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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:14:24 UTC

Update Date

2022-03-07 02:53:44 UTC

HMDB ID

HMDB0033504

Secondary Accession Numbers

HMDB33504

Metabolite Identification

Common Name

AF Toxin II

Description

AF Toxin II belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review a significant number of articles have been published on AF Toxin II.

Structure

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

HMDB0033504
     RDKit          3D
AF Toxin II
 47 47  0  0  0  0  0  0  0  0999 V2000
   -5.5798   -0.9993    0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154   -0.3215   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1616    1.0558    0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2973    1.9211   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8446    1.7082   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6457    1.8649   -1.4566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368    0.8742    0.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475    0.5625    1.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661    0.4521   -0.2448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.3404    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990    0.0484    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489    0.8336   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157    1.7271   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8083    1.6090   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1845    0.5175    0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4337    0.2919    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7467   -0.8179    1.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391   -1.5509    2.1952 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0131   -1.0928    2.2629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -1.7567   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4947   -2.5163   -0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8442   -1.8775   -1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -2.4743   -0.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4967   -0.4198   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228   -1.9866   -0.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4830   -1.2070    1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682   -0.9330    0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3465   -0.2787   -1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2614    1.0153    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3213    1.9785   -1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2919    1.5908    0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1537    2.9872    0.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8282    2.6794    0.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074    1.0568   -1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -0.4735    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.7100    0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5261    1.5529   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3357    2.5705   -1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5608    2.3095   -0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4428   -0.1679    0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1776    0.9760    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6236   -0.4337    2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1018   -2.0866   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -3.5834   -0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531   -2.6214    0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5041   -1.0001   -1.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974   -2.5339   -2.2256 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 20  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
M  END


  Mrv0541 02241216522D          

 23 23  0  0  0  0            999 V2000
   -2.9660    2.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1310    2.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6294    1.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638    1.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973    0.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9630    0.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9630    1.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432    2.6736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936    1.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7103    0.5004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5424    1.3362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8767   -0.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0416   -0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920   -1.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2927   -1.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0438   -1.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287   -2.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645   -2.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9660   -2.6736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7149   -1.2530    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
  3 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033504

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)C(O)C(=O)OC(\C=C\C=C/C=C/C(O)=O)C1(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O6/c1-4-12(2)15(20)16(21)23-13(17(3)11-22-17)9-7-5-6-8-10-14(18)19/h5-10,12-13,15,20H,4,11H2,1-3H3,(H,18,19)/b6-5-,9-7+,10-8+

> <INCHI_KEY>
PXZGUAVTZUPRMI-WDGPHVMXSA-N

> <FORMULA>
C17H24O6

> <MOLECULAR_WEIGHT>
324.3689

> <EXACT_MASS>
324.1572885

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
34.56328261259373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4Z,6E)-8-[(2-hydroxy-3-methylpentanoyl)oxy]-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.3995583270000003

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.47886827413743

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.150558717723623

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9015430177842676

> <JCHEM_POLAR_SURFACE_AREA>
96.36

> <JCHEM_REFRACTIVITY>
87.3741

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4Z,6E)-8-[(2-hydroxy-3-methylpentanoyl)oxy]-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033504
     RDKit          3D
AF Toxin II
 47 47  0  0  0  0  0  0  0  0999 V2000
   -5.5798   -0.9993    0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154   -0.3215   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1616    1.0558    0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2973    1.9211   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8446    1.7082   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6457    1.8649   -1.4566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368    0.8742    0.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475    0.5625    1.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661    0.4521   -0.2448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.3404    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990    0.0484    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489    0.8336   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157    1.7271   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8083    1.6090   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1845    0.5175    0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4337    0.2919    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7467   -0.8179    1.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391   -1.5509    2.1952 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0131   -1.0928    2.2629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -1.7567   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4947   -2.5163   -0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8442   -1.8775   -1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -2.4743   -0.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4967   -0.4198   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228   -1.9866   -0.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4830   -1.2070    1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682   -0.9330    0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3465   -0.2787   -1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2614    1.0153    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3213    1.9785   -1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2919    1.5908    0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1537    2.9872    0.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8282    2.6794    0.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074    1.0568   -1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -0.4735    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.7100    0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5261    1.5529   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3357    2.5705   -1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5608    2.3095   -0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4428   -0.1679    0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1776    0.9760    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6236   -0.4337    2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1018   -2.0866   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -3.5834   -0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531   -2.6214    0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5041   -1.0001   -1.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974   -2.5339   -2.2256 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 20  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.537   4.210   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.978   4.367   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.042   3.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.666   1.870   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.288   0.156   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.664   1.558   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.912   2.339   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.664   3.118   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.014   4.991   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.481   3.431   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.545   2.339   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.326   0.934   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.012   2.494   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.104   1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.637  -0.156   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.078  -0.623   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.545  -2.027   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.546  -3.275   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.948  -2.963   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.040  -4.055   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.600  -3.744   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.537  -4.991   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.068  -2.339   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    5    7    8   14                                             
CONECT    7    6    8                                                       
CONECT    8    6    7                                                       
CONECT    9   10                                                            
CONECT   10    3    9   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14    6   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0033504
HETATM    1  C1  UNL     1      -5.580  -0.999   0.088  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.315  -0.322  -0.366  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.162   1.056   0.211  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.297   1.921  -0.236  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.845   1.708  -0.119  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.646   1.865  -1.457  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.737   0.874   0.462  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.847   0.563   1.697  1.00  0.00           O  
HETATM    9  O3  UNL     1      -0.666   0.452  -0.245  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.326  -0.340   0.303  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.699   0.048   0.274  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.549   0.834  -0.148  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.516   1.727  -0.629  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.808   1.609  -0.308  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.185   0.517   0.563  1.00  0.00           C  
HETATM   16  C13 UNL     1       6.434   0.292   0.962  1.00  0.00           C  
HETATM   17  C14 UNL     1       6.747  -0.818   1.835  1.00  0.00           C  
HETATM   18  O4  UNL     1       5.739  -1.551   2.195  1.00  0.00           O  
HETATM   19  O5  UNL     1       8.013  -1.093   2.263  1.00  0.00           O  
HETATM   20  C15 UNL     1       0.240  -1.757  -0.296  1.00  0.00           C  
HETATM   21  C16 UNL     1       1.495  -2.516  -0.518  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.844  -1.878  -1.341  1.00  0.00           C  
HETATM   23  O6  UNL     1      -0.915  -2.474  -0.078  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.497  -0.420  -0.091  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.623  -1.987  -0.428  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.483  -1.207   1.201  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.468  -0.933   0.012  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.347  -0.279  -1.467  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.261   1.015   1.340  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.321   1.978  -1.337  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.292   1.591   0.172  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.154   2.987   0.096  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.828   2.679   0.412  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.907   1.057  -1.965  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.012  -0.473   1.404  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.322  -0.710   0.958  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.526   1.553  -0.759  1.00  0.00           H  
HETATM   38  H15 UNL     1       3.336   2.571  -1.293  1.00  0.00           H  
HETATM   39  H16 UNL     1       5.561   2.309  -0.697  1.00  0.00           H  
HETATM   40  H17 UNL     1       4.443  -0.168   0.929  1.00  0.00           H  
HETATM   41  H18 UNL     1       7.178   0.976   0.590  1.00  0.00           H  
HETATM   42  H19 UNL     1       8.624  -0.434   2.734  1.00  0.00           H  
HETATM   43  H20 UNL     1       2.102  -2.087  -1.346  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.255  -3.583  -0.833  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.153  -2.621   0.346  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.504  -1.000  -1.526  1.00  0.00           H  
HETATM   47  H24 UNL     1      -0.697  -2.534  -2.226  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    5   29
CONECT    4   30   31   32
CONECT    5    6    7   33
CONECT    6   34
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   20   35
CONECT   11   12   12   36
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   15   39
CONECT   15   16   16   40
CONECT   16   17   41
CONECT   17   18   18   19
CONECT   19   42
CONECT   20   21   22   23
CONECT   21   43   44   45
CONECT   22   23   46   47
END

HMDB0033504
     RDKit          3D
AF Toxin II
 47 47  0  0  0  0  0  0  0  0999 V2000
   -5.5798   -0.9993    0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3154   -0.3215   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1616    1.0558    0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2973    1.9211   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8446    1.7082   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6457    1.8649   -1.4566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368    0.8742    0.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475    0.5625    1.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661    0.4521   -0.2448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.3404    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990    0.0484    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489    0.8336   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157    1.7271   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8083    1.6090   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1845    0.5175    0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4337    0.2919    0.9624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7467   -0.8179    1.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391   -1.5509    2.1952 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0131   -1.0928    2.2629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -1.7567   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4947   -2.5163   -0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8442   -1.8775   -1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -2.4743   -0.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4967   -0.4198   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228   -1.9866   -0.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4830   -1.2070    1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4682   -0.9330    0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3465   -0.2787   -1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2614    1.0153    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3213    1.9785   -1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2919    1.5908    0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1537    2.9872    0.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8282    2.6794    0.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074    1.0568   -1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -0.4735    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.7100    0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5261    1.5529   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3357    2.5705   -1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5608    2.3095   -0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4428   -0.1679    0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1776    0.9760    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6236   -0.4337    2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1018   -2.0866   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2554   -3.5834   -0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531   -2.6214    0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5041   -1.0001   -1.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974   -2.5339   -2.2256 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 20  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  6 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E,4Z)-8-[(2-Hydroxy-3-methylpentanoyl)oxy]-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoate	HMDB

Chemical Formula

C₁₇H₂₄O₆

Average Molecular Weight

324.3689

Monoisotopic Molecular Weight

324.1572885

IUPAC Name

(2E,4Z,6E)-8-[(2-hydroxy-3-methylpentanoyl)oxy]-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid

Traditional Name

(2E,4Z,6E)-8-[(2-hydroxy-3-methylpentanoyl)oxy]-8-(2-methyloxiran-2-yl)octa-2,4,6-trienoic acid

CAS Registry Number

Not Available

SMILES

CCC(C)C(O)C(=O)OC(\C=C\C=C/C=C/C(O)=O)C1(C)CO1

InChI Identifier

InChI=1S/C17H24O6/c1-4-12(2)15(20)16(21)23-13(17(3)11-22-17)9-7-5-6-8-10-14(18)19/h5-10,12-13,15,20H,4,11H2,1-3H3,(H,18,19)/b6-5-,9-7+,10-8+

InChI Key

PXZGUAVTZUPRMI-WDGPHVMXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Branched fatty acid
Fatty acid ester
Heterocyclic fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0033504)

Cellular substructure

Extracellular (HMDB: HMDB0033504)
Membrane (HMDB: HMDB0033504)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033504)

Source

Endogenous

Endogenous (HMDB: HMDB0033504)

Plant

Plant (HMDB: HMDB0033504)

Animal

Animal (HMDB: HMDB0033504)

Exogenous

Food

Food (HMDB: HMDB0033504)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033504)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033504)

Cellular process

Cell signaling (HMDB: HMDB0033504)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033504)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033504)

Nutrient

Nutrient (HMDB: HMDB0033504)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033504)

Emulsifier (HMDB: HMDB0033504)

Physical Properties

State

Not Available

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	0.14 g/L	ALOGPS
logP	2.9	ALOGPS
logP	2.4	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.36 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	87.37 m³·mol⁻¹	ChemAxon
Polarizability	34.56 Å³	ChemAxon
Number of Rings	1	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]+	179.509	31661259
DarkChem	[M-H]-	175.282	31661259
DeepCCS	[M+H]+	178.978	30932474
DeepCCS	[M-H]-	176.62	30932474
DeepCCS	[M-2H]-	210.853	30932474
DeepCCS	[M+Na]+	186.081	30932474
AllCCS	[M+H]+	180.1	32859911
AllCCS	[M+H-H2O]+	177.2	32859911
AllCCS	[M+NH4]+	182.7	32859911
AllCCS	[M+Na]+	183.5	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	179.7	32859911
AllCCS	[M+HCOO]-	180.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
AF Toxin II	CCC(C)C(O)C(=O)OC(\C=C\C=C/C=C/C(O)=O)C1(C)CO1	4292.8	Standard polar	33892256
AF Toxin II	CCC(C)C(O)C(=O)OC(\C=C\C=C/C=C/C(O)=O)C1(C)CO1	2285.1	Standard non polar	33892256
AF Toxin II	CCC(C)C(O)C(=O)OC(\C=C\C=C/C=C/C(O)=O)C1(C)CO1	2408.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
AF Toxin II,1TMS,isomer #1	CCC(C)C(O[Si](C)(C)C)C(=O)OC(/C=C/C=C\C=C\C(=O)O)C1(C)CO1	2584.5	Semi standard non polar	33892256
AF Toxin II,1TMS,isomer #2	CCC(C)C(O)C(=O)OC(/C=C/C=C\C=C\C(=O)O[Si](C)(C)C)C1(C)CO1	2556.0	Semi standard non polar	33892256
AF Toxin II,2TMS,isomer #1	CCC(C)C(O[Si](C)(C)C)C(=O)OC(/C=C/C=C\C=C\C(=O)O[Si](C)(C)C)C1(C)CO1	2570.8	Semi standard non polar	33892256
AF Toxin II,1TBDMS,isomer #1	CCC(C)C(O[Si](C)(C)C(C)(C)C)C(=O)OC(/C=C/C=C\C=C\C(=O)O)C1(C)CO1	2831.7	Semi standard non polar	33892256
AF Toxin II,1TBDMS,isomer #2	CCC(C)C(O)C(=O)OC(/C=C/C=C\C=C\C(=O)O[Si](C)(C)C(C)(C)C)C1(C)CO1	2781.3	Semi standard non polar	33892256
AF Toxin II,2TBDMS,isomer #1	CCC(C)C(O[Si](C)(C)C(C)(C)C)C(=O)OC(/C=C/C=C\C=C\C(=O)O[Si](C)(C)C(C)(C)C)C1(C)CO1	3044.7	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 - AF Toxin II GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-9501000000-0da4db8b6231e8f784a3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - AF Toxin II GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-9680100000-2f4df8ec423fc108ab8c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - AF Toxin II 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 - AF Toxin II 10V, Positive-QTOF	splash10-0570-5947000000-ec03eca296cf93122b63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 20V, Positive-QTOF	splash10-0a4i-9620000000-1764177b291ba1bedced	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 40V, Positive-QTOF	splash10-0a4i-9500000000-4a4f63a30cc8410cdd8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 10V, Negative-QTOF	splash10-05fr-6898000000-dd7c423dca936dad70af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 20V, Negative-QTOF	splash10-0a4i-3951000000-32df125136ea8b43eb65	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 40V, Negative-QTOF	splash10-0a4i-9200000000-5aa2f873ab07850e2363	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 10V, Positive-QTOF	splash10-056r-2915000000-6b23e1e2c96755d514e4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 20V, Positive-QTOF	splash10-0a4i-9402000000-40ff59cdceabd2ad5b28	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 40V, Positive-QTOF	splash10-0691-9400000000-98efa50bf21bce88e8c6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 10V, Negative-QTOF	splash10-00e9-1739000000-7acd74357127e7fded48	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 20V, Negative-QTOF	splash10-06r2-3920000000-d6e4d7d396bddbc32421	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - AF Toxin II 40V, Negative-QTOF	splash10-03dr-9700000000-0f713218106dcae08662	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011556

KNApSAcK ID

Not Available

Chemspider ID

35013614

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751442

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

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for AF Toxin II (HMDB0033504)

MOL for HMDB0033504 (AF Toxin II)

3D MOL for HMDB0033504 (AF Toxin II)

3D SDF for HMDB0033504 (AF Toxin II)

3D-SDF for HMDB0033504 (AF Toxin II)

PDB for HMDB0033504 (AF Toxin II)

3D PDB for HMDB0033504 (AF Toxin II)

SMILES for HMDB0033504 (AF Toxin II)

INCHI for HMDB0033504 (AF Toxin II)

Structure for HMDB0033504 (AF Toxin II)

3D Structure for HMDB0033504 (AF Toxin II)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra