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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 17:56:48 UTC

Update Date

2022-07-12 23:05:07 UTC

HMDB ID

HMDB0004385

Secondary Accession Numbers

HMDB04385

Metabolite Identification

Common Name

Lipoxin A4

Description

Lipoxin A4 (LXA4) was first identified in 1984 by Serhan and colleagues as 5-lipoxygenase interaction product of activated leukocytes. Endogenous transcellular biosynthesis of LXA4 occurs via interaction of leukocytes with epithelium, endothelium or platelets. Lipoxins (LXs) or the lipoxygenase interaction products are generated from arachidonic acid via sequential actions of lipoxygenases and subsequent reactions to give specific trihydroxytetraene-containing eicosanoids. These unique structures are formed during cell-cell interactions and appear to act at both temporal and spatially distinct sites from other eicosanoids produced during the course of inflammatory responses and to stimulate natural resolution. Lipoxin A4 (LXA4) and lipoxin B4 (LXB4) are positional isomers that each possesses potent cellular and in vivo actions. These LX structures are conserved across species. The results of numerous studies reviewed in this work now confirm that they are the first recognized eicosanoid chemical mediators that display both potent anti-inflammatory and pro-resolving actions in vivo in disease models that include rabbit, rat, and mouse systems. LXs act at specific GPCRs as agonists to regulate cellular responses of interest in inflammation and resolution. Aspirin has a direct impact in the LX circuit by triggering the biosynthesis of endogenous epimers of LX, termed the aspirin-triggered 15-epi-LX, that share the potent anti-inflammatory actions of LX. (PMID: 16005201 , 16613568 ).

Structure

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

HMDB0004385
     RDKit          3D
Lipoxin A4
 57 56  0  0  0  0  0  0  0  0999 V2000
   -8.2887    0.4251    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4488    0.6868    1.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1699    0.2320    2.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0514    1.0590    1.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    0.7775    2.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    1.6347    1.6466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9990    2.9449    1.8553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282    1.2259    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528    0.8649   -0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7429    0.4899   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8012    0.0993   -2.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314   -0.0422   -2.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6940   -0.1587   -2.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -0.1379   -1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068   -0.6446   -2.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4784   -0.5877   -1.6815 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5848    0.5567   -0.8735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8705   -1.8060   -0.9144 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8935   -2.9225   -1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1010   -1.6268   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3387   -1.2500   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -1.1105    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1830   -0.0323    1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2332    0.7609    0.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9265    0.1720    2.3426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3177    0.3285   -0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7738    1.3234   -0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6617   -0.4716    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3313    0.1312    2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5544    1.7790    1.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1966    0.2666    3.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0529   -0.8471    2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525    0.7565    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2731    2.1381    1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952    0.8816    3.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4653   -0.3172    2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    1.4438    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773    3.3854    2.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5704    1.2300   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312    0.8719    0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7869    0.5406   -2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1672   -0.1365   -3.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -0.8599   -3.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220    0.5534   -0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190    0.2406   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380   -1.0646   -3.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1891   -0.4468   -2.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260    0.4538    0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9962   -1.9968   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273   -2.7197   -2.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3160   -2.6827    0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8969   -1.0632    0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2628   -0.2714   -1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6066   -2.0259   -1.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6542   -2.0538    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3774   -0.7979   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9447    0.1052    2.2887 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  2  0
  9 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  1  0
 16 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  1
  7 38  1  0
  8 39  1  0
  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  6
 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 02231219562D          

 25 24  0  0  1  0            999 V2000
   22.8653  -10.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5797  -12.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8666  -14.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2928  -11.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0073  -10.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8653  -11.5874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.1507  -11.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2956  -15.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4363  -11.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2956  -14.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0101  -15.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5797  -11.9999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.5812  -14.0624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.0101  -16.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7218  -11.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2942  -11.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7246  -16.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5812  -13.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0073  -11.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0087  -11.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8666  -12.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7232  -11.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8666  -11.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4377  -11.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1522  -11.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
 12  2  1  1  0  0  0
 13  3  1  6  0  0  0
  4 19  1  0  0  0  0
  5 19  2  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 15  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 16  1  0  0  0  0
 13 18  1  0  0  0  0
 14 17  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 18 21  2  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004385

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1

> <INCHI_KEY>
IXAQOQZEOGMIQS-SSQFXEBMSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.4651

> <EXACT_MASS>
352.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.536298981291516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid

> <ALOGPS_LOGP>
4.61

> <JCHEM_LOGP>
3.0506450699999985

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.658863253317975

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475339418208748

> <JCHEM_PKA_STRONGEST_BASIC>
-1.575973533829957

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
104.3465

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lipoxin A4

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004385
     RDKit          3D
Lipoxin A4
 57 56  0  0  0  0  0  0  0  0999 V2000
   -8.2887    0.4251    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4488    0.6868    1.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1699    0.2320    2.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0514    1.0590    1.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    0.7775    2.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    1.6347    1.6466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9990    2.9449    1.8553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282    1.2259    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528    0.8649   -0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7429    0.4899   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8012    0.0993   -2.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314   -0.0422   -2.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6940   -0.1587   -2.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -0.1379   -1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068   -0.6446   -2.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4784   -0.5877   -1.6815 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5848    0.5567   -0.8735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8705   -1.8060   -0.9144 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8935   -2.9225   -1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1010   -1.6268   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3387   -1.2500   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -1.1105    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1830   -0.0323    1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2332    0.7609    0.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9265    0.1720    2.3426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3177    0.3285   -0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7738    1.3234   -0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6617   -0.4716    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3313    0.1312    2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5544    1.7790    1.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1966    0.2666    3.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0529   -0.8471    2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525    0.7565    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2731    2.1381    1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952    0.8816    3.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4653   -0.3172    2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    1.4438    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773    3.3854    2.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5704    1.2300   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312    0.8719    0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7869    0.5406   -2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1672   -0.1365   -3.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -0.8599   -3.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220    0.5534   -0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190    0.2406   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380   -1.0646   -3.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1891   -0.4468   -2.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260    0.4538    0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9962   -1.9968   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273   -2.7197   -2.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3160   -2.6827    0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8969   -1.0632    0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2628   -0.2714   -1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6066   -2.0259   -1.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6542   -2.0538    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3774   -0.7979   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9447    0.1052    2.2887 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  2  0
  9 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  1  0
 16 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  1
  7 38  1  0
  8 39  1  0
  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  6
 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  O   UNK     0      42.682 -20.090   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      44.015 -23.940   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      52.018 -27.020   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      36.013 -22.400   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      37.347 -20.090   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      42.682 -21.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.348 -22.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      54.685 -28.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      40.014 -21.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      54.685 -27.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      56.019 -29.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      44.015 -22.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      53.352 -26.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      56.019 -30.870   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      38.681 -22.400   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.349 -21.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      57.353 -31.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      53.352 -24.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.347 -21.630   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      46.683 -22.400   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      52.018 -23.940   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      48.017 -21.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      52.018 -22.400   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      49.350 -22.400   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      50.684 -21.630   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   19                                                            
CONECT    5   19                                                            
CONECT    6    1    7   12                                                  
CONECT    7    6    9                                                       
CONECT    8   10   11                                                       
CONECT    9    7   15                                                       
CONECT   10    8   13                                                       
CONECT   11    8   14                                                       
CONECT   12    2    6   16                                                  
CONECT   13    3   10   18                                                  
CONECT   14   11   17                                                       
CONECT   15    9   19                                                       
CONECT   16   12   20                                                       
CONECT   17   14                                                            
CONECT   18   13   21                                                       
CONECT   19    4    5   15                                                  
CONECT   20   16   22                                                       
CONECT   21   18   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   25                                                       
CONECT   25   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0004385
HETATM    1  C1  UNL     1      -8.289   0.425   0.198  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.449   0.687   1.687  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.170   0.232   2.368  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.051   1.059   1.742  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.698   0.777   2.327  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.617   1.635   1.647  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.999   2.945   1.855  1.00  0.00           O  
HETATM    8  C7  UNL     1      -3.628   1.226   0.225  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.553   0.865  -0.480  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.743   0.490  -1.831  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.801   0.099  -2.611  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.431  -0.042  -2.372  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.694  -0.159  -2.176  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.077  -0.138  -1.597  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.107  -0.645  -2.283  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.478  -0.588  -1.681  1.00  0.00           C  
HETATM   17  O2  UNL     1       4.585   0.557  -0.873  1.00  0.00           O  
HETATM   18  C16 UNL     1       4.870  -1.806  -0.914  1.00  0.00           C  
HETATM   19  O3  UNL     1       4.894  -2.923  -1.725  1.00  0.00           O  
HETATM   20  C17 UNL     1       6.101  -1.627  -0.092  1.00  0.00           C  
HETATM   21  C18 UNL     1       7.339  -1.250  -0.822  1.00  0.00           C  
HETATM   22  C19 UNL     1       8.442  -1.111   0.216  1.00  0.00           C  
HETATM   23  C20 UNL     1       8.183  -0.032   1.188  1.00  0.00           C  
HETATM   24  O4  UNL     1       7.233   0.761   0.981  1.00  0.00           O  
HETATM   25  O5  UNL     1       8.927   0.172   2.343  1.00  0.00           O  
HETATM   26  H1  UNL     1      -9.318   0.329  -0.239  1.00  0.00           H  
HETATM   27  H2  UNL     1      -7.774   1.323  -0.231  1.00  0.00           H  
HETATM   28  H3  UNL     1      -7.662  -0.472   0.075  1.00  0.00           H  
HETATM   29  H4  UNL     1      -9.331   0.131   2.096  1.00  0.00           H  
HETATM   30  H5  UNL     1      -8.554   1.779   1.850  1.00  0.00           H  
HETATM   31  H6  UNL     1      -7.197   0.267   3.448  1.00  0.00           H  
HETATM   32  H7  UNL     1      -7.053  -0.847   2.033  1.00  0.00           H  
HETATM   33  H8  UNL     1      -6.053   0.757   0.660  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.273   2.138   1.752  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.695   0.882   3.417  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.465  -0.317   2.121  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.626   1.444   2.105  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.377   3.385   2.517  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.570   1.230  -0.347  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.631   0.872   0.023  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.787   0.541  -2.267  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.167  -0.137  -3.686  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.243  -0.860  -3.483  1.00  0.00           H  
HETATM   44  H19 UNL     1       0.322   0.553  -0.922  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.319   0.241  -0.651  1.00  0.00           H  
HETATM   46  H21 UNL     1       2.938  -1.065  -3.228  1.00  0.00           H  
HETATM   47  H22 UNL     1       5.189  -0.447  -2.518  1.00  0.00           H  
HETATM   48  H23 UNL     1       4.226   0.454   0.023  1.00  0.00           H  
HETATM   49  H24 UNL     1       3.996  -1.997  -0.170  1.00  0.00           H  
HETATM   50  H25 UNL     1       5.227  -2.720  -2.614  1.00  0.00           H  
HETATM   51  H26 UNL     1       6.316  -2.683   0.328  1.00  0.00           H  
HETATM   52  H27 UNL     1       5.897  -1.063   0.836  1.00  0.00           H  
HETATM   53  H28 UNL     1       7.263  -0.271  -1.349  1.00  0.00           H  
HETATM   54  H29 UNL     1       7.607  -2.026  -1.553  1.00  0.00           H  
HETATM   55  H30 UNL     1       8.654  -2.054   0.695  1.00  0.00           H  
HETATM   56  H31 UNL     1       9.377  -0.798  -0.330  1.00  0.00           H  
HETATM   57  H32 UNL     1       9.945   0.105   2.289  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    9   39
CONECT    9   10   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   18   47
CONECT   17   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

HMDB0004385
     RDKit          3D
Lipoxin A4
 57 56  0  0  0  0  0  0  0  0999 V2000
   -8.2887    0.4251    0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4488    0.6868    1.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1699    0.2320    2.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0514    1.0590    1.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    0.7775    2.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169    1.6347    1.6466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9990    2.9449    1.8553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282    1.2259    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528    0.8649   -0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7429    0.4899   -1.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8012    0.0993   -2.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4314   -0.0422   -2.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6940   -0.1587   -2.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -0.1379   -1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068   -0.6446   -2.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4784   -0.5877   -1.6815 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5848    0.5567   -0.8735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8705   -1.8060   -0.9144 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8935   -2.9225   -1.7248 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1010   -1.6268   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3387   -1.2500   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -1.1105    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1830   -0.0323    1.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2332    0.7609    0.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9265    0.1720    2.3426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3177    0.3285   -0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7738    1.3234   -0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6617   -0.4716    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3313    0.1312    2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5544    1.7790    1.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1966    0.2666    3.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0529   -0.8471    2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0525    0.7565    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2731    2.1381    1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952    0.8816    3.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4653   -0.3172    2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    1.4438    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773    3.3854    2.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5704    1.2300   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312    0.8719    0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7869    0.5406   -2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1672   -0.1365   -3.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -0.8599   -3.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220    0.5534   -0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190    0.2406   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380   -1.0646   -3.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1891   -0.4468   -2.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260    0.4538    0.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9962   -1.9968   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273   -2.7197   -2.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3160   -2.6827    0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8969   -1.0632    0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2628   -0.2714   -1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6066   -2.0259   -1.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6542   -2.0538    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3774   -0.7979   -0.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9447    0.1052    2.2887 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  2  0
  9 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  1  0
 16 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  1
  7 38  1  0
  8 39  1  0
  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  6
 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,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid	ChEBI
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoic acid	ChEBI
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxyeicosa-7,9,11,13-tetraenoic acid	ChEBI
(7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoic acid	ChEBI
5(S),6(R),15(S)-Trihydroxyeicosa-7E,9E,11Z,13E-tetraenoic acid	ChEBI
5S,6R,15S-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid	ChEBI
5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid	ChEBI
5S,6R-LipoxinA4	ChEBI
6R-LXA4	ChEBI
LXA4	ChEBI
(5S,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoate	Generator
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoate	Generator
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxyeicosa-7,9,11,13-tetraenoate	Generator
(7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoate	Generator
5(S),6(R),15(S)-Trihydroxyeicosa-7E,9E,11Z,13E-tetraenoate	Generator
5S,6R,15S-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoate	Generator
5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoate	Generator
5S,6S-Lipoxin a4	HMDB
15-Epi-lxa4	HMDB
15-Epi-lipoxin a4	HMDB
5,6,15-Tri-hete	HMDB
5,6,15-TriHETE	HMDB
5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoic acid	HMDB

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid

Traditional Name

lipoxin A4

CAS Registry Number

89663-86-5

SMILES

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

InChI Identifier

InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1

InChI Key

IXAQOQZEOGMIQS-SSQFXEBMSA-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:6498 )
polyunsaturated fatty acid (CHEBI:6498 )
hydroxy fatty acid (CHEBI:6498 )
lipoxin (CHEBI:6498 )
Lipoxins (C06314 )
Lipoxins (LMFA03040001 )

Ontology

Not Available

Platelet (HMDB: HMDB0004385)

Leukocyte (HMDB: HMDB0004385)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 1617790)

Cellular substructure

Membrane (HMDB: HMDB0004385)
Extracellular (HMDB: HMDB0004385)

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Coronary artery disease (MarkerDB: MDB00000449)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	194.004	30932474
[M-H]-	Not Available	194.004	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001870

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	4.61	ALOGPS
logP	3.05	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-1.6	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	41.54 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]+	192.209	31661259
DarkChem	[M-H]-	192.455	31661259
DeepCCS	[M+H]+	201.872	30932474
DeepCCS	[M-H]-	199.514	30932474
DeepCCS	[M-2H]-	233.562	30932474
DeepCCS	[M+Na]+	208.79	30932474
AllCCS	[M+H]+	194.5	32859911
AllCCS	[M+H-H2O]+	191.8	32859911
AllCCS	[M+NH4]+	197.1	32859911
AllCCS	[M+Na]+	197.8	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 A4	CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O	4963.4	Standard polar	33892256
Lipoxin A4	CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O	2873.2	Standard non polar	33892256
Lipoxin A4	CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O	3099.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lipoxin A4,1TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C	3198.8	Semi standard non polar	33892256
Lipoxin A4,1TMS,isomer #2	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O	3157.1	Semi standard non polar	33892256
Lipoxin A4,1TMS,isomer #3	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C	3154.4	Semi standard non polar	33892256
Lipoxin A4,1TMS,isomer #4	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C	3112.7	Semi standard non polar	33892256
Lipoxin A4,2TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C	3188.5	Semi standard non polar	33892256
Lipoxin A4,2TMS,isomer #2	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3182.2	Semi standard non polar	33892256
Lipoxin A4,2TMS,isomer #3	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3156.1	Semi standard non polar	33892256
Lipoxin A4,2TMS,isomer #4	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C	3175.2	Semi standard non polar	33892256
Lipoxin A4,2TMS,isomer #5	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C	3109.6	Semi standard non polar	33892256
Lipoxin A4,2TMS,isomer #6	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3105.1	Semi standard non polar	33892256
Lipoxin A4,3TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3187.2	Semi standard non polar	33892256
Lipoxin A4,3TMS,isomer #2	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3143.5	Semi standard non polar	33892256
Lipoxin A4,3TMS,isomer #3	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3130.5	Semi standard non polar	33892256
Lipoxin A4,3TMS,isomer #4	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3127.3	Semi standard non polar	33892256
Lipoxin A4,4TMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3155.9	Semi standard non polar	33892256
Lipoxin A4,1TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3450.6	Semi standard non polar	33892256
Lipoxin A4,1TBDMS,isomer #2	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O	3413.6	Semi standard non polar	33892256
Lipoxin A4,1TBDMS,isomer #3	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3408.0	Semi standard non polar	33892256
Lipoxin A4,1TBDMS,isomer #4	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3377.5	Semi standard non polar	33892256
Lipoxin A4,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3676.6	Semi standard non polar	33892256
Lipoxin A4,2TBDMS,isomer #2	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)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 A4,2TBDMS,isomer #3	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3667.6	Semi standard non polar	33892256
Lipoxin A4,2TBDMS,isomer #4	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3671.2	Semi standard non polar	33892256
Lipoxin A4,2TBDMS,isomer #5	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3619.3	Semi standard non polar	33892256
Lipoxin A4,2TBDMS,isomer #6	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3616.4	Semi standard non polar	33892256
Lipoxin A4,3TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](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	3954.0	Semi standard non polar	33892256
Lipoxin A4,3TBDMS,isomer #2	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](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	3914.5	Semi standard non polar	33892256
Lipoxin A4,3TBDMS,isomer #3	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[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	3913.7	Semi standard non polar	33892256
Lipoxin A4,3TBDMS,isomer #4	CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](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	3903.6	Semi standard non polar	33892256
Lipoxin A4,4TBDMS,isomer #1	CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](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	4175.2	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 A4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-02ti-3942000000-539dee31c556f111beef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoxin A4 GC-MS (4 TMS) - 70eV, Positive	splash10-004i-9023156000-8244ac03abe716c2ce53	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoxin A4 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lipoxin A4 LC-ESI-QQ , negative-QTOF	splash10-0fri-0796000000-05d19d6a20bf1380d76e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lipoxin A4 LC-ESI-QQ , negative-QTOF	splash10-0avl-0985000000-f36e867fda44da442a8e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 10V, Positive-QTOF	splash10-00kr-0019000000-19caadde5e524b5ae250	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 20V, Positive-QTOF	splash10-00kr-9466000000-dc971dc55975b569912b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 40V, Positive-QTOF	splash10-000f-9430000000-bc82bb195c4947fa53cf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 10V, Negative-QTOF	splash10-0udi-0009000000-009f9c82d818546c6102	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 20V, Negative-QTOF	splash10-0kai-4379000000-52c1e5333adc5555ffef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 40V, Negative-QTOF	splash10-0a4i-9340000000-ca0cb5410468b7dee5f8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 10V, Negative-QTOF	splash10-0ue9-0009000000-cb99b6286e5f411abaa3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 20V, Negative-QTOF	splash10-0gc0-4459000000-b29437cc7614015ca29b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 40V, Negative-QTOF	splash10-014j-9320000000-477457ab7d09daaade6b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 10V, Positive-QTOF	splash10-014r-0119000000-a8a3218eed37097e38da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 20V, Positive-QTOF	splash10-00kr-1936000000-0ece3e36fd898b1f9097	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoxin A4 40V, Positive-QTOF	splash10-059f-9600000000-18d8014a43feca3a38b6	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Leukocyte
Platelet

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.00007 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000104 +/- 0.000119 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	<0.00007 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.000053 +/- 0.000013 uM	Adult (>18 years old)	Both	Normal	20671299	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.044 +/- 0.0068 uM	Adult (>18 years old)	Both	Coronary artery disease	1617790	details

Associated Disorders and Diseases

Disease References

Coronary artery disease
Brezinski DA, Nesto RW, Serhan CN: Angioplasty triggers intracoronary leukotrienes and lipoxin A4. Impact of aspirin therapy. Circulation. 1992 Jul;86(1):56-63. [PubMed:1617790 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023370

KNApSAcK ID

Not Available

Chemspider ID

4444429

KEGG Compound ID

C06314

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lipoxin

METLIN ID

7058

PubChem Compound

5280914

PDB ID

Not Available

ChEBI ID

6498

Food Biomarker Ontology

Not Available

VMH ID

C06314

MarkerDB ID

MDB00000449

Good Scents ID

Not Available

References

Synthesis Reference

Rodriguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. J.; Lee, T. H. Total synthesis of lipoxin A4 and lipoxin B4 from butadiene. Tetrahedron Letters (2000), 41(6), 823-826.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Nicolaou KC, Marron BE, Veale CA, Webber SE, Dahlen SE, Samuelsson B, Serhan CN: Identification of a novel 7-cis-11-trans-lipoxin A4 generated by human neutrophils: total synthesis, spasmogenic activities and comparison with other geometric isomers of lipoxins A4 and B4. Biochim Biophys Acta. 1989 May 15;1003(1):44-53. [PubMed:2713393 ]
Wu SH, Wu XH, Lu C, Dong L, Chen ZQ: Lipoxin A4 inhibits proliferation of human lung fibroblasts induced by connective tissue growth factor. Am J Respir Cell Mol Biol. 2006 Jan;34(1):65-72. Epub 2005 Sep 1. [PubMed:16141446 ]
Moores KE, Merritt JE: Lipoxin A4 elevates cytosolic calcium in human neutrophils. Eicosanoids. 1991;4(2):89-94. [PubMed:1910866 ]
Sumimoto H, Isobe R, Mizukami Y, Minakami S: Formation of a novel 20-hydroxylated metabolite of lipoxin A4 by human neutrophil microsomes. FEBS Lett. 1993 Jan 11;315(3):205-10. [PubMed:8422907 ]
Bae YS, Park JC, He R, Ye RD, Kwak JY, Suh PG, Ho Ryu S: Differential signaling of formyl peptide receptor-like 1 by Trp-Lys-Tyr-Met-Val-Met-CONH2 or lipoxin A4 in human neutrophils. Mol Pharmacol. 2003 Sep;64(3):721-30. [PubMed:12920210 ]
Tran U, Boyle T, Shupp JW, Hammamieh R, Jett M: Staphylococcal enterotoxin B initiates protein kinase C translocation and eicosanoid metabolism while inhibiting thrombin-induced aggregation in human platelets. Mol Cell Biochem. 2006 Aug;288(1-2):171-8. Epub 2006 Mar 21. [PubMed:16550298 ]
Parkinson JF: Lipoxin and synthetic lipoxin analogs: an overview of anti-inflammatory functions and new concepts in immunomodulation. Inflamm Allergy Drug Targets. 2006 Apr;5(2):91-106. [PubMed:16613568 ]
Andersson P, Serhan CN, Petasis NA, Palmblad J: Interactions between lipoxin A4, the stable analogue 16-phenoxy-lipoxin A4 and leukotriene B4 in cytokine generation by human monocytes. Scand J Immunol. 2004 Sep;60(3):249-56. [PubMed:15320881 ]
Serhan CN: Lipoxins and aspirin-triggered 15-epi-lipoxins are the first lipid mediators of endogenous anti-inflammation and resolution. Prostaglandins Leukot Essent Fatty Acids. 2005 Sep-Oct;73(3-4):141-62. [PubMed:16005201 ]

Enzymes

Enzyme Details

1. Aryl hydrocarbon receptor

General function:: Involved in transcription regulator activity
Specific function:: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:: AHR
Uniprot ID:: P35869
Molecular weight:: 96146.7

Showing metabocard for Lipoxin A4 (HMDB0004385)

MOL for HMDB0004385 (Lipoxin A4)

3D MOL for HMDB0004385 (Lipoxin A4)

3D SDF for HMDB0004385 (Lipoxin A4)

3D-SDF for HMDB0004385 (Lipoxin A4)

PDB for HMDB0004385 (Lipoxin A4)

3D PDB for HMDB0004385 (Lipoxin A4)

SMILES for HMDB0004385 (Lipoxin A4)

INCHI for HMDB0004385 (Lipoxin A4)

Structure for HMDB0004385 (Lipoxin A4)

3D Structure for HMDB0004385 (Lipoxin A4)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes