Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-25 10:54:12 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005082

Secondary Accession Numbers

HMDB0062299
HMDB05082
HMDB62299

Metabolite Identification

Common Name

Lipoxin B4

Description

Lipoxins (LXs) and aspirin-triggered lipoxin (ATL) are trihydroxytetraene-containing eicosanoids generated from arachidonic acid that are distinct in structure, formation, and function from the many other proinflammatory lipid-derived mediators. These endogenous eicosanoids have now emerged as founding members of the first class of lipid/chemical mediators involved in the resolution of the inflammatory response. Lipoxin A4 (LXA4), ATL, and their metabolic stable analogs elicit cellular responses and regulate leukocyte trafficking in vivo by activating the specific receptor, ALX. Many of the eicosanoids derived from arachidonic acid (AA2), including prostaglandins (PGs) and leukotrienes (LTs), play important roles as local mediators exerting a wide range of actions relevant in immune hypersensitivity and inflammation. However, recent observations indicate that other agents derived from the lipoxygenase (LO) pathways are formed and play a key role in initiating the resolution of acute inflammation. This phenomenon is an active process that is governed by specific lipid mediators and involves a series of well-orchestrated temporal events. Thus, potent locally released mediators serve as checkpoint controllers of inflammation. In addition to the well-appreciated ability of aspirin to inhibit PGs, aspirin also acetylates cyclooxygenase (COX)-2, triggering the formation of a 15-epimeric form of lipoxins, termed aspirin-triggered LXA4 (ATL). These eicosanoids (i.e. LXA4 and ATL) with a unique trihydroxytetraene structure function as 'stop signals' in inflammation and actively participate in dampening host responses to bring the inflammation to a close, namely, resolution. LXA4 and ATL elicit the multicellular responses via a specific G protein-coupled receptor (GPCR) termed ALX that has been identified in human (PMID: 16968948 , 11478982 ).

Structure

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

HMDB0005082
     RDKit          3D
Lipoxin B4
 57 56  0  0  0  0  0  0  0  0999 V2000
   -9.2619    0.9625   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6378    1.8395    0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4727    1.1401    1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3926    0.7849    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2361    0.0897    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1516   -0.2632   -0.1288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6551   -1.1108   -1.1156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0327   -0.9284    0.6450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5796   -0.0454    1.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -1.5169   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7204   -1.2207   -0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2184   -1.8700   -1.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5023   -1.6524   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -2.3595   -2.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -2.1410   -2.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3309   -1.1801   -1.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6344   -1.0207   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5020   -0.0680   -0.7407 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5587    0.2961   -1.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7672    1.1006   -0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4414    2.1544    0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0857    1.8530    1.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2680    1.0224    1.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9900    0.6499    0.9130 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6776    0.5559    3.1261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6122    0.0048   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5198    0.8295   -1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0969    1.5638   -1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4276    2.0647    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2870    2.7738   -0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9174    0.2292    1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1056    1.7750    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9861    1.7208   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7682    0.1666   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7969    0.8776    1.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5633   -0.7810    1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7700    0.6804   -0.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8979   -1.9837   -0.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5290   -1.7664    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850   -0.2999    2.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978   -2.2756   -0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3711   -0.4942    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689   -2.6246   -1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353   -0.9325   -0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619   -3.1174   -2.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1589   -2.7388   -2.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8607   -0.5877   -0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1186   -1.6428   -2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9473   -0.6802    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8919   -0.5716   -2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3363    1.6226   -1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8229    0.8045    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2077    2.6296   -0.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6462    2.9683    0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2929    1.4501    2.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3587    2.8413    2.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6744    0.6032    3.3723 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  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  1
  9 40  1  0
 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  0
 18 49  1  1
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END


  Mrv0541 02231220212D          

 25 24  0  0  1  0            999 V2000
   10.2213  -16.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3963  -16.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9838  -16.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3963  -18.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9838  -17.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2213  -18.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1588  -17.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1588  -16.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6338  -17.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7463  -16.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8713  -15.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4588  -17.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4588  -16.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7463  -15.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9213  -16.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4588  -14.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8713  -16.7552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9213  -15.3262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5088  -16.0407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8713  -13.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6963  -16.7552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5088  -14.6117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6838  -16.0407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6963  -13.8973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4588  -13.1828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 14  1  0  0  0  0
  9 12  2  0  0  0  0
 10 15  2  0  0  0  0
 11 13  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  6  0  0  0
 18 22  1  1  0  0  0
 18 19  1  0  0  0  0
 19 23  1  1  0  0  0
 20 24  1  0  0  0  0
 20 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005082

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h4-7,9-10,12,15,17-19,21-23H,2-3,8,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,12-9+,15-10+/t17-,18+,19-/m1/s1

> <INCHI_KEY>
UXVRTOKOJOMENI-WLPVFMORSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.221743560171845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-trihydroxyicosa-6,8,10,12-tetraenoic acid

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
3.0506450699999985

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.658633405132488

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6463447307767485

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5455178992223582

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
104.34649999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lipoxin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005082
     RDKit          3D
Lipoxin B4
 57 56  0  0  0  0  0  0  0  0999 V2000
   -9.2619    0.9625   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6378    1.8395    0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4727    1.1401    1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3926    0.7849    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2361    0.0897    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1516   -0.2632   -0.1288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6551   -1.1108   -1.1156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0327   -0.9284    0.6450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5796   -0.0454    1.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -1.5169   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7204   -1.2207   -0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2184   -1.8700   -1.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5023   -1.6524   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -2.3595   -2.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -2.1410   -2.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3309   -1.1801   -1.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6344   -1.0207   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5020   -0.0680   -0.7407 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5587    0.2961   -1.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7672    1.1006   -0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4414    2.1544    0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0857    1.8530    1.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2680    1.0224    1.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9900    0.6499    0.9130 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6776    0.5559    3.1261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6122    0.0048   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5198    0.8295   -1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0969    1.5638   -1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4276    2.0647    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2870    2.7738   -0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9174    0.2292    1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1056    1.7750    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9861    1.7208   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7682    0.1666   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7969    0.8776    1.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5633   -0.7810    1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7700    0.6804   -0.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8979   -1.9837   -0.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5290   -1.7664    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850   -0.2999    2.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978   -2.2756   -0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3711   -0.4942    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689   -2.6246   -1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353   -0.9325   -0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619   -3.1174   -2.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1589   -2.7388   -2.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8607   -0.5877   -0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1186   -1.6428   -2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9473   -0.6802    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8919   -0.5716   -2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3363    1.6226   -1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8229    0.8045    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2077    2.6296   -0.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6462    2.9683    0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2929    1.4501    2.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3587    2.8413    2.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6744    0.6032    3.3723 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  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  1
  9 40  1  0
 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  0
 18 49  1  1
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  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  C   UNK     0      19.080 -31.276   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.540 -31.276   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.770 -29.943   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.540 -33.944   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.770 -32.610   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.080 -33.944   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.230 -32.610   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.230 -29.943   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.850 -32.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.460 -31.276   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.160 -28.609   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.390 -32.610   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.390 -29.943   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.460 -28.609   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.920 -31.276   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.390 -27.275   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.160 -31.276   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.920 -28.609   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.150 -29.943   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.160 -25.942   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      23.700 -31.276   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.150 -27.275   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.610 -29.943   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      23.700 -25.942   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      21.390 -24.608   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8    3   14                                                       
CONECT    9    6   12                                                       
CONECT   10    7   15                                                       
CONECT   11   13   16                                                       
CONECT   12    9   17                                                       
CONECT   13   11   17                                                       
CONECT   14    8   18                                                       
CONECT   15   10   19                                                       
CONECT   16   11   20                                                       
CONECT   17   12   13   21                                                  
CONECT   18   14   22   19                                                  
CONECT   19   15   18   23                                                  
CONECT   20   16   24   25                                                  
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   20                                                            
CONECT   25   20                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0005082
HETATM    1  C1  UNL     1      -9.262   0.963  -0.586  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.638   1.840   0.482  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.473   1.140   1.157  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.393   0.785   0.186  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.236   0.090   0.886  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.152  -0.263  -0.129  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.655  -1.111  -1.116  1.00  0.00           O  
HETATM    8  C7  UNL     1      -3.033  -0.928   0.645  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.580  -0.045   1.598  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.012  -1.517  -0.219  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.720  -1.221  -0.207  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.218  -1.870  -1.114  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.502  -1.652  -1.189  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.346  -2.359  -2.134  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.617  -2.141  -2.211  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.331  -1.180  -1.377  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.634  -1.021  -1.528  1.00  0.00           C  
HETATM   18  C16 UNL     1       6.502  -0.068  -0.741  1.00  0.00           C  
HETATM   19  O3  UNL     1       7.559   0.296  -1.629  1.00  0.00           O  
HETATM   20  C17 UNL     1       5.767   1.101  -0.252  1.00  0.00           C  
HETATM   21  C18 UNL     1       6.441   2.154   0.521  1.00  0.00           C  
HETATM   22  C19 UNL     1       7.086   1.853   1.821  1.00  0.00           C  
HETATM   23  C20 UNL     1       8.268   1.022   1.844  1.00  0.00           C  
HETATM   24  O4  UNL     1       8.990   0.650   0.913  1.00  0.00           O  
HETATM   25  O5  UNL     1       8.678   0.556   3.126  1.00  0.00           O  
HETATM   26  H1  UNL     1      -9.612   0.005  -0.168  1.00  0.00           H  
HETATM   27  H2  UNL     1      -8.520   0.830  -1.417  1.00  0.00           H  
HETATM   28  H3  UNL     1     -10.097   1.564  -1.045  1.00  0.00           H  
HETATM   29  H4  UNL     1      -9.428   2.065   1.250  1.00  0.00           H  
HETATM   30  H5  UNL     1      -8.287   2.774  -0.001  1.00  0.00           H  
HETATM   31  H6  UNL     1      -7.917   0.229   1.645  1.00  0.00           H  
HETATM   32  H7  UNL     1      -7.106   1.775   1.989  1.00  0.00           H  
HETATM   33  H8  UNL     1      -5.986   1.721  -0.267  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.768   0.167  -0.641  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.797   0.878   1.553  1.00  0.00           H  
HETATM   36  H11 UNL     1      -5.563  -0.781   1.459  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.770   0.680  -0.544  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.898  -1.984  -0.724  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.529  -1.766   1.221  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.785  -0.300   2.529  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.298  -2.276  -0.958  1.00  0.00           H  
HETATM   42  H17 UNL     1      -0.371  -0.494   0.482  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.169  -2.625  -1.822  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.935  -0.933  -0.528  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.862  -3.117  -2.811  1.00  0.00           H  
HETATM   46  H21 UNL     1       4.159  -2.739  -2.967  1.00  0.00           H  
HETATM   47  H22 UNL     1       3.861  -0.588  -0.639  1.00  0.00           H  
HETATM   48  H23 UNL     1       6.119  -1.643  -2.294  1.00  0.00           H  
HETATM   49  H24 UNL     1       6.947  -0.680   0.051  1.00  0.00           H  
HETATM   50  H25 UNL     1       7.892  -0.572  -2.024  1.00  0.00           H  
HETATM   51  H26 UNL     1       5.336   1.623  -1.182  1.00  0.00           H  
HETATM   52  H27 UNL     1       4.823   0.805   0.310  1.00  0.00           H  
HETATM   53  H28 UNL     1       7.208   2.630  -0.186  1.00  0.00           H  
HETATM   54  H29 UNL     1       5.646   2.968   0.704  1.00  0.00           H  
HETATM   55  H30 UNL     1       6.293   1.450   2.556  1.00  0.00           H  
HETATM   56  H31 UNL     1       7.359   2.841   2.349  1.00  0.00           H  
HETATM   57  H32 UNL     1       9.674   0.603   3.372  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9   10   39
CONECT    9   40
CONECT   10   11   11   41
CONECT   11   12   42
CONECT   12   13   13   43
CONECT   13   14   44
CONECT   14   15   15   45
CONECT   15   16   46
CONECT   16   17   17   47
CONECT   17   18   48
CONECT   18   19   20   49
CONECT   19   50
CONECT   20   21   51   52
CONECT   21   22   53   54
CONECT   22   23   55   56
CONECT   23   24   24   25
CONECT   25   57
END

HMDB0005082
     RDKit          3D
Lipoxin B4
 57 56  0  0  0  0  0  0  0  0999 V2000
   -9.2619    0.9625   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6378    1.8395    0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4727    1.1401    1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3926    0.7849    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2361    0.0897    0.8864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1516   -0.2632   -0.1288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6551   -1.1108   -1.1156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0327   -0.9284    0.6450 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5796   -0.0454    1.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -1.5169   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7204   -1.2207   -0.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2184   -1.8700   -1.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5023   -1.6524   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3459   -2.3595   -2.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6173   -2.1410   -2.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3309   -1.1801   -1.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6344   -1.0207   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5020   -0.0680   -0.7407 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5587    0.2961   -1.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7672    1.1006   -0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4414    2.1544    0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0857    1.8530    1.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2680    1.0224    1.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9900    0.6499    0.9130 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6776    0.5559    3.1261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6122    0.0048   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5198    0.8295   -1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0969    1.5638   -1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4276    2.0647    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2870    2.7738   -0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9174    0.2292    1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1056    1.7750    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9861    1.7208   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7682    0.1666   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7969    0.8776    1.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5633   -0.7810    1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7700    0.6804   -0.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8979   -1.9837   -0.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5290   -1.7664    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850   -0.2999    2.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978   -2.2756   -0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3711   -0.4942    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689   -2.6246   -1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353   -0.9325   -0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619   -3.1174   -2.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1589   -2.7388   -2.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8607   -0.5877   -0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1186   -1.6428   -2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9473   -0.6802    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8919   -0.5716   -2.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3363    1.6226   -1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8229    0.8045    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2077    2.6296   -0.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6462    2.9683    0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2929    1.4501    2.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3587    2.8413    2.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6744    0.6032    3.3723 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  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  1
  9 40  1  0
 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  0
 18 49  1  1
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5S,14R,6E,8Z,10E,12E,15S)-5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acid	ChEBI
(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-Trihydroxyeicosa-6,8,10,12-tetraenoic acid	ChEBI
(6E,8Z,10E,12E)-(5S,14R,15S)-Trihydroxyicosa-6,8,10,12-tetraenoic acid	ChEBI
5(S),14(R)-Lipoxin b4	ChEBI
5,14,15-Thet	ChEBI
5S,14R,15S-6,10,12-trans-8-cis-TriHETE	ChEBI
5S,14R,15S-8-cis-Lipoxin b	ChEBI
5S,14R,15S-Trihydroxy-6E,8Z,10E,12E-eicosatetraenoic acid	ChEBI
LipoxinB4	ChEBI
LXB4	ChEBI
(5S,14R,6E,8Z,10E,12E,15S)-5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoate	Generator
(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-Trihydroxyeicosa-6,8,10,12-tetraenoate	Generator
(6E,8Z,10E,12E)-(5S,14R,15S)-Trihydroxyicosa-6,8,10,12-tetraenoate	Generator
5S,14R,15S-Trihydroxy-6E,8Z,10E,12E-eicosatetraenoate	Generator
(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-Trihydroxyicosa-6,8,10,12-tetraenoate	HMDB
(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-Trihydroxyicosa-6,8,10,12-tetraenoic acid	HMDB
15-Epi-lipoxin b4	HMDB
15-Epi-LXB(4)	HMDB
5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acid	HMDB
5-Methyl-LXB4	HMDB
5D,14,15l-Trihydroxy-6,8,10,12-eicosatetraenoic acid	HMDB
Lipoxin b4	MeSH

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-trihydroxyicosa-6,8,10,12-tetraenoic acid

Traditional Name

lipoxin

CAS Registry Number

98049-69-5

SMILES

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

InChI Identifier

InChI=1S/C20H32O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h4-7,9-10,12,15,17-19,21-23H,2-3,8,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,12-9+,15-10+/t17-,18+,19-/m1/s1

InChI Key

UXVRTOKOJOMENI-WLPVFMORSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lipoxins. These are eicosanoids with a trihydroxyicosatetraenoic acid skeleton (a c20-fatty acid, with the chain bearing three hydroxyl groups and four double bonds). Lipoxins have four double bonds, which are all conjugated. In some cases a hydroxyl group is substituted by a C=O group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Lipoxins

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:6499 )
polyunsaturated fatty acid (CHEBI:6499 )
hydroxy fatty acid (CHEBI:6499 )
lipoxin (CHEBI:6499 )
Lipoxins (C06315 )
Lipoxins (LMFA03040002 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	3.104	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.047 g/L	ALOGPS
logP	4.54	ALOGPS
logP	3.05	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	104.35 m³·mol⁻¹	ChemAxon
Polarizability	41.22 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	193.126	31661259
DarkChem	[M-H]-	190.399	31661259
DeepCCS	[M+H]+	199.008	30932474
DeepCCS	[M-H]-	196.65	30932474
DeepCCS	[M-2H]-	230.935	30932474
DeepCCS	[M+Na]+	206.163	30932474
AllCCS	[M+H]+	194.4	32859911
AllCCS	[M+H-H2O]+	191.7	32859911
AllCCS	[M+NH4]+	196.9	32859911
AllCCS	[M+Na]+	197.7	32859911
AllCCS	[M-H]-	189.7	32859911
AllCCS	[M+Na-2H]-	191.6	32859911
AllCCS	[M+HCOO]-	193.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lipoxin B4	CCCCC[C@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@@H](O)CCCC(O)=O	4973.9	Standard polar	33892256
Lipoxin B4	CCCCC[C@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@@H](O)CCCC(O)=O	2873.9	Standard non polar	33892256
Lipoxin B4	CCCCC[C@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@@H](O)CCCC(O)=O	3092.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lipoxin B4,1TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O	3151.5	Semi standard non polar	33892256
Lipoxin B4,1TMS,isomer #2	CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C	3156.3	Semi standard non polar	33892256
Lipoxin B4,1TMS,isomer #3	CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C	3213.5	Semi standard non polar	33892256
Lipoxin B4,1TMS,isomer #4	CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C	3113.8	Semi standard non polar	33892256
Lipoxin B4,2TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C	3174.9	Semi standard non polar	33892256
Lipoxin B4,2TMS,isomer #2	CCCCC[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C	3184.3	Semi standard non polar	33892256
Lipoxin B4,2TMS,isomer #3	CCCCC[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C	3100.9	Semi standard non polar	33892256
Lipoxin B4,2TMS,isomer #4	CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3192.7	Semi standard non polar	33892256
Lipoxin B4,2TMS,isomer #5	CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3108.5	Semi standard non polar	33892256
Lipoxin B4,2TMS,isomer #6	CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3163.2	Semi standard non polar	33892256
Lipoxin B4,3TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3186.3	Semi standard non polar	33892256
Lipoxin B4,3TMS,isomer #2	CCCCC[C@H](O[Si](C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3128.6	Semi standard non polar	33892256
Lipoxin B4,3TMS,isomer #3	CCCCC[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3127.8	Semi standard non polar	33892256
Lipoxin B4,3TMS,isomer #4	CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3143.9	Semi standard non polar	33892256
Lipoxin B4,4TMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3155.6	Semi standard non polar	33892256
Lipoxin B4,1TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O	3404.9	Semi standard non polar	33892256
Lipoxin B4,1TBDMS,isomer #2	CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3408.1	Semi standard non polar	33892256
Lipoxin B4,1TBDMS,isomer #3	CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3461.2	Semi standard non polar	33892256
Lipoxin B4,1TBDMS,isomer #4	CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3378.6	Semi standard non polar	33892256
Lipoxin B4,2TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3671.3	Semi standard non polar	33892256
Lipoxin B4,2TBDMS,isomer #2	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3677.3	Semi standard non polar	33892256
Lipoxin B4,2TBDMS,isomer #3	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3615.5	Semi standard non polar	33892256
Lipoxin B4,2TBDMS,isomer #4	CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3672.5	Semi standard non polar	33892256
Lipoxin B4,2TBDMS,isomer #5	CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3616.6	Semi standard non polar	33892256
Lipoxin B4,2TBDMS,isomer #6	CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3675.1	Semi standard non polar	33892256
Lipoxin B4,3TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3952.6	Semi standard non polar	33892256
Lipoxin B4,3TBDMS,isomer #2	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3911.6	Semi standard non polar	33892256
Lipoxin B4,3TBDMS,isomer #3	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3909.1	Semi standard non polar	33892256
Lipoxin B4,3TBDMS,isomer #4	CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3909.4	Semi standard non polar	33892256
Lipoxin B4,4TBDMS,isomer #1	CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4175.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoxin B4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-3392000000-a452e50dffe416dac561	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoxin B4 GC-MS (4 TMS) - 70eV, Positive	splash10-00or-8110966000-fed14b9f9421b815655e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoxin B4 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 10V, Positive-QTOF	splash10-00kr-0019000000-f75597717f15f296bd15	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 20V, Positive-QTOF	splash10-00y0-9386000000-2e771a40b3840c1ead4e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 40V, Positive-QTOF	splash10-05tf-9330000000-dd7c3658c32ea3f12c60	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 10V, Negative-QTOF	splash10-0udi-0009000000-db43773198bd1de17252	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 20V, Negative-QTOF	splash10-0f89-4289000000-ab08cb7957857fbc6083	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 40V, Negative-QTOF	splash10-0a4i-9340000000-bfb62be3534dfa6e6cb7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 10V, Positive-QTOF	splash10-014r-0019000000-9d44e47386ca0709d2ae	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 20V, Positive-QTOF	splash10-014i-3159000000-064a21e6051966543d09	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 40V, Positive-QTOF	splash10-0036-9520000000-ea9cf5d384d9aafb4ccb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 10V, Negative-QTOF	splash10-0udi-0019000000-4a996556cba0a2d6d02a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 20V, Negative-QTOF	splash10-0ue9-3298000000-0edc1c1c64c88a9e1fb3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin B4 40V, Negative-QTOF	splash10-067m-9426000000-32a8e0706ca036a6d4c2	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023621

KNApSAcK ID

Not Available

Chemspider ID

4444430

KEGG Compound ID

C06315

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lipoxin

METLIN ID

Not Available

PubChem Compound

5280915

PDB ID

Not Available

ChEBI ID

6499

Food Biomarker Ontology

Not Available

VMH ID

C06315

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

McMahon B, Mitchell S, Brady HR, Godson C: Lipoxins: revelations on resolution. Trends Pharmacol Sci. 2001 Aug;22(8):391-5. [PubMed:11478982 ]
Chiang N, Serhan CN, Dahlen SE, Drazen JM, Hay DW, Rovati GE, Shimizu T, Yokomizo T, Brink C: The lipoxin receptor ALX: potent ligand-specific and stereoselective actions in vivo. Pharmacol Rev. 2006 Sep;58(3):463-87. [PubMed:16968948 ]
Lipid Maps (LMFA03040002) [Link]

Showing metabocard for Lipoxin B4 (HMDB0005082)

MOL for HMDB0005082 (Lipoxin B4)

3D MOL for HMDB0005082 (Lipoxin B4)

3D SDF for HMDB0005082 (Lipoxin B4)

3D-SDF for HMDB0005082 (Lipoxin B4)

PDB for HMDB0005082 (Lipoxin B4)

3D PDB for HMDB0005082 (Lipoxin B4)

SMILES for HMDB0005082 (Lipoxin B4)

INCHI for HMDB0005082 (Lipoxin B4)

Structure for HMDB0005082 (Lipoxin B4)

3D Structure for HMDB0005082 (Lipoxin B4)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra