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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:30 UTC

Update Date

2022-03-07 02:49:12 UTC

HMDB ID

HMDB0001977

Secondary Accession Numbers

HMDB01977

Metabolite Identification

Common Name

Trioxilin A3

Description

Trioxilin A3 is the enzymatically formed derivative of Hepoxilin A3. Normal human epidermis incubated with exogenous AA produces 12-oxo-eicosatetraenoic acid (12-oxo-ETE), hepoxilin A3 (HxA3), and hepoxilin B3 (HxB3) through the 12- Lipoxygenase (LO) pathway. 12-LO is the major arachidonic acid (AA) oxygenation pathway in epidermal cells with total product formation generally exceeding cyclooxygenase activity. Platelet-type 12-LO has been found to be the predominant isoenzyme expressed in human and murine skin epidermis. Increased levels of nonesterified hepoxilins and trioxilins occur in the psoriatic scales. Normal human epidermis synthesized only one of the two possible 10-hydroxy epimers of HxB3 whose formation is probably catalyzed by 12-LO. Hepoxilins exert action on plasma permeability on skin, and induce a specific-receptor-dependent Ca2+ mobilization from endogenous sources and the release of AA and diacylglycerols. (PMID: 11851887 ).

Structure

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

HMDB0001977
     RDKit          3D
Trioxilin A3
 59 58  0  0  0  0  0  0  0  0999 V2000
   -7.3731   -2.1544   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0506   -1.6659    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6032   -1.8976    0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6539   -1.2037   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9052    0.3004   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7081    0.7924    1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    1.6836    1.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    2.3240    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954    1.9880    0.9585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2966    2.4787    2.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257    2.7387    0.0727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6865    2.2855   -1.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504    2.4385    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4243    1.2652    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.0163    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1318    1.8503    1.8955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524    1.2106   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347    0.2737   -1.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -0.6528   -1.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5838   -0.8349   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7147   -2.2327   -0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0665   -2.5192   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3764   -1.6289    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5910   -0.7804    1.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6405   -1.7286    1.3785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3369   -1.3382   -1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3982   -2.6148   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6795   -2.9376   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3457   -0.6136    0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6532   -2.2577    0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4098   -2.9975    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4601   -1.5861    1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6201   -1.3389    0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671   -1.6019   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9693    0.5014   -0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2772    0.7208   -1.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3505    0.3932    1.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8023    1.9550    2.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881    2.0544   -0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    3.4428    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3402    0.9110    0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475    3.4636    2.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194    3.8253    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6391    1.3091   -1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4223    3.1698    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329    0.4736   -0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8716   -0.0541    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8162    2.4712    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7820    1.2986   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    2.2373   -0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    0.3611   -1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370   -1.2779   -2.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2478   -0.8288   -2.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873   -0.0421   -0.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4413   -2.9175   -1.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705   -2.4608   -0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0654   -3.6031   -0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7958   -2.3729   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3539   -1.0580    1.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 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  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  1
 10 42  1  0
 11 43  1  6
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 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 02231219182D          

 25 24  0  0  1  0            999 V2000
   15.9886   -3.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7031   -5.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8464   -3.1900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4188   -7.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1333   -6.4900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9886   -4.0150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7031   -4.4274    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2741   -4.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1306   -5.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1306   -6.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8453   -5.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5596   -4.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4162   -6.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8453   -4.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4175   -4.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8464   -4.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1319   -4.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5609   -4.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4162   -7.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9899   -5.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2753   -4.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7042   -5.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9899   -4.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7042   -6.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4188   -6.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  7  2  1  1  0  0  0
  3 16  1  0  0  0  0
  4 25  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 15  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 14  2  0  0  0  0
 13 19  1  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001977

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/c1-2-3-4-5-6-10-13-18(22)19(23)16-15-17(21)12-9-7-8-11-14-20(24)25/h6-7,9-10,15-19,21-23H,2-5,8,11-14H2,1H3,(H,24,25)/b9-7-,10-6-,16-15+/t17?,18-,19+/m0/s1

> <INCHI_KEY>
WPLPEZUSILBTGP-CIQDQOFUSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.59373251455416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,9E,11R,12S,14Z)-8,11,12-trihydroxyicosa-5,9,14-trienoic acid

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
3.4125667266666655

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.607742863193021

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.676900471667817

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8712367806303405

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
103.22989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trioxilin A3

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001977
     RDKit          3D
Trioxilin A3
 59 58  0  0  0  0  0  0  0  0999 V2000
   -7.3731   -2.1544   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0506   -1.6659    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6032   -1.8976    0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6539   -1.2037   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9052    0.3004   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7081    0.7924    1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    1.6836    1.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    2.3240    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954    1.9880    0.9585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2966    2.4787    2.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257    2.7387    0.0727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6865    2.2855   -1.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504    2.4385    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4243    1.2652    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.0163    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1318    1.8503    1.8955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524    1.2106   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347    0.2737   -1.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -0.6528   -1.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5838   -0.8349   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7147   -2.2327   -0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0665   -2.5192   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3764   -1.6289    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5910   -0.7804    1.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6405   -1.7286    1.3785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3369   -1.3382   -1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3982   -2.6148   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6795   -2.9376   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3457   -0.6136    0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6532   -2.2577    0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4098   -2.9975    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4601   -1.5861    1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6201   -1.3389    0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671   -1.6019   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9693    0.5014   -0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2772    0.7208   -1.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3505    0.3932    1.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8023    1.9550    2.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881    2.0544   -0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    3.4428    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3402    0.9110    0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475    3.4636    2.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194    3.8253    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6391    1.3091   -1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4223    3.1698    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329    0.4736   -0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8716   -0.0541    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8162    2.4712    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7820    1.2986   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    2.2373   -0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    0.3611   -1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370   -1.2779   -2.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2478   -0.8288   -2.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873   -0.0421   -0.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4413   -2.9175   -1.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705   -2.4608   -0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0654   -3.6031   -0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7958   -2.3729   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3539   -1.0580    1.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 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  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  1
 10 42  1  0
 11 43  1  6
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 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                                 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      29.845  -5.955   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.179  -9.805   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.180  -5.955   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      41.848 -14.425   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      43.182 -12.115   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      29.845  -7.495   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.179  -8.265   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.512  -8.265   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.511 -10.575   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.511 -12.115   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.845  -9.805   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.178  -7.495   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.177 -12.885   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.845  -8.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.513  -7.495   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      35.180  -7.495   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.846  -8.265   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.514  -8.265   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.177 -14.425   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.181  -9.805   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.847  -7.495   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      40.514 -10.575   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      39.181  -8.265   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      40.514 -12.115   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      41.848 -12.885   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   16                                                            
CONECT    4   25                                                            
CONECT    5   25                                                            
CONECT    6    1    7    8                                                  
CONECT    7    2    6   15                                                  
CONECT    8    6   12                                                       
CONECT    9   10   11                                                       
CONECT   10    9   13                                                       
CONECT   11    9   14                                                       
CONECT   12    8   14                                                       
CONECT   13   10   19                                                       
CONECT   14   11   12                                                       
CONECT   15    7   17                                                       
CONECT   16    3   17   18                                                  
CONECT   17   15   16                                                       
CONECT   18   16   21                                                       
CONECT   19   13                                                            
CONECT   20   22   23                                                       
CONECT   21   18   23                                                       
CONECT   22   20   24                                                       
CONECT   23   20   21                                                       
CONECT   24   22   25                                                       
CONECT   25    4    5   24                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0001977
HETATM    1  C1  UNL     1      -7.373  -2.154  -1.191  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.051  -1.666   0.196  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.603  -1.898   0.578  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.654  -1.204  -0.334  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.905   0.300  -0.320  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.708   0.792   1.050  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.832   1.684   1.419  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.908   2.324   0.484  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.495   1.988   0.959  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.297   2.479   2.264  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.526   2.739   0.073  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.687   2.285  -1.227  1.00  0.00           O  
HETATM   13  C11 UNL     1       0.850   2.438   0.563  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.424   1.265   0.333  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.796   1.016   0.842  1.00  0.00           C  
HETATM   16  O3  UNL     1       3.132   1.850   1.895  1.00  0.00           O  
HETATM   17  C14 UNL     1       3.752   1.211  -0.339  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.435   0.274  -1.416  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.216  -0.653  -1.933  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.584  -0.835  -1.428  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.715  -2.233  -0.894  1.00  0.00           C  
HETATM   22  C19 UNL     1       7.066  -2.519  -0.353  1.00  0.00           C  
HETATM   23  C20 UNL     1       7.376  -1.629   0.779  1.00  0.00           C  
HETATM   24  O4  UNL     1       6.591  -0.780   1.253  1.00  0.00           O  
HETATM   25  O5  UNL     1       8.640  -1.729   1.378  1.00  0.00           O  
HETATM   26  H1  UNL     1      -7.337  -1.338  -1.949  1.00  0.00           H  
HETATM   27  H2  UNL     1      -8.398  -2.615  -1.238  1.00  0.00           H  
HETATM   28  H3  UNL     1      -6.679  -2.938  -1.542  1.00  0.00           H  
HETATM   29  H4  UNL     1      -7.346  -0.614   0.361  1.00  0.00           H  
HETATM   30  H5  UNL     1      -7.653  -2.258   0.946  1.00  0.00           H  
HETATM   31  H6  UNL     1      -5.410  -2.997   0.545  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.460  -1.586   1.608  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.620  -1.339   0.044  1.00  0.00           H  
HETATM   34  H9  UNL     1      -4.667  -1.602  -1.371  1.00  0.00           H  
HETATM   35  H10 UNL     1      -5.969   0.501  -0.678  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.277   0.721  -1.095  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.350   0.393   1.865  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.802   1.955   2.496  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.988   2.054  -0.567  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.049   3.443   0.533  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.340   0.911   0.945  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.248   3.464   2.268  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.719   3.825   0.163  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.639   1.309  -1.251  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.422   3.170   1.121  1.00  0.00           H  
HETATM   46  H21 UNL     1       0.933   0.474  -0.215  1.00  0.00           H  
HETATM   47  H22 UNL     1       2.872  -0.054   1.177  1.00  0.00           H  
HETATM   48  H23 UNL     1       3.816   2.471   1.569  1.00  0.00           H  
HETATM   49  H24 UNL     1       4.782   1.299  -0.026  1.00  0.00           H  
HETATM   50  H25 UNL     1       3.472   2.237  -0.731  1.00  0.00           H  
HETATM   51  H26 UNL     1       2.418   0.361  -1.840  1.00  0.00           H  
HETATM   52  H27 UNL     1       3.837  -1.278  -2.737  1.00  0.00           H  
HETATM   53  H28 UNL     1       6.248  -0.829  -2.359  1.00  0.00           H  
HETATM   54  H29 UNL     1       5.987  -0.042  -0.809  1.00  0.00           H  
HETATM   55  H30 UNL     1       5.441  -2.917  -1.744  1.00  0.00           H  
HETATM   56  H31 UNL     1       4.971  -2.461  -0.102  1.00  0.00           H  
HETATM   57  H32 UNL     1       7.065  -3.603  -0.039  1.00  0.00           H  
HETATM   58  H33 UNL     1       7.796  -2.373  -1.192  1.00  0.00           H  
HETATM   59  H34 UNL     1       9.354  -1.058   1.215  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    7   37
CONECT    7    8   38
CONECT    8    9   39   40
CONECT    9   10   11   41
CONECT   10   42
CONECT   11   12   13   43
CONECT   12   44
CONECT   13   14   14   45
CONECT   14   15   46
CONECT   15   16   17   47
CONECT   16   48
CONECT   17   18   49   50
CONECT   18   19   19   51
CONECT   19   20   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

HMDB0001977
     RDKit          3D
Trioxilin A3
 59 58  0  0  0  0  0  0  0  0999 V2000
   -7.3731   -2.1544   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0506   -1.6659    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6032   -1.8976    0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6539   -1.2037   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9052    0.3004   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7081    0.7924    1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    1.6836    1.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    2.3240    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954    1.9880    0.9585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2966    2.4787    2.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257    2.7387    0.0727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6865    2.2855   -1.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504    2.4385    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4243    1.2652    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.0163    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1318    1.8503    1.8955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524    1.2106   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347    0.2737   -1.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -0.6528   -1.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5838   -0.8349   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7147   -2.2327   -0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0665   -2.5192   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3764   -1.6289    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5910   -0.7804    1.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6405   -1.7286    1.3785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3369   -1.3382   -1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3982   -2.6148   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6795   -2.9376   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3457   -0.6136    0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6532   -2.2577    0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4098   -2.9975    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4601   -1.5861    1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6201   -1.3389    0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671   -1.6019   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9693    0.5014   -0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2772    0.7208   -1.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3505    0.3932    1.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8023    1.9550    2.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881    2.0544   -0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    3.4428    0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3402    0.9110    0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475    3.4636    2.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194    3.8253    0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6391    1.3091   -1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4223    3.1698    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329    0.4736   -0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8716   -0.0541    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8162    2.4712    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7820    1.2986   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717    2.2373   -0.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    0.3611   -1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370   -1.2779   -2.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2478   -0.8288   -2.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873   -0.0421   -0.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4413   -2.9175   -1.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705   -2.4608   -0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0654   -3.6031   -0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7958   -2.3729   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3539   -1.0580    1.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 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  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  1
 10 42  1  0
 11 43  1  6
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 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
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyeicosa-5,9,14-trienoic acid	ChEBI
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyicosa-5,9,14-trienoic acid	ChEBI
(8,11R,12S)-OH 5c9t14t-20:3	ChEBI
(8,11R,12S)-OH 5c9t14t-C20:3	ChEBI
8,11,12-Teta	ChEBI
8,11R,12S-TriOH 5c9t14c-20:3	ChEBI
8,11R,12S-TriOH 5c9t14c-C20:3	ChEBI
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyeicosa-5,9,14-trienoate	Generator
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyicosa-5,9,14-trienoate	Generator
(5Z,9E,11R,12S,14Z)-8,11,12-Trihydroxyicosa-5,9,14-trienoate	HMDB
(5Z,9E,11R,12S,14Z)-8,11,12-Trihydroxyicosa-5,9,14-trienoic acid	HMDB
8,11,12-Trihydroxy-5,9,14-eicosatrienoate	HMDB
8,11,12-Trihydroxy-5,9,14-eicosatrienoic acid	HMDB
8,11R,12S-Trihydroxy-5Z,9E,14Z-eicosatrienoate	HMDB
8,11R,12S-Trihydroxy-5Z,9E,14Z-eicosatrienoic acid	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

(5Z,9E,11R,12S,14Z)-8,11,12-trihydroxyicosa-5,9,14-trienoic acid

Traditional Name

trioxilin A3

CAS Registry Number

68860-46-8

SMILES

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

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-4-5-6-10-13-18(22)19(23)16-15-17(21)12-9-7-8-11-14-20(24)25/h6-7,9-10,15-19,21-23H,2-5,8,11-14H2,1H3,(H,24,25)/b9-7-,10-6-,16-15+/t17?,18-,19+/m0/s1

InChI Key

WPLPEZUSILBTGP-CIQDQOFUSA-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

trioxilin (CHEBI:36203 )
Hepoxilins (C14809 )
Hepoxilins (LMFA03090002 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0001977)
Membrane (HMDB: HMDB0001977)

Source

Exogenous

Exogenous (HMDB: HMDB0001977)

Food

Animal origin

Poultry

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0001977)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.047 g/L	ALOGPS
logP	4.53	ALOGPS
logP	3.41	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-2.9	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	103.23 m³·mol⁻¹	ChemAxon
Polarizability	40.59 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]+	197.342	31661259
DarkChem	[M-H]-	194.095	31661259
AllCCS	[M+H]+	196.058	32859911
AllCCS	[M-H]-	191.492	32859911
DeepCCS	[M+H]+	201.191	30932474
DeepCCS	[M-H]-	198.582	30932474
DeepCCS	[M-2H]-	233.124	30932474
DeepCCS	[M+Na]+	208.352	30932474
AllCCS	[M+H]+	196.1	32859911
AllCCS	[M+H-H2O]+	193.4	32859911
AllCCS	[M+NH4]+	198.5	32859911
AllCCS	[M+Na]+	199.2	32859911
AllCCS	[M-H]-	191.5	32859911
AllCCS	[M+Na-2H]-	193.5	32859911
AllCCS	[M+HCOO]-	195.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.52 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4428 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.98 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	53.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2719.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	216.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	265.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	610.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	476.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	144.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1303.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	547.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1403.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	400.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	393.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	167.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trioxilin A3	CCCCC\C=C/C[C@H](O)[C@H](O)\C=C\C(O)C\C=C/CCCC(O)=O	4490.8	Standard polar	33892256
Trioxilin A3	CCCCC\C=C/C[C@H](O)[C@H](O)\C=C\C(O)C\C=C/CCCC(O)=O	2635.0	Standard non polar	33892256
Trioxilin A3	CCCCC\C=C/C[C@H](O)[C@H](O)\C=C\C(O)C\C=C/CCCC(O)=O	2821.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trioxilin A3,1TMS,isomer #1	CCCCC/C=C\C[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C(O)C/C=C\CCCC(=O)O	2890.0	Semi standard non polar	33892256
Trioxilin A3,1TMS,isomer #2	CCCCC/C=C\C[C@H](O)[C@@H](/C=C/C(O)C/C=C\CCCC(=O)O)O[Si](C)(C)C	2923.6	Semi standard non polar	33892256
Trioxilin A3,1TMS,isomer #3	CCCCC/C=C\C[C@H](O)[C@H](O)/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C	2995.7	Semi standard non polar	33892256
Trioxilin A3,1TMS,isomer #4	CCCCC/C=C\C[C@H](O)[C@H](O)/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C	2897.5	Semi standard non polar	33892256
Trioxilin A3,2TMS,isomer #1	CCCCC/C=C\C[C@H](O[Si](C)(C)C)[C@@H](/C=C/C(O)C/C=C\CCCC(=O)O)O[Si](C)(C)C	2887.7	Semi standard non polar	33892256
Trioxilin A3,2TMS,isomer #2	CCCCC/C=C\C[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C	2916.8	Semi standard non polar	33892256
Trioxilin A3,2TMS,isomer #3	CCCCC/C=C\C[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C	2849.6	Semi standard non polar	33892256
Trioxilin A3,2TMS,isomer #4	CCCCC/C=C\C[C@H](O)[C@@H](/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2918.1	Semi standard non polar	33892256
Trioxilin A3,2TMS,isomer #5	CCCCC/C=C\C[C@H](O)[C@@H](/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2869.6	Semi standard non polar	33892256
Trioxilin A3,2TMS,isomer #6	CCCCC/C=C\C[C@H](O)[C@H](O)/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2908.0	Semi standard non polar	33892256
Trioxilin A3,3TMS,isomer #1	CCCCC/C=C\C[C@H](O[Si](C)(C)C)[C@@H](/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2862.1	Semi standard non polar	33892256
Trioxilin A3,3TMS,isomer #2	CCCCC/C=C\C[C@H](O[Si](C)(C)C)[C@@H](/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2822.8	Semi standard non polar	33892256
Trioxilin A3,3TMS,isomer #3	CCCCC/C=C\C[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2833.5	Semi standard non polar	33892256
Trioxilin A3,3TMS,isomer #4	CCCCC/C=C\C[C@H](O)[C@@H](/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2844.8	Semi standard non polar	33892256
Trioxilin A3,4TMS,isomer #1	CCCCC/C=C\C[C@H](O[Si](C)(C)C)[C@@H](/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2813.4	Semi standard non polar	33892256
Trioxilin A3,1TBDMS,isomer #1	CCCCC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C(O)C/C=C\CCCC(=O)O	3162.3	Semi standard non polar	33892256
Trioxilin A3,1TBDMS,isomer #2	CCCCC/C=C\C[C@H](O)[C@@H](/C=C/C(O)C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3171.4	Semi standard non polar	33892256
Trioxilin A3,1TBDMS,isomer #3	CCCCC/C=C\C[C@H](O)[C@H](O)/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3237.2	Semi standard non polar	33892256
Trioxilin A3,1TBDMS,isomer #4	CCCCC/C=C\C[C@H](O)[C@H](O)/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3156.6	Semi standard non polar	33892256
Trioxilin A3,2TBDMS,isomer #1	CCCCC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C(O)C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3373.3	Semi standard non polar	33892256
Trioxilin A3,2TBDMS,isomer #2	CCCCC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	3399.4	Semi standard non polar	33892256
Trioxilin A3,2TBDMS,isomer #3	CCCCC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	3352.7	Semi standard non polar	33892256
Trioxilin A3,2TBDMS,isomer #4	CCCCC/C=C\C[C@H](O)[C@@H](/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3383.5	Semi standard non polar	33892256
Trioxilin A3,2TBDMS,isomer #5	CCCCC/C=C\C[C@H](O)[C@@H](/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3356.7	Semi standard non polar	33892256
Trioxilin A3,2TBDMS,isomer #6	CCCCC/C=C\C[C@H](O)[C@H](O)/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3398.1	Semi standard non polar	33892256
Trioxilin A3,3TBDMS,isomer #1	CCCCC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3562.6	Semi standard non polar	33892256
Trioxilin A3,3TBDMS,isomer #2	CCCCC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3566.8	Semi standard non polar	33892256
Trioxilin A3,3TBDMS,isomer #3	CCCCC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3589.3	Semi standard non polar	33892256
Trioxilin A3,3TBDMS,isomer #4	CCCCC/C=C\C[C@H](O)[C@@H](/C=C/C(C/C=C\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	3580.3	Semi standard non polar	33892256
Trioxilin A3,4TBDMS,isomer #1	CCCCC/C=C\C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C(C/C=C\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	3729.3	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 - Trioxilin A3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-01p9-5893000000-667fa646d16ff3ad7e48	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trioxilin A3 GC-MS (4 TMS) - 70eV, Positive	splash10-004i-9310777000-178d62278397333a4459	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trioxilin A3 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 - Trioxilin A3 10V, Positive-QTOF	splash10-00kr-0109000000-32057b85f8b26ed1923e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 20V, Positive-QTOF	splash10-02ti-1913000000-317db6ad761ac5229259	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 40V, Positive-QTOF	splash10-00kf-9810000000-a6f6761b8cb7bd092125	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 10V, Negative-QTOF	splash10-0udi-0009000000-be9e9136d023c2d0c23d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 20V, Negative-QTOF	splash10-000l-0936000000-bc633eb61e3eadac39b4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 40V, Negative-QTOF	splash10-0a4i-8920000000-a441615b390fda432670	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 10V, Negative-QTOF	splash10-0udi-0009000000-8ab28281d1aca995297b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 20V, Negative-QTOF	splash10-0udr-0928000000-8b962f22aefddb5f5780	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 40V, Negative-QTOF	splash10-0f6t-2920000000-51f129a191bb5e81edf5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 10V, Positive-QTOF	splash10-00kr-0219000000-2c228f383c6dc0dd0ba4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 20V, Positive-QTOF	splash10-066r-9614000000-fd2c09f329fd6f33cd86	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trioxilin A3 40V, Positive-QTOF	splash10-067i-9500000000-3532b544f7e8849544a0	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

FDB022775

KNApSAcK ID

Not Available

Chemspider ID

4446329

KEGG Compound ID

C14809

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283208

PDB ID

Not Available

ChEBI ID

36203

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

Anton R, Camacho M, Puig L, Vila L: Hepoxilin B3 and its enzymatically formed derivative trioxilin B3 are incorporated into phospholipids in psoriatic lesions. J Invest Dermatol. 2002 Jan;118(1):139-46. [PubMed:11851887 ]

Showing metabocard for Trioxilin A3 (HMDB0001977)

MOL for HMDB0001977 (Trioxilin A3)

3D MOL for HMDB0001977 (Trioxilin A3)

3D SDF for HMDB0001977 (Trioxilin A3)

3D-SDF for HMDB0001977 (Trioxilin A3)

PDB for HMDB0001977 (Trioxilin A3)

3D PDB for HMDB0001977 (Trioxilin A3)

SMILES for HMDB0001977 (Trioxilin A3)

INCHI for HMDB0001977 (Trioxilin A3)

Structure for HMDB0001977 (Trioxilin A3)

3D Structure for HMDB0001977 (Trioxilin A3)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra