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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-16 03:44:25 UTC

Update Date

2022-03-07 03:17:53 UTC

HMDB ID

HMDB0062334

Secondary Accession Numbers

HMDB62334

Metabolite Identification

Common Name

N-Linoleoyl GABA

Description

GABA linoleamide, also known as gabalid or gaba-linoleamide, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. GABA linoleamide is a very strong basic compound (based on its pKa).

Structure

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


  Mrv1652303161704442D          

 30 29  0  0  0  0            999 V2000
    0.1401    0.9059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    0.0809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    0.0809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    0.9059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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  1  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  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
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  END

HMDB0062334
     RDKit          3D
N-Linoleoyl GABA
 65 64  0  0  0  0  0  0  0  0999 V2000
   -8.7310   -2.7721   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2907   -2.3013   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8005   -2.3191    0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3722   -1.8667    1.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1768   -0.4507    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9772    0.5290    1.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4708    1.5453    1.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0271    1.8630    2.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215    3.2071    1.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838    3.4043    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1420    2.3571   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513    2.6428    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2037    1.6010   -0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6473    1.9819   -0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131    1.0027   -1.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101    1.5111   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0802    0.6154   -1.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3892    1.1959   -0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6835    2.4812   -1.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2448    0.5434   -0.2423 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0424   -0.8168    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3611   -1.8147   -0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1265   -3.2047   -0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999   -3.4444    0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6364   -3.1320    2.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2523   -4.0235    0.6970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2629   -2.4475    0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7537   -3.8828   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2607   -2.2959   -1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6696   -3.0392   -1.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2782   -1.2972   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8437   -3.3705    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4887   -1.7475    1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623   -1.9601    2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7543   -2.5759    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -0.5019   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0926   -0.2668    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0562    0.4170    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1682    2.2284    2.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462    1.0713    1.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8788    1.9793    3.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2682    4.0347    2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7283    4.4350    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    2.4986   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951    1.3263    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3700    2.6721    1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528    3.6284   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0328    1.5220   -1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381    0.6258   -0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896    3.0035   -0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7930    2.0442    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598    0.9420   -2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741    0.0184   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1407    2.5103   -1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1141    1.6195    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9127   -0.4017   -0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9616    0.7175   -2.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0603    2.7508   -2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7696   -1.0296    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0353   -1.0030    0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4568   -1.6800   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7971   -1.6275   -1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3037   -3.9685   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0421   -3.3279   -0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7868   -3.9570   -0.1646 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  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
 18 20  2  3
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 19 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 26 65  1  0
M  END


  Mrv1652303161704442D          

 30 29  0  0  0  0            999 V2000
    0.1401    0.9059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    0.0809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    0.0809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    0.9059    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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  1  0  0  0  0
  2  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  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
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062334

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(O)=NCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-21(24)23-20-17-19-22(25)26/h6-7,9-10H,2-5,8,11-20H2,1H3,(H,23,24)(H,25,26)/b7-6-,10-9-

> <INCHI_KEY>
YGFYZZQGVSUXJE-HZJYTTRNSA-N

> <FORMULA>
C22H39NO3

> <MOLECULAR_WEIGHT>
365.558

> <EXACT_MASS>
365.29299412

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.928848012418094

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}butanoic acid

> <ALOGPS_LOGP>
6.85

> <JCHEM_LOGP>
5.202402681480774

> <ALOGPS_LOGS>
-6.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.879763240000003

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.128624306872153

> <JCHEM_PKA_STRONGEST_BASIC>
6.852827885357378

> <JCHEM_POLAR_SURFACE_AREA>
69.89000000000001

> <JCHEM_REFRACTIVITY>
111.29839999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.92e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062334
     RDKit          3D
N-Linoleoyl GABA
 65 64  0  0  0  0  0  0  0  0999 V2000
   -8.7310   -2.7721   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2907   -2.3013   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8005   -2.3191    0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3722   -1.8667    1.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1768   -0.4507    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9772    0.5290    1.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4708    1.5453    1.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0271    1.8630    2.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215    3.2071    1.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838    3.4043    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1420    2.3571   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513    2.6428    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2037    1.6010   -0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6473    1.9819   -0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131    1.0027   -1.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101    1.5111   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0802    0.6154   -1.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3892    1.1959   -0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6835    2.4812   -1.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2448    0.5434   -0.2423 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0424   -0.8168    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3611   -1.8147   -0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1265   -3.2047   -0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999   -3.4444    0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6364   -3.1320    2.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2523   -4.0235    0.6970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2629   -2.4475    0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7537   -3.8828   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2607   -2.2959   -1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6696   -3.0392   -1.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2782   -1.2972   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8437   -3.3705    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4887   -1.7475    1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623   -1.9601    2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7543   -2.5759    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -0.5019   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0926   -0.2668    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0562    0.4170    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1682    2.2284    2.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462    1.0713    1.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8788    1.9793    3.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2682    4.0347    2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7283    4.4350    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    2.4986   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951    1.3263    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3700    2.6721    1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528    3.6284   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0328    1.5220   -1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381    0.6258   -0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896    3.0035   -0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7930    2.0442    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598    0.9420   -2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741    0.0184   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1407    2.5103   -1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1141    1.6195    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9127   -0.4017   -0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9616    0.7175   -2.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0603    2.7508   -2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7696   -1.0296    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0353   -1.0030    0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4568   -1.6800   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7971   -1.6275   -1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3037   -3.9685   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0421   -3.3279   -0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7868   -3.9570   -0.1646 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  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
 18 20  2  3
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 19 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 26 65  1  0
M  END

HEADER    PROTEIN                                 16-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAR-17         0                                  
HETATM    1  H   UNK     0       0.262   1.691   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.595   2.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.595   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.262   6.311   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.072   7.081   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.072   8.621   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.929   1.691   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       2.929   0.151   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       4.263   2.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.596   1.691   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       5.596   0.151   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       6.930   2.461   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       8.264   1.691   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.266   6.311   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0      17.599   4.001   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      18.933   4.771   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.267   4.001   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.600   4.771   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.934   4.001   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      24.268   4.771   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      22.934   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   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   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

COMPND    HMDB0062334
HETATM    1  C1  UNL     1      -8.731  -2.772  -0.510  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.291  -2.301  -0.503  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.800  -2.319   0.927  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.372  -1.867   1.051  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.177  -0.451   0.547  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.977   0.529   1.270  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.471   1.545   1.940  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.027   1.863   2.074  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.722   3.207   1.529  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.884   3.404   0.550  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.142   2.357  -0.137  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.651   2.643   0.048  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.204   1.601  -0.638  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.647   1.982  -0.391  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.613   1.003  -1.040  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.010   1.511  -0.708  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.080   0.615  -1.305  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.389   1.196  -0.925  1.00  0.00           C  
HETATM   19  O1  UNL     1       6.683   2.481  -1.326  1.00  0.00           O  
HETATM   20  N1  UNL     1       7.245   0.543  -0.242  1.00  0.00           N  
HETATM   21  C19 UNL     1       7.042  -0.817   0.234  1.00  0.00           C  
HETATM   22  C20 UNL     1       7.361  -1.815  -0.851  1.00  0.00           C  
HETATM   23  C21 UNL     1       7.127  -3.205  -0.317  1.00  0.00           C  
HETATM   24  C22 UNL     1       8.000  -3.444   0.849  1.00  0.00           C  
HETATM   25  O2  UNL     1       7.636  -3.132   2.010  1.00  0.00           O  
HETATM   26  O3  UNL     1       9.252  -4.023   0.697  1.00  0.00           O  
HETATM   27  H1  UNL     1      -9.263  -2.448   0.417  1.00  0.00           H  
HETATM   28  H2  UNL     1      -8.754  -3.883  -0.559  1.00  0.00           H  
HETATM   29  H3  UNL     1      -9.261  -2.296  -1.347  1.00  0.00           H  
HETATM   30  H4  UNL     1      -6.670  -3.039  -1.067  1.00  0.00           H  
HETATM   31  H5  UNL     1      -7.278  -1.297  -0.952  1.00  0.00           H  
HETATM   32  H6  UNL     1      -6.844  -3.371   1.277  1.00  0.00           H  
HETATM   33  H7  UNL     1      -7.489  -1.747   1.602  1.00  0.00           H  
HETATM   34  H8  UNL     1      -5.062  -1.960   2.097  1.00  0.00           H  
HETATM   35  H9  UNL     1      -4.754  -2.576   0.464  1.00  0.00           H  
HETATM   36  H10 UNL     1      -5.442  -0.502  -0.554  1.00  0.00           H  
HETATM   37  H11 UNL     1      -4.093  -0.267   0.554  1.00  0.00           H  
HETATM   38  H12 UNL     1      -7.056   0.417   1.256  1.00  0.00           H  
HETATM   39  H13 UNL     1      -6.168   2.228   2.452  1.00  0.00           H  
HETATM   40  H14 UNL     1      -3.346   1.071   1.798  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.879   1.979   3.203  1.00  0.00           H  
HETATM   42  H16 UNL     1      -4.268   4.035   2.026  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.728   4.435   0.220  1.00  0.00           H  
HETATM   44  H18 UNL     1      -2.300   2.499  -1.252  1.00  0.00           H  
HETATM   45  H19 UNL     1      -2.395   1.326   0.067  1.00  0.00           H  
HETATM   46  H20 UNL     1      -0.370   2.672   1.117  1.00  0.00           H  
HETATM   47  H21 UNL     1      -0.453   3.628  -0.374  1.00  0.00           H  
HETATM   48  H22 UNL     1      -0.033   1.522  -1.715  1.00  0.00           H  
HETATM   49  H23 UNL     1      -0.038   0.626  -0.150  1.00  0.00           H  
HETATM   50  H24 UNL     1       1.790   3.004  -0.812  1.00  0.00           H  
HETATM   51  H25 UNL     1       1.793   2.044   0.693  1.00  0.00           H  
HETATM   52  H26 UNL     1       2.460   0.942  -2.128  1.00  0.00           H  
HETATM   53  H27 UNL     1       2.474   0.018  -0.546  1.00  0.00           H  
HETATM   54  H28 UNL     1       4.141   2.510  -1.163  1.00  0.00           H  
HETATM   55  H29 UNL     1       4.114   1.619   0.385  1.00  0.00           H  
HETATM   56  H30 UNL     1       4.913  -0.402  -0.958  1.00  0.00           H  
HETATM   57  H31 UNL     1       4.962   0.717  -2.419  1.00  0.00           H  
HETATM   58  H32 UNL     1       7.060   2.751  -2.208  1.00  0.00           H  
HETATM   59  H33 UNL     1       7.770  -1.030   1.070  1.00  0.00           H  
HETATM   60  H34 UNL     1       6.035  -1.003   0.623  1.00  0.00           H  
HETATM   61  H35 UNL     1       8.457  -1.680  -1.088  1.00  0.00           H  
HETATM   62  H36 UNL     1       6.797  -1.628  -1.787  1.00  0.00           H  
HETATM   63  H37 UNL     1       7.304  -3.968  -1.120  1.00  0.00           H  
HETATM   64  H38 UNL     1       6.042  -3.328  -0.058  1.00  0.00           H  
HETATM   65  H39 UNL     1       9.787  -3.957  -0.165  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7    7   38
CONECT    7    8   39
CONECT    8    9   40   41
CONECT    9   10   10   42
CONECT   10   11   43
CONECT   11   12   44   45
CONECT   12   13   46   47
CONECT   13   14   48   49
CONECT   14   15   50   51
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18   56   57
CONECT   18   19   20   20
CONECT   19   58
CONECT   20   21
CONECT   21   22   59   60
CONECT   22   23   61   62
CONECT   23   24   63   64
CONECT   24   25   25   26
CONECT   26   65
END

HMDB0062334
     RDKit          3D
N-Linoleoyl GABA
 65 64  0  0  0  0  0  0  0  0999 V2000
   -8.7310   -2.7721   -0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2907   -2.3013   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8005   -2.3191    0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3722   -1.8667    1.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1768   -0.4507    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9772    0.5290    1.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4708    1.5453    1.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0271    1.8630    2.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215    3.2071    1.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838    3.4043    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1420    2.3571   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513    2.6428    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2037    1.6010   -0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6473    1.9819   -0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131    1.0027   -1.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101    1.5111   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0802    0.6154   -1.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3892    1.1959   -0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6835    2.4812   -1.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2448    0.5434   -0.2423 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0424   -0.8168    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3611   -1.8147   -0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1265   -3.2047   -0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999   -3.4444    0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6364   -3.1320    2.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2523   -4.0235    0.6970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2629   -2.4475    0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7537   -3.8828   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2607   -2.2959   -1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6696   -3.0392   -1.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2782   -1.2972   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8437   -3.3705    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4887   -1.7475    1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0623   -1.9601    2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7543   -2.5759    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -0.5019   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0926   -0.2668    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0562    0.4170    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1682    2.2284    2.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462    1.0713    1.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8788    1.9793    3.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2682    4.0347    2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7283    4.4350    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    2.4986   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951    1.3263    0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3700    2.6721    1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528    3.6284   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0328    1.5220   -1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381    0.6258   -0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896    3.0035   -0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7930    2.0442    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598    0.9420   -2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741    0.0184   -0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1407    2.5103   -1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1141    1.6195    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9127   -0.4017   -0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9616    0.7175   -2.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0603    2.7508   -2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7696   -1.0296    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0353   -1.0030    0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4568   -1.6800   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7971   -1.6275   -1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3037   -3.9685   -1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0421   -3.3279   -0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7868   -3.9570   -0.1646 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  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
 18 20  2  3
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 19 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 26 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Gabalid	MeSH
GABA-linoleamide	MeSH
GABA linoleamide	HMDB

Chemical Formula

C₂₂H₃₉NO₃

Average Molecular Weight

365.558

Monoisotopic Molecular Weight

365.29299412

IUPAC Name

4-{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}butanoic acid

Traditional Name

4-{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}butanoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(O)=NCCCC(O)=O

InChI Identifier

InChI=1S/C22H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-21(24)23-20-17-19-22(25)26/h6-7,9-10H,2-5,8,11-20H2,1H3,(H,23,24)(H,25,26)/b7-6-,10-9-

InChI Key

YGFYZZQGVSUXJE-HZJYTTRNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Fatty amide
N-acyl-amine
Straight chain fatty acid
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0062334)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00024 g/l	ALOGPS
LogP	6.64	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.85	ALOGPS
logP	5.2	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	6.85	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	111.3 m³·mol⁻¹	ChemAxon
Polarizability	45.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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]+	198.277	31661259
DarkChem	[M-H]-	196.52	31661259
DeepCCS	[M+H]+	202.757	30932474
DeepCCS	[M-H]-	200.399	30932474
DeepCCS	[M-2H]-	234.191	30932474
DeepCCS	[M+Na]+	209.421	30932474
AllCCS	[M+H]+	198.5	32859911
AllCCS	[M+H-H2O]+	196.2	32859911
AllCCS	[M+NH4]+	200.7	32859911
AllCCS	[M+Na]+	201.3	32859911
AllCCS	[M-H]-	194.6	32859911
AllCCS	[M+Na-2H]-	196.9	32859911
AllCCS	[M+HCOO]-	199.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.36 minutes	32390414
Predicted by Siyang on May 30, 2022	20.9198 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.45 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3090.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	353.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	220.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	669.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	980.8 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	645.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	124.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2001.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	677.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1836.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	671.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	498.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	337.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	402.3 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Linoleoyl GABA	[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(O)=NCCCC(O)=O	4264.6	Standard polar	33892256
N-Linoleoyl GABA	[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(O)=NCCCC(O)=O	2685.7	Standard non polar	33892256
N-Linoleoyl GABA	[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(O)=NCCCC(O)=O	2897.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Linoleoyl GABA,1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=NCCCC(=O)O)O[Si](C)(C)C	2929.0	Semi standard non polar	33892256
N-Linoleoyl GABA,1TMS,isomer #2	CCCCC/C=C\C/C=C\CCCCCCCC(O)=NCCCC(=O)O[Si](C)(C)C	2849.5	Semi standard non polar	33892256
N-Linoleoyl GABA,2TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=NCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2901.3	Semi standard non polar	33892256
N-Linoleoyl GABA,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=NCCCC(=O)O)O[Si](C)(C)C(C)(C)C	3149.7	Semi standard non polar	33892256
N-Linoleoyl GABA,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\CCCCCCCC(O)=NCCCC(=O)O[Si](C)(C)C(C)(C)C	3101.8	Semi standard non polar	33892256
N-Linoleoyl GABA,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=NCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3354.5	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 - N-Linoleoyl GABA GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7982000000-81228bc8eb89d0dcba7a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Linoleoyl GABA GC-MS (2 TMS) - 70eV, Positive	splash10-0fkc-7825900000-276d3e3f6690f0ce7c19	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Linoleoyl GABA 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 - N-Linoleoyl GABA 10V, Positive-QTOF	splash10-0f6t-4319000000-ef0af39feffff1d598a7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 20V, Positive-QTOF	splash10-0udr-9411000000-b036c286ac42cdff7f8a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 40V, Positive-QTOF	splash10-0zg3-9310000000-dae6763424008faddd3a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 10V, Negative-QTOF	splash10-03di-0019000000-07e1cc302df1eb9eabf3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 20V, Negative-QTOF	splash10-0imj-2359000000-10de7de23763421e9278	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 40V, Negative-QTOF	splash10-0006-9130000000-826f93892c14b262d230	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 10V, Negative-QTOF	splash10-03dj-0009000000-c7f46e59cc007cab327f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 20V, Negative-QTOF	splash10-03di-4349000000-e36cbb226d674f4a5570	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 40V, Negative-QTOF	splash10-0gx0-9540000000-d13f5b0ad540664c5883	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 10V, Positive-QTOF	splash10-0gb9-4429000000-e1f822e2fbe8d93c7923	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 20V, Positive-QTOF	splash10-0uei-9513000000-425ab30a3c9cd4ff7d29	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl GABA 40V, Positive-QTOF	splash10-0f7o-9500000000-d22cf429f4fb423bcb42	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438152

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for N-Linoleoyl GABA (HMDB0062334)

MOL for HMDB0062334 (N-Linoleoyl GABA)

3D MOL for HMDB0062334 (N-Linoleoyl GABA)

3D SDF for HMDB0062334 (N-Linoleoyl GABA)

3D-SDF for HMDB0062334 (N-Linoleoyl GABA)

PDB for HMDB0062334 (N-Linoleoyl GABA)

3D PDB for HMDB0062334 (N-Linoleoyl GABA)

SMILES for HMDB0062334 (N-Linoleoyl GABA)

INCHI for HMDB0062334 (N-Linoleoyl GABA)

Structure for HMDB0062334 (N-Linoleoyl GABA)

3D Structure for HMDB0062334 (N-Linoleoyl GABA)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra