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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-05-23 14:34:40 UTC

Update Date

2022-03-07 02:49:32 UTC

HMDB ID

HMDB0006528

Secondary Accession Numbers

HMDB06528

Metabolite Identification

Common Name

Docosapentaenoic acid (22n-3)

Description

Docosapentaenoic acid (22n-3) (also known as clupanodonic acid) is an essential omega-3 fatty acid (EFA) which is prevalent in fish oils. Docosapentaenoic acid, commonly called DPA, is an intermediary between eicosapentaenoic acid (EPA, 20:5 ω-3) and docosahexaenoic acid (DHA, 22:6 ω-3). Seal oil is a rich source of this metabolite. There are three functions of docosapentaenoic acid. Most importantly, it is a component of phospholipids found in all animal cell membranes, and a deficiency of docosapentaenoic acid leads to faulty membranes being formed. Secondly, it is involved in the transport and oxidation of cholesterol, and clupanodonic acid tends to lower plasma cholesterol. A third function is as a precursor of prostanoids which are only formed from docosapentaenoic acid. Deficiency of this in experimental animals causes lesions mainly attributable to faulty cellular membranes. Outcomes include sudden failure of growth, lesions of the skin, kidney, and connective tissue, erythrocyte fragility, impaired fertility, and the uncoupling of oxidation and phosphorylation. In humans, pure deficiency of docosapentaenoic acid has been studied particularly in persons fed intravenously. A relative deficiency (that is, a low ratio in the body of docosapentaenoic to long-chain saturated fatty acids and isomers of docosapentaenoate) is common in Western diets and plays an important part in the causation of atherosclerosis, coronary thrombosis, multiple sclerosis, the triopathy of diabetes mellitus, hypertension, and certain forms of malignant disease. Various factors affect the dietary requirement of docosapentaenoic acid (PMID: 6469703 ).

Structure

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

HMDB0006528
     RDKit          3D
Docosapentaenoic acid (22n-3)
 58 57  0  0  0  0  0  0  0  0999 V2000
   -7.2264    1.0253   -2.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2179    0.3279   -2.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3891    1.3300   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2908    1.4993   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0205    0.6852    0.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4207   -0.1760    1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815   -0.4524    2.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    0.0501    1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2491   -1.1076    0.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087   -1.2824    1.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -0.3522    2.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -1.0694    3.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3712   -1.1305    3.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928   -0.4874    2.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4359   -1.5734    2.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7722   -1.7994    1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3265   -1.0799    0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5296   -0.4652   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0074    0.2618   -1.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    0.8954   -2.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8858    1.9147   -1.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9488    2.4956   -2.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7153    3.3755   -2.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1403    2.1249   -4.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0448    1.4922   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6864    0.2243   -3.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7157    1.7458   -3.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6931   -0.4304   -1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5681   -0.2767   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7872    2.0093   -1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6529    2.3278    0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6305    1.4904    1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9325    0.1855    0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -0.7065    2.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9078   -1.1628    2.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    0.7041    1.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2448    0.6513    0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7490   -1.7799    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4216   -2.1364    0.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.0806    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7622    0.6065    2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6144   -1.6050    3.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121   -1.7089    4.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2823    0.2342    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083    0.1325    3.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8395   -2.1795    3.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798   -2.6348    1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8764   -1.8315   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812   -0.3038    0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2067   -1.2801   -0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9937    0.2831   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -0.4938   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    1.0088   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8326    0.1482   -3.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6780    1.3823   -3.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3930    1.3497   -1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2664    2.7345   -1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0583    1.8614   -4.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
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 18 50  1  0
 18 51  1  0
 19 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

LMFA04000044
  Mrv1652303312018252D          

 24 23  0  0  0  0            999 V2000
   19.8432    5.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5536    5.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8432    6.1157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1277    5.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4118    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6960    5.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9801    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2642    5.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5484    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8326    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1167    5.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4009    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6850    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9691    5.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2533    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5375    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8216    5.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1057    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3899    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6740    5.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9582    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2424    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5264    5.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8106    5.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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  1  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  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006528

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(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/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
YUFFSWGQGVEMMI-JLNKQSITSA-N

> <FORMULA>
C22H34O2

> <MOLECULAR_WEIGHT>
330.5042

> <EXACT_MASS>
330.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.102772290562484

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid

> <ALOGPS_LOGP>
7.08

> <JCHEM_LOGP>
7.114386484333333

> <ALOGPS_LOGS>
-6.45

> <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>
110.27260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clupanodonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006528
     RDKit          3D
Docosapentaenoic acid (22n-3)
 58 57  0  0  0  0  0  0  0  0999 V2000
   -7.2264    1.0253   -2.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2179    0.3279   -2.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3891    1.3300   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2908    1.4993   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0205    0.6852    0.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4207   -0.1760    1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815   -0.4524    2.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    0.0501    1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2491   -1.1076    0.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087   -1.2824    1.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -0.3522    2.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -1.0694    3.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3712   -1.1305    3.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928   -0.4874    2.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4359   -1.5734    2.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7722   -1.7994    1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3265   -1.0799    0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5296   -0.4652   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0074    0.2618   -1.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    0.8954   -2.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8858    1.9147   -1.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9488    2.4956   -2.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7153    3.3755   -2.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1403    2.1249   -4.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0448    1.4922   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6864    0.2243   -3.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7157    1.7458   -3.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6931   -0.4304   -1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5681   -0.2767   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7872    2.0093   -1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6529    2.3278    0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6305    1.4904    1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9325    0.1855    0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -0.7065    2.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9078   -1.1628    2.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    0.7041    1.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2448    0.6513    0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7490   -1.7799    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4216   -2.1364    0.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.0806    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7622    0.6065    2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6144   -1.6050    3.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121   -1.7089    4.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2823    0.2342    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083    0.1325    3.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8395   -2.1795    3.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798   -2.6348    1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8764   -1.8315   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812   -0.3038    0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2067   -1.2801   -0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9937    0.2831   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -0.4938   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    1.0088   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8326    0.1482   -3.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6780    1.3823   -3.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3930    1.3497   -1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2664    2.7345   -1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0583    1.8614   -4.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 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                                 31-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LMFA04000044                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-20         0                                  
HETATM    1  C   UNK     0      37.041  10.190   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      38.367   9.424   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      37.041  11.416   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      35.705   9.424   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      34.369  10.190   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.033   9.424   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.696  10.190   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.360   9.424   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.024  10.190   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.688  10.190   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.351   9.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.015  10.190   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.679  10.190   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.342   9.424   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.006  10.190   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.670  10.190   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.334   9.424   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.997  10.190   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.661  10.190   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.325   9.424   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.989  10.190   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.652  10.190   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.316   9.424   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.980  10.190   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    HMDB0006528
HETATM    1  C1  UNL     1      -7.226   1.025  -2.914  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.218   0.328  -2.018  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.389   1.330  -1.320  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.291   1.499  -0.024  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.020   0.685   0.927  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.421  -0.176   1.896  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.182  -0.452   2.083  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.031   0.050   1.326  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.249  -1.108   0.754  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.009  -1.282   1.073  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.317  -0.352   2.005  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.136  -1.069   3.212  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.371  -1.130   3.604  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.493  -0.487   2.893  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.436  -1.573   2.514  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.772  -1.799   1.279  1.00  0.00           C  
HETATM   17  C17 UNL     1       3.327  -1.080   0.083  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.530  -0.465  -0.663  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.007   0.262  -1.884  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.101   0.895  -2.678  1.00  0.00           C  
HETATM   21  C21 UNL     1       5.886   1.915  -1.880  1.00  0.00           C  
HETATM   22  C22 UNL     1       6.949   2.496  -2.736  1.00  0.00           C  
HETATM   23  O1  UNL     1       7.715   3.376  -2.237  1.00  0.00           O  
HETATM   24  O2  UNL     1       7.140   2.125  -4.040  1.00  0.00           O  
HETATM   25  H1  UNL     1      -8.045   1.492  -2.351  1.00  0.00           H  
HETATM   26  H2  UNL     1      -7.686   0.224  -3.541  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.716   1.746  -3.562  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.693  -0.430  -1.389  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.568  -0.277  -2.730  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.787   2.009  -1.959  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.653   2.328   0.327  1.00  0.00           H  
HETATM   32  H8  UNL     1      -6.631   1.490   1.540  1.00  0.00           H  
HETATM   33  H9  UNL     1      -6.932   0.185   0.425  1.00  0.00           H  
HETATM   34  H10 UNL     1      -6.132  -0.706   2.622  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.908  -1.163   2.919  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.471   0.704   1.987  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.245   0.651   0.427  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.749  -1.780   0.078  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.422  -2.136   0.656  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.640  -0.081   1.431  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.762   0.607   2.188  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.614  -1.605   3.851  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.612  -1.709   4.547  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.282   0.234   2.134  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.008   0.133   3.728  1.00  0.00           H  
HETATM   46  H22 UNL     1       3.840  -2.179   3.316  1.00  0.00           H  
HETATM   47  H23 UNL     1       4.480  -2.635   1.107  1.00  0.00           H  
HETATM   48  H24 UNL     1       2.876  -1.831  -0.629  1.00  0.00           H  
HETATM   49  H25 UNL     1       2.581  -0.304   0.218  1.00  0.00           H  
HETATM   50  H26 UNL     1       5.207  -1.280  -0.908  1.00  0.00           H  
HETATM   51  H27 UNL     1       4.994   0.283  -0.000  1.00  0.00           H  
HETATM   52  H28 UNL     1       3.514  -0.494  -2.526  1.00  0.00           H  
HETATM   53  H29 UNL     1       3.242   1.009  -1.620  1.00  0.00           H  
HETATM   54  H30 UNL     1       5.833   0.148  -3.041  1.00  0.00           H  
HETATM   55  H31 UNL     1       4.678   1.382  -3.579  1.00  0.00           H  
HETATM   56  H32 UNL     1       6.393   1.350  -1.053  1.00  0.00           H  
HETATM   57  H33 UNL     1       5.266   2.734  -1.495  1.00  0.00           H  
HETATM   58  H34 UNL     1       8.058   1.861  -4.371  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4    4   30
CONECT    4    5   31
CONECT    5    6   32   33
CONECT    6    7    7   34
CONECT    7    8   35
CONECT    8    9   36   37
CONECT    9   10   10   38
CONECT   10   11   39
CONECT   11   12   40   41
CONECT   12   13   13   42
CONECT   13   14   43
CONECT   14   15   44   45
CONECT   15   16   16   46
CONECT   16   17   47
CONECT   17   18   48   49
CONECT   18   19   50   51
CONECT   19   20   52   53
CONECT   20   21   54   55
CONECT   21   22   56   57
CONECT   22   23   23   24
CONECT   24   58
END

HMDB0006528
     RDKit          3D
Docosapentaenoic acid (22n-3)
 58 57  0  0  0  0  0  0  0  0999 V2000
   -7.2264    1.0253   -2.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2179    0.3279   -2.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3891    1.3300   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2908    1.4993   -0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0205    0.6852    0.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4207   -0.1760    1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815   -0.4524    2.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    0.0501    1.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2491   -1.1076    0.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087   -1.2824    1.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -0.3522    2.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -1.0694    3.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3712   -1.1305    3.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928   -0.4874    2.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4359   -1.5734    2.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7722   -1.7994    1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3265   -1.0799    0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5296   -0.4652   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0074    0.2618   -1.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1014    0.8954   -2.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8858    1.9147   -1.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9488    2.4956   -2.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7153    3.3755   -2.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1403    2.1249   -4.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0448    1.4922   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6864    0.2243   -3.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7157    1.7458   -3.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6931   -0.4304   -1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5681   -0.2767   -2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7872    2.0093   -1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6529    2.3278    0.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6305    1.4904    1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9325    0.1855    0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -0.7065    2.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9078   -1.1628    2.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4705    0.7041    1.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2448    0.6513    0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7490   -1.7799    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4216   -2.1364    0.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.0806    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7622    0.6065    2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6144   -1.6050    3.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121   -1.7089    4.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2823    0.2342    2.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083    0.1325    3.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8395   -2.1795    3.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798   -2.6348    1.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8764   -1.8315   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812   -0.3038    0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2067   -1.2801   -0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9937    0.2831   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -0.4938   -2.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    1.0088   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8326    0.1482   -3.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6780    1.3823   -3.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3930    1.3497   -1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2664    2.7345   -1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0583    1.8614   -4.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 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
(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acid	ChEBI
(all Z)-7,10,13,16,19-Docosapentaenoic acid	ChEBI
all-cis-7,10,13,16,19-Docosapentaenoic acid	ChEBI
cis-7,10,13,16,19-Docosapentaenoic acid	ChEBI
Clupanodonic acid	ChEBI
Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acid	ChEBI
Docosapentaenoic acid	ChEBI
DPA	ChEBI
DPAn-3	ChEBI
7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid	Kegg
(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoate	Generator
(all Z)-7,10,13,16,19-Docosapentaenoate	Generator
all-cis-7,10,13,16,19-Docosapentaenoate	Generator
cis-7,10,13,16,19-Docosapentaenoate	Generator
Clupanodonate	Generator
Docosa-7Z,10Z,13Z,16Z,19Z-pentaenoate	Generator
Docosapentaenoate	Generator
7Z,10Z,13Z,16Z,19Z-Docosapentaenoate	Generator
Docosapentaenoate (22N-3)	Generator
7,10,13,16,19-Docosapentaenoic acid, (all-Z)-isomer	MeSH
Docosapentaenoic acid (C22:5 N3)	MeSH
Osbond acid	MeSH
(all-Z)-7, 10, 13, 16, 19-Docosapentaenoic acid	MeSH
7,10,13,16,19-Docosapentaenoic acid	MeSH
Docosapentaenoic acid, (all Z)-isomer	MeSH
(7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoate	HMDB
(7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoic acid	HMDB
7,10,13,16,19-Docosapentaenoate	HMDB
FA(22:5(7Z,10Z,13Z,16Z,19Z))	HMDB
(7Z,10Z,13Z,16Z,19Z)-7,10,13,16,19-Docosapentaenoic acid	HMDB
(all-Z)-7,10,13,16,19-Docosapentaenoic acid	HMDB
FA(22:5n3)	HMDB
delta7,10,13,16,19-Docosapentaenoic acid	HMDB
omega3-Docosapentaenoic acid	HMDB
Δ7,10,13,16,19-Docosapentaenoic acid	HMDB
ω3-Docosapentaenoic acid	HMDB

Chemical Formula

C₂₂H₃₄O₂

Average Molecular Weight

330.5042

Monoisotopic Molecular Weight

330.255880332

IUPAC Name

(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid

Traditional Name

clupanodonic acid

CAS Registry Number

24880-45-3

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(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/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-

InChI Key

YUFFSWGQGVEMMI-JLNKQSITSA-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

omega-3 fatty acid (CHEBI:53488 )
docosapentaenoic acid (CHEBI:53488 )
Docosanoids (C16513 )
Polyunsaturated fatty acids (C16513 )
Docosanoids (LMFA04000044 )

Ontology

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	0.00012 g/L	ALOGPS
logP	7.08	ALOGPS
logP	7.11	ChemAxon
logS	-6.4	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	15	ChemAxon
Refractivity	110.27 m³·mol⁻¹	ChemAxon
Polarizability	40.1 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]+	192.516	31661259
DarkChem	[M-H]-	190.663	31661259
DeepCCS	[M+H]+	188.95	30932474
DeepCCS	[M-H]-	186.592	30932474
DeepCCS	[M-2H]-	219.478	30932474
DeepCCS	[M+Na]+	195.043	30932474
AllCCS	[M+H]+	190.0	32859911
AllCCS	[M+H-H2O]+	187.2	32859911
AllCCS	[M+NH4]+	192.7	32859911
AllCCS	[M+Na]+	193.4	32859911
AllCCS	[M-H]-	189.6	32859911
AllCCS	[M+Na-2H]-	191.7	32859911
AllCCS	[M+HCOO]-	194.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Docosapentaenoic acid (22n-3)	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O	3993.9	Standard polar	33892256
Docosapentaenoic acid (22n-3)	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O	2283.2	Standard non polar	33892256
Docosapentaenoic acid (22n-3)	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O	2524.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Docosapentaenoic acid (22n-3),1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[Si](C)(C)C	2559.7	Semi standard non polar	33892256
Docosapentaenoic acid (22n-3),1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[Si](C)(C)C(C)(C)C	2808.7	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 - Docosapentaenoic acid (22n-3) GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-5491000000-56de363323dabc6f26e3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Docosapentaenoic acid (22n-3) GC-MS (1 TMS) - 70eV, Positive	splash10-009i-9583000000-943203f8659c9ab3cac4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Docosapentaenoic acid (22n-3) 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) LC-ESI-IT , negative-QTOF	splash10-000i-0090000000-260dcf8cd2e9cacf0e81	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) Linear Ion Trap , negative-QTOF	splash10-000i-0090000000-b359128b4a9edc7dc9ca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) Linear Ion Trap , positive-QTOF	splash10-01x3-0492000000-89d3794a87bea421691b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 10V, Positive-QTOF	splash10-03di-0039000000-405cbfa338b34ddb7441	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 20V, Positive-QTOF	splash10-000i-5793000000-59855762e7bce0a8ec9d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 40V, Positive-QTOF	splash10-0avv-8970000000-49596865551dfe04eaa1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 10V, Negative-QTOF	splash10-004i-0019000000-4d8832b1fd953fd8ec08	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 20V, Negative-QTOF	splash10-01ti-1039000000-f6df0e4a8ec7c01d9955	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 40V, Negative-QTOF	splash10-0a4l-9130000000-a69f7e9f82c75012f728	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 10V, Negative-QTOF	splash10-004i-0009000000-f4bd181f937819513660	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 20V, Negative-QTOF	splash10-01t9-1009000000-fd8104aee9b78a72f4db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 40V, Negative-QTOF	splash10-0006-9221000000-a71d2d6e07928441d5ef	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 10V, Positive-QTOF	splash10-01q9-2329000000-918ad0c35d9079c18ee1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 20V, Positive-QTOF	splash10-001i-4911000000-cca43fd70d0980b4845e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-3) 40V, Positive-QTOF	splash10-001i-9700000000-ca068d510d72f2bb000e	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

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	39.334 +/- 6.0514 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	36.308 +/- 6.0514 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	33.282 +/- 6.0514 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	30.257 +/- 9.0770 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	45.779 +/- 12.768 uM	Adult (>18 years old)	Both	Normal	17313719	details
Blood	Detected and Quantified	48.925 +/- 11.256 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	60 +/- 20 uM	Adult (>18 years old)	Female	Normal	14608088	details
Blood	Detected and Quantified	0.993 +/- 0.46 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	60 +/- 20 uM	Adult (>18 years old)	Male	Normal	14608088	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected and Quantified	0.400 +/- 0.005 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	9.0 (7.3-11.5) uM	Adult (>18 years old)	Both	Normal	10022638	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	34.8 +/- 12.2 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Blood	Detected and Quantified	0.386 +/- 0.229 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	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	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26476344	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	18.7 +/- 10.4 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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	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
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] 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 ]

Associated OMIM IDs

243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Docosapentaenoic acid

METLIN ID

194

PubChem Compound

5497182

PDB ID

Not Available

ChEBI ID

53488

Food Biomarker Ontology

Not Available

VMH ID

CLPND

MarkerDB ID

MDB00000486

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sinclair HM: Essential fatty acids in perspective. Hum Nutr Clin Nutr. 1984 Jul;38(4):245-60. [PubMed:6469703 ]
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-3) (HMDB0006528)

MOL for HMDB0006528 (Docosapentaenoic acid (22n-3))

3D MOL for HMDB0006528 (Docosapentaenoic acid (22n-3))

3D SDF for HMDB0006528 (Docosapentaenoic acid (22n-3))

3D-SDF for HMDB0006528 (Docosapentaenoic acid (22n-3))

PDB for HMDB0006528 (Docosapentaenoic acid (22n-3))

3D PDB for HMDB0006528 (Docosapentaenoic acid (22n-3))

SMILES for HMDB0006528 (Docosapentaenoic acid (22n-3))

INCHI for HMDB0006528 (Docosapentaenoic acid (22n-3))

Structure for HMDB0006528 (Docosapentaenoic acid (22n-3))

3D Structure for HMDB0006528 (Docosapentaenoic acid (22n-3))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra