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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:43 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002226

Secondary Accession Numbers

HMDB0062580
HMDB02226
HMDB62580

Metabolite Identification

Common Name

Adrenic acid

Description

Adrenic acid, also known as 7,10,13,16-docosatetraenoic acid or adrenate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Adrenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Adrenic acid can be found in blood and in human myelin tissue. Within the cell, adrenic acid is primarily located in the cytoplasm, in the membrane (predicted from logP), and in the peroxisome. It can also be found in the extracellular space. In humans, adrenic acid is involved in alpha-linolenic acid and linoleic acid metabolism. Docosatetraenoic acid designates any straight chain 22:4 fatty acid. In particular, all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the trivial name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells into biologically active products, such as dihomoprostaglandins and dihomo-epoxyeicosatrienoic acids (dihomo-EETs) (Wikipedia ). Adrenic acid, which is a prostacyclin inhibitor, appears to be a potential prothrombotic agent (PMID: 1642692 ).

Structure

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

HMDB0002226
     RDKit          3D
Adrenic acid
 60 59  0  0  0  0  0  0  0  0999 V2000
    8.1368   -2.4675    0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7115   -2.0995   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2240   -0.6649   -0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0536   -0.5903    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4916    0.8359    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3616    0.8054    1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277    1.1055    1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7806    1.4983   -0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2217    2.8658   -0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0556    3.2374   -0.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0306    2.3381   -1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2321    2.3957   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042    1.3906   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    0.0503    0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0006   -1.0800   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301   -1.1281   -1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9821    0.0273   -1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3459   -0.1449   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2824   -0.2801    0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6286   -0.4559    1.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3514   -1.6747    0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6731   -1.7917    1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4768   -2.7218    1.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0365   -0.8179    2.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0726   -3.0675    0.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2982   -3.0968    1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3266   -1.5774    1.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8957   -2.7410   -0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5695   -2.1791   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0460   -0.0001   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8317   -0.4014   -1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3124   -0.9170    1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2622   -1.2736   -0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592    1.5039    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898    1.2400   -0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5577    0.5142    2.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3395    1.0569    1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    1.3179   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548    0.7788   -0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881    3.6629   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876    4.3105   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724    2.6700   -2.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3845    1.3323   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584    3.3754   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599    1.5781    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -0.1926    1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801    0.0111   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956   -2.1116   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -2.1477   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5789    1.0101   -1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2500   -0.1424   -2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8344   -1.0493   -1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0168    0.7021   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8201    0.6340    1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6444   -1.1242    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4536   -0.5734    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2615    0.4741    1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4593   -1.7259   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7516   -2.5583    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3977    0.0738    2.1103 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 24 60  1  0
M  END

LMFA01030178
  Mrv1652303312018252D          

 24 23  0  0  0  0            999 V2000
   11.4648    6.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7502    6.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0358    6.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3212    6.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6067    6.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815    6.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0671    6.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3526    6.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    6.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440    5.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    5.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3526    5.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0671    5.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815    5.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6067    5.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1820    6.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3116    5.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0164    5.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7214    5.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4263    5.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1313    5.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8851    6.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5884    6.0385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8851    7.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 11  1  0  0  0  0
  1 16  1  0  0  0  0
 17 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 16  1  0  0  0  0
 23 22  1  0  0  0  0
 22 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002226

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
TWSWSIQAPQLDBP-DOFZRALJSA-N

> <FORMULA>
C22H36O2

> <MOLECULAR_WEIGHT>
332.52

> <EXACT_MASS>
332.271530396

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.3694022249114

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acid

> <ALOGPS_LOGP>
7.42

> <JCHEM_LOGP>
7.4763081410000005

> <ALOGPS_LOGS>
-6.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.955292438746737

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
109.15599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.77e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
docosatetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002226
     RDKit          3D
Adrenic acid
 60 59  0  0  0  0  0  0  0  0999 V2000
    8.1368   -2.4675    0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7115   -2.0995   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2240   -0.6649   -0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0536   -0.5903    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4916    0.8359    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3616    0.8054    1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277    1.1055    1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7806    1.4983   -0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2217    2.8658   -0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0556    3.2374   -0.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0306    2.3381   -1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2321    2.3957   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042    1.3906   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    0.0503    0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0006   -1.0800   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301   -1.1281   -1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9821    0.0273   -1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3459   -0.1449   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2824   -0.2801    0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6286   -0.4559    1.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3514   -1.6747    0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6731   -1.7917    1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4768   -2.7218    1.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0365   -0.8179    2.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0726   -3.0675    0.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2982   -3.0968    1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3266   -1.5774    1.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8957   -2.7410   -0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5695   -2.1791   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0460   -0.0001   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8317   -0.4014   -1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3124   -0.9170    1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2622   -1.2736   -0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592    1.5039    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898    1.2400   -0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5577    0.5142    2.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3395    1.0569    1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    1.3179   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548    0.7788   -0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881    3.6629   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876    4.3105   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724    2.6700   -2.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3845    1.3323   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584    3.3754   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599    1.5781    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -0.1926    1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801    0.0111   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956   -2.1116   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -2.1477   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5789    1.0101   -1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2500   -0.1424   -2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8344   -1.0493   -1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0168    0.7021   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8201    0.6340    1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6444   -1.1242    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4536   -0.5734    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2615    0.4741    1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4593   -1.7259   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7516   -2.5583    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3977    0.0738    2.1103 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 24 60  1  0
M  END

HEADER    PROTEIN                                 31-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LMFA01030178                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-20         0                                  
HETATM    1  C   UNK     0      21.401  12.045   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.067  11.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.733  12.045   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.400  11.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.066  12.045   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.525  12.045   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.192  11.275   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.858  12.045   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.318  12.045   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.229  10.956   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.318   9.686   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.858   9.686   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.192  10.456   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.525   9.686   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.066   9.686   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.740  11.272   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.382  10.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.697   9.686   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.013  10.445   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.329   9.686   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.645  10.445   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.052  12.030   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      25.365  11.272   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      24.052  13.185   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   12   10                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   17                                                       
CONECT   16    1   22                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   16   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0002226
HETATM    1  C1  UNL     1       8.137  -2.467   0.812  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.712  -2.100  -0.593  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.224  -0.665  -0.605  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.054  -0.590   0.349  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.492   0.836   0.401  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.362   0.805   1.352  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.128   1.106   1.007  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.781   1.498  -0.381  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.222   2.866  -0.431  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.056   3.237  -0.856  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.031   2.338  -1.388  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.232   2.396  -0.629  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.804   1.391  -0.018  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.298   0.050   0.020  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.001  -1.080  -0.535  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.130  -1.128  -1.164  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.982   0.027  -1.465  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.346  -0.145  -0.813  1.00  0.00           C  
HETATM   19  C19 UNL     1      -5.282  -0.280   0.683  1.00  0.00           C  
HETATM   20  C20 UNL     1      -6.629  -0.456   1.310  1.00  0.00           C  
HETATM   21  C21 UNL     1      -7.351  -1.675   0.834  1.00  0.00           C  
HETATM   22  C22 UNL     1      -8.673  -1.792   1.499  1.00  0.00           C  
HETATM   23  O1  UNL     1      -9.477  -2.722   1.278  1.00  0.00           O  
HETATM   24  O2  UNL     1      -9.037  -0.818   2.414  1.00  0.00           O  
HETATM   25  H1  UNL     1       9.073  -3.067   0.813  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.298  -3.097   1.231  1.00  0.00           H  
HETATM   27  H3  UNL     1       8.327  -1.577   1.427  1.00  0.00           H  
HETATM   28  H4  UNL     1       6.896  -2.741  -0.975  1.00  0.00           H  
HETATM   29  H5  UNL     1       8.569  -2.179  -1.301  1.00  0.00           H  
HETATM   30  H6  UNL     1       8.046  -0.000  -0.321  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.832  -0.401  -1.608  1.00  0.00           H  
HETATM   32  H8  UNL     1       6.312  -0.917   1.372  1.00  0.00           H  
HETATM   33  H9  UNL     1       5.262  -1.274  -0.020  1.00  0.00           H  
HETATM   34  H10 UNL     1       6.259   1.504   0.891  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.290   1.240  -0.566  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.558   0.514   2.419  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.339   1.057   1.791  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.548   1.318  -1.131  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.955   0.779  -0.663  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.888   3.663  -0.056  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.788   4.310  -0.827  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.172   2.670  -2.471  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.384   1.332  -1.500  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.758   3.375  -0.560  1.00  0.00           H  
HETATM   45  H21 UNL     1      -2.760   1.578   0.561  1.00  0.00           H  
HETATM   46  H22 UNL     1      -1.226  -0.193   1.168  1.00  0.00           H  
HETATM   47  H23 UNL     1      -0.180   0.011  -0.215  1.00  0.00           H  
HETATM   48  H24 UNL     1      -1.496  -2.112  -0.410  1.00  0.00           H  
HETATM   49  H25 UNL     1      -3.516  -2.148  -1.525  1.00  0.00           H  
HETATM   50  H26 UNL     1      -3.579   1.010  -1.476  1.00  0.00           H  
HETATM   51  H27 UNL     1      -4.250  -0.142  -2.597  1.00  0.00           H  
HETATM   52  H28 UNL     1      -5.834  -1.049  -1.230  1.00  0.00           H  
HETATM   53  H29 UNL     1      -6.017   0.702  -1.039  1.00  0.00           H  
HETATM   54  H30 UNL     1      -4.820   0.634   1.159  1.00  0.00           H  
HETATM   55  H31 UNL     1      -4.644  -1.124   1.011  1.00  0.00           H  
HETATM   56  H32 UNL     1      -6.454  -0.573   2.416  1.00  0.00           H  
HETATM   57  H33 UNL     1      -7.262   0.474   1.208  1.00  0.00           H  
HETATM   58  H34 UNL     1      -7.459  -1.726  -0.262  1.00  0.00           H  
HETATM   59  H35 UNL     1      -6.752  -2.558   1.134  1.00  0.00           H  
HETATM   60  H36 UNL     1      -9.398   0.074   2.110  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7   36
CONECT    7    8   37
CONECT    8    9   38   39
CONECT    9   10   10   40
CONECT   10   11   41
CONECT   11   12   42   43
CONECT   12   13   13   44
CONECT   13   14   45
CONECT   14   15   46   47
CONECT   15   16   16   48
CONECT   16   17   49
CONECT   17   18   50   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   56   57
CONECT   21   22   58   59
CONECT   22   23   23   24
CONECT   24   60
END

HMDB0002226
     RDKit          3D
Adrenic acid
 60 59  0  0  0  0  0  0  0  0999 V2000
    8.1368   -2.4675    0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7115   -2.0995   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2240   -0.6649   -0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0536   -0.5903    0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4916    0.8359    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3616    0.8054    1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277    1.1055    1.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7806    1.4983   -0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2217    2.8658   -0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0556    3.2374   -0.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0306    2.3381   -1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2321    2.3957   -0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8042    1.3906   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    0.0503    0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0006   -1.0800   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301   -1.1281   -1.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9821    0.0273   -1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3459   -0.1449   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2824   -0.2801    0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6286   -0.4559    1.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3514   -1.6747    0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6731   -1.7917    1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4768   -2.7218    1.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0365   -0.8179    2.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0726   -3.0675    0.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2982   -3.0968    1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3266   -1.5774    1.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8957   -2.7410   -0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5695   -2.1791   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0460   -0.0001   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8317   -0.4014   -1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3124   -0.9170    1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2622   -1.2736   -0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592    1.5039    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2898    1.2400   -0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5577    0.5142    2.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3395    1.0569    1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    1.3179   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548    0.7788   -0.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881    3.6629   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876    4.3105   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724    2.6700   -2.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3845    1.3323   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584    3.3754   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599    1.5781    0.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -0.1926    1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1801    0.0111   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956   -2.1116   -0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -2.1477   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5789    1.0101   -1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2500   -0.1424   -2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8344   -1.0493   -1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0168    0.7021   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8201    0.6340    1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6444   -1.1242    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4536   -0.5734    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2615    0.4741    1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4593   -1.7259   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7516   -2.5583    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3977    0.0738    2.1103 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 24 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid	ChEBI
7,10,13,16-Docosatetraenoic acid	ChEBI
7Z,10Z,13Z,16Z-Docosatetraenoic acid	ChEBI
all-cis-7,10,13,16-Docosatetraenoic acid	ChEBI
cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeure	ChEBI
(7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoate	Generator
7,10,13,16-Docosatetraenoate	Generator
7Z,10Z,13Z,16Z-Docosatetraenoate	Generator
all-cis-7,10,13,16-Docosatetraenoate	Generator
Adrenate	Generator
Adrenic acid, (Z)-isomer	HMDB
7,10,13,16-Docosatetraenoic acid (van) adrenate	HMDB
7,10,13,16-Docosatetraenoic acid (van) adrenic acid	HMDB
FA(22:4(7Z,10Z,13Z,16Z))	HMDB
(7Z,10Z,13Z,16Z)-Docosatetraenoate	HMDB

Chemical Formula

C₂₂H₃₆O₂

Average Molecular Weight

332.52

Monoisotopic Molecular Weight

332.271530396

IUPAC Name

(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoic acid

Traditional Name

docosatetraenoic acid

CAS Registry Number

28874-58-0

SMILES

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O

InChI Identifier

InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-

InChI Key

TWSWSIQAPQLDBP-DOFZRALJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

docosatetraenoic acid (CHEBI:53487 )
Docosanoids (C16527 )
Polyunsaturated fatty acids (C16527 )
Unsaturated fatty acids (LMFA01030178 )

Ontology

Not Available

Endogenous (HMDB: HMDB0139879)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	190.921	30932474
[M+H]+	Baker	189.413	30932474
[M-H]-	Not Available	190.921	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001853

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.8e-05 g/L	ALOGPS
logP	7.42	ALOGPS
logP	7.48	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	4.96	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	109.16 m³·mol⁻¹	ChemAxon
Polarizability	41.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	194.604	31661259
DarkChem	[M-H]-	196.94	31661259
DeepCCS	[M+H]+	193.853	30932474
DeepCCS	[M-H]-	191.496	30932474
DeepCCS	[M-2H]-	224.382	30932474
DeepCCS	[M+Na]+	199.947	30932474
AllCCS	[M+H]+	191.6	32859911
AllCCS	[M+H-H2O]+	188.8	32859911
AllCCS	[M+NH4]+	194.1	32859911
AllCCS	[M+Na]+	194.9	32859911
AllCCS	[M-H]-	191.8	32859911
AllCCS	[M+Na-2H]-	194.0	32859911
AllCCS	[M+HCOO]-	196.7	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.	7.96 minutes	32390414
Predicted by Siyang on May 30, 2022	29.1109 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.6 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	41.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3475.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	727.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	296.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	535.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	813.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1372.4 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	783.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2709.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	885.6 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	2196.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1028.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	611.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	603.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	705.5 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	9.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Adrenic acid	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O	3822.9	Standard polar	33892256
Adrenic acid	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O	2318.1	Standard non polar	33892256
Adrenic acid	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O	2517.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Adrenic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[Si](C)(C)C	2569.4	Semi standard non polar	33892256
Adrenic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[Si](C)(C)C(C)(C)C	2816.0	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Peroxisome

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Neuron
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
alpha-Linolenic acid metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.417 +/- 0.070 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.364 +/- 0.005 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	1.01 +/- 0.48 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	8.657 +/- 3.137 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	14.5 +/- 4.6 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	16.1 +/- 6.5 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details

Associated Disorders and Diseases

Disease References

Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]

Associated OMIM IDs

243500 (Isovaleric acidemia)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

53487

Food Biomarker Ontology

Not Available

VMH ID

ADRN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Martinez M, Mougan I: Fatty acid composition of brain glycerophospholipids in peroxisomal disorders. Lipids. 1999 Jul;34(7):733-40. [PubMed:10478932 ]
Ren H, Magulike N, Ghebremeskel K, Crawford M: Primary open-angle glaucoma patients have reduced levels of blood docosahexaenoic and eicosapentaenoic acids. Prostaglandins Leukot Essent Fatty Acids. 2006 Mar;74(3):157-63. Epub 2006 Jan 10. [PubMed:16410047 ]
Tardy B, Bordet JC, Berruyer M, Ffrench P, Dechavanne M: Priming effect of adrenic acid (22:4(n-6)) on tissue factor activity expressed by thrombin-stimulated endothelial cells. Atherosclerosis. 1992 Jul;95(1):51-8. [PubMed:1642692 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Adrenic acid (HMDB0002226)

MOL for HMDB0002226 (Adrenic acid)

3D MOL for HMDB0002226 (Adrenic acid)

3D SDF for HMDB0002226 (Adrenic acid)

3D-SDF for HMDB0002226 (Adrenic acid)

PDB for HMDB0002226 (Adrenic acid)

3D PDB for HMDB0002226 (Adrenic acid)

SMILES for HMDB0002226 (Adrenic acid)

INCHI for HMDB0002226 (Adrenic acid)

Structure for HMDB0002226 (Adrenic acid)

3D Structure for HMDB0002226 (Adrenic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized