MiMeDB: Showing metabocard for Leukotriene B4 (MMDBc0000772)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:54:36 UTC

Update Date

2024-04-30 19:33:38 UTC

Metabolite ID

MMDBc0000772

Metabolite Identification

Common Name

Leukotriene B4

Description

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 omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-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 in 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 omega-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. The term leukotriene was coined to indicate the presence of three conjugated double bonds within the 20-carbon structure of arachidonic acid as well as the fact that these compounds were derived from leucocytes such as PMNNs or transformed mast cells. Interestingly, most of the cells known to express 5-LO are of myeloid origin, which includes neutrophils, eosinophils, mast cells, macrophages, basophils, and monocytes. Leukotriene biosynthesis begins with the specific oxidation of arachidonic acid by a free radical mechanism as a consequence of interaction with 5-LO. The first enzymatic step involves the abstraction of a hydrogen atom from C-7 of arachidonate followed by the addition of molecular oxygen to form 5-HpETE (5-hydroperoxyeicosatetraenoic acid). A second enzymatic step is also catalyzed by 5-LO and involves removal of a hydrogen atom from C-10, resulting in the formation of the conjugated triene epoxide LTA4. LTA4 must then be released by 5-LO and encounter either LTA4-H (LTA4 hydrolase) or LTC4-S [LTC4 (leukotriene C4) synthase]. LTA4-H can stereospecifically add water to C-12 while retaining a specific double-bond geometry, leading to LTB4 [leukotriene B4, 5(S),12(R)-dihydroxy-6,8,10,14-(Z,E,E,Z)-eicosatetraenoic acid]. If LTA4 encounters LTC4-S, then the reactive epoxide is opened at C-6 by the thiol anion of glutathione to form the product LTC4 [5(S)-hydroxy-6(R)-S-glutathyionyl-7,9,11,14- (E,E,Z,Z)-eicosatetraenoic acid], essentially a glutathionyl adduct of oxidized arachidonic acid. Both of these terminal leukotrienes are biologically active in that specific GPCRs recognize these chemical structures and receptor recognition initiates complex intracellular signalling cascades. In order for these molecules to serve as lipid mediators, however, they must be released from the biosynthetic cell into the extracellular milieu so that they can encounter the corresponding GPCRs. Surprising features of this cascade include the recognition of the assembly of critical enzymes at the perinuclear region of the cell and even localization of 5-LO within the nucleus of some cells. Under some situations, the budding phagosome has been found to assemble these proteins. Non-enzymatic proteins such as FLAP are now known as critical partners of this protein-machine assembly. An unexpected pathway of leukotriene biosynthesis involves the transfer of the chemically reactive intermediate, LTA4, from the biosynthetic cell followed by conversion into LTB4 or LTC4 by other cells that do not express 5-LO (PMID: 17623009 ). 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

HMDB0001085
     RDKit          3D
Leukotriene B4
 56 55  0  0  0  0  0  0  0  0999 V2000
    8.8585    0.1471    0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9151   -0.3361   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1704    0.8357   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1945    0.5247   -1.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -0.4527   -1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699    0.1058   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0817    0.3188   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503    0.0229   -1.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604   -0.9924   -1.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6731   -2.2045   -0.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -0.4952   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623   -0.1218   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.3588    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0521    0.7327    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    1.2210    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1684    1.5842    1.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7812    1.5381   -0.0378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9525    2.2544   -0.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2337    0.2860   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2672   -0.5716   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1122   -1.2504    1.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9451   -0.5061    2.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9364   -0.7119    3.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8605    0.4598    2.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8501   -0.5370    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5661    1.1748    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9043    0.2127    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5339   -0.8043   -0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525   -1.1023    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6290    1.3661    0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9165    1.5640   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696    1.4309   -2.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7461    0.0432   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6593   -1.3706   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5806   -0.7624   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9706    0.3499    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    0.7490    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -0.1957   -2.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    0.9791   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -1.1397   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3900   -2.0533   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -0.4426    0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -0.1828   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.4202    1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    0.6629   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5644    1.2932    2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7361    1.9790    2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7055    2.2153    0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2950    2.1386   -1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3461   -0.3815   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6021    0.5740   -1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2712    0.0063   -0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5441   -1.3851   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487   -1.9993    1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9929   -1.9737    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5457    1.1863    3.4903 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
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  6
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  1
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END


  Mrv1652303192023122D          

 24 23  0  0  0  0            999 V2000
10001.736610004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.561910004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.277010004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.991810004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.706610004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.422410004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.135910004.4998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10006.851710004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.565210004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.392310004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.105910004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.821610004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.537210004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.250810004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.968610004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.135910005.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.021710004.4998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.306710004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.591810004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.877010004.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.162210004.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.445010004.0882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.162210005.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.021710005.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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  1  0  0  0  0
  7 16  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 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
 17 18  1  0  0  0  0
 17 24  1  6  0  0  0
 18 19  1  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
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000772

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1

> <INCHI_KEY>
VNYSSYRCGWBHLG-AMOLWHMGSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.514010035725704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
4.125548676999999

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720820347637158

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6463449725928205

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2749373349576958

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
102.985

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
leukotriene B4

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001085
     RDKit          3D
Leukotriene B4
 56 55  0  0  0  0  0  0  0  0999 V2000
    8.8585    0.1471    0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9151   -0.3361   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1704    0.8357   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1945    0.5247   -1.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -0.4527   -1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699    0.1058   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0817    0.3188   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503    0.0229   -1.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604   -0.9924   -1.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6731   -2.2045   -0.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -0.4952   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623   -0.1218   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.3588    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0521    0.7327    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    1.2210    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1684    1.5842    1.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7812    1.5381   -0.0378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9525    2.2544   -0.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2337    0.2860   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2672   -0.5716   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1122   -1.2504    1.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9451   -0.5061    2.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9364   -0.7119    3.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8605    0.4598    2.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8501   -0.5370    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5661    1.1748    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9043    0.2127    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5339   -0.8043   -0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525   -1.1023    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6290    1.3661    0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9165    1.5640   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696    1.4309   -2.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7461    0.0432   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6593   -1.3706   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5806   -0.7624   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9706    0.3499    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    0.7490    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -0.1957   -2.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    0.9791   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -1.1397   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3900   -2.0533   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -0.4426    0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -0.1828   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.4202    1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    0.6629   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5644    1.2932    2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7361    1.9790    2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7055    2.2153    0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2950    2.1386   -1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3461   -0.3815   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6021    0.5740   -1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2712    0.0063   -0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5441   -1.3851   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487   -1.9993    1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9929   -1.9737    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5457    1.1863    3.4903 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
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  6
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  1
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8669.9088674.298   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8671.4498674.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8672.7848675.066   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8674.1188674.298   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8675.4528675.066   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8676.7888674.298   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8678.1208675.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8679.4578674.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8680.7888675.066   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8682.3328675.066   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8683.6648674.298   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8685.0008675.066   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8686.3368674.298   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8687.6688675.066   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8689.0088674.298   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8678.1208676.607   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8668.5748675.066   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.2398674.298   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.9058675.066   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.5708674.298   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8663.2368675.066   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8661.8978674.298   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8663.2368676.607   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8668.5748676.607   0.000  0.00  0.00           O+0
CONECT    1    2   17                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    7                                                            
CONECT   17    1   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0001085
HETATM    1  C1  UNL     1       8.859   0.147   0.883  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.915  -0.336  -0.195  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.170   0.836  -0.745  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.195   0.525  -1.826  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.110  -0.453  -1.346  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.370   0.106  -0.227  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.082   0.319  -0.259  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.250   0.023  -1.413  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.160  -0.992  -1.122  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.673  -2.204  -0.705  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.281  -0.495  -0.049  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.962  -0.122  -0.299  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.807   0.359   0.752  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.052   0.733   0.496  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.932   1.221   1.524  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.168   1.584   1.265  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.781   1.538  -0.038  1.00  0.00           C  
HETATM   18  O2  UNL     1      -4.952   2.254  -0.945  1.00  0.00           O  
HETATM   19  C17 UNL     1      -6.234   0.286  -0.645  1.00  0.00           C  
HETATM   20  C18 UNL     1      -7.267  -0.572  -0.051  1.00  0.00           C  
HETATM   21  C19 UNL     1      -7.112  -1.250   1.234  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.945  -0.506   2.467  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.936  -0.712   3.233  1.00  0.00           O  
HETATM   24  O4  UNL     1      -7.861   0.460   2.882  1.00  0.00           O  
HETATM   25  H1  UNL     1       8.850  -0.537   1.756  1.00  0.00           H  
HETATM   26  H2  UNL     1       8.566   1.175   1.172  1.00  0.00           H  
HETATM   27  H3  UNL     1       9.904   0.213   0.487  1.00  0.00           H  
HETATM   28  H4  UNL     1       8.534  -0.804  -0.994  1.00  0.00           H  
HETATM   29  H5  UNL     1       7.253  -1.102   0.266  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.629   1.366   0.071  1.00  0.00           H  
HETATM   31  H7  UNL     1       7.917   1.564  -1.124  1.00  0.00           H  
HETATM   32  H8  UNL     1       5.670   1.431  -2.134  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.746   0.043  -2.668  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.659  -1.371  -0.962  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.581  -0.762  -2.231  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.971   0.350   0.686  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.644   0.749   0.664  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.719  -0.196  -2.358  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.657   0.979  -1.614  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.562  -1.140  -2.033  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.390  -2.053  -0.061  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.676  -0.443   0.952  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.342  -0.183  -1.317  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.423   0.420   1.783  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.365   0.663  -0.518  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.564   1.293   2.555  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.736   1.979   2.145  1.00  0.00           H  
HETATM   48  H24 UNL     1      -6.706   2.215   0.014  1.00  0.00           H  
HETATM   49  H25 UNL     1      -5.295   2.139  -1.861  1.00  0.00           H  
HETATM   50  H26 UNL     1      -5.346  -0.381  -0.941  1.00  0.00           H  
HETATM   51  H27 UNL     1      -6.602   0.574  -1.713  1.00  0.00           H  
HETATM   52  H28 UNL     1      -8.271   0.006  -0.046  1.00  0.00           H  
HETATM   53  H29 UNL     1      -7.544  -1.385  -0.830  1.00  0.00           H  
HETATM   54  H30 UNL     1      -6.249  -1.999   1.155  1.00  0.00           H  
HETATM   55  H31 UNL     1      -7.993  -1.974   1.339  1.00  0.00           H  
HETATM   56  H32 UNL     1      -7.546   1.186   3.490  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7   36
CONECT    7    8   37
CONECT    8    9   38   39
CONECT    9   10   11   40
CONECT   10   41
CONECT   11   12   12   42
CONECT   12   13   43
CONECT   13   14   14   44
CONECT   14   15   45
CONECT   15   16   16   46
CONECT   16   17   47
CONECT   17   18   19   48
CONECT   18   49
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   54   55
CONECT   22   23   23   24
CONECT   24   56
END

HMDB0001085
     RDKit          3D
Leukotriene B4
 56 55  0  0  0  0  0  0  0  0999 V2000
    8.8585    0.1471    0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9151   -0.3361   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1704    0.8357   -0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1945    0.5247   -1.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -0.4527   -1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699    0.1058   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0817    0.3188   -0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503    0.0229   -1.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604   -0.9924   -1.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6731   -2.2045   -0.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -0.4952   -0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623   -0.1218   -0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.3588    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0521    0.7327    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    1.2210    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1684    1.5842    1.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7812    1.5381   -0.0378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9525    2.2544   -0.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2337    0.2860   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2672   -0.5716   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1122   -1.2504    1.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9451   -0.5061    2.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9364   -0.7119    3.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8605    0.4598    2.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8501   -0.5370    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5661    1.1748    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9043    0.2127    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5339   -0.8043   -0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525   -1.1023    0.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6290    1.3661    0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9165    1.5640   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696    1.4309   -2.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7461    0.0432   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6593   -1.3706   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5806   -0.7624   -2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9706    0.3499    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    0.7490    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191   -0.1957   -2.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573    0.9791   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -1.1397   -2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3900   -2.0533   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759   -0.4426    0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -0.1828   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.4202    1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3646    0.6629   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5644    1.2932    2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7361    1.9790    2.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7055    2.2153    0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2950    2.1386   -1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3461   -0.3815   -0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6021    0.5740   -1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2712    0.0063   -0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5441   -1.3851   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2487   -1.9993    1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9929   -1.9737    1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5457    1.1863    3.4903 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
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  6
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  1
 18 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 24 56  1  0
M  END

Synonyms

Value	Source
(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acid	ChEBI
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acid	ChEBI
(S-(R,s-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid	ChEBI
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acid	ChEBI
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoic acid	ChEBI
5,12-Dihete	ChEBI
5,12-Hete	ChEBI
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid	ChEBI
LTB4	ChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate	Kegg
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoate	Kegg
(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoate	Generator
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate	Generator
(S-(R,s-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoate	Generator
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoate	Generator
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoate	Generator
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoate	Generator
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acid	Generator
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid	Generator
5,12 HETE	HMDB
5,12 DiHETE	HMDB
Leukotriene b-4	HMDB
Leukotrienes b	HMDB
b-4, Leukotriene	HMDB
Leukotriene b 4	HMDB
Leukotriene b	HMDB
5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoate	HMDB
5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoic acid	HMDB
Leukotriene b4 ethanol solution	HMDB
(+)-Leukotriene b4	HMDB
(5S,12R)-Leukotriene b4	HMDB
5(S),12(R)-Dihydroxy-6-cis,8,10-trans,14-cis-eicosatetraenoic acid	HMDB
Leucotriene b4	HMDB
cis-Leukotriene b4	HMDB
Leukotriene B4	HMDB

Molecular Formula

C₂₀H₃₂O₄

Average Mass

336.4657

Monoisotopic Mass

336.230059512

IUPAC Name

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

Traditional Name

leukotriene B4

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1

InChI Key

VNYSSYRCGWBHLG-AMOLWHMGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Leukotrienes

Alternative Parents

Substituents

Leukotriene
Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:15647 )
leukotriene (CHEBI:15647 )
dihydroxy monocarboxylic acid (CHEBI:15647 )
polyunsaturated fatty acid (CHEBI:15647 )
hydroxy fatty acid (CHEBI:15647 )
Leukotrienes (C02165 )
Leukotrienes (LMFA03020001 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	5.46	ALOGPS
logP	4.13	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	102.98 m³·mol⁻¹	ChemAxon
Polarizability	39.51 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-7896000000-60973fb1d8ff05c73e4e	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-01rl-9113530000-205b0d713aeb42a9afc2	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-000i-0419000000-061132d646cd5dd85a1b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00ks-0829000000-7da7ab59ee0d4812767b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0002-0933000000-3fb381ce0f3609a90222	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0udj-0931000000-ccfdaa3226146fe9edc3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0udj-1940000000-ef988be204f5c54f4b21	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0r00-1910000000-e16cc958487f06dc4287	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0006-6900000000-a356f0334bf220eb54cc	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-052f-9700000000-66a6a217eba63b4874d1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0a4l-7900000000-aeb350579ea4a84117d0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0619000000-dc49d3f4ab097db18f18	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0019000000-39d0f0947681f1f7fc37	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0v4i-5498000000-4599d3006831091f926c	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9450000000-b6647dcbb40f3175983d	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kr-0029000000-d2d2e17f68f90518361e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-2269000000-1a60fcc2f712b3beea2a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9340000000-edfb4e3fd8a8f4667ead	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-74962f74765b30de04ac	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-3659000000-98607094f1fa036e16e2	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-5191000000-91a6c7d4dfff9bd70967	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-0019000000-bbfb0bde6a04ea9b05bc	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-3439000000-d8140c418a63ad2159a3	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ar0-9320000000-afb563cb7a2b51e02836	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Leukocyte
Platelet
Urine

Tissue Locations

Epidermis
Leukocyte
Platelet

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192625	Leukotriene-B(4) omega-hydroxylase 1	Unknown	P78329	Homo sapiens
MMDBp0192626	Leukotriene-B(4) omega-hydroxylase 2	Unknown	Q08477	Homo sapiens
MMDBp0192627	Leukotriene A-4 hydrolase	Unknown	P09960	Homo sapiens
MMDBp0193100	Cytochrome P450 4F11	Unknown	Q9HBI6	Homo sapiens
MMDBp0193119	Cytochrome P450 4F8	Unknown	P98187	Homo sapiens
MMDBp0193291	Leukotriene B4 receptor 1	Unknown	Q15722	Homo sapiens
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo sapiens
MMDBp0194559	Leukotriene B4 receptor 2	Unknown	Q9NPC1	Homo sapiens
MMDBp0195407	Cytochrome P450 4F22	Unknown	Q6NT55	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001593	leukotriene A4	Leukotriene B4	leukotriene A4 hydrolase	VMH	7918238
MMDBr0001876	Leukotriene B4	20-Hydroxy-leukotriene B4	cytochrome P450, family 4, subfamily F, polypeptide 12	VMH	15145985 15579107 8026587 8486631
MMDBr0004439	Leukotriene B4	12-Oxo-Leukotriene B4	carbonyl reductase 1	VMH	11368003 9799565 9862787
MMDBr0004440	Leukotriene B4	12-Oxo-Leukotriene B4	dehydrogenase/reductase (SDR family) member 4	VMH	11368003 9799565 9862787
MMDBr0004441	Leukotriene B4	12-Oxo-Leukotriene B4	Not Available	VMH	11368003 9799565 9862787
MMDBr0004442	Leukotriene B4	12-Oxo-Leukotriene B4	dehydrogenase/reductase (SDR family) member 4	VMH	11368003 9799565 9862787
MMDBr0004828	Leukotriene B4	5-Oxo-12(S)-Hydroxy-Eicosa-6E,8Z,10E,14Z-Tetraenoate	carbonyl reductase 1	VMH	1326548 7929234
MMDBr0004829	Leukotriene B4	5-Oxo-12(S)-Hydroxy-Eicosa-6E,8Z,10E,14Z-Tetraenoate	dehydrogenase/reductase (SDR family) member 4	VMH	1326548 7929234
MMDBr0004830	Leukotriene B4	5-Oxo-12(S)-Hydroxy-Eicosa-6E,8Z,10E,14Z-Tetraenoate	dehydrogenase/reductase (SDR family) member 4	VMH	1326548 7929234
MMDBr0004868	12-Hydroxyeicosatetraenoate	Leukotriene B4	Not Available	VMH	10224163 2377602 9837935
MMDBr0004869	12-Hydroxyeicosatetraenoate	Leukotriene B4	arachidonate 5-lipoxygenase	VMH	10224163 2377602 9837935
MMDBr0004870	12-Hydroxyeicosatetraenoate	Leukotriene B4	Not Available	VMH	10224163 2377602 9837935
MMDBr0004871	Leukotriene B4	5,12,20-Trihete	Not Available	VMH	10224163 2377602 9837935
MMDBr0004872	Leukotriene B4	5,12,20-Trihete	cytochrome P450, family 4, subfamily F, polypeptide 2	VMH	10224163 2377602 9837935
MMDBr0004890	5-HETE	Leukotriene B4	arachidonate 12-lipoxygenase	VMH	1326548 7929234
MMDBr0004891	5-HETE	Leukotriene B4	Not Available	VMH	1326548 7929234
MMDBr0004892	5-HETE	Leukotriene B4	Not Available	VMH	1326548 7929234
MMDBr0004893	5-HETE	Leukotriene B4	Not Available	VMH	1326548 7929234
MMDBr0004894	5-HETE	Leukotriene B4	Not Available	VMH	1326548 7929234
MMDBr0009400	Leukotriene B4	5,12,20-Trihete	cytochrome P450, family 4, subfamily F, polypeptide 11	VMH	30371894
MMDBr0009435	12-Hydroxyeicosatetraenoate	Leukotriene B4	arachidonate 5-lipoxygenase	VMH	30371894
MMDBr0009445	Leukotriene B4	12-Oxo-Leukotriene B4	carbonyl reductase 1	VMH; KEGG	30371894
MMDBr0009449	Leukotriene B4	20-Hydroxy-leukotriene B4	cytochrome P450, family 4, subfamily F, polypeptide 11	VMH; KEGG	30371894
MMDBr0009450	Leukotriene B4	20-Hydroxy-leukotriene B4	cytochrome P450, family 4, subfamily F, polypeptide 11	VMH; KEGG	30371894
MMDBr0010827	Leukotriene B4	5-Oxo-(6E,8Z,11Z,14Z)-Eicosatetraenoic Acid	carbonyl reductase 1	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Aseptic meningitis	Slight Increase	Association	Human Cerebrospinal Fluid (CSF)	HMDB	8703223
Hydrocephalus		Association	Human Cerebrospinal Fluid (CSF)	HMDB	2835791
Meningitis		Association	Human Cerebrospinal Fluid (CSF)	HMDB	2835791

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1		Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00477	0.000813			uM	Children (1-13 years old)	Not Specified	Aseptic meningitis	HMDB	8703223
Human Blood	Detected and Quantified	0.00015	0.00005			uM	Infant (0-1 year old)	Both	Postoperative pulmonary hypertension	HMDB	10543508
Human Blood	Detected and Quantified	0.00016	0.00006			uM	Infant (0-1 year old)	Both	Postoperative pulmonary hypertension	HMDB	10543508
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.000177				uM	Adult (>18 years old)	Male	glutathione synthetase deficiency, acute metabolic crisis	HMDB	15243994
Human Cerebrospinal fluid (csf)	Detected and Quantified	<0.000595				uM	Not Specified	Not Specified	hydrocephalus	HMDB	2835791
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0002				uM	Infant (0-1 year old)	Female	Leukotriene C4-Synthesis Deficiency	HMDB	9820300
Human Blood	Detected and Quantified	0.082				uM	Infant (0-1 year old)	Female	Leukotriene C4-Synthesis Deficiency	HMDB	9820300
Human Urine	Detected and Quantified	<0.000000005				umol/mmol creatinine	Infant (0-1 year old)	Female	Leukotriene C4-Synthesis Deficiency	HMDB	9820300
Human Cerebrospinal fluid (csf)	Detected and Quantified	<0.000297				uM	Not Specified	Not Specified	meningitis	HMDB	2835791
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00014	0.00002			uM	Children (1-13 years old)	Both	Sjögren-Larsson syndrome	HMDB	11166796
Human Urine	Detected and Quantified	<0.000000005				umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	9820300
Human Blood	Detected and Quantified	<0.0001				uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Urine	Detected and Quantified			0	0.000005	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	11166796
Human Urine	Detected and Quantified	0.00003	0.000014			umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	11166796
Human Blood	Detected and Quantified	0.000037	0.000007			uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	0.00009686	0.0000062			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00011	0.00006			uM	Children (1-13 years old)	Both	Normal	HMDB	11166796
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.000115	0.00005706			uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	9820300
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.000115	0.00005710			uM	Not Specified	Not Specified	Normal	HMDB	15243994
Human Blood	Detected and Quantified	0.000296	0.000292			uM	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human Blood	Detected and Quantified	0.000296	0.000292			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.00363	0.000480			uM	Children (1-13 years old)	Not Specified	Normal	HMDB	8703223
Human Blood	Detected and Quantified	0.0309	0.00178			uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	9820300
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Leukocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001085

DrugBank ID

DB12961

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02165

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Leukotriene_B4

METLIN ID

Not Available

PubChem Compound

5280492

PDB ID

Not Available

ChEBI ID

15647

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Nieminen MM, Moilanen EK, Koskinen MO, Karvonen JI, Tuomisto L, Metsa-Ketela TJ, Vapaatalo H: Inhaled budesonide fails to inhibit the PAF-induced increase in plasma leukotriene B4 in man. Br J Clin Pharmacol. 1992 Jun;33(6):645-52. doi: 10.1111/j.1365-2125.1992.tb04095.x. [PubMed:1327049 ]
Sieunarine K, Lawrence-Brown MM, Goodman MA, Prendergast FJ, Rocchetta S: Plasma levels of the lipid mediators, leukotriene B4 and lyso platelet-activating factor, in intraoperative salvaged blood. Vox Sang. 1992;63(3):168-71. doi: 10.1111/j.1423-0410.1992.tb05095.x. [PubMed:1333134 ]
Pacheco Y, Hosni R, Chabannes B, Gormand F, Moliere P, Grosclaude M, Piperno D, Lagarde M, Perrin-Fayolle M: Leukotriene B4 level in stimulated blood neutrophils and alveolar macrophages from healthy and asthmatic subjects. Effect of beta-2 agonist therapy. Eur J Clin Invest. 1992 Nov;22(11):732-9. doi: 10.1111/j.1365-2362.1992.tb01437.x. [PubMed:1335872 ]
Fogh J, Poulsen LK, Bisgaard H: A specific assay for leukotriene B4 in human whole blood. J Pharmacol Toxicol Methods. 1992 Dec;28(4):185-90. doi: 10.1016/1056-8719(92)90002-i. [PubMed:1338371 ]
Ahmadzadeh N, Shingu M, Nobunaga M, Tawara T: Relationship between leukotriene B4 and immunological parameters in rheumatoid synovial fluids. Inflammation. 1991 Dec;15(6):497-503. doi: 10.1007/BF00923346. [PubMed:1661709 ]
Blackburn WD Jr, Heck LW, Loose LD, Eskra JD, Carty TJ: Inhibition of 5-lipoxygenase product formation and polymorphonuclear cell degranulation by tenidap sodium in patients with rheumatoid arthritis. Arthritis Rheum. 1991 Feb;34(2):204-10. doi: 10.1002/art.1780340212. [PubMed:1847289 ]
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Showing metabocard for Leukotriene B4 (MMDBc0000772)

MOL for #<Metabolite:0x00007fdb4967a698>

3D MOL for #<Metabolite:0x00007fdb4967a698>

3D SDF for #<Metabolite:0x00007fdb4967a698>

3D-SDF for #<Metabolite:0x00007fdb4967a698>

PDB for #<Metabolite:0x00007fdb4967a698>

3D PDB for #<Metabolite:0x00007fdb4967a698>

SMILES for #<Metabolite:0x00007fdb4967a698>

INCHI for #<Metabolite:0x00007fdb4967a698>

Structure for #<Metabolite:0x00007fdb4967a698>

3D Structure for #<Metabolite:0x00007fdb4967a698>