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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-07-28 16:26:48 UTC

Update Date

2021-09-16 22:46:31 UTC

HMDB ID

HMDB0241978

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Linoleoyl Isoleucine

Description

N-linoleoyl isoleucine belongs to the class of compounds known as N-acylamides. These are molecules characterized by a fatty acyl group linked to a primary amine by an amide bond. More specifically, it is a Linoleic acid amide of Isoleucine. It is believed that there are more than 800 types of N-acylamides in the human body. N-acylamides fall into several categories: amino acid conjugates (e.g., those acyl amides conjugated with amino acids), neurotransmitter conjugates (e.g., those acylamides conjugated with neurotransmitters), ethanolamine conjugates (e.g., those acylamides conjugated to ethanolamine), and taurine conjugates (e.g., those acyamides conjugated to taurine). N-Linoleoyl Isoleucine is an amino acid conjugate. N-acylamides can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain N-acylamides; 2) medium-chain N-acylamides; 3) long-chain N-acylamides; and 4) very long-chain N-acylamides; 5) hydroxy N-acylamides; 6) branched chain N-acylamides; 7) unsaturated N-acylamides; 8) dicarboxylic N-acylamides and 9) miscellaneous N-acylamides. N-Linoleoyl Isoleucine is therefore classified as a long chain N-acylamide. N-acyl amides have a variety of signaling functions in physiology, including in cardiovascular activity, metabolic homeostasis, memory, cognition, pain, motor control and others (PMID: 15655504 ). N-acyl amides have also been shown to play a role in cell migration, inflammation and certain pathological conditions such as diabetes, cancer, neurodegenerative disease, and obesity (PMID: 23144998 ; PMID: 25136293 ; PMID: 28854168 ).N-acyl amides can be synthesized both endogenously and by gut microbiota (PMID: 28854168 ). N-acylamides can be biosynthesized via different routes, depending on the parent amine group. N-acyl ethanolamines (NAEs) are formed via the hydrolysis of an unusual phospholipid precursor, N-acyl-phosphatidylethanolamine (NAPE), by a specific phospholipase D. N-acyl amino acids are synthesized via a circulating peptidase M20 domain containing 1 (PM20D1), which can catalyze the bidirectional the condensation and hydrolysis of a variety of N-acyl amino acids. The degradation of N-acylamides is largely mediated by an enzyme called fatty acid amide hydrolase (FAAH), which catalyzes the hydrolysis of N-acylamides into fatty acids and the biogenic amines. Many N-acylamides are involved in lipid signaling system through interactions with transient receptor potential channels (TRP). TRP channel proteins interact with N-acyl amides such as N-arachidonoyl ethanolamide (Anandamide), N-arachidonoyl dopamine and others in an opportunistic fashion (PMID: 23178153 ). This signaling system has been shown to play a role in the physiological processes involved in inflammation (PMID: 25136293 ). Other N-acyl amides, including N-oleoyl-glutamine, have also been characterized as TRP channel antagonists (PMID: 29967167 ). N-acylamides have also been shown to have G-protein-coupled receptors (GPCRs) binding activity (PMID: 28854168 ). The study of N-acylamides is an active area of research and it is likely that many novel N-acylamides will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.

Structure

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


  Mrv1652307282118362D          

 28 27  0  0  0  0            999 V2000
   12.6177    2.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    2.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007    5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007    6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    7.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  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  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0241978
     RDKit          3D
N-Linoleoyl Isoleucine
 71 70  0  0  0  0  0  0  0  0999 V2000
   -7.9294   -4.2058   -2.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6134   -3.2681   -3.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3111   -1.9367   -3.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8465   -1.2641   -2.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3535   -0.9903   -2.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9974   -0.3494   -1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4809    0.8334   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1452    1.7756   -2.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6934    2.1200   -2.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7914    1.6223   -1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583    2.0067   -1.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    0.8312   -1.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5578   -0.2894   -0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543    0.0560    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    0.5635    0.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783    0.8341    2.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9221    1.3499    2.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0138    0.4710    2.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169   -0.5045    1.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3593    0.6221    2.5142 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4251   -0.2492    2.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6012   -1.3585    3.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8316   -1.3946    4.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5733   -2.3005    2.9786 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7359    0.4399    1.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7851    1.5966    1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5321    0.6533    3.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9408    1.4437    4.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7373   -5.2495   -3.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2982   -3.8530   -1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9868   -4.0705   -2.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5183   -3.1426   -4.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9725   -3.7304   -4.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0528   -1.2977   -4.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3942   -2.1453   -3.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3416   -0.2788   -2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0607   -1.9120   -1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0876   -0.3537   -3.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7953   -1.9755   -2.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1788   -0.9056   -0.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2638    1.1997   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4091    1.4311   -3.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6790    2.7639   -2.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749    2.8305   -2.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0791    0.8950   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756    2.7605   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0543    2.5101   -0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5620    1.1863   -1.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7896    0.4226   -2.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193   -1.1469   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437   -0.5891   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -0.7736    1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    0.8594    0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3807    1.5185    0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9137   -0.1607    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086    1.5823    2.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -0.1157    2.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8997    1.5665    3.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957    2.3264    1.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5536    1.4098    3.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1457   -0.7491    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7926   -3.0439    3.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3801   -0.3647    1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8704    1.9057    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1809    2.4705    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4343    1.3290    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4594    1.2242    2.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9533   -0.2862    3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0734    0.9209    4.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7189    1.4240    5.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7528    2.4992    4.1299 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  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 20 60  1  0
 21 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
M  END


  Mrv1652307282118362D          

 28 27  0  0  0  0            999 V2000
   12.6177    2.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    2.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007    5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007    6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    7.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  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  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0241978

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC=CCC=CCCCCCCCC(=O)NC(C(C)CC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H43NO3/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22(26)25-23(24(27)28)21(3)5-2/h9-10,12-13,21,23H,4-8,11,14-20H2,1-3H3,(H,25,26)(H,27,28)

> <INCHI_KEY>
NLHYAAGTDKOGDG-UHFFFAOYSA-N

> <FORMULA>
C24H43NO3

> <MOLECULAR_WEIGHT>
393.612

> <EXACT_MASS>
393.324294249

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.80499314414091

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyl-2-(octadeca-9,12-dienamido)pentanoic acid

> <ALOGPS_LOGP>
7.19

> <JCHEM_LOGP>
7.217421683333335

> <ALOGPS_LOGS>
-6.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.603164676068204

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.259026161816989

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1307686509303183

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
119.4128

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-2-(octadeca-9,12-dienamido)pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241978
     RDKit          3D
N-Linoleoyl Isoleucine
 71 70  0  0  0  0  0  0  0  0999 V2000
   -7.9294   -4.2058   -2.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6134   -3.2681   -3.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3111   -1.9367   -3.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8465   -1.2641   -2.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3535   -0.9903   -2.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9974   -0.3494   -1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4809    0.8334   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1452    1.7756   -2.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6934    2.1200   -2.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7914    1.6223   -1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583    2.0067   -1.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    0.8312   -1.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5578   -0.2894   -0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543    0.0560    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    0.5635    0.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783    0.8341    2.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9221    1.3499    2.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0138    0.4710    2.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169   -0.5045    1.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3593    0.6221    2.5142 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4251   -0.2492    2.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6012   -1.3585    3.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8316   -1.3946    4.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5733   -2.3005    2.9786 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7359    0.4399    1.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7851    1.5966    1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5321    0.6533    3.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9408    1.4437    4.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7373   -5.2495   -3.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2982   -3.8530   -1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9868   -4.0705   -2.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5183   -3.1426   -4.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9725   -3.7304   -4.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0528   -1.2977   -4.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3942   -2.1453   -3.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3416   -0.2788   -2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0607   -1.9120   -1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0876   -0.3537   -3.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7953   -1.9755   -2.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1788   -0.9056   -0.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2638    1.1997   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4091    1.4311   -3.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6790    2.7639   -2.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749    2.8305   -2.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0791    0.8950   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756    2.7605   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0543    2.5101   -0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5620    1.1863   -1.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7896    0.4226   -2.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193   -1.1469   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437   -0.5891   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -0.7736    1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    0.8594    0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3807    1.5185    0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9137   -0.1607    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086    1.5823    2.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -0.1157    2.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8997    1.5665    3.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957    2.3264    1.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5536    1.4098    3.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1457   -0.7491    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7926   -3.0439    3.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3801   -0.3647    1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8704    1.9057    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1809    2.4705    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4343    1.3290    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4594    1.2242    2.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9533   -0.2862    3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0734    0.9209    4.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7189    1.4240    5.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7528    2.4992    4.1299 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  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 20 60  1  0
 21 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
M  END

HEADER    PROTEIN                                 28-JUL-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-21         0                                  
HETATM    1  O   UNK     0      23.553   4.358   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      22.219   5.128   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      20.886   4.358   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      20.886   7.438   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      19.552   5.128   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.883   6.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.549   7.438   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.215   6.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.882   7.438   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.882   8.978   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.548   9.748   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.548  11.288   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.214  12.058   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.214  13.598   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.881  14.368   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.553   8.978   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.220   7.438   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25    4   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

COMPND    HMDB0241978
HETATM    1  C1  UNL     1      -7.929  -4.206  -2.761  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.613  -3.268  -3.929  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.311  -1.937  -3.733  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.847  -1.264  -2.456  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.353  -0.990  -2.484  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.997  -0.349  -1.207  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.481   0.833  -1.082  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.145   1.776  -2.154  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.693   2.120  -2.199  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.791   1.622  -1.395  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.358   2.007  -1.488  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.489   0.831  -1.804  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.558  -0.289  -0.815  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.154   0.056   0.576  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.299   0.564   0.647  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.578   0.834   2.075  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.922   1.350   2.437  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.014   0.471   2.062  1.00  0.00           C  
HETATM   19  O1  UNL     1       3.817  -0.504   1.290  1.00  0.00           O  
HETATM   20  N1  UNL     1       5.359   0.622   2.514  1.00  0.00           N  
HETATM   21  C19 UNL     1       6.425  -0.249   2.114  1.00  0.00           C  
HETATM   22  C20 UNL     1       6.601  -1.359   3.124  1.00  0.00           C  
HETATM   23  O2  UNL     1       5.832  -1.395   4.104  1.00  0.00           O  
HETATM   24  O3  UNL     1       7.573  -2.301   2.979  1.00  0.00           O  
HETATM   25  C21 UNL     1       7.736   0.440   1.984  1.00  0.00           C  
HETATM   26  C22 UNL     1       7.785   1.597   1.042  1.00  0.00           C  
HETATM   27  C23 UNL     1       8.532   0.653   3.210  1.00  0.00           C  
HETATM   28  C24 UNL     1       7.941   1.444   4.313  1.00  0.00           C  
HETATM   29  H1  UNL     1      -7.737  -5.249  -3.062  1.00  0.00           H  
HETATM   30  H2  UNL     1      -7.298  -3.853  -1.927  1.00  0.00           H  
HETATM   31  H3  UNL     1      -8.987  -4.070  -2.452  1.00  0.00           H  
HETATM   32  H4  UNL     1      -6.518  -3.143  -4.016  1.00  0.00           H  
HETATM   33  H5  UNL     1      -7.972  -3.730  -4.863  1.00  0.00           H  
HETATM   34  H6  UNL     1      -8.053  -1.298  -4.592  1.00  0.00           H  
HETATM   35  H7  UNL     1      -9.394  -2.145  -3.671  1.00  0.00           H  
HETATM   36  H8  UNL     1      -8.342  -0.279  -2.348  1.00  0.00           H  
HETATM   37  H9  UNL     1      -8.061  -1.912  -1.595  1.00  0.00           H  
HETATM   38  H10 UNL     1      -6.088  -0.354  -3.327  1.00  0.00           H  
HETATM   39  H11 UNL     1      -5.795  -1.975  -2.514  1.00  0.00           H  
HETATM   40  H12 UNL     1      -6.179  -0.906  -0.261  1.00  0.00           H  
HETATM   41  H13 UNL     1      -5.264   1.200  -0.053  1.00  0.00           H  
HETATM   42  H14 UNL     1      -5.409   1.431  -3.157  1.00  0.00           H  
HETATM   43  H15 UNL     1      -5.679   2.764  -2.017  1.00  0.00           H  
HETATM   44  H16 UNL     1      -3.375   2.830  -2.957  1.00  0.00           H  
HETATM   45  H17 UNL     1      -3.079   0.895  -0.615  1.00  0.00           H  
HETATM   46  H18 UNL     1      -1.276   2.760  -2.307  1.00  0.00           H  
HETATM   47  H19 UNL     1      -1.054   2.510  -0.535  1.00  0.00           H  
HETATM   48  H20 UNL     1       0.562   1.186  -1.947  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.790   0.423  -2.789  1.00  0.00           H  
HETATM   50  H22 UNL     1       0.019  -1.147  -1.236  1.00  0.00           H  
HETATM   51  H23 UNL     1      -1.644  -0.589  -0.767  1.00  0.00           H  
HETATM   52  H24 UNL     1      -0.248  -0.774   1.289  1.00  0.00           H  
HETATM   53  H25 UNL     1      -0.823   0.859   0.946  1.00  0.00           H  
HETATM   54  H26 UNL     1       1.381   1.519   0.044  1.00  0.00           H  
HETATM   55  H27 UNL     1       1.914  -0.161   0.128  1.00  0.00           H  
HETATM   56  H28 UNL     1       0.809   1.582   2.422  1.00  0.00           H  
HETATM   57  H29 UNL     1       1.377  -0.116   2.654  1.00  0.00           H  
HETATM   58  H30 UNL     1       2.900   1.567   3.537  1.00  0.00           H  
HETATM   59  H31 UNL     1       3.096   2.326   1.884  1.00  0.00           H  
HETATM   60  H32 UNL     1       5.554   1.410   3.153  1.00  0.00           H  
HETATM   61  H33 UNL     1       6.146  -0.749   1.177  1.00  0.00           H  
HETATM   62  H34 UNL     1       7.793  -3.044   3.598  1.00  0.00           H  
HETATM   63  H35 UNL     1       8.380  -0.365   1.405  1.00  0.00           H  
HETATM   64  H36 UNL     1       8.870   1.906   0.988  1.00  0.00           H  
HETATM   65  H37 UNL     1       7.181   2.471   1.366  1.00  0.00           H  
HETATM   66  H38 UNL     1       7.434   1.329   0.033  1.00  0.00           H  
HETATM   67  H39 UNL     1       9.459   1.224   2.879  1.00  0.00           H  
HETATM   68  H40 UNL     1       8.953  -0.286   3.645  1.00  0.00           H  
HETATM   69  H41 UNL     1       7.073   0.921   4.825  1.00  0.00           H  
HETATM   70  H42 UNL     1       8.719   1.424   5.157  1.00  0.00           H  
HETATM   71  H43 UNL     1       7.753   2.499   4.130  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7    7   40
CONECT    7    8   41
CONECT    8    9   42   43
CONECT    9   10   10   44
CONECT   10   11   45
CONECT   11   12   46   47
CONECT   12   13   48   49
CONECT   13   14   50   51
CONECT   14   15   52   53
CONECT   15   16   54   55
CONECT   16   17   56   57
CONECT   17   18   58   59
CONECT   18   19   19   20
CONECT   20   21   60
CONECT   21   22   25   61
CONECT   22   23   23   24
CONECT   24   62
CONECT   25   26   27   63
CONECT   26   64   65   66
CONECT   27   28   67   68
CONECT   28   69   70   71
END

HMDB0241978
     RDKit          3D
N-Linoleoyl Isoleucine
 71 70  0  0  0  0  0  0  0  0999 V2000
   -7.9294   -4.2058   -2.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6134   -3.2681   -3.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3111   -1.9367   -3.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8465   -1.2641   -2.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3535   -0.9903   -2.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9974   -0.3494   -1.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4809    0.8334   -1.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1452    1.7756   -2.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6934    2.1200   -2.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7914    1.6223   -1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583    2.0067   -1.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    0.8312   -1.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5578   -0.2894   -0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543    0.0560    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    0.5635    0.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783    0.8341    2.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9221    1.3499    2.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0138    0.4710    2.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169   -0.5045    1.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3593    0.6221    2.5142 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4251   -0.2492    2.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6012   -1.3585    3.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8316   -1.3946    4.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5733   -2.3005    2.9786 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7359    0.4399    1.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7851    1.5966    1.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5321    0.6533    3.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9408    1.4437    4.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7373   -5.2495   -3.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2982   -3.8530   -1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9868   -4.0705   -2.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5183   -3.1426   -4.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9725   -3.7304   -4.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0528   -1.2977   -4.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3942   -2.1453   -3.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3416   -0.2788   -2.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0607   -1.9120   -1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0876   -0.3537   -3.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7953   -1.9755   -2.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1788   -0.9056   -0.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2638    1.1997   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4091    1.4311   -3.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6790    2.7639   -2.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749    2.8305   -2.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0791    0.8950   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756    2.7605   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0543    2.5101   -0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5620    1.1863   -1.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7896    0.4226   -2.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193   -1.1469   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437   -0.5891   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -0.7736    1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    0.8594    0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3807    1.5185    0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9137   -0.1607    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086    1.5823    2.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769   -0.1157    2.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8997    1.5665    3.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957    2.3264    1.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5536    1.4098    3.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1457   -0.7491    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7926   -3.0439    3.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3801   -0.3647    1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8704    1.9057    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1809    2.4705    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4343    1.3290    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4594    1.2242    2.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9533   -0.2862    3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0734    0.9209    4.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7189    1.4240    5.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7528    2.4992    4.1299 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  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 20 60  1  0
 21 61  1  0
 24 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(1-Hydroxyoctadeca-9,12-dien-1-ylidene)amino]-3-methylpentanoate	Generator

Chemical Formula

C₂₄H₄₃NO₃

Average Molecular Weight

393.612

Monoisotopic Molecular Weight

393.324294249

IUPAC Name

3-methyl-2-(octadeca-9,12-dienamido)pentanoic acid

Traditional Name

3-methyl-2-(octadeca-9,12-dienamido)pentanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC=CCC=CCCCCCCCC(=O)NC(C(C)CC)C(O)=O

InChI Identifier

InChI=1S/C24H43NO3/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22(26)25-23(24(27)28)21(3)5-2/h9-10,12-13,21,23H,4-8,11,14-20H2,1-3H3,(H,25,26)(H,27,28)

InChI Key

NLHYAAGTDKOGDG-UHFFFAOYSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Not Available

Not Available

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	7.19	ALOGPS
logP	7.22	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	119.41 m³·mol⁻¹	ChemAxon
Polarizability	49.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	206.966	30932474
DeepCCS	[M-H]-	204.608	30932474
DeepCCS	[M-2H]-	237.595	30932474
DeepCCS	[M+Na]+	213.285	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Linoleoyl Isoleucine	CCCCCC=CCC=CCCCCCCCC(=O)NC(C(C)CC)C(O)=O	3657.4	Standard polar	33892256
N-Linoleoyl Isoleucine	CCCCCC=CCC=CCCCCCCCC(=O)NC(C(C)CC)C(O)=O	2688.7	Standard non polar	33892256
N-Linoleoyl Isoleucine	CCCCCC=CCC=CCCCCCCCC(=O)NC(C(C)CC)C(O)=O	2832.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Linoleoyl Isoleucine,2TMS,isomer #1	CCCCCC=CCC=CCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)CC)[Si](C)(C)C	2902.8	Semi standard non polar	33892256
N-Linoleoyl Isoleucine,2TMS,isomer #1	CCCCCC=CCC=CCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)CC)[Si](C)(C)C	2850.0	Standard non polar	33892256
N-Linoleoyl Isoleucine,2TMS,isomer #1	CCCCCC=CCC=CCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)CC)[Si](C)(C)C	2998.3	Standard polar	33892256
N-Linoleoyl Isoleucine,2TBDMS,isomer #1	CCCCCC=CCC=CCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)CC)[Si](C)(C)C(C)(C)C	3381.8	Semi standard non polar	33892256
N-Linoleoyl Isoleucine,2TBDMS,isomer #1	CCCCCC=CCC=CCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)CC)[Si](C)(C)C(C)(C)C	3190.0	Standard non polar	33892256
N-Linoleoyl Isoleucine,2TBDMS,isomer #1	CCCCCC=CCC=CCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)CC)[Si](C)(C)C(C)(C)C	3122.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Linoleoyl Isoleucine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03kj-5698000000-cbad283f190fa755ff84	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Linoleoyl Isoleucine 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 Isoleucine 10V, Positive-QTOF	splash10-0006-0119000000-8ae5c158954b9a247c32	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl Isoleucine 20V, Positive-QTOF	splash10-01s7-5769000000-d31131b0ace217d1035e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl Isoleucine 40V, Positive-QTOF	splash10-05ne-9500000000-32f44a31532e7fc7d319	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl Isoleucine 10V, Negative-QTOF	splash10-0006-0009000000-a5294d208c6a854af1d6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl Isoleucine 20V, Negative-QTOF	splash10-001i-0903000000-a4e563ecf186898637f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Linoleoyl Isoleucine 40V, Negative-QTOF	splash10-000x-8940000000-c917e2ffd9373a661cfe	2021-10-12	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

Not Available

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

Bradshaw HB, Walker JM: The expanding field of cannabimimetic and related lipid mediators. Br J Pharmacol. 2005 Feb;144(4):459-65. doi: 10.1038/sj.bjp.0706093. [PubMed:15655504 ]
Grapov D, Adams SH, Pedersen TL, Garvey WT, Newman JW: Type 2 diabetes associated changes in the plasma non-esterified fatty acids, oxylipins and endocannabinoids. PLoS One. 2012;7(11):e48852. doi: 10.1371/journal.pone.0048852. Epub 2012 Nov 8. [PubMed:23144998 ]
Raboune S, Stuart JM, Leishman E, Takacs SM, Rhodes B, Basnet A, Jameyfield E, McHugh D, Widlanski T, Bradshaw HB: Novel endogenous N-acyl amides activate TRPV1-4 receptors, BV-2 microglia, and are regulated in brain in an acute model of inflammation. Front Cell Neurosci. 2014 Aug 1;8:195. doi: 10.3389/fncel.2014.00195. eCollection 2014. [PubMed:25136293 ]
Cohen LJ, Esterhazy D, Kim SH, Lemetre C, Aguilar RR, Gordon EA, Pickard AJ, Cross JR, Emiliano AB, Han SM, Chu J, Vila-Farres X, Kaplitt J, Rogoz A, Calle PY, Hunter C, Bitok JK, Brady SF: Commensal bacteria make GPCR ligands that mimic human signalling molecules. Nature. 2017 Sep 7;549(7670):48-53. doi: 10.1038/nature23874. Epub 2017 Aug 30. [PubMed:28854168 ]
Bradshaw HB, Raboune S, Hollis JL: Opportunistic activation of TRP receptors by endogenous lipids: exploiting lipidomics to understand TRP receptor cellular communication. Life Sci. 2013 Mar 19;92(8-9):404-9. doi: 10.1016/j.lfs.2012.11.008. Epub 2012 Nov 20. [PubMed:23178153 ]
Long JZ, Roche AM, Berdan CA, Louie SM, Roberts AJ, Svensson KJ, Dou FY, Bateman LA, Mina AI, Deng Z, Jedrychowski MP, Lin H, Kamenecka TM, Asara JM, Griffin PR, Banks AS, Nomura DK, Spiegelman BM: Ablation of PM20D1 reveals N-acyl amino acid control of metabolism and nociception. Proc Natl Acad Sci U S A. 2018 Jul 17;115(29):E6937-E6945. doi: 10.1073/pnas.1803389115. Epub 2018 Jul 2. [PubMed:29967167 ]

Showing metabocard for N-Linoleoyl Isoleucine (HMDB0241978)

MOL for HMDB0241978 (N-Linoleoyl Isoleucine)

3D MOL for HMDB0241978 (N-Linoleoyl Isoleucine)

3D SDF for HMDB0241978 (N-Linoleoyl Isoleucine)

3D-SDF for HMDB0241978 (N-Linoleoyl Isoleucine)

PDB for HMDB0241978 (N-Linoleoyl Isoleucine)

3D PDB for HMDB0241978 (N-Linoleoyl Isoleucine)

SMILES for HMDB0241978 (N-Linoleoyl Isoleucine)

INCHI for HMDB0241978 (N-Linoleoyl Isoleucine)

Structure for HMDB0241978 (N-Linoleoyl Isoleucine)

3D Structure for HMDB0241978 (N-Linoleoyl Isoleucine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra