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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2011-07-06 15:20:02 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013650

Secondary Accession Numbers

HMDB13650

Metabolite Identification

Common Name

Arachidonoyl Serinol

Description

2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor (PMID: 8954083 , 9399597 ). Replacement of the sn-2 oxygen in the glycerol moiety of 2-AG with a nitrogen atom gives arachidonoyl serinol (PMID: 8893848 ). Arachidonoyl serinol is much more stable than 2-AG. However, it is at least a log less potent as a CB1 receptor agonist than 2-AG (PMID: 9399597 ).

Structure

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

  Mrv0541 02271200292D          

 27 26  0  0  0  0            999 V2000
    9.0763  -10.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9014  -10.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139  -11.5566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389  -11.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515  -12.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765  -12.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515  -10.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765  -10.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139  -10.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389  -10.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515   -9.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765   -9.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7890   -8.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3771   -7.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5521   -7.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1395   -7.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765   -6.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7884   -5.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3759   -5.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5509   -5.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389   -4.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5509   -3.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3759   -3.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7877   -2.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6116   -2.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0235   -2.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0013650
     RDKit          3D
Arachidonoyl Serinol
 66 65  0  0  0  0  0  0  0  0999 V2000
    9.9547   -2.5913    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3701   -1.6943   -0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4878   -0.6267   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3102   -1.1744    0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4744    0.0120    1.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410   -0.5634    1.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0856   -0.3854    1.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    0.4696    0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9421    1.6288    0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554    1.8524    0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558    1.0030   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722    1.8302   -2.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959    2.0706   -2.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6367    1.5480   -1.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5646    2.6385   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9755    2.7826   -0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6532    1.9758    0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9693    1.4122    1.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    0.5547    0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9118   -0.0084    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960    0.2680    1.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7463   -0.8447    0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9863   -1.3948    0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0848   -0.8048   -0.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3270   -1.2817   -0.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0437   -2.8978    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0288   -3.4355    1.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5628   -2.0120    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6948   -3.2654   -0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1987   -3.2341    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2147   -1.1917   -1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8507   -2.3214   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1020   -0.0306   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0546    0.0361    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6695   -1.8504   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6990   -1.7498    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2765    0.7563    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1738    0.5543    1.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5980   -1.1944    2.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2564   -0.8348    2.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5845    0.6946   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937   -0.2441   -0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3321    2.3397    1.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919    2.7451    0.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006    0.7334   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.1149   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670    2.2615   -2.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379    2.7051   -3.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1966    1.0030   -2.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875    0.8602   -1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9075    3.3416   -2.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6662    3.6322   -0.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447    1.1709    0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2910    2.7038    1.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059    0.7497    2.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5880    2.2380    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8277    1.2117   -0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9883   -0.2734    0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4249   -1.0715   -0.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2529   -1.1098    1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0728    0.3029   -0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8555   -0.9284   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9882   -0.5528   -0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9397   -3.2582   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0424   -3.1966    0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3516   -4.1787    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 22 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
M  END

  Mrv0541 02271200292D          

 27 26  0  0  0  0            999 V2000
    9.0763  -10.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9014  -10.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139  -11.5566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389  -11.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515  -12.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765  -12.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515  -10.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765  -10.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139  -10.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389  -10.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515   -9.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765   -9.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7890   -8.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3771   -7.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5521   -7.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1395   -7.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765   -6.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7884   -5.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3759   -5.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5509   -5.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389   -4.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5509   -3.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3759   -3.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7877   -2.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6116   -2.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0235   -2.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013650

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC(CO)CO

> <INCHI_IDENTIFIER>
InChI=1S/C23H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(27)24-22(20-25)21-26/h6-7,9-10,12-13,15-16,22,25-26H,2-5,8,11,14,17-21H2,1H3,(H,24,27)/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
QHELXIATGZYOIB-DOFZRALJSA-N

> <FORMULA>
C23H39NO3

> <MOLECULAR_WEIGHT>
377.5607

> <EXACT_MASS>
377.292994119

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
45.31883375417432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z)-N-(1,3-dihydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
4.683467309000001

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.738556460778891

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.82357253696766

> <JCHEM_PKA_STRONGEST_BASIC>
-0.26695465114214023

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
118.9277

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
AA dihydroxypropylamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013650
     RDKit          3D
Arachidonoyl Serinol
 66 65  0  0  0  0  0  0  0  0999 V2000
    9.9547   -2.5913    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3701   -1.6943   -0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4878   -0.6267   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3102   -1.1744    0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4744    0.0120    1.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410   -0.5634    1.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0856   -0.3854    1.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    0.4696    0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9421    1.6288    0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554    1.8524    0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558    1.0030   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722    1.8302   -2.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959    2.0706   -2.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6367    1.5480   -1.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5646    2.6385   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9755    2.7826   -0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6532    1.9758    0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9693    1.4122    1.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    0.5547    0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9118   -0.0084    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960    0.2680    1.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7463   -0.8447    0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9863   -1.3948    0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0848   -0.8048   -0.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3270   -1.2817   -0.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0437   -2.8978    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0288   -3.4355    1.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5628   -2.0120    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6948   -3.2654   -0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1987   -3.2341    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2147   -1.1917   -1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8507   -2.3214   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1020   -0.0306   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0546    0.0361    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6695   -1.8504   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6990   -1.7498    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2765    0.7563    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1738    0.5543    1.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5980   -1.1944    2.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2564   -0.8348    2.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5845    0.6946   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937   -0.2441   -0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3321    2.3397    1.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919    2.7451    0.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006    0.7334   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.1149   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670    2.2615   -2.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379    2.7051   -3.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1966    1.0030   -2.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875    0.8602   -1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9075    3.3416   -2.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6662    3.6322   -0.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447    1.1709    0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2910    2.7038    1.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059    0.7497    2.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5880    2.2380    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8277    1.2117   -0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9883   -0.2734    0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4249   -1.0715   -0.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2529   -1.1098    1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0728    0.3029   -0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8555   -0.9284   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9882   -0.5528   -0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9397   -3.2582   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0424   -3.1966    0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3516   -4.1787    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 22 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0      16.942 -20.238   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      18.483 -20.238   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      19.253 -21.572   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      20.793 -21.572   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.563 -22.906   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      23.103 -22.906   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      21.563 -20.238   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      23.103 -20.238   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      19.253 -18.904   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.793 -18.904   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.563 -17.571   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.103 -17.571   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.873 -16.238   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.104 -14.904   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.564 -14.903   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.794 -13.568   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.563 -12.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.103 -12.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.872 -10.899   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.102  -9.565   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.562  -9.563   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.793  -8.230   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.562  -6.896   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.102  -6.893   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.870  -5.559   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      25.408  -5.557   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.177  -4.223   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7                                                            
CONECT    9    2   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   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

COMPND    HMDB0013650
HETATM    1  C1  UNL     1       9.955  -2.591   0.298  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.370  -1.694  -0.755  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.488  -0.627  -0.197  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.310  -1.174   0.567  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.474   0.012   1.093  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.341  -0.563   1.828  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.086  -0.385   1.522  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.742   0.470   0.323  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.942   1.629   0.721  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.755   1.852   0.225  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.056   1.003  -0.783  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.772   1.830  -2.008  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.396   2.071  -2.514  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.637   1.548  -1.938  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.565   2.638  -1.537  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.975   2.783  -0.312  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.653   1.976   0.868  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.969   1.412   1.394  1.00  0.00           C  
HETATM   19  C19 UNL     1      -4.643   0.555   0.346  1.00  0.00           C  
HETATM   20  C20 UNL     1      -5.912  -0.008   0.806  1.00  0.00           C  
HETATM   21  O1  UNL     1      -6.296   0.268   1.974  1.00  0.00           O  
HETATM   22  N1  UNL     1      -6.746  -0.845   0.035  1.00  0.00           N  
HETATM   23  C21 UNL     1      -7.986  -1.395   0.484  1.00  0.00           C  
HETATM   24  C22 UNL     1      -9.085  -0.805  -0.404  1.00  0.00           C  
HETATM   25  O2  UNL     1     -10.327  -1.282  -0.042  1.00  0.00           O  
HETATM   26  C23 UNL     1      -8.044  -2.898   0.395  1.00  0.00           C  
HETATM   27  O3  UNL     1      -7.029  -3.435   1.186  1.00  0.00           O  
HETATM   28  H1  UNL     1      10.563  -2.012   1.026  1.00  0.00           H  
HETATM   29  H2  UNL     1      10.695  -3.265  -0.221  1.00  0.00           H  
HETATM   30  H3  UNL     1       9.199  -3.234   0.786  1.00  0.00           H  
HETATM   31  H4  UNL     1      10.215  -1.192  -1.277  1.00  0.00           H  
HETATM   32  H5  UNL     1       8.851  -2.321  -1.507  1.00  0.00           H  
HETATM   33  H6  UNL     1       8.102  -0.031  -1.060  1.00  0.00           H  
HETATM   34  H7  UNL     1       9.055   0.036   0.456  1.00  0.00           H  
HETATM   35  H8  UNL     1       6.670  -1.850  -0.031  1.00  0.00           H  
HETATM   36  H9  UNL     1       7.699  -1.750   1.431  1.00  0.00           H  
HETATM   37  H10 UNL     1       6.277   0.756   0.336  1.00  0.00           H  
HETATM   38  H11 UNL     1       7.174   0.554   1.838  1.00  0.00           H  
HETATM   39  H12 UNL     1       5.598  -1.194   2.710  1.00  0.00           H  
HETATM   40  H13 UNL     1       3.256  -0.835   2.101  1.00  0.00           H  
HETATM   41  H14 UNL     1       4.585   0.695  -0.318  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.094  -0.244  -0.276  1.00  0.00           H  
HETATM   43  H16 UNL     1       3.332   2.340   1.453  1.00  0.00           H  
HETATM   44  H17 UNL     1       1.192   2.745   0.563  1.00  0.00           H  
HETATM   45  H18 UNL     1       0.101   0.733  -0.318  1.00  0.00           H  
HETATM   46  H19 UNL     1       1.619   0.115  -1.085  1.00  0.00           H  
HETATM   47  H20 UNL     1       1.667   2.261  -2.503  1.00  0.00           H  
HETATM   48  H21 UNL     1      -0.438   2.705  -3.429  1.00  0.00           H  
HETATM   49  H22 UNL     1      -2.197   1.003  -2.775  1.00  0.00           H  
HETATM   50  H23 UNL     1      -1.487   0.860  -1.127  1.00  0.00           H  
HETATM   51  H24 UNL     1      -2.907   3.342  -2.317  1.00  0.00           H  
HETATM   52  H25 UNL     1      -3.666   3.632  -0.125  1.00  0.00           H  
HETATM   53  H26 UNL     1      -1.945   1.171   0.753  1.00  0.00           H  
HETATM   54  H27 UNL     1      -2.291   2.704   1.658  1.00  0.00           H  
HETATM   55  H28 UNL     1      -3.706   0.750   2.244  1.00  0.00           H  
HETATM   56  H29 UNL     1      -4.588   2.238   1.736  1.00  0.00           H  
HETATM   57  H30 UNL     1      -4.828   1.212  -0.536  1.00  0.00           H  
HETATM   58  H31 UNL     1      -3.988  -0.273   0.013  1.00  0.00           H  
HETATM   59  H32 UNL     1      -6.425  -1.072  -0.932  1.00  0.00           H  
HETATM   60  H33 UNL     1      -8.253  -1.110   1.515  1.00  0.00           H  
HETATM   61  H34 UNL     1      -9.073   0.303  -0.208  1.00  0.00           H  
HETATM   62  H35 UNL     1      -8.856  -0.928  -1.474  1.00  0.00           H  
HETATM   63  H36 UNL     1     -10.988  -0.553  -0.162  1.00  0.00           H  
HETATM   64  H37 UNL     1      -7.940  -3.258  -0.653  1.00  0.00           H  
HETATM   65  H38 UNL     1      -9.042  -3.197   0.820  1.00  0.00           H  
HETATM   66  H39 UNL     1      -7.352  -4.179   1.752  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6   37   38
CONECT    6    7    7   39
CONECT    7    8   40
CONECT    8    9   41   42
CONECT    9   10   10   43
CONECT   10   11   44
CONECT   11   12   45   46
CONECT   12   13   13   47
CONECT   13   14   48
CONECT   14   15   49   50
CONECT   15   16   16   51
CONECT   16   17   52
CONECT   17   18   53   54
CONECT   18   19   55   56
CONECT   19   20   57   58
CONECT   20   21   21   22
CONECT   22   23   59
CONECT   23   24   26   60
CONECT   24   25   61   62
CONECT   25   63
CONECT   26   27   64   65
CONECT   27   66
END

HMDB0013650
     RDKit          3D
Arachidonoyl Serinol
 66 65  0  0  0  0  0  0  0  0999 V2000
    9.9547   -2.5913    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3701   -1.6943   -0.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4878   -0.6267   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3102   -1.1744    0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4744    0.0120    1.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410   -0.5634    1.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0856   -0.3854    1.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    0.4696    0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9421    1.6288    0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554    1.8524    0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558    1.0030   -0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722    1.8302   -2.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959    2.0706   -2.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6367    1.5480   -1.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5646    2.6385   -1.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9755    2.7826   -0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6532    1.9758    0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9693    1.4122    1.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    0.5547    0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9118   -0.0084    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960    0.2680    1.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7463   -0.8447    0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9863   -1.3948    0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0848   -0.8048   -0.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3270   -1.2817   -0.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0437   -2.8978    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0288   -3.4355    1.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5628   -2.0120    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6948   -3.2654   -0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1987   -3.2341    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2147   -1.1917   -1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8507   -2.3214   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1020   -0.0306   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0546    0.0361    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6695   -1.8504   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6990   -1.7498    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2765    0.7563    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1738    0.5543    1.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5980   -1.1944    2.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2564   -0.8348    2.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5845    0.6946   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937   -0.2441   -0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3321    2.3397    1.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1919    2.7451    0.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1006    0.7334   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6195    0.1149   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670    2.2615   -2.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379    2.7051   -3.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1966    1.0030   -2.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875    0.8602   -1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9075    3.3416   -2.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6662    3.6322   -0.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447    1.1709    0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2910    2.7038    1.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059    0.7497    2.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5880    2.2380    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8277    1.2117   -0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9883   -0.2734    0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4249   -1.0715   -0.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2529   -1.1098    1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0728    0.3029   -0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8555   -0.9284   -1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9882   -0.5528   -0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9397   -3.2582   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0424   -3.1966    0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3516   -4.1787    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 22 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[(2-Hydroxy-1-hydroxymethyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide	HMDB

Chemical Formula

C₂₃H₃₉NO₃

Average Molecular Weight

377.5607

Monoisotopic Molecular Weight

377.292994119

IUPAC Name

(5Z,8Z,11Z,14Z)-N-(1,3-dihydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide

Traditional Name

AA dihydroxypropylamine

CAS Registry Number

183718-70-9

SMILES

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC(CO)CO

InChI Identifier

InChI=1S/C23H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(27)24-22(20-25)21-26/h6-7,9-10,12-13,15-16,22,25-26H,2-5,8,11,14,17-21H2,1H3,(H,24,27)/b7-6-,10-9-,13-12-,16-15-

InChI Key

QHELXIATGZYOIB-DOFZRALJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acyl amines (LMFA08020072 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013650)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013650)

Source

Endogenous

Endogenous (HMDB: HMDB0013650)

Animal

Animal (HMDB: HMDB0013650)

Exogenous

Food

Food (HMDB: HMDB0013650)

Exogenous (HMDB: HMDB0013650)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013650)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013650)

Lipid metabolism pathway (HMDB: HMDB0013650)

Cellular process

Cell signaling (HMDB: HMDB0013650)

Biochemical process

Lipid transport (HMDB: HMDB0013650)

Role

Biological role

Energy source (HMDB: HMDB0013650)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013650)

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	0.0023 g/L	ALOGPS
logP	5.35	ALOGPS
logP	4.68	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.82	ChemAxon
pKa (Strongest Basic)	-0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	118.93 m³·mol⁻¹	ChemAxon
Polarizability	45.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	203.513	31661259
DarkChem	[M-H]-	202.887	31661259
DeepCCS	[M+H]+	202.196	30932474
DeepCCS	[M-H]-	199.838	30932474
DeepCCS	[M-2H]-	233.811	30932474
DeepCCS	[M+Na]+	209.142	30932474
AllCCS	[M+H]+	202.2	32859911
AllCCS	[M+H-H2O]+	199.8	32859911
AllCCS	[M+NH4]+	204.4	32859911
AllCCS	[M+Na]+	205.0	32859911
AllCCS	[M-H]-	197.5	32859911
AllCCS	[M+Na-2H]-	200.1	32859911
AllCCS	[M+HCOO]-	203.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arachidonoyl Serinol	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC(CO)CO	3551.6	Standard polar	33892256
Arachidonoyl Serinol	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC(CO)CO	2735.5	Standard non polar	33892256
Arachidonoyl Serinol	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC(CO)CO	3102.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Arachidonoyl Serinol,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC(CO)CO[Si](C)(C)C	3094.5	Semi standard non polar	33892256
Arachidonoyl Serinol,1TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(C(CO)CO)[Si](C)(C)C	3011.4	Semi standard non polar	33892256
Arachidonoyl Serinol,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC(CO[Si](C)(C)C)CO[Si](C)(C)C	3070.8	Semi standard non polar	33892256
Arachidonoyl Serinol,2TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(C(CO)CO[Si](C)(C)C)[Si](C)(C)C	3048.2	Semi standard non polar	33892256
Arachidonoyl Serinol,3TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(C(CO[Si](C)(C)C)CO[Si](C)(C)C)[Si](C)(C)C	3062.4	Semi standard non polar	33892256
Arachidonoyl Serinol,3TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(C(CO[Si](C)(C)C)CO[Si](C)(C)C)[Si](C)(C)C	3064.1	Standard non polar	33892256
Arachidonoyl Serinol,3TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(C(CO[Si](C)(C)C)CO[Si](C)(C)C)[Si](C)(C)C	2978.1	Standard polar	33892256
Arachidonoyl Serinol,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC(CO)CO[Si](C)(C)C(C)(C)C	3347.4	Semi standard non polar	33892256
Arachidonoyl Serinol,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(C(CO)CO)[Si](C)(C)C(C)(C)C	3292.9	Semi standard non polar	33892256
Arachidonoyl Serinol,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	3599.4	Semi standard non polar	33892256
Arachidonoyl Serinol,2TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(C(CO)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3535.4	Semi standard non polar	33892256
Arachidonoyl Serinol,3TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(C(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3799.9	Semi standard non polar	33892256
Arachidonoyl Serinol,3TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(C(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3601.6	Standard non polar	33892256
Arachidonoyl Serinol,3TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(C(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3118.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Arachidonoyl Serinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-009e-8394000000-ee975369d3eb3fd9c364	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arachidonoyl Serinol GC-MS (2 TMS) - 70eV, Positive	splash10-0avi-8291330000-6d7f0c815e7f37d353e0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arachidonoyl Serinol 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 - Arachidonoyl Serinol 10V, Positive-QTOF	splash10-01t9-3039000000-f862936c3f34b1dec568	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 20V, Positive-QTOF	splash10-022l-9253000000-5d214947ccbaa7dd64fd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 40V, Positive-QTOF	splash10-05fu-9440000000-45a9bf0530671947f808	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 10V, Negative-QTOF	splash10-004i-0009000000-250c1e3347cdf3a2b1ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 20V, Negative-QTOF	splash10-004l-4019000000-05fcf810b81f91aa4bb0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 40V, Negative-QTOF	splash10-0596-9110000000-f847e55771698d03c31d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 10V, Positive-QTOF	splash10-004i-7149000000-2c9afb8661bb65299aed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 20V, Positive-QTOF	splash10-00dl-9111000000-f2e0dce0e74bd4b489ad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 40V, Positive-QTOF	splash10-006x-9100000000-e117b29e6bf0fd5d944e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 10V, Negative-QTOF	splash10-004i-0009000000-d2bf266ec49b9577dcff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 20V, Negative-QTOF	splash10-056r-3039000000-b851578cb8583b68067a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arachidonoyl Serinol 40V, Negative-QTOF	splash10-052f-9112000000-80adfac02ed1365cf330	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029620

KNApSAcK ID

Not Available

Chemspider ID

8771144

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10595770

PDB ID

Not Available

ChEBI ID

332319

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

Sugiura T, Kodaka T, Kondo S, Tonegawa T, Nakane S, Kishimoto S, Yamashita A, Waku K: 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma x glioma hybrid NG108-15 cells. Biochem Biophys Res Commun. 1996 Dec 4;229(1):58-64. [PubMed:8954083 ]
Sugiura T, Kodaka T, Kondo S, Nakane S, Kondo H, Waku K, Ishima Y, Watanabe K, Yamamoto I: Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J Biochem. 1997 Oct;122(4):890-5. [PubMed:9399597 ]
Khanolkar AD, Abadji V, Lin S, Hill WA, Taha G, Abouzid K, Meng Z, Fan P, Makriyannis A: Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem. 1996 Oct 25;39(22):4515-9. [PubMed:8893848 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Arachidonoyl Serinol (HMDB0013650)

MOL for HMDB0013650 (Arachidonoyl Serinol)

3D MOL for HMDB0013650 (Arachidonoyl Serinol)

3D SDF for HMDB0013650 (Arachidonoyl Serinol)

3D-SDF for HMDB0013650 (Arachidonoyl Serinol)

PDB for HMDB0013650 (Arachidonoyl Serinol)

3D PDB for HMDB0013650 (Arachidonoyl Serinol)

SMILES for HMDB0013650 (Arachidonoyl Serinol)

INCHI for HMDB0013650 (Arachidonoyl Serinol)

Structure for HMDB0013650 (Arachidonoyl Serinol)

3D Structure for HMDB0013650 (Arachidonoyl Serinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra