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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:02:59 UTC

Update Date

2022-03-07 02:51:26 UTC

HMDB ID

HMDB0012563

Secondary Accession Numbers

HMDB12563

Metabolite Identification

Common Name

13,14-Dihydro- lipoxin A4

Description

13,14-Dihydro- lipoxin A4 is a lipoxin derivative. 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

HMDB0012563
     RDKit          3D
13,14-Dihydro- lipoxin A4
 59 58  0  0  0  0  0  0  0  0999 V2000
   -9.1540   -0.7435    0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6882   -0.5440    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9718   -1.8524    0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6109   -1.9946    0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4129   -1.3566    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1350    0.0732    0.4823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9597    0.9046    1.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    0.3502    1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345   -0.2995    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980    0.1299   -1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5515    0.7177   -1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6840    1.0440   -1.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6747    1.6474   -1.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    1.9574   -0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9340    2.5544   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2005    2.8987   -0.8359 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9634    3.2073    0.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2240    1.8101   -0.8659 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5539    1.4046   -2.1580 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    0.6276    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9449   -0.3974   -0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7423   -1.6337    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5471   -2.4176    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7871   -2.0644   -0.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2926   -3.5655    1.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6104   -1.4919    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5979    0.2615    0.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0269   -1.1158    1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8186   -0.2717   -0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3397    0.2586    1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1620   -2.3492    1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6069   -2.5488   -0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3908   -3.1411    0.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6739   -1.9105   -1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1343   -1.7461    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5502   -1.8320   -0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712    0.4463   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676    0.4462    2.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5520    1.4277    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6757   -0.0428    2.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    0.0086    0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6455   -1.4145    0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.0798   -1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    0.9997   -2.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8503    0.8084    0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553    1.9009   -2.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103    1.6891    0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    2.8179   -2.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742    3.8122   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6832    3.7543    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1730    2.2505   -0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7754    0.9692   -2.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    1.0312    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727    0.2166   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1625   -0.5879   -1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8770    0.1095    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8087   -1.4026    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6385   -2.2915    0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771   -3.4398    2.1171 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
  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  6
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  6
 17 50  1  0
 18 51  1  1
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
M  END

  Mrv0541 02251208072D          

 25 24  0  0  1  0            999 V2000
   10.6877  -13.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1002  -12.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9252  -12.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3377  -11.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1627  -11.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5752  -11.2645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1627  -10.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4002  -11.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8127  -11.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6377  -11.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0502  -12.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6377  -13.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0502  -14.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6377  -14.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0502  -15.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6377  -16.2659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0502  -16.9803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8127  -16.2659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4002  -16.9803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4002  -15.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5752  -15.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1627  -14.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3377  -14.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9252  -14.1224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9252  -15.5514    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012563

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/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/h4-7,10,14,17-19,21-23H,2-3,8-9,11-13,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,14-10+/t17-,18-,19-/m1/s1

> <INCHI_KEY>
WRFBDEURXXFJRY-WYMHFOEZSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.915463747707065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.76

> <JCHEM_LOGP>
3.256659266666666

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.658865131639597

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475339880627137

> <JCHEM_PKA_STRONGEST_BASIC>
-1.233888113707776

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
103.3839

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6R,7E,9E,11Z,15R)-5,6,15-trihydroxyicosa-7,9,11-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012563
     RDKit          3D
13,14-Dihydro- lipoxin A4
 59 58  0  0  0  0  0  0  0  0999 V2000
   -9.1540   -0.7435    0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6882   -0.5440    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9718   -1.8524    0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6109   -1.9946    0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4129   -1.3566    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1350    0.0732    0.4823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9597    0.9046    1.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    0.3502    1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345   -0.2995    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980    0.1299   -1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5515    0.7177   -1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6840    1.0440   -1.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6747    1.6474   -1.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    1.9574   -0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9340    2.5544   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2005    2.8987   -0.8359 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9634    3.2073    0.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2240    1.8101   -0.8659 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5539    1.4046   -2.1580 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    0.6276    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9449   -0.3974   -0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7423   -1.6337    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5471   -2.4176    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7871   -2.0644   -0.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2926   -3.5655    1.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6104   -1.4919    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5979    0.2615    0.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0269   -1.1158    1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8186   -0.2717   -0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3397    0.2586    1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1620   -2.3492    1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6069   -2.5488   -0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3908   -3.1411    0.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6739   -1.9105   -1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1343   -1.7461    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5502   -1.8320   -0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712    0.4463   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676    0.4462    2.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5520    1.4277    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6757   -0.0428    2.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    0.0086    0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6455   -1.4145    0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.0798   -1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    0.9997   -2.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8503    0.8084    0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553    1.9009   -2.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103    1.6891    0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    2.8179   -2.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742    3.8122   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6832    3.7543    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1730    2.2505   -0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7754    0.9692   -2.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    1.0312    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727    0.2166   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1625   -0.5879   -1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8770    0.1095    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8087   -1.4026    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6385   -2.2915    0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771   -3.4398    2.1171 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
  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  6
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  6
 17 50  1  0
 18 51  1  1
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      19.950 -25.028   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.720 -23.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.260 -23.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.030 -22.361   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.570 -22.361   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.340 -21.027   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      24.570 -19.693   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      26.880 -21.027   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.650 -22.361   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.190 -22.361   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.960 -23.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.190 -25.028   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.960 -26.362   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.190 -27.696   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.960 -29.029   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.190 -30.363   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      29.960 -31.697   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      27.650 -30.363   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      26.880 -31.697   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      26.880 -29.029   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.340 -29.029   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.570 -27.696   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.030 -27.696   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      22.260 -26.362   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      22.260 -29.029   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0012563
HETATM    1  C1  UNL     1      -9.154  -0.743   0.911  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.688  -0.544   0.394  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.972  -1.852   0.470  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.611  -1.995   0.004  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.413  -1.357   0.484  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.135   0.073   0.482  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.960   0.905   1.214  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.741   0.350   1.022  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.635  -0.300   0.233  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.598   0.130  -1.171  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.552   0.718  -1.667  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.684   1.044  -1.008  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.675   1.647  -1.635  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.921   1.957  -0.905  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.934   2.554  -1.479  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.201   2.899  -0.836  1.00  0.00           C  
HETATM   17  O2  UNL     1       4.963   3.207   0.513  1.00  0.00           O  
HETATM   18  C16 UNL     1       6.224   1.810  -0.866  1.00  0.00           C  
HETATM   19  O3  UNL     1       6.554   1.405  -2.158  1.00  0.00           O  
HETATM   20  C17 UNL     1       5.850   0.628   0.004  1.00  0.00           C  
HETATM   21  C18 UNL     1       6.945  -0.397  -0.104  1.00  0.00           C  
HETATM   22  C19 UNL     1       6.742  -1.634   0.695  1.00  0.00           C  
HETATM   23  C20 UNL     1       5.547  -2.418   0.359  1.00  0.00           C  
HETATM   24  O4  UNL     1       4.787  -2.064  -0.555  1.00  0.00           O  
HETATM   25  O5  UNL     1       5.293  -3.566   1.093  1.00  0.00           O  
HETATM   26  H1  UNL     1      -9.610  -1.492   0.265  1.00  0.00           H  
HETATM   27  H2  UNL     1      -9.598   0.261   0.857  1.00  0.00           H  
HETATM   28  H3  UNL     1      -9.027  -1.116   1.949  1.00  0.00           H  
HETATM   29  H4  UNL     1      -7.819  -0.272  -0.668  1.00  0.00           H  
HETATM   30  H5  UNL     1      -7.340   0.259   1.032  1.00  0.00           H  
HETATM   31  H6  UNL     1      -7.162  -2.349   1.481  1.00  0.00           H  
HETATM   32  H7  UNL     1      -7.607  -2.549  -0.195  1.00  0.00           H  
HETATM   33  H8  UNL     1      -5.391  -3.141   0.050  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.674  -1.910  -1.158  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.134  -1.746   1.521  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.550  -1.832  -0.128  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.071   0.446  -0.600  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.168   0.446   2.066  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.552   1.428   1.061  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.676  -0.043   2.057  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.702   0.009   0.732  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.646  -1.414   0.339  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.500  -0.080  -1.759  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.628   1.000  -2.732  1.00  0.00           H  
HETATM   45  H20 UNL     1       0.850   0.808   0.022  1.00  0.00           H  
HETATM   46  H21 UNL     1       1.555   1.901  -2.663  1.00  0.00           H  
HETATM   47  H22 UNL     1       3.010   1.689   0.130  1.00  0.00           H  
HETATM   48  H23 UNL     1       3.815   2.818  -2.541  1.00  0.00           H  
HETATM   49  H24 UNL     1       5.674   3.812  -1.268  1.00  0.00           H  
HETATM   50  H25 UNL     1       5.683   3.754   0.897  1.00  0.00           H  
HETATM   51  H26 UNL     1       7.173   2.250  -0.441  1.00  0.00           H  
HETATM   52  H27 UNL     1       5.775   0.969  -2.612  1.00  0.00           H  
HETATM   53  H28 UNL     1       5.820   1.031   1.058  1.00  0.00           H  
HETATM   54  H29 UNL     1       4.873   0.217  -0.277  1.00  0.00           H  
HETATM   55  H30 UNL     1       7.162  -0.588  -1.176  1.00  0.00           H  
HETATM   56  H31 UNL     1       7.877   0.109   0.284  1.00  0.00           H  
HETATM   57  H32 UNL     1       6.809  -1.403   1.787  1.00  0.00           H  
HETATM   58  H33 UNL     1       7.638  -2.292   0.509  1.00  0.00           H  
HETATM   59  H34 UNL     1       5.277  -3.440   2.117  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   39   40
CONECT    9   10   41   42
CONECT   10   11   11   43
CONECT   11   12   44
CONECT   12   13   13   45
CONECT   13   14   46
CONECT   14   15   15   47
CONECT   15   16   48
CONECT   16   17   18   49
CONECT   17   50
CONECT   18   19   20   51
CONECT   19   52
CONECT   20   21   53   54
CONECT   21   22   55   56
CONECT   22   23   57   58
CONECT   23   24   24   25
CONECT   25   59
END

HMDB0012563
     RDKit          3D
13,14-Dihydro- lipoxin A4
 59 58  0  0  0  0  0  0  0  0999 V2000
   -9.1540   -0.7435    0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6882   -0.5440    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9718   -1.8524    0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6109   -1.9946    0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4129   -1.3566    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1350    0.0732    0.4823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9597    0.9046    1.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    0.3502    1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345   -0.2995    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980    0.1299   -1.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5515    0.7177   -1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6840    1.0440   -1.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6747    1.6474   -1.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    1.9574   -0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9340    2.5544   -1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2005    2.8987   -0.8359 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9634    3.2073    0.5128 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2240    1.8101   -0.8659 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5539    1.4046   -2.1580 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    0.6276    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9449   -0.3974   -0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7423   -1.6337    0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5471   -2.4176    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7871   -2.0644   -0.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2926   -3.5655    1.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6104   -1.4919    0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5979    0.2615    0.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0269   -1.1158    1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8186   -0.2717   -0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3397    0.2586    1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1620   -2.3492    1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6069   -2.5488   -0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3908   -3.1411    0.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6739   -1.9105   -1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1343   -1.7461    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5502   -1.8320   -0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712    0.4463   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676    0.4462    2.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5520    1.4277    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6757   -0.0428    2.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    0.0086    0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6455   -1.4145    0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.0798   -1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    0.9997   -2.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8503    0.8084    0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553    1.9009   -2.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103    1.6891    0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    2.8179   -2.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742    3.8122   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6832    3.7543    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1730    2.2505   -0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7754    0.9692   -2.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    1.0312    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727    0.2166   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1625   -0.5879   -1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8770    0.1095    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8087   -1.4026    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6385   -2.2915    0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771   -3.4398    2.1171 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
  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  6
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  6
 17 50  1  0
 18 51  1  1
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5S,6R,15S)-Trihydroxy-(7E,9E,11Z)-eicosatrienoate	HMDB
(5S,6R,15S)-Trihydroxy-(7E,9E,11Z)-eicosatrienoic acid	HMDB
13,14-dihydro-LXA(,4)	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

(5R,6R,7E,9E,11Z,15R)-5,6,15-trihydroxyicosa-7,9,11-trienoic acid

Traditional Name

(5R,6R,7E,9E,11Z,15R)-5,6,15-trihydroxyicosa-7,9,11-trienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H34O5/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/h4-7,10,14,17-19,21-23H,2-3,8-9,11-13,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,14-10+/t17-,18-,19-/m1/s1

InChI Key

WRFBDEURXXFJRY-WYMHFOEZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatrienoic acids

Alternative Parents

Substituents

Hydroxyeicosatrienoic acid
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012563)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012563)

Source

Endogenous

Endogenous (HMDB: HMDB0012563)

Animal

Animal (HMDB: HMDB0012563)

Exogenous

Food

Food (HMDB: HMDB0012563)

Exogenous (HMDB: HMDB0012563)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012563)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012563)

Lipid metabolism pathway (HMDB: HMDB0012563)

Cellular process

Cell signaling (HMDB: HMDB0012563)

Biochemical process

Lipid transport (HMDB: HMDB0012563)

Role

Biological role

Energy source (HMDB: HMDB0012563)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012563)

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	4.76	ALOGPS
logP	3.26	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-1.2	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	15	ChemAxon
Refractivity	103.38 m³·mol⁻¹	ChemAxon
Polarizability	41.92 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]+	190.968	31661259
DarkChem	[M-H]-	191.032	31661259
DeepCCS	[M+H]+	202.86	30932474
DeepCCS	[M-H]-	200.502	30932474
DeepCCS	[M-2H]-	234.656	30932474
DeepCCS	[M+Na]+	210.208	30932474
AllCCS	[M+H]+	195.9	32859911
AllCCS	[M+H-H2O]+	193.3	32859911
AllCCS	[M+NH4]+	198.4	32859911
AllCCS	[M+Na]+	199.1	32859911
AllCCS	[M-H]-	190.9	32859911
AllCCS	[M+Na-2H]-	192.9	32859911
AllCCS	[M+HCOO]-	195.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13,14-Dihydro- lipoxin A4	CCCCC[C@@H](O)CC\C=C/C=C/C=C/[C@@H](O)[C@H](O)CCCC(O)=O	4805.1	Standard polar	33892256
13,14-Dihydro- lipoxin A4	CCCCC[C@@H](O)CC\C=C/C=C/C=C/[C@@H](O)[C@H](O)CCCC(O)=O	2838.2	Standard non polar	33892256
13,14-Dihydro- lipoxin A4	CCCCC[C@@H](O)CC\C=C/C=C/C=C/[C@@H](O)[C@H](O)CCCC(O)=O	3007.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13,14-Dihydro- lipoxin A4,1TMS,isomer #1	CCCCC[C@H](CC/C=C\C=C\C=C\[C@@H](O)[C@H](O)CCCC(=O)O)O[Si](C)(C)C	3138.4	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,1TMS,isomer #2	CCCCC[C@@H](O)CC/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](O)CCCC(=O)O	3136.7	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,1TMS,isomer #3	CCCCC[C@@H](O)CC/C=C\C=C\C=C\[C@@H](O)[C@@H](CCCC(=O)O)O[Si](C)(C)C	3126.4	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,1TMS,isomer #4	CCCCC[C@@H](O)CC/C=C\C=C\C=C\[C@@H](O)[C@H](O)CCCC(=O)O[Si](C)(C)C	3091.5	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TMS,isomer #1	CCCCC[C@H](CC/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](O)CCCC(=O)O)O[Si](C)(C)C	3135.5	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TMS,isomer #2	CCCCC[C@H](CC/C=C\C=C\C=C\[C@@H](O)[C@@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	3126.0	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TMS,isomer #3	CCCCC[C@H](CC/C=C\C=C\C=C\[C@@H](O)[C@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3102.9	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TMS,isomer #4	CCCCC[C@@H](O)CC/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](CCCC(=O)O)O[Si](C)(C)C	3152.3	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TMS,isomer #5	CCCCC[C@@H](O)CC/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](O)CCCC(=O)O[Si](C)(C)C	3099.5	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TMS,isomer #6	CCCCC[C@@H](O)CC/C=C\C=C\C=C\[C@@H](O)[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3094.5	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,3TMS,isomer #1	CCCCC[C@H](CC/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	3136.4	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,3TMS,isomer #2	CCCCC[C@H](CC/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	3096.4	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,3TMS,isomer #3	CCCCC[C@H](CC/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	3082.3	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,3TMS,isomer #4	CCCCC[C@@H](O)CC/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	3120.6	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,4TMS,isomer #1	CCCCC[C@H](CC/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	3110.0	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,1TBDMS,isomer #1	CCCCC[C@H](CC/C=C\C=C\C=C\[C@@H](O)[C@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3398.0	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,1TBDMS,isomer #2	CCCCC[C@@H](O)CC/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CCCC(=O)O	3394.7	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,1TBDMS,isomer #3	CCCCC[C@@H](O)CC/C=C\C=C\C=C\[C@@H](O)[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3385.0	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,1TBDMS,isomer #4	CCCCC[C@@H](O)CC/C=C\C=C\C=C\[C@@H](O)[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C	3361.4	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TBDMS,isomer #1	CCCCC[C@H](CC/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	3626.0	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TBDMS,isomer #2	CCCCC[C@H](CC/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	3614.2	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TBDMS,isomer #3	CCCCC[C@H](CC/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	3606.0	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TBDMS,isomer #4	CCCCC[C@@H](O)CC/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	3639.3	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TBDMS,isomer #5	CCCCC[C@@H](O)CC/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	3591.0	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,2TBDMS,isomer #6	CCCCC[C@@H](O)CC/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	3588.2	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,3TBDMS,isomer #1	CCCCC[C@H](CC/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	3899.3	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,3TBDMS,isomer #2	CCCCC[C@H](CC/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	3861.0	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,3TBDMS,isomer #3	CCCCC[C@H](CC/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	3848.9	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,3TBDMS,isomer #4	CCCCC[C@@H](O)CC/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	3863.1	Semi standard non polar	33892256
13,14-Dihydro- lipoxin A4,4TBDMS,isomer #1	CCCCC[C@H](CC/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	4103.3	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 - 13,14-Dihydro- lipoxin A4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-014r-3944000000-5c2b75cf67ef5146bc9c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13,14-Dihydro- lipoxin A4 GC-MS (4 TMS) - 70eV, Positive	splash10-00b9-6313289000-ae71cdb726adc265eef4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13,14-Dihydro- 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 10V, Positive-QTOF	splash10-00kr-0019000000-6c77b52c82fb0309bb39	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 20V, Positive-QTOF	splash10-00ku-9456000000-5787e1ac9fccd0739dfe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 40V, Positive-QTOF	splash10-0006-9330000000-801cc2c10d467dfc03ed	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 10V, Negative-QTOF	splash10-0udi-0009000000-0d49f4b58ebb31b682df	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 20V, Negative-QTOF	splash10-000i-4379000000-9766432761c6dd2738e9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 40V, Negative-QTOF	splash10-0a4i-9340000000-669904acdb57de8f8aeb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 10V, Positive-QTOF	splash10-014r-0119000000-fa2fb724fbc2943a8eb7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 20V, Positive-QTOF	splash10-014r-1739000000-7885143353316f514d46	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 40V, Positive-QTOF	splash10-00r6-9400000000-1032bdd6cb9a1074205d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 10V, Negative-QTOF	splash10-0udr-0009000000-0a1436f9efc7e2aab2d6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 20V, Negative-QTOF	splash10-0fri-4349000000-62c84297c96217a0441e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13,14-Dihydro- lipoxin A4 40V, Negative-QTOF	splash10-066v-9320000000-4a445e2526a91ccd3c88	2021-09-23	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

FDB029129

KNApSAcK ID

Not Available

Chemspider ID

30776635

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481469

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 13,14-Dihydro- lipoxin A4 (HMDB0012563)

MOL for HMDB0012563 (13,14-Dihydro- lipoxin A4)

3D MOL for HMDB0012563 (13,14-Dihydro- lipoxin A4)

3D SDF for HMDB0012563 (13,14-Dihydro- lipoxin A4)

3D-SDF for HMDB0012563 (13,14-Dihydro- lipoxin A4)

PDB for HMDB0012563 (13,14-Dihydro- lipoxin A4)

3D PDB for HMDB0012563 (13,14-Dihydro- lipoxin A4)

SMILES for HMDB0012563 (13,14-Dihydro- lipoxin A4)

INCHI for HMDB0012563 (13,14-Dihydro- lipoxin A4)

Structure for HMDB0012563 (13,14-Dihydro- lipoxin A4)

3D Structure for HMDB0012563 (13,14-Dihydro- lipoxin A4)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra