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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-07-27 21:58:21 UTC

Update Date

2021-09-16 22:46:28 UTC

HMDB ID

HMDB0241927

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Palmitoyl Isoleucine

Description

N-palmitoyl 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 Palmitic 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-Palmitoyl 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-Palmitoyl 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


  Mrv1652307282100072D          

 26 25  0  0  0  0            999 V2000
   13.9954    5.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9954    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809    6.8427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5664    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5664    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    5.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809    5.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    7.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4230    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7099    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4243    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1388    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8533    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5677    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2822    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9967    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7112    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4256    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1401    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8546    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5690    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7124    6.8427    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  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
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0241927
     RDKit          3D
N-Palmitoyl Isoleucine
 69 68  0  0  0  0  0  0  0  0999 V2000
    8.4556    2.0854   -2.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4151    2.6071   -1.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3541    1.6541   -0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3226    2.1291    0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792    1.1865    1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9247   -0.2241    1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5455   -0.2447    0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2487   -1.6808    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -1.7583   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022   -1.2347    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4505   -1.3266   -0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -2.7109   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117   -2.9641   -1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4970   -2.7274   -0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8554   -1.3774   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2902   -1.3943    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754   -2.4336    0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7801   -0.1926    0.7537 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1560   -0.1564    1.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1032    0.2230    2.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0042    0.4538    3.2628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2369    0.3495    3.4942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9104    0.8170    0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657    2.1597    0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3906    0.8178    0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0217    1.8382   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0419    2.9216   -3.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088    1.5885   -3.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1058    1.3225   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7266    3.6171   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4270    2.6460   -2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1379    0.6581   -1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3482    1.7320   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275    2.2624   -0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7076    3.1127    0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5632    1.5182    2.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3134    1.1620    1.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8569   -0.8030    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6892   -0.7085    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5308    0.4033   -0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    0.1438    1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913   -2.1155   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1737   -2.3100    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866   -1.2832   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203   -2.8592   -0.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849   -1.6758    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9853   -0.1280    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -0.7881   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -0.7670    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1506   -3.4051    0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8699   -3.1867   -1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648   -4.0718   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1982   -2.4400   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168   -3.5209   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044   -2.9862   -1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7821   -0.5445   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2947   -1.2551    0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2008    0.6846    0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6171   -1.1656    1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4217    1.2532    3.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7811    0.4478   -0.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0111    2.3717    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8870    2.9608    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3219    2.1438   -0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7749   -0.1905    0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5902    1.0715    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9266    2.8518    0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4054    1.8585   -1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0732    1.5780   -0.4914 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  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  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 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
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 18 58  1  0
 19 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
M  END


  Mrv1652307282100072D          

 26 25  0  0  0  0            999 V2000
   13.9954    5.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9954    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809    6.8427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5664    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5664    5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    5.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809    5.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    7.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4230    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7099    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4243    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1388    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8533    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5677    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2822    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9967    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7112    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4256    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1401    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8546    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5690    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7124    6.8427    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  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
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0241927

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H43NO3/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-20(24)23-21(22(25)26)19(3)5-2/h19,21H,4-18H2,1-3H3,(H,23,24)(H,25,26)

> <INCHI_KEY>
NGYZAEAXQQNUBZ-UHFFFAOYSA-N

> <FORMULA>
C22H43NO3

> <MOLECULAR_WEIGHT>
369.59

> <EXACT_MASS>
369.324294249

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
46.99031576241621

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hexadecanamido-3-methylpentanoic acid

> <ALOGPS_LOGP>
7.06

> <JCHEM_LOGP>
7.052127666666668

> <ALOGPS_LOGS>
-6.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.582775397714645

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.259026161764947

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1307686508516666

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
107.97759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.03e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hexadecanamido-3-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241927
     RDKit          3D
N-Palmitoyl Isoleucine
 69 68  0  0  0  0  0  0  0  0999 V2000
    8.4556    2.0854   -2.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4151    2.6071   -1.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3541    1.6541   -0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3226    2.1291    0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792    1.1865    1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9247   -0.2241    1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5455   -0.2447    0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2487   -1.6808    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -1.7583   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022   -1.2347    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4505   -1.3266   -0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -2.7109   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117   -2.9641   -1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4970   -2.7274   -0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8554   -1.3774   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2902   -1.3943    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754   -2.4336    0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7801   -0.1926    0.7537 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1560   -0.1564    1.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1032    0.2230    2.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0042    0.4538    3.2628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2369    0.3495    3.4942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9104    0.8170    0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657    2.1597    0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3906    0.8178    0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0217    1.8382   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0419    2.9216   -3.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088    1.5885   -3.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1058    1.3225   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7266    3.6171   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4270    2.6460   -2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1379    0.6581   -1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3482    1.7320   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275    2.2624   -0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7076    3.1127    0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5632    1.5182    2.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3134    1.1620    1.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8569   -0.8030    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6892   -0.7085    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5308    0.4033   -0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    0.1438    1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913   -2.1155   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1737   -2.3100    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866   -1.2832   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203   -2.8592   -0.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849   -1.6758    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9853   -0.1280    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -0.7881   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -0.7670    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1506   -3.4051    0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8699   -3.1867   -1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648   -4.0718   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1982   -2.4400   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168   -3.5209   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044   -2.9862   -1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7821   -0.5445   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2947   -1.2551    0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2008    0.6846    0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6171   -1.1656    1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4217    1.2532    3.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7811    0.4478   -0.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0111    2.3717    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8870    2.9608    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3219    2.1438   -0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7749   -0.1905    0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5902    1.0715    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9266    2.8518    0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4054    1.8585   -1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0732    1.5780   -0.4914 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  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  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 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
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 18 58  1  0
 19 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  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      26.125  10.463   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      26.125  12.003   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      24.791  12.773   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      23.457  12.003   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.457  10.463   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      22.124   9.693   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      24.791   9.693   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      22.124  12.773   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.124  14.313   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.790  12.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.456  12.773   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.458  12.773   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.792  12.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.126  12.773   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.459  12.003   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.793  12.773   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      34.127  12.003   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.460  12.773   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.794  12.003   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.128  12.773   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.462  12.003   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      40.795  12.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      42.129  12.003   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      43.463  12.773   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      44.796  12.003   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      46.130  12.773   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0241927
HETATM    1  C1  UNL     1       8.456   2.085  -2.932  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.415   2.607  -1.978  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.354   1.654  -0.778  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.323   2.129   0.215  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.279   1.187   1.378  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.925  -0.224   1.020  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.546  -0.245   0.373  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.249  -1.681   0.049  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.873  -1.758  -0.617  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.802  -1.235   0.276  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.451  -1.327  -0.425  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.080  -2.711  -0.779  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.212  -2.964  -1.453  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.497  -2.727  -0.802  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.855  -1.377  -0.294  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.290  -1.394   0.236  1.00  0.00           C  
HETATM   17  O1  UNL     1      -4.975  -2.434   0.201  1.00  0.00           O  
HETATM   18  N1  UNL     1      -4.780  -0.193   0.754  1.00  0.00           N  
HETATM   19  C17 UNL     1      -6.156  -0.156   1.277  1.00  0.00           C  
HETATM   20  C18 UNL     1      -6.103   0.223   2.698  1.00  0.00           C  
HETATM   21  O2  UNL     1      -5.004   0.454   3.263  1.00  0.00           O  
HETATM   22  O3  UNL     1      -7.237   0.349   3.494  1.00  0.00           O  
HETATM   23  C19 UNL     1      -6.910   0.817   0.415  1.00  0.00           C  
HETATM   24  C20 UNL     1      -6.266   2.160   0.507  1.00  0.00           C  
HETATM   25  C21 UNL     1      -8.391   0.818   0.677  1.00  0.00           C  
HETATM   26  C22 UNL     1      -9.022   1.838  -0.256  1.00  0.00           C  
HETATM   27  H1  UNL     1       9.042   2.922  -3.352  1.00  0.00           H  
HETATM   28  H2  UNL     1       7.909   1.588  -3.771  1.00  0.00           H  
HETATM   29  H3  UNL     1       9.106   1.322  -2.466  1.00  0.00           H  
HETATM   30  H4  UNL     1       7.727   3.617  -1.610  1.00  0.00           H  
HETATM   31  H5  UNL     1       6.427   2.646  -2.441  1.00  0.00           H  
HETATM   32  H6  UNL     1       7.138   0.658  -1.187  1.00  0.00           H  
HETATM   33  H7  UNL     1       8.348   1.732  -0.294  1.00  0.00           H  
HETATM   34  H8  UNL     1       5.327   2.262  -0.273  1.00  0.00           H  
HETATM   35  H9  UNL     1       6.708   3.113   0.599  1.00  0.00           H  
HETATM   36  H10 UNL     1       5.563   1.518   2.163  1.00  0.00           H  
HETATM   37  H11 UNL     1       7.313   1.162   1.809  1.00  0.00           H  
HETATM   38  H12 UNL     1       5.857  -0.803   1.958  1.00  0.00           H  
HETATM   39  H13 UNL     1       6.689  -0.708   0.379  1.00  0.00           H  
HETATM   40  H14 UNL     1       4.531   0.403  -0.514  1.00  0.00           H  
HETATM   41  H15 UNL     1       3.835   0.144   1.129  1.00  0.00           H  
HETATM   42  H16 UNL     1       4.991  -2.116  -0.651  1.00  0.00           H  
HETATM   43  H17 UNL     1       4.174  -2.310   0.952  1.00  0.00           H  
HETATM   44  H18 UNL     1       2.887  -1.283  -1.610  1.00  0.00           H  
HETATM   45  H19 UNL     1       2.720  -2.859  -0.827  1.00  0.00           H  
HETATM   46  H20 UNL     1       1.785  -1.676   1.271  1.00  0.00           H  
HETATM   47  H21 UNL     1       1.985  -0.128   0.414  1.00  0.00           H  
HETATM   48  H22 UNL     1       0.640  -0.788  -1.415  1.00  0.00           H  
HETATM   49  H23 UNL     1      -0.303  -0.767   0.095  1.00  0.00           H  
HETATM   50  H24 UNL     1       0.151  -3.405   0.129  1.00  0.00           H  
HETATM   51  H25 UNL     1       0.870  -3.187  -1.461  1.00  0.00           H  
HETATM   52  H26 UNL     1      -1.165  -4.072  -1.776  1.00  0.00           H  
HETATM   53  H27 UNL     1      -1.198  -2.440  -2.465  1.00  0.00           H  
HETATM   54  H28 UNL     1      -2.717  -3.521  -0.011  1.00  0.00           H  
HETATM   55  H29 UNL     1      -3.304  -2.986  -1.577  1.00  0.00           H  
HETATM   56  H30 UNL     1      -2.782  -0.545  -0.967  1.00  0.00           H  
HETATM   57  H31 UNL     1      -2.295  -1.255   0.686  1.00  0.00           H  
HETATM   58  H32 UNL     1      -4.201   0.685   0.782  1.00  0.00           H  
HETATM   59  H33 UNL     1      -6.617  -1.166   1.178  1.00  0.00           H  
HETATM   60  H34 UNL     1      -7.422   1.253   3.938  1.00  0.00           H  
HETATM   61  H35 UNL     1      -6.781   0.448  -0.645  1.00  0.00           H  
HETATM   62  H36 UNL     1      -6.011   2.372   1.565  1.00  0.00           H  
HETATM   63  H37 UNL     1      -6.887   2.961   0.057  1.00  0.00           H  
HETATM   64  H38 UNL     1      -5.322   2.144  -0.092  1.00  0.00           H  
HETATM   65  H39 UNL     1      -8.775  -0.190   0.423  1.00  0.00           H  
HETATM   66  H40 UNL     1      -8.590   1.072   1.736  1.00  0.00           H  
HETATM   67  H41 UNL     1      -8.927   2.852   0.202  1.00  0.00           H  
HETATM   68  H42 UNL     1      -8.405   1.858  -1.175  1.00  0.00           H  
HETATM   69  H43 UNL     1     -10.073   1.578  -0.491  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   38   39
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   52   53
CONECT   14   15   54   55
CONECT   15   16   56   57
CONECT   16   17   17   18
CONECT   18   19   58
CONECT   19   20   23   59
CONECT   20   21   21   22
CONECT   22   60
CONECT   23   24   25   61
CONECT   24   62   63   64
CONECT   25   26   65   66
CONECT   26   67   68   69
END

HMDB0241927
     RDKit          3D
N-Palmitoyl Isoleucine
 69 68  0  0  0  0  0  0  0  0999 V2000
    8.4556    2.0854   -2.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4151    2.6071   -1.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3541    1.6541   -0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3226    2.1291    0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792    1.1865    1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9247   -0.2241    1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5455   -0.2447    0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2487   -1.6808    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -1.7583   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022   -1.2347    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4505   -1.3266   -0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -2.7109   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117   -2.9641   -1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4970   -2.7274   -0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8554   -1.3774   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2902   -1.3943    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754   -2.4336    0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7801   -0.1926    0.7537 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1560   -0.1564    1.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1032    0.2230    2.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0042    0.4538    3.2628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2369    0.3495    3.4942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9104    0.8170    0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2657    2.1597    0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3906    0.8178    0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0217    1.8382   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0419    2.9216   -3.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088    1.5885   -3.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1058    1.3225   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7266    3.6171   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4270    2.6460   -2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1379    0.6581   -1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3482    1.7320   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275    2.2624   -0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7076    3.1127    0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5632    1.5182    2.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3134    1.1620    1.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8569   -0.8030    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6892   -0.7085    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5308    0.4033   -0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    0.1438    1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913   -2.1155   -0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1737   -2.3100    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866   -1.2832   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203   -2.8592   -0.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849   -1.6758    1.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9853   -0.1280    0.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -0.7881   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -0.7670    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1506   -3.4051    0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8699   -3.1867   -1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1648   -4.0718   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1982   -2.4400   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168   -3.5209   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044   -2.9862   -1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7821   -0.5445   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2947   -1.2551    0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2008    0.6846    0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6171   -1.1656    1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4217    1.2532    3.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7811    0.4478   -0.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0111    2.3717    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8870    2.9608    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3219    2.1438   -0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7749   -0.1905    0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5902    1.0715    1.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9266    2.8518    0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4054    1.8585   -1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0732    1.5780   -0.4914 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  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  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 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
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 18 58  1  0
 19 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₂H₄₃NO₃

Average Molecular Weight

369.59

Monoisotopic Molecular Weight

369.324294249

IUPAC Name

2-hexadecanamido-3-methylpentanoic acid

Traditional Name

2-hexadecanamido-3-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O

InChI Identifier

InChI=1S/C22H43NO3/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-20(24)23-21(22(25)26)19(3)5-2/h19,21H,4-18H2,1-3H3,(H,23,24)(H,25,26)

InChI Key

NGYZAEAXQQNUBZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Isoleucine and derivatives

Alternative Parents

Substituents

Isoleucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Branched fatty acid
Methyl-branched fatty acid
Fatty amide
N-acyl-amine
Fatty acid
Fatty acyl
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	7.06	ALOGPS
logP	7.05	ChemAxon
logS	-6.1	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	107.98 m³·mol⁻¹	ChemAxon
Polarizability	46.99 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]+	199.239	30932474
DeepCCS	[M-H]-	196.739	30932474
DeepCCS	[M-2H]-	229.892	30932474
DeepCCS	[M+Na]+	205.582	30932474
AllCCS	[M+H]+	206.2	32859911
AllCCS	[M+H-H2O]+	204.0	32859911
AllCCS	[M+NH4]+	208.3	32859911
AllCCS	[M+Na]+	208.9	32859911
AllCCS	[M-H]-	199.1	32859911
AllCCS	[M+Na-2H]-	200.9	32859911
AllCCS	[M+HCOO]-	203.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Palmitoyl Isoleucine	CCCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O	3590.1	Standard polar	33892256
N-Palmitoyl Isoleucine	CCCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O	2562.2	Standard non polar	33892256
N-Palmitoyl Isoleucine	CCCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O	2712.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Palmitoyl Isoleucine,2TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)CC)[Si](C)(C)C	2797.4	Semi standard non polar	33892256
N-Palmitoyl Isoleucine,2TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)CC)[Si](C)(C)C	2713.6	Standard non polar	33892256
N-Palmitoyl Isoleucine,2TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)CC)[Si](C)(C)C	2804.7	Standard polar	33892256
N-Palmitoyl Isoleucine,2TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)CC)[Si](C)(C)C(C)(C)C	3273.1	Semi standard non polar	33892256
N-Palmitoyl Isoleucine,2TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)CC)[Si](C)(C)C(C)(C)C	3028.8	Standard non polar	33892256
N-Palmitoyl Isoleucine,2TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)CC)[Si](C)(C)C(C)(C)C	3052.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Palmitoyl Isoleucine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01w3-6595000000-7b9422c68011711085d3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Palmitoyl 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-Palmitoyl Isoleucine 10V, Positive-QTOF	splash10-00di-0119000000-81bf0775dfe8d15f71d7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl Isoleucine 20V, Positive-QTOF	splash10-00dr-4469000000-0157dae5e870caae7858	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl Isoleucine 40V, Positive-QTOF	splash10-0a4l-9200000000-477500e99aa0239052cf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl Isoleucine 10V, Negative-QTOF	splash10-014i-0009000000-2904f7751435e2f912e9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl Isoleucine 20V, Negative-QTOF	splash10-001i-0903000000-96ed334ed8bc948871d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Palmitoyl Isoleucine 40V, Negative-QTOF	splash10-0ff3-7930000000-754b255839cbb5828fca	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

3463058

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4255222

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-Palmitoyl Isoleucine (HMDB0241927)

MOL for HMDB0241927 (N-Palmitoyl Isoleucine)

3D MOL for HMDB0241927 (N-Palmitoyl Isoleucine)

3D SDF for HMDB0241927 (N-Palmitoyl Isoleucine)

3D-SDF for HMDB0241927 (N-Palmitoyl Isoleucine)

PDB for HMDB0241927 (N-Palmitoyl Isoleucine)

3D PDB for HMDB0241927 (N-Palmitoyl Isoleucine)

SMILES for HMDB0241927 (N-Palmitoyl Isoleucine)

INCHI for HMDB0241927 (N-Palmitoyl Isoleucine)

Structure for HMDB0241927 (N-Palmitoyl Isoleucine)

3D Structure for HMDB0241927 (N-Palmitoyl Isoleucine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra