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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:30 UTC

Update Date

2022-03-07 02:49:12 UTC

HMDB ID

HMDB0001976

Secondary Accession Numbers

HMDB0060113
HMDB01976
HMDB60113

Metabolite Identification

Common Name

Docosapentaenoic acid (22n-6)

Description

Docosapentaenoic acid is an unsaturated fatty acid found in fish oils. It is a minor constituent of the total serum unsaturated fatty acids in humans. Docosapentaenoic acid (22n-6) is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Docosapentaenoic acid (22n-6) can be found in blood and urine, as well as in human adipose tissue, fibroblasts, and platelet tissues. Within the cell, docosapentaenoic acid (22n-6) is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. In humans, docosapentaenoic acid (22n-6) is involved in alpha-linolenic acid and linoleic acid metabolism. Docosapentaenoic acid (22n-6) is found to be associated with thyroid cancer.

Structure

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

HMDB0001976
     RDKit          3D
Docosapentaenoic acid (22n-6)
 58 57  0  0  0  0  0  0  0  0999 V2000
   -8.2918   -3.2237   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0284   -1.9183   -0.8621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5194   -1.6437   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3168   -0.3427   -1.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419    0.0531   -1.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610    0.2324   -0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7350    1.3481    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6624    2.5571   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    3.2612   -0.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283    2.9975   -0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722    1.7630   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139    2.1095    1.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283    1.7213    1.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9152    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560   -0.3632    0.9667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7412   -0.6364    0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681    0.2215    0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6959    0.6492    1.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9811    0.4288    1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6567   -0.2846    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3009   -1.5338    0.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0076   -2.3286   -0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4334   -3.1133   -0.8524 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4034   -2.2238   -0.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5008   -3.5167    0.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2872   -4.0068   -0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2790   -3.1681    0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5558   -1.0673   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3621   -1.9101   -1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1358   -1.6520    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0175   -2.4832   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9486    0.4675   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6063   -0.4888   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7069    0.8042   -2.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3547   -0.8819   -2.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2544   -0.6412    0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632    1.3241    1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548    2.4696   -1.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2704    3.3844    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579    4.2303   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4635    3.6813   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0530    1.3094   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.9605    0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960    2.7057    1.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    2.0326    2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5300    0.7385   -0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8673    1.5783    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -1.0566    1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0633   -1.5746    1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4918    1.0921   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3081   -0.5024   -0.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2879    1.2004    2.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792    0.7845    2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1082   -0.4995   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5098    0.4196    0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5350   -2.1685    1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0213   -1.1748    1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8677   -1.3265   -0.0295 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  2  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
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 24 58  1  0
M  END

LMFA04000064
  Mrv1652304091817242D          

 24 23  0  0  0  0            999 V2000
    5.8729    5.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625    5.2327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8729    6.4630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5884    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3043    5.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0201    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7362    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4521    5.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1680    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8838    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5997    5.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3156    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0316    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7476    5.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4634    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1793    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8951    5.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6110    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3271    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0429    5.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7588    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4748    5.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1905    5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9065    5.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001976

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16,18-19H,2-5,8,11,14,17,20-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-,19-18-

> <INCHI_KEY>
AVKOENOBFIYBSA-WMPRHZDHSA-N

> <FORMULA>
C22H34O2

> <MOLECULAR_WEIGHT>
330.5042

> <EXACT_MASS>
330.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.577538424973

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid

> <ALOGPS_LOGP>
7.18

> <JCHEM_LOGP>
7.114386484333333

> <ALOGPS_LOGS>
-6.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885498414345382

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
110.2726

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001976
     RDKit          3D
Docosapentaenoic acid (22n-6)
 58 57  0  0  0  0  0  0  0  0999 V2000
   -8.2918   -3.2237   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0284   -1.9183   -0.8621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5194   -1.6437   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3168   -0.3427   -1.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419    0.0531   -1.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610    0.2324   -0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7350    1.3481    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6624    2.5571   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    3.2612   -0.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283    2.9975   -0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722    1.7630   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139    2.1095    1.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283    1.7213    1.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9152    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560   -0.3632    0.9667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7412   -0.6364    0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681    0.2215    0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6959    0.6492    1.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9811    0.4288    1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6567   -0.2846    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3009   -1.5338    0.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0076   -2.3286   -0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4334   -3.1133   -0.8524 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4034   -2.2238   -0.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5008   -3.5167    0.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2872   -4.0068   -0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2790   -3.1681    0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5558   -1.0673   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3621   -1.9101   -1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1358   -1.6520    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0175   -2.4832   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9486    0.4675   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6063   -0.4888   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7069    0.8042   -2.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3547   -0.8819   -2.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2544   -0.6412    0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632    1.3241    1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548    2.4696   -1.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2704    3.3844    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579    4.2303   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4635    3.6813   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0530    1.3094   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.9605    0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960    2.7057    1.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    2.0326    2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5300    0.7385   -0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8673    1.5783    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -1.0566    1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0633   -1.5746    1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4918    1.0921   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3081   -0.5024   -0.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2879    1.2004    2.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792    0.7845    2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1082   -0.4995   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5098    0.4196    0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5350   -2.1685    1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0213   -1.1748    1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8677   -1.3265   -0.0295 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  2  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
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 24 58  1  0
M  END

HEADER    PROTEIN                                 09-APR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LMFA04000064                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-18         0                                  
HETATM    1  C   UNK     0      10.963  10.533   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.637   9.768   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.963  12.064   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.298   9.768   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.635  10.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.971   9.768   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.308   9.768   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.644  10.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.980   9.768   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.316   9.768   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.653  10.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.989   9.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.326   9.768   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.662  10.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.998   9.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.335   9.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.671  10.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.007   9.768   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.344   9.768   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.680  10.533   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      35.016   9.768   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.353  10.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.689   9.768   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      39.026  10.533   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    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   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   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                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0001976
HETATM    1  C1  UNL     1      -8.292  -3.224  -0.180  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.028  -1.918  -0.862  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.519  -1.644  -0.830  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.317  -0.343  -1.538  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.842   0.053  -1.565  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.261   0.232  -0.244  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.735   1.348   0.222  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.662   2.557  -0.517  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.474   3.261  -0.910  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.228   2.998  -0.739  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.772   1.763  -0.021  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.014   2.109   1.185  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.228   1.721   1.328  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.971   0.915   0.322  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.456  -0.363   0.967  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.741  -0.636   0.966  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.768   0.222   0.367  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.696   0.649   1.453  1.00  0.00           C  
HETATM   19  C19 UNL     1       6.981   0.429   1.468  1.00  0.00           C  
HETATM   20  C20 UNL     1       7.657  -0.285   0.375  1.00  0.00           C  
HETATM   21  C21 UNL     1       8.301  -1.534   0.980  1.00  0.00           C  
HETATM   22  C22 UNL     1       9.008  -2.329  -0.038  1.00  0.00           C  
HETATM   23  O1  UNL     1       8.433  -3.113  -0.852  1.00  0.00           O  
HETATM   24  O2  UNL     1      10.403  -2.224  -0.128  1.00  0.00           O  
HETATM   25  H1  UNL     1      -7.501  -3.517   0.534  1.00  0.00           H  
HETATM   26  H2  UNL     1      -8.287  -4.007  -0.995  1.00  0.00           H  
HETATM   27  H3  UNL     1      -9.279  -3.168   0.296  1.00  0.00           H  
HETATM   28  H4  UNL     1      -8.556  -1.067  -0.336  1.00  0.00           H  
HETATM   29  H5  UNL     1      -8.362  -1.910  -1.895  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.136  -1.652   0.209  1.00  0.00           H  
HETATM   31  H7  UNL     1      -6.017  -2.483  -1.370  1.00  0.00           H  
HETATM   32  H8  UNL     1      -6.949   0.468  -1.155  1.00  0.00           H  
HETATM   33  H9  UNL     1      -6.606  -0.489  -2.598  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.707   0.804  -2.319  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.355  -0.882  -2.019  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.254  -0.641   0.438  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.363   1.324   1.267  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.355   2.470  -1.408  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.270   3.384   0.071  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.658   4.230  -1.477  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.463   3.681  -1.124  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.053   1.309  -0.796  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.500   0.960   0.069  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.496   2.706   1.984  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.722   2.033   2.270  1.00  0.00           H  
HETATM   46  H22 UNL     1       1.530   0.738  -0.632  1.00  0.00           H  
HETATM   47  H23 UNL     1       2.867   1.578   0.103  1.00  0.00           H  
HETATM   48  H24 UNL     1       1.777  -1.057   1.426  1.00  0.00           H  
HETATM   49  H25 UNL     1       4.063  -1.575   1.448  1.00  0.00           H  
HETATM   50  H26 UNL     1       4.492   1.092  -0.192  1.00  0.00           H  
HETATM   51  H27 UNL     1       5.308  -0.502  -0.350  1.00  0.00           H  
HETATM   52  H28 UNL     1       5.288   1.200   2.326  1.00  0.00           H  
HETATM   53  H29 UNL     1       7.579   0.785   2.318  1.00  0.00           H  
HETATM   54  H30 UNL     1       7.108  -0.500  -0.517  1.00  0.00           H  
HETATM   55  H31 UNL     1       8.510   0.420   0.067  1.00  0.00           H  
HETATM   56  H32 UNL     1       7.535  -2.168   1.454  1.00  0.00           H  
HETATM   57  H33 UNL     1       9.021  -1.175   1.726  1.00  0.00           H  
HETATM   58  H34 UNL     1      10.868  -1.327  -0.030  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   19   52
CONECT   19   20   53
CONECT   20   21   54   55
CONECT   21   22   56   57
CONECT   22   23   23   24
CONECT   24   58
END

HMDB0001976
     RDKit          3D
Docosapentaenoic acid (22n-6)
 58 57  0  0  0  0  0  0  0  0999 V2000
   -8.2918   -3.2237   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0284   -1.9183   -0.8621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5194   -1.6437   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3168   -0.3427   -1.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419    0.0531   -1.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2610    0.2324   -0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7350    1.3481    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6624    2.5571   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    3.2612   -0.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283    2.9975   -0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722    1.7630   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139    2.1095    1.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2283    1.7213    1.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9152    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560   -0.3632    0.9667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7412   -0.6364    0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7681    0.2215    0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6959    0.6492    1.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9811    0.4288    1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6567   -0.2846    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3009   -1.5338    0.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0076   -2.3286   -0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4334   -3.1133   -0.8524 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4034   -2.2238   -0.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5008   -3.5167    0.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2872   -4.0068   -0.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2790   -3.1681    0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5558   -1.0673   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3621   -1.9101   -1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1358   -1.6520    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0175   -2.4832   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9486    0.4675   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6063   -0.4888   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7069    0.8042   -2.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3547   -0.8819   -2.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2544   -0.6412    0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632    1.3241    1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548    2.4696   -1.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2704    3.3844    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579    4.2303   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4635    3.6813   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0530    1.3094   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.9605    0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960    2.7057    1.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219    2.0326    2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5300    0.7385   -0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8673    1.5783    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -1.0566    1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0633   -1.5746    1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4918    1.0921   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3081   -0.5024   -0.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2879    1.2004    2.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792    0.7845    2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1082   -0.4995   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5098    0.4196    0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5350   -2.1685    1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0213   -1.1748    1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8677   -1.3265   -0.0295 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  2  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
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 24 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(all-Z)-4,7,10,13,16-Docosapentaenoic acid	ChEBI
22:5(4Z,7Z,10Z,13Z,16Z)	ChEBI
4Z,7Z,10Z,13Z,16Z-Docosapentaenoic acid	ChEBI
all-cis-Docosa-4,7,10,13,16-pentaenoic acid	ChEBI
DPAn-6	ChEBI
(all-Z)-4,7,10,13,16-Docosapentaenoate	Generator
4Z,7Z,10Z,13Z,16Z-Docosapentaenoate	Generator
all-cis-Docosa-4,7,10,13,16-pentaenoate	Generator
Docosapentaenoate (22N-6)	Generator
Docosa-4,7,10,13,16-pentaenoic acid	HMDB
Docosapentaenoate	HMDB
Docosapentaenoic acid	HMDB
Osbond acid	HMDB
FA(22:5(4Z,7Z,10Z,13Z,16Z))	HMDB
(all-Z)-7, 10, 13, 16, 19-Docosapentaenoic acid	HMDB
Docosapentaenoic acid (C22:5 N6)	HMDB
Docosapentaenoic acid, (all Z)-isomer	HMDB
Docosa-4,7,10,13,16-pentaenoic acid, (all-Z)-isomer	HMDB
(4Z,7Z,10Z,13Z,16Z)-4,7,10,13,16-Docosapentaenoic acid	HMDB
DPA	HMDB
FA(22:5n6)	HMDB

Chemical Formula

C₂₂H₃₄O₂

Average Molecular Weight

330.5042

Monoisotopic Molecular Weight

330.255880332

IUPAC Name

(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid

Traditional Name

(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid

CAS Registry Number

25448-00-4

SMILES

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

InChI Identifier

InChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16,18-19H,2-5,8,11,14,17,20-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-,19-18-

InChI Key

AVKOENOBFIYBSA-WMPRHZDHSA-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

docosapentaenoic acid (CHEBI:65136 )
Docosanoids (LMFA04000064 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060113)

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	0.0001 g/L	ALOGPS
logP	7.18	ALOGPS
logP	7.11	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	4.89	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	15	ChemAxon
Refractivity	110.27 m³·mol⁻¹	ChemAxon
Polarizability	40.58 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]+	195.247	31661259
DarkChem	[M-H]-	194.721	31661259
AllCCS	[M+H]+	190.075	32859911
AllCCS	[M-H]-	189.011	32859911
DeepCCS	[M+H]+	194.194	30932474
DeepCCS	[M-H]-	191.836	30932474
DeepCCS	[M-2H]-	224.722	30932474
DeepCCS	[M+Na]+	200.287	30932474
AllCCS	[M+H]+	190.1	32859911
AllCCS	[M+H-H2O]+	187.2	32859911
AllCCS	[M+NH4]+	192.7	32859911
AllCCS	[M+Na]+	193.4	32859911
AllCCS	[M-H]-	189.0	32859911
AllCCS	[M+Na-2H]-	191.0	32859911
AllCCS	[M+HCOO]-	193.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Docosapentaenoic acid (22n-6)	CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	3962.9	Standard polar	33892256
Docosapentaenoic acid (22n-6)	CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	2272.3	Standard non polar	33892256
Docosapentaenoic acid (22n-6)	CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O	2510.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Docosapentaenoic acid (22n-6),1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C	2560.5	Semi standard non polar	33892256
Docosapentaenoic acid (22n-6),1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C	2808.9	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 - Docosapentaenoic acid (22n-6) GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-7490000000-97ad3e356a5f908f9003	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Docosapentaenoic acid (22n-6) GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9244000000-8e631b61a994e509b114	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Docosapentaenoic acid (22n-6) 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 - Docosapentaenoic acid (22n-6) 10V, Positive-QTOF	splash10-01q9-0139000000-31a18234c1c393f0a6a7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 20V, Positive-QTOF	splash10-0239-4592000000-fa33f23033ae64b97560	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 40V, Positive-QTOF	splash10-006x-7960000000-ccf21f4fdb0af5b5c619	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 10V, Negative-QTOF	splash10-004i-0019000000-fa512c1688ce00ffd41d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 20V, Negative-QTOF	splash10-004r-1059000000-8f65bcb90bc078a7912d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 40V, Negative-QTOF	splash10-0a4l-9140000000-4ded7c8842575d2752c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 10V, Negative-QTOF	splash10-004i-0009000000-f4bd181f937819513660	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 20V, Negative-QTOF	splash10-01t9-1019000000-a6b85cd3220846053c5c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 40V, Negative-QTOF	splash10-052f-9041000000-f6b90f282a7eccd547fd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 10V, Positive-QTOF	splash10-01q9-1239000000-b1d4cd921a69d9f8653f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 20V, Positive-QTOF	splash10-01q9-6933000000-1d63fd3f377179dddb82	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 40V, Positive-QTOF	splash10-053u-9800000000-eeb640c3008512e3c40a	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Adipose Tissue
Fibroblasts
Placenta
Platelet

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	10.0 +/- 4.1 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	6.4 +/- 5.6 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	14643447	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	13.9 +/- 5.2 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Urine	Detected and Quantified	3.0 +/- 2.3 umol/mmol creatinine	Adult (>18 years old)	Both	Thyroid cancer	14643447	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 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Thyroid cancer
Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]

Associated OMIM IDs

243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022774

KNApSAcK ID

Not Available

Chemspider ID

4945614

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6412

PubChem Compound

6441454

PDB ID

Not Available

ChEBI ID

65136

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

Williard DE, Nwankwo JO, Kaduce TL, Harmon SD, Irons M, Moser HW, Raymond GV, Spector AA: Identification of a fatty acid delta6-desaturase deficiency in human skin fibroblasts. J Lipid Res. 2001 Apr;42(4):501-8. [PubMed:11290821 ]
Marckmann P, Lassen A, Haraldsdottir J, Sandstrom B: Biomarkers of habitual fish intake in adipose tissue. Am J Clin Nutr. 1995 Nov;62(5):956-9. [PubMed:7572741 ]
Pedersen JI, Ringstad J, Almendingen K, Haugen TS, Stensvold I, Thelle DS: Adipose tissue fatty acids and risk of myocardial infarction--a case-control study. Eur J Clin Nutr. 2000 Aug;54(8):618-25. [PubMed:10951510 ]
Park Y, Harris W: EPA, but not DHA, decreases mean platelet volume in normal subjects. Lipids. 2002 Oct;37(10):941-6. [PubMed:12530552 ]
Francois CA, Connor SL, Bolewicz LC, Connor WE: Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk. Am J Clin Nutr. 2003 Jan;77(1):226-33. [PubMed:12499346 ]
Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
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 ]

Showing metabocard for Docosapentaenoic acid (22n-6) (HMDB0001976)

MOL for HMDB0001976 (Docosapentaenoic acid (22n-6))

3D MOL for HMDB0001976 (Docosapentaenoic acid (22n-6))

3D SDF for HMDB0001976 (Docosapentaenoic acid (22n-6))

3D-SDF for HMDB0001976 (Docosapentaenoic acid (22n-6))

PDB for HMDB0001976 (Docosapentaenoic acid (22n-6))

3D PDB for HMDB0001976 (Docosapentaenoic acid (22n-6))

SMILES for HMDB0001976 (Docosapentaenoic acid (22n-6))

INCHI for HMDB0001976 (Docosapentaenoic acid (22n-6))

Structure for HMDB0001976 (Docosapentaenoic acid (22n-6))

3D Structure for HMDB0001976 (Docosapentaenoic acid (22n-6))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra