -0.7381   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    0.4411   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094    1.1666   -1.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    0.7160   -1.0943 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1193   -0.5283   -1.7695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0160    1.6089   -1.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3873    1.1000   -1.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7411    1.0894    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325    0.5368    0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7883    0.2578   -0.9171 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6679    0.3423    1.4183 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9998   -0.1898    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0888    0.6540    1.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0334    1.9346    1.6412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4156    3.7715   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2800    2.7120    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1492    3.2065   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6566    1.8894   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2349    0.8212   -0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3092    1.2988    0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6140    2.3980   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6975    0.4475   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4411   -0.5479   -0.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8757   -0.9080   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842    0.8112   -0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4299    0.5158    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8673   -1.5359    2.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8029   -2.6927   -0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2280   -3.5169    1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180   -3.3648    2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -4.1605   -0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026   -1.3513    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7407   -3.3934    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604   -2.4929    0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -0.8867    0.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291    0.8025   -1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542    2.0565   -1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    0.6525   -0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878   -1.0877   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9212    1.5168   -2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658    2.6476   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4290    0.0237   -1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1837    1.6049   -2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0456    0.4855    0.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7297    2.1266    0.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.5890    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1244   -0.4340    2.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0472   -1.1793    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0898    0.2641    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0007    0.7798   -0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5123    2.5844    1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  1
 10 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  1
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  0
M  END


  Mrv0541 02231219282D          

 27 26  0  0  1  0            999 V2000
   27.2724  -12.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6999  -12.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7014  -10.0024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8449   -7.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1304  -10.0024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7014  -12.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7014  -11.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8420  -15.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8420  -16.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9869  -12.8899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.4158  -11.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5566  -14.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1275  -16.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5566  -14.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4158  -10.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9869  -13.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9855  -14.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1275  -17.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2710  -13.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6999  -13.7150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.1304   -9.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2724  -14.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4145  -14.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5579  -13.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8449   -8.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1290  -13.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8434  -14.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  1  0  0  0
 20  2  1  1  0  0  0
  3 15  2  0  0  0  0
  4 25  1  0  0  0  0
  5 15  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 16  1  0  0  0  0
 11 15  1  0  0  0  0
 12 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  2  0  0  0  0
 16 22  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 23  1  0  0  0  0
 21 25  1  0  0  0  0
 22 24  1  0  0  0  0
 23 26  2  0  0  0  0
 24 27  2  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002304

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H37NO4/c1-2-3-4-5-6-9-13-20(25)14-10-7-8-11-15-21(26)16-12-17-22(27)23-18-19-24/h6-11,14-15,20-21,24-26H,2-5,12-13,16-19H2,1H3,(H,23,27)/b8-7+,9-6-,14-10+,15-11-/t20-,21-/m1/s1

> <INCHI_KEY>
DQLVVNIINUTUIU-XLFGVTECSA-N

> <FORMULA>
C22H37NO4

> <MOLECULAR_WEIGHT>
379.5335

> <EXACT_MASS>
379.272258677

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.08741932140663

> <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-dihydroxy-N-(2-hydroxyethyl)icosa-6,8,10,14-tetraenamide

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
2.8521801169999996

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.27296221649774

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.391616181556316

> <JCHEM_PKA_STRONGEST_BASIC>
-0.28368012078589977

> <JCHEM_POLAR_SURFACE_AREA>
89.79

> <JCHEM_REFRACTIVITY>
115.99619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
LTB4 ethanol amide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002304
     RDKit          3D
Leukotriene B4 ethanolamide
 64 63  0  0  0  0  0  0  0  0999 V2000
   -9.1582    2.9791    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6582    1.7329   -0.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2275    1.4973   -0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7195    0.2705   -0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2976   -0.1051   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2177   -0.3212    0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9037   -1.4645    1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5902   -2.6941    0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1841   -3.1645    1.0755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0146   -4.3558    0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2099   -2.2168    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953   -2.4647    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088   -1.5563    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234   -0.7381   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    0.4411   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094    1.1666   -1.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    0.7160   -1.0943 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1193   -0.5283   -1.7695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0160    1.6089   -1.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3873    1.1000   -1.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7411    1.0894    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325    0.5368    0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7883    0.2578   -0.9171 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6679    0.3423    1.4183 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9998   -0.1898    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0888    0.6540    1.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0334    1.9346    1.6412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4156    3.7715   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2800    2.7120    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1492    3.2065   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6566    1.8894   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2349    0.8212   -0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3092    1.2988    0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6140    2.3980   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6975    0.4475   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4411   -0.5479   -0.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8757   -0.9080   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842    0.8112   -0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4299    0.5158    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8673   -1.5359    2.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8029   -2.6927   -0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2280   -3.5169    1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180   -3.3648    2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -4.1605   -0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026   -1.3513    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7407   -3.3934    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604   -2.4929    0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -0.8867    0.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291    0.8025   -1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542    2.0565   -1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    0.6525   -0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878   -1.0877   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9212    1.5168   -2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658    2.6476   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4290    0.0237   -1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1837    1.6049   -2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0456    0.4855    0.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7297    2.1266    0.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.5890    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1244   -0.4340    2.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0472   -1.1793    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0898    0.2641    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0007    0.7798   -0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5123    2.5844    1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  1
 10 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  1
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      50.908 -23.291   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      44.240 -24.061   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      53.576 -18.671   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      57.577 -14.821   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      56.243 -18.671   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      53.576 -23.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      53.576 -21.751   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.905 -28.681   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      38.905 -30.221   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      52.242 -24.061   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      54.909 -20.981   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      40.239 -27.911   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      37.571 -30.991   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      40.239 -26.371   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      54.909 -19.441   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      52.242 -25.601   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      42.906 -26.371   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.571 -32.531   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.573 -25.601   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.240 -25.601   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      56.243 -17.131   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      50.908 -26.371   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.574 -26.371   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      49.575 -25.601   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      57.577 -16.361   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      46.907 -25.601   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      48.241 -26.371   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   20                                                            
CONECT    3   15                                                            
CONECT    4   25                                                            
CONECT    5   15   21                                                       
CONECT    6    7   10                                                       
CONECT    7    6   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10    1    6   16                                                  
CONECT   11    7   15                                                       
CONECT   12    8   14                                                       
CONECT   13    9   18                                                       
CONECT   14   12   19                                                       
CONECT   15    3    5   11                                                  
CONECT   16   10   22                                                       
CONECT   17   19   20                                                       
CONECT   18   13                                                            
CONECT   19   14   17                                                       
CONECT   20    2   17   23                                                  
CONECT   21    5   25                                                       
CONECT   22   16   24                                                       
CONECT   23   20   26                                                       
CONECT   24   22   27                                                       
CONECT   25    4   21                                                       
CONECT   26   23   27                                                       
CONECT   27   24   26                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

COMPND    HMDB0002304
HETATM    1  C1  UNL     1      -9.158   2.979   0.073  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.658   1.733  -0.637  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.227   1.497  -0.174  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.720   0.271  -0.859  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.298  -0.105  -0.491  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.218  -0.321   0.952  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.904  -1.464   1.494  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.590  -2.694   0.747  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.184  -3.165   1.075  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.015  -4.356   0.311  1.00  0.00           O  
HETATM   11  C10 UNL     1      -2.210  -2.217   0.541  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.895  -2.465   0.744  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.009  -1.556   0.232  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.823  -0.738  -0.229  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.576   0.441  -0.981  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.609   1.167  -1.411  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.972   0.716  -1.094  1.00  0.00           C  
HETATM   18  O2  UNL     1       3.119  -0.528  -1.769  1.00  0.00           O  
HETATM   19  C17 UNL     1       4.016   1.609  -1.764  1.00  0.00           C  
HETATM   20  C18 UNL     1       5.387   1.100  -1.426  1.00  0.00           C  
HETATM   21  C19 UNL     1       5.741   1.089   0.017  1.00  0.00           C  
HETATM   22  C20 UNL     1       7.132   0.537   0.127  1.00  0.00           C  
HETATM   23  O3  UNL     1       7.788   0.258  -0.917  1.00  0.00           O  
HETATM   24  N1  UNL     1       7.668   0.342   1.418  1.00  0.00           N  
HETATM   25  C21 UNL     1       9.000  -0.190   1.645  1.00  0.00           C  
HETATM   26  C22 UNL     1      10.089   0.654   1.057  1.00  0.00           C  
HETATM   27  O4  UNL     1      10.033   1.935   1.641  1.00  0.00           O  
HETATM   28  H1  UNL     1      -8.416   3.772  -0.072  1.00  0.00           H  
HETATM   29  H2  UNL     1      -9.280   2.712   1.133  1.00  0.00           H  
HETATM   30  H3  UNL     1     -10.149   3.207  -0.420  1.00  0.00           H  
HETATM   31  H4  UNL     1      -8.657   1.889  -1.729  1.00  0.00           H  
HETATM   32  H5  UNL     1      -9.235   0.821  -0.330  1.00  0.00           H  
HETATM   33  H6  UNL     1      -7.309   1.299   0.927  1.00  0.00           H  
HETATM   34  H7  UNL     1      -6.614   2.398  -0.361  1.00  0.00           H  
HETATM   35  H8  UNL     1      -6.698   0.448  -1.970  1.00  0.00           H  
HETATM   36  H9  UNL     1      -7.441  -0.548  -0.706  1.00  0.00           H  
HETATM   37  H10 UNL     1      -4.876  -0.908  -1.096  1.00  0.00           H  
HETATM   38  H11 UNL     1      -4.684   0.811  -0.787  1.00  0.00           H  
HETATM   39  H12 UNL     1      -5.430   0.516   1.643  1.00  0.00           H  
HETATM   40  H13 UNL     1      -4.867  -1.536   2.599  1.00  0.00           H  
HETATM   41  H14 UNL     1      -4.803  -2.693  -0.313  1.00  0.00           H  
HETATM   42  H15 UNL     1      -5.228  -3.517   1.209  1.00  0.00           H  
HETATM   43  H16 UNL     1      -3.118  -3.365   2.149  1.00  0.00           H  
HETATM   44  H17 UNL     1      -2.802  -4.161  -0.614  1.00  0.00           H  
HETATM   45  H18 UNL     1      -2.503  -1.351   0.004  1.00  0.00           H  
HETATM   46  H19 UNL     1      -0.741  -3.393   1.320  1.00  0.00           H  
HETATM   47  H20 UNL     1       1.060  -2.493   0.255  1.00  0.00           H  
HETATM   48  H21 UNL     1       1.861  -0.887   0.089  1.00  0.00           H  
HETATM   49  H22 UNL     1      -0.429   0.802  -1.240  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.454   2.057  -1.981  1.00  0.00           H  
HETATM   51  H24 UNL     1       3.183   0.652  -0.033  1.00  0.00           H  
HETATM   52  H25 UNL     1       3.788  -1.088  -1.341  1.00  0.00           H  
HETATM   53  H26 UNL     1       3.921   1.517  -2.881  1.00  0.00           H  
HETATM   54  H27 UNL     1       3.866   2.648  -1.429  1.00  0.00           H  
HETATM   55  H28 UNL     1       5.429   0.024  -1.778  1.00  0.00           H  
HETATM   56  H29 UNL     1       6.184   1.605  -2.014  1.00  0.00           H  
HETATM   57  H30 UNL     1       5.046   0.486   0.631  1.00  0.00           H  
HETATM   58  H31 UNL     1       5.730   2.127   0.458  1.00  0.00           H  
HETATM   59  H32 UNL     1       7.094   0.589   2.254  1.00  0.00           H  
HETATM   60  H33 UNL     1       9.124  -0.434   2.712  1.00  0.00           H  
HETATM   61  H34 UNL     1       9.047  -1.179   1.111  1.00  0.00           H  
HETATM   62  H35 UNL     1      11.090   0.264   1.267  1.00  0.00           H  
HETATM   63  H36 UNL     1      10.001   0.780  -0.031  1.00  0.00           H  
HETATM   64  H37 UNL     1      10.512   2.584   1.044  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6   37   38
CONECT    6    7    7   39
CONECT    7    8   40
CONECT    8    9   41   42
CONECT    9   10   11   43
CONECT   10   44
CONECT   11   12   12   45
CONECT   12   13   46
CONECT   13   14   14   47
CONECT   14   15   48
CONECT   15   16   16   49
CONECT   16   17   50
CONECT   17   18   19   51
CONECT   18   52
CONECT   19   20   53   54
CONECT   20   21   55   56
CONECT   21   22   57   58
CONECT   22   23   23   24
CONECT   24   25   59
CONECT   25   26   60   61
CONECT   26   27   62   63
CONECT   27   64
END

HMDB0002304
     RDKit          3D
Leukotriene B4 ethanolamide
 64 63  0  0  0  0  0  0  0  0999 V2000
   -9.1582    2.9791    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6582    1.7329   -0.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2275    1.4973   -0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7195    0.2705   -0.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2976   -0.1051   -0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2177   -0.3212    0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9037   -1.4645    1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5902   -2.6941    0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1841   -3.1645    1.0755 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0146   -4.3558    0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2099   -2.2168    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953   -2.4647    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088   -1.5563    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8234   -0.7381   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757    0.4411   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094    1.1666   -1.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    0.7160   -1.0943 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1193   -0.5283   -1.7695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0160    1.6089   -1.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3873    1.1000   -1.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7411    1.0894    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325    0.5368    0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7883    0.2578   -0.9171 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6679    0.3423    1.4183 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9998   -0.1898    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0888    0.6540    1.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0334    1.9346    1.6412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4156    3.7715   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2800    2.7120    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1492    3.2065   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6566    1.8894   -1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2349    0.8212   -0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3092    1.2988    0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6140    2.3980   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6975    0.4475   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4411   -0.5479   -0.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8757   -0.9080   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842    0.8112   -0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4299    0.5158    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8673   -1.5359    2.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8029   -2.6927   -0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2280   -3.5169    1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180   -3.3648    2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8016   -4.1605   -0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5026   -1.3513    0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7407   -3.3934    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604   -2.4929    0.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -0.8867    0.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291    0.8025   -1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542    2.0565   -1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    0.6525   -0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878   -1.0877   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9212    1.5168   -2.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658    2.6476   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4290    0.0237   -1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1837    1.6049   -2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0456    0.4855    0.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7297    2.1266    0.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    0.5890    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1244   -0.4340    2.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0472   -1.1793    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0898    0.2641    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0007    0.7798   -0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5123    2.5844    1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  1
 10 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  1
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
LTB4 Ethanol amide	HMDB
N-(2-Hydroxyethyl)-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraen-1-amide	HMDB

Chemical Formula

C₂₂H₃₇NO₄

Average Molecular Weight

379.5335

Monoisotopic Molecular Weight

379.272258677

IUPAC Name

(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-N-(2-hydroxyethyl)icosa-6,8,10,14-tetraenamide

Traditional Name

LTB4 ethanol amide

CAS Registry Number

877459-63-7

SMILES

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

InChI Identifier

InChI=1S/C22H37NO4/c1-2-3-4-5-6-9-13-20(25)14-10-7-8-11-15-21(26)16-12-17-22(27)23-18-19-24/h6-11,14-15,20-21,24-26H,2-5,12-13,16-19H2,1H3,(H,23,27)/b8-7+,9-6-,14-10+,15-11-/t20-,21-/m1/s1

InChI Key

DQLVVNIINUTUIU-XLFGVTECSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

N-acylethanolamines

Alternative Parents

Substituents

N-acylethanolamine
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Leukotrienes (LMFA03020012 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0002304)
Membrane (HMDB: HMDB0002304)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

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	0.013 g/L	ALOGPS
logP	3.99	ALOGPS
logP	2.85	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	15.39	ChemAxon
pKa (Strongest Basic)	-0.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	116 m³·mol⁻¹	ChemAxon
Polarizability	45.09 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]+	201.075	31661259
DarkChem	[M-H]-	196.645	31661259
DeepCCS	[M+H]+	202.787	30932474
DeepCCS	[M-H]-	200.429	30932474
DeepCCS	[M-2H]-	234.532	30932474
DeepCCS	[M+Na]+	209.761	30932474
AllCCS	[M+H]+	201.2	32859911
AllCCS	[M+H-H2O]+	198.7	32859911
AllCCS	[M+NH4]+	203.4	32859911
AllCCS	[M+Na]+	204.1	32859911
AllCCS	[M-H]-	196.7	32859911
AllCCS	[M+Na-2H]-	199.1	32859911
AllCCS	[M+HCOO]-	202.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Leukotriene B4 ethanolamide	CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(=O)NCCO	4413.3	Standard polar	33892256
Leukotriene B4 ethanolamide	CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(=O)NCCO	3052.2	Standard non polar	33892256
Leukotriene B4 ethanolamide	CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(=O)NCCO	3409.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leukotriene B4 ethanolamide,1TMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)NCCO)O[Si](C)(C)C	3424.7	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,1TMS,isomer #2	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)NCCO)O[Si](C)(C)C	3418.0	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,1TMS,isomer #3	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)NCCO[Si](C)(C)C	3397.3	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,1TMS,isomer #4	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)N(CCO)[Si](C)(C)C	3326.2	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)NCCO)O[Si](C)(C)C)O[Si](C)(C)C	3454.9	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TMS,isomer #2	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)NCCO[Si](C)(C)C)O[Si](C)(C)C	3410.5	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TMS,isomer #3	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)N(CCO)[Si](C)(C)C)O[Si](C)(C)C	3348.7	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TMS,isomer #4	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)NCCO[Si](C)(C)C)O[Si](C)(C)C	3412.1	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TMS,isomer #5	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO)[Si](C)(C)C)O[Si](C)(C)C	3344.5	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TMS,isomer #6	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3377.5	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,3TMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)NCCO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3410.0	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,3TMS,isomer #2	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3340.2	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,3TMS,isomer #3	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3377.7	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,3TMS,isomer #4	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3367.0	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,4TMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3359.1	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,4TMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3196.4	Standard non polar	33892256
Leukotriene B4 ethanolamide,4TMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3304.9	Standard polar	33892256
Leukotriene B4 ethanolamide,1TBDMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)NCCO)O[Si](C)(C)C(C)(C)C	3660.2	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,1TBDMS,isomer #2	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)NCCO)O[Si](C)(C)C(C)(C)C	3661.2	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,1TBDMS,isomer #3	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)NCCO[Si](C)(C)C(C)(C)C	3632.5	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,1TBDMS,isomer #4	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	3556.1	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)NCCO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3935.1	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TBDMS,isomer #2	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)NCCO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3900.4	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TBDMS,isomer #3	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3820.5	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TBDMS,isomer #4	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)NCCO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3890.5	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TBDMS,isomer #5	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3817.0	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,2TBDMS,isomer #6	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3848.1	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,3TBDMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)NCCO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4153.0	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,3TBDMS,isomer #2	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4071.7	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,3TBDMS,isomer #3	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4106.7	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,3TBDMS,isomer #4	CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4094.9	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,4TBDMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4297.9	Semi standard non polar	33892256
Leukotriene B4 ethanolamide,4TBDMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3903.8	Standard non polar	33892256
Leukotriene B4 ethanolamide,4TBDMS,isomer #1	CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3486.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene B4 ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-4569000000-07bbcd45df0fab107131	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene B4 ethanolamide GC-MS (3 TMS) - 70eV, Positive	splash10-00al-9403580000-183af0e09936b9778485	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene B4 ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leukotriene B4 ethanolamide 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 - Leukotriene B4 ethanolamide 10V, Positive-QTOF	splash10-03di-2019000000-4f352551829a8f9e3932	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 20V, Positive-QTOF	splash10-03dl-9114000000-a9957a9113512b82fed1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 40V, Positive-QTOF	splash10-01ox-9211000000-bf01e60a47f738449f5c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 10V, Negative-QTOF	splash10-004i-0009000000-103935c4a5640462193d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 20V, Negative-QTOF	splash10-03di-3119000000-77b68bbcfe920f285fb9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 40V, Negative-QTOF	splash10-01ox-9010000000-8161d2163618ea5160ce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 10V, Positive-QTOF	splash10-03dl-0019000000-680ed762e070f11a0bd6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 20V, Positive-QTOF	splash10-03dl-4249000000-001753066a308396c126	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 40V, Positive-QTOF	splash10-0cdi-9221000000-e87198640faaf65d8d77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 10V, Negative-QTOF	splash10-004i-0009000000-12014e2c88deaf8a4a75	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 20V, Negative-QTOF	splash10-01t9-4339000000-639b80e888b3e42bb90c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leukotriene B4 ethanolamide 40V, Negative-QTOF	splash10-067l-9237000000-ed1d0e834f57d6d5ea83	2021-09-22	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

FDB022956

KNApSAcK ID

Not Available

Chemspider ID

4446251

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283127

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)

Download (PDF)

General References

Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]
McHugh D, McMaster RS, Pertwee RG, Roy S, Mahadevan A, Razdan RK, Ross RA: Novel compounds that interact with both leukotriene B4 receptors and vanilloid TRPV1 receptors. J Pharmacol Exp Ther. 2006 Feb;316(2):955-65. Epub 2005 Oct 5. [PubMed:16207832 ]
Lipid Maps (LMFA03020012) [Link]

Showing metabocard for Leukotriene B4 ethanolamide (HMDB0002304)

MOL for HMDB0002304 (Leukotriene B4 ethanolamide)

3D MOL for HMDB0002304 (Leukotriene B4 ethanolamide)

3D SDF for HMDB0002304 (Leukotriene B4 ethanolamide)

3D-SDF for HMDB0002304 (Leukotriene B4 ethanolamide)

PDB for HMDB0002304 (Leukotriene B4 ethanolamide)

3D PDB for HMDB0002304 (Leukotriene B4 ethanolamide)

SMILES for HMDB0002304 (Leukotriene B4 ethanolamide)

INCHI for HMDB0002304 (Leukotriene B4 ethanolamide)

Structure for HMDB0002304 (Leukotriene B4 ethanolamide)

3D Structure for HMDB0002304 (Leukotriene B4 ethanolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra