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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:12 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0002823

Secondary Accession Numbers

HMDB02823

Metabolite Identification

Common Name

Docosatrienoic acid

Description

Docosatrienoic acid, also known as docosatrienoate, 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. Docosatrienoic acid is a very hydrophobic molecule, is practically insoluble (in water), and is relatively neutral. Application of docosatrienoic acid was shown to dose-dependently decrease the peak K+ current amplitude and accelerate the potassium activation and inactivation kinetics at all membrane potentials.

Structure

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

HMDB0002823
     RDKit          3D
Docosatrienoic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
    9.6316   -1.0408    0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2111   -1.6194    0.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5639   -1.4435   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4725   -0.7601   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7185   -0.0584    0.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900    1.3687    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717    2.0016    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2500    1.3708    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    1.5082   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4747    2.1697   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728    2.8168   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    2.1721   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    0.7000    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9838    0.2033    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9790   -1.2494    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820   -1.8875    0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2838   -1.9705   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8988   -0.7821   -0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5899    0.1401    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6954   -0.5194    0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8112   -1.0671   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5197   -0.0366   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1955    1.1676   -0.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5522   -0.3560   -1.7118 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2148   -1.4471    1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5230    0.0510    1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1701   -1.3062    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6448   -1.3725    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4064   -2.7470    1.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9947   -1.8988   -1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0102   -0.6468   -1.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7612   -0.5833    0.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2494   -0.1574    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6619    1.9153    0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441    3.0732   -0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249    0.3031    0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6579    1.8322    1.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835    1.0305   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958    2.2613   -2.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367    2.9911    0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215    3.8766   -0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2416    2.6569    0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554    2.2729   -1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213    0.4602    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278    0.1852   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4737    0.4379   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    0.7372    1.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4082   -1.7961   -0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3953   -1.3966    1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636   -2.9417    1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8199   -1.4129    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145   -2.5736   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0798   -2.7094    0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -0.2102   -1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7416   -1.1519   -1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8160    0.5016    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9462    1.0113   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3546   -1.3030    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1513    0.2708    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5518   -1.5109    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4522   -1.8382   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8556    0.3071   -2.4106 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  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
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 24 62  1  0
M  END


  Mrv1652304202022022D          

 24 23  0  0  0  0            999 V2000
 9996.3582 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0731 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7879 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5030 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2174 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9331 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7581 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4737 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1873 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0143 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7279 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.4436 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2685 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.9863 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.6998 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6434 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9284 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2136 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.4987 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.7839 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.0689 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.3520 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.6372 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.3520 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  1  0  0  0  0
  3  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  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
 22 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002823

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10H,2,5,8,11-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-

> <INCHI_KEY>
WBBQTNCISCKUMU-PDBXOOCHSA-N

> <FORMULA>
C22H38O2

> <MOLECULAR_WEIGHT>
334.5359

> <EXACT_MASS>
334.28718046

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.32642059215165

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(13Z,16Z,19Z)-docosa-13,16,19-trienoic acid

> <ALOGPS_LOGP>
7.92

> <JCHEM_LOGP>
7.838229797666668

> <ALOGPS_LOGS>
-6.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
108.0394

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.44e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DTrE

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002823
     RDKit          3D
Docosatrienoic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
    9.6316   -1.0408    0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2111   -1.6194    0.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5639   -1.4435   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4725   -0.7601   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7185   -0.0584    0.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900    1.3687    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717    2.0016    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2500    1.3708    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    1.5082   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4747    2.1697   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728    2.8168   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    2.1721   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    0.7000    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9838    0.2033    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9790   -1.2494    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820   -1.8875    0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2838   -1.9705   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8988   -0.7821   -0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5899    0.1401    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6954   -0.5194    0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8112   -1.0671   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5197   -0.0366   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1955    1.1676   -0.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5522   -0.3560   -1.7118 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2148   -1.4471    1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5230    0.0510    1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1701   -1.3062    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6448   -1.3725    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4064   -2.7470    1.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9947   -1.8988   -1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0102   -0.6468   -1.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7612   -0.5833    0.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2494   -0.1574    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6619    1.9153    0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441    3.0732   -0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249    0.3031    0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6579    1.8322    1.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835    1.0305   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958    2.2613   -2.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367    2.9911    0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215    3.8766   -0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2416    2.6569    0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554    2.2729   -1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213    0.4602    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278    0.1852   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4737    0.4379   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    0.7372    1.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4082   -1.7961   -0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3953   -1.3966    1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636   -2.9417    1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8199   -1.4129    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145   -2.5736   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0798   -2.7094    0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -0.2102   -1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7416   -1.1519   -1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8160    0.5016    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9462    1.0113   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3546   -1.3030    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1513    0.2708    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5518   -1.5109    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4522   -1.8382   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8556    0.3071   -2.4106 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  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
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 24 62  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8659.8698663.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8661.2038663.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.5378663.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.8728663.832   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8665.2068663.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8666.5428663.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8668.0828663.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8669.4188663.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8670.7508663.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8672.2938663.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8673.6258663.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8674.9618663.832   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8676.5018663.832   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8677.8418663.064   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8679.1738663.832   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8658.5348663.832   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8657.2008663.064   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8655.8658663.832   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8654.5318663.064   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8653.1978663.832   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8651.8628663.064   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8650.5248663.832   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8649.1898663.064   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8650.5248665.373   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   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    1   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   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0002823
HETATM    1  C1  UNL     1       9.632  -1.041   0.974  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.211  -1.619   0.960  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.564  -1.443  -0.336  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.472  -0.760  -0.479  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.718  -0.058   0.623  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.690   1.369   0.239  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.572   2.002   0.055  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.250   1.371   0.209  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.589   1.508  -1.139  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.475   2.170  -1.242  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.773   2.817  -0.158  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.605   2.172  -0.054  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.507   0.700   0.222  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.984   0.203   0.298  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.979  -1.249   0.568  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.282  -1.887   0.723  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.284  -1.970  -0.332  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.899  -0.782  -0.935  1.00  0.00           C  
HETATM   19  C19 UNL     1      -5.590   0.140   0.045  1.00  0.00           C  
HETATM   20  C20 UNL     1      -6.695  -0.519   0.787  1.00  0.00           C  
HETATM   21  C21 UNL     1      -7.811  -1.067  -0.047  1.00  0.00           C  
HETATM   22  C22 UNL     1      -8.520  -0.037  -0.828  1.00  0.00           C  
HETATM   23  O1  UNL     1      -8.195   1.168  -0.705  1.00  0.00           O  
HETATM   24  O2  UNL     1      -9.552  -0.356  -1.712  1.00  0.00           O  
HETATM   25  H1  UNL     1      10.215  -1.447   1.819  1.00  0.00           H  
HETATM   26  H2  UNL     1       9.523   0.051   1.131  1.00  0.00           H  
HETATM   27  H3  UNL     1      10.170  -1.306   0.053  1.00  0.00           H  
HETATM   28  H4  UNL     1       7.645  -1.372   1.848  1.00  0.00           H  
HETATM   29  H5  UNL     1       8.406  -2.747   1.042  1.00  0.00           H  
HETATM   30  H6  UNL     1       7.995  -1.899  -1.255  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.010  -0.647  -1.462  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.761  -0.583   0.654  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.249  -0.157   1.616  1.00  0.00           H  
HETATM   34  H10 UNL     1       6.662   1.915   0.103  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.544   3.073  -0.234  1.00  0.00           H  
HETATM   36  H12 UNL     1       3.225   0.303   0.416  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.658   1.832   1.025  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.083   1.030  -2.018  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.996   2.261  -2.249  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.237   2.991   0.790  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.522   3.877  -0.540  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.242   2.657   0.688  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.055   2.273  -1.083  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.021   0.460   1.151  1.00  0.00           H  
HETATM   45  H21 UNL     1      -0.028   0.185  -0.630  1.00  0.00           H  
HETATM   46  H22 UNL     1      -2.474   0.438  -0.639  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.457   0.737   1.138  1.00  0.00           H  
HETATM   48  H24 UNL     1      -1.408  -1.796  -0.257  1.00  0.00           H  
HETATM   49  H25 UNL     1      -1.395  -1.397   1.524  1.00  0.00           H  
HETATM   50  H26 UNL     1      -3.064  -2.942   1.160  1.00  0.00           H  
HETATM   51  H27 UNL     1      -3.820  -1.413   1.625  1.00  0.00           H  
HETATM   52  H28 UNL     1      -3.815  -2.574  -1.198  1.00  0.00           H  
HETATM   53  H29 UNL     1      -5.080  -2.709   0.026  1.00  0.00           H  
HETATM   54  H30 UNL     1      -4.259  -0.210  -1.592  1.00  0.00           H  
HETATM   55  H31 UNL     1      -5.742  -1.152  -1.654  1.00  0.00           H  
HETATM   56  H32 UNL     1      -4.816   0.502   0.760  1.00  0.00           H  
HETATM   57  H33 UNL     1      -5.946   1.011  -0.502  1.00  0.00           H  
HETATM   58  H34 UNL     1      -6.355  -1.303   1.497  1.00  0.00           H  
HETATM   59  H35 UNL     1      -7.151   0.271   1.454  1.00  0.00           H  
HETATM   60  H36 UNL     1      -8.552  -1.511   0.659  1.00  0.00           H  
HETATM   61  H37 UNL     1      -7.452  -1.838  -0.777  1.00  0.00           H  
HETATM   62  H38 UNL     1      -9.856   0.307  -2.411  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   42   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   54   55
CONECT   19   20   56   57
CONECT   20   21   58   59
CONECT   21   22   60   61
CONECT   22   23   23   24
CONECT   24   62
END

HMDB0002823
     RDKit          3D
Docosatrienoic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
    9.6316   -1.0408    0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2111   -1.6194    0.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5639   -1.4435   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4725   -0.7601   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7185   -0.0584    0.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900    1.3687    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5717    2.0016    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2500    1.3708    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    1.5082   -1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4747    2.1697   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728    2.8168   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    2.1721   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    0.7000    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9838    0.2033    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9790   -1.2494    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820   -1.8875    0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2838   -1.9705   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8988   -0.7821   -0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5899    0.1401    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6954   -0.5194    0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8112   -1.0671   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5197   -0.0366   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1955    1.1676   -0.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5522   -0.3560   -1.7118 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2148   -1.4471    1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5230    0.0510    1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1701   -1.3062    0.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6448   -1.3725    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4064   -2.7470    1.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9947   -1.8988   -1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0102   -0.6468   -1.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7612   -0.5833    0.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2494   -0.1574    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6619    1.9153    0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441    3.0732   -0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249    0.3031    0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6579    1.8322    1.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835    1.0305   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958    2.2613   -2.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367    2.9911    0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215    3.8766   -0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2416    2.6569    0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554    2.2729   -1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0213    0.4602    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278    0.1852   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4737    0.4379   -0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    0.7372    1.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4082   -1.7961   -0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3953   -1.3966    1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636   -2.9417    1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8199   -1.4129    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145   -2.5736   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0798   -2.7094    0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -0.2102   -1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7416   -1.1519   -1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8160    0.5016    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9462    1.0113   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3546   -1.3030    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1513    0.2708    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5518   -1.5109    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4522   -1.8382   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8556    0.3071   -2.4106 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  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
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 24 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(13Z,16Z,19Z) Docosatrienoic acid	ChEBI
all-cis-13,16,19 Docosatrienoic acid	ChEBI
(13Z,16Z,19Z) Docosatrienoate	Generator
all-cis-13,16,19 Docosatrienoate	Generator
Docosatrienoate	Generator
13,16,19-Docosatrienoate	HMDB
13,16,19-Docosatrienoic acid	HMDB
(13Z,16Z,19Z)-Docosatrienoate	HMDB
(13Z,16Z,19Z)-13,16,19-Docosatrienoic acid	HMDB
FA(22:3(13Z,16Z,19Z))	HMDB
FA(22:3n3)	HMDB
cis-13,cis-16,cis-19-Docosatrienoic acid	HMDB
Docosatrienoic acid	HMDB

Chemical Formula

C₂₂H₃₈O₂

Average Molecular Weight

334.5359

Monoisotopic Molecular Weight

334.28718046

IUPAC Name

(13Z,16Z,19Z)-docosa-13,16,19-trienoic acid

Traditional Name

DTrE

CAS Registry Number

28845-86-5

SMILES

CC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C22H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10H,2,5,8,11-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-

InChI Key

WBBQTNCISCKUMU-PDBXOOCHSA-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:77807 )
docosatrienoic acid (CHEBI:77807 )
Unsaturated fatty acids (LMFA01030408 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Organ

Placenta (HMDB: HMDB0002823)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)

Cellular substructure

Membrane (HMDB: HMDB0002823)
Extracellular (HMDB: HMDB0002823)

Source

Exogenous

Exogenous (HMDB: HMDB0002823)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002823)

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	3.4e-05 g/L	ALOGPS
logP	7.92	ALOGPS
logP	7.84	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	4.95	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	17	ChemAxon
Refractivity	108.04 m³·mol⁻¹	ChemAxon
Polarizability	43.33 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]+	192.64	31661259
DarkChem	[M-H]-	191.887	31661259
DeepCCS	[M+H]+	190.026	30932474
DeepCCS	[M-H]-	187.668	30932474
DeepCCS	[M-2H]-	220.555	30932474
DeepCCS	[M+Na]+	196.119	30932474
AllCCS	[M+H]+	193.4	32859911
AllCCS	[M+H-H2O]+	190.7	32859911
AllCCS	[M+NH4]+	195.9	32859911
AllCCS	[M+Na]+	196.6	32859911
AllCCS	[M-H]-	193.0	32859911
AllCCS	[M+Na-2H]-	195.3	32859911
AllCCS	[M+HCOO]-	198.1	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.	9.2 minutes	32390414
Predicted by Siyang on May 30, 2022	28.3658 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.64 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	42.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3459.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	719.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	287.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	477.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	766.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1280.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	850.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2647.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	820.1 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	2151.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1005.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	589.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	640.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	668.5 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	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Docosatrienoic acid	CC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O	3761.1	Standard polar	33892256
Docosatrienoic acid	CC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O	2416.7	Standard non polar	33892256
Docosatrienoic acid	CC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O	2555.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Docosatrienoic acid,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCCCCCC(=O)O[Si](C)(C)C	2610.6	Semi standard non polar	33892256
Docosatrienoic acid,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2861.4	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.004 +/- 0.001 uM	Adult (>18 years old)	Both	Normal	20671299	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

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

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 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112372

KNApSAcK ID

Not Available

Chemspider ID

4471982

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

195

PubChem Compound

5312557

PDB ID

Not Available

ChEBI ID

77807

Food Biomarker Ontology

Not Available

VMH ID

M00341

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Soares MC, Alessio ML, Leger CL, Bluet-Pajot MT, Clauser H, Enjalbert A, Kordon C, Wandscheer DE: Effect of essential fatty acid deficiency on membrane fatty acid content and growth hormone stimulation of rat pituitaries during postnatal development. J Lipid Res. 1995 Jun;36(6):1401-6. [PubMed:7666016 ]
Krutetskaia ZI, Lebedev OE, Roshchina NG, Butov SN: [The effect of docosatrienoic acid on the potassium channels of outward rectification in the membrane of rat peritoneal macrophages]. Fiziol Zh Im I M Sechenova. 1995 Jul;81(7):111-9. [PubMed:8714386 ]
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 Docosatrienoic acid (HMDB0002823)

MOL for HMDB0002823 (Docosatrienoic acid)

3D MOL for HMDB0002823 (Docosatrienoic acid)

3D SDF for HMDB0002823 (Docosatrienoic acid)

3D-SDF for HMDB0002823 (Docosatrienoic acid)

PDB for HMDB0002823 (Docosatrienoic acid)

3D PDB for HMDB0002823 (Docosatrienoic acid)

SMILES for HMDB0002823 (Docosatrienoic acid)

INCHI for HMDB0002823 (Docosatrienoic acid)

Structure for HMDB0002823 (Docosatrienoic acid)

3D Structure for HMDB0002823 (Docosatrienoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized