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Showing metabocard for N-Nervonoyl Isoleucine (HMDB0242093)

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Record Information
Version5.0
StatusPredicted
Creation Date2021-08-24 04:08:05 UTC
Update Date2021-09-16 22:46:47 UTC
HMDB IDHMDB0242093
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Nervonoyl Isoleucine
DescriptionN-nervonoyl 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 Nervonic 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-Nervonoyl 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-Nervonoyl Isoleucine is therefore classified as a very 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0242093 (N-Nervonoyl Isoleucine)


  Mrv1652308242106182D          

 34 33  0  0  0  0            999 V2000
   12.0434    6.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    7.3658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    7.3658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D MOL for HMDB0242093 (N-Nervonoyl Isoleucine)

HMDB0242093
     RDKit          3D
N-Nervonoyl Isoleucine
 91 90  0  0  0  0  0  0  0  0999 V2000
   11.2153   -2.0323    4.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4666   -1.0736    3.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1688   -0.3519    2.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042   -1.3171    2.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
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3D SDF for HMDB0242093 (N-Nervonoyl Isoleucine)


  Mrv1652308242106182D          

 34 33  0  0  0  0            999 V2000
   12.0434    6.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    7.3658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    7.3658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4711    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7605    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4749    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4749    6.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1894    7.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1894    8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9039    8.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9039    9.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6184    9.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6184   10.6658    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
 25 24  1  4  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242093

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H57NO3/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-28(32)31-29(30(33)34)27(3)5-2/h12-13,27,29H,4-11,14-26H2,1-3H3,(H,31,32)(H,33,34)

> <INCHI_KEY>
MBNAEHFLAWUAIS-UHFFFAOYSA-N

> <FORMULA>
C30H57NO3

> <MOLECULAR_WEIGHT>
479.79

> <EXACT_MASS>
479.433844699

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
63.10195301973391

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyl-2-(tetracos-15-enamido)pentanoic acid

> <ALOGPS_LOGP>
9.37

> <JCHEM_LOGP>
10.246755330000003

> <ALOGPS_LOGS>
-7.34

> <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>
145.9022

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.20e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-2-(tetracos-15-enamido)pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0242093 (N-Nervonoyl Isoleucine)

HMDB0242093
     RDKit          3D
N-Nervonoyl Isoleucine
 91 90  0  0  0  0  0  0  0  0999 V2000
   11.2153   -2.0323    4.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4666   -1.0736    3.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1688   -0.3519    2.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042   -1.3171    2.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8116   -0.6250    1.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0173    0.3173    0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7372    1.0325    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    0.0384    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1313   -0.7492   -1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731   -0.8046   -2.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3575   -0.0903   -2.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3437   -1.1710   -3.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822   -0.5137   -3.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4762    0.3124   -2.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1697    1.0182   -2.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    0.0277   -3.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1533    0.4874   -3.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1130    1.2663   -3.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8070    2.5931   -2.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0095    3.2079   -1.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4686    2.3712   -0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6500    3.0607   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1353    2.2559    1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6843    0.9490    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8086    0.6644   -0.5671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0691    0.0262    1.6575 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6119   -1.2521    1.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8240   -2.3985    1.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7970   -2.1928    2.4728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1648   -3.7153    1.5153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0891   -1.3561    1.5818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7579   -0.2258    0.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4176   -1.1220    3.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7803   -2.0701    3.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2229   -1.8820    4.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3028   -3.0530    3.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9937   -1.9303    4.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8241   -1.5660    2.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1745   -0.2915    3.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8084    0.2917    3.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4120    0.2888    1.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4308   -1.8467    1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9090   -2.0916    3.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0557   -1.4185    1.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5072   -0.0874    2.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7095    1.1248    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4241   -0.2121   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3258    1.6376    1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9340    1.6866   -0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3913   -0.6266    0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7706    0.6293   -0.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0559   -1.3615   -0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0228   -1.4422   -3.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    0.5075   -1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516    0.5447   -3.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0974   -1.6788   -2.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7776   -1.8802   -3.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2597    0.0373   -4.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3646   -1.3409   -3.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250    1.1301   -2.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1819   -0.2763   -1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758    1.6390   -2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865    1.6961   -3.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805   -0.5296   -4.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9429   -0.8223   -2.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6980   -0.4508   -4.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9397    1.0010   -4.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0500    1.3713   -3.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    0.6117   -2.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    2.6674   -1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798    3.3003   -3.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274    4.2085   -1.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8313    3.3594   -2.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7884    1.3666   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516    2.2159    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3205    4.0774    0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4126    3.2223   -0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8645    2.8410    1.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3026    2.0342    1.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9419    0.3142    2.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5758   -1.3391    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5734   -3.8840    0.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4804   -2.2930    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8199   -0.1136    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5210   -0.4116   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2275    0.7187    1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2324   -0.0491    3.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5284   -1.2422    3.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8891   -3.0938    3.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7840   -1.8071    4.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4358   -2.0685    4.9015 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  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  1  0
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 21 22  1  0
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 28 30  1  0
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 31 32  1  0
 31 33  1  0
 33 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
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  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
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  7 48  1  0
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  8 50  1  0
  8 51  1  0
  9 52  1  0
 10 53  1  0
 11 54  1  0
 11 55  1  0
 12 56  1  0
 12 57  1  0
 13 58  1  0
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 32 85  1  0
 32 86  1  0
 33 87  1  0
 33 88  1  0
 34 89  1  0
 34 90  1  0
 34 91  1  0
M  END
Download

PDB for HMDB0242093 (N-Nervonoyl Isoleucine)

HEADER    PROTEIN                                 24-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-AUG-21         0                                  
HETATM    1  O   UNK     0      22.481  12.979   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      22.481  11.439   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      21.147  10.669   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.814  12.979   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      18.480  13.749   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      21.147  13.749   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.480   9.129   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.146  11.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.813  10.669   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.815  10.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.148  11.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.483  11.439   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.150  11.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      35.818  11.439   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      41.153  11.439   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      42.486  10.669   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      43.820  11.439   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      43.820  12.979   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      45.154  13.749   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      45.154  15.289   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      46.487  16.059   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      46.487  17.599   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      47.821  18.369   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      47.821  19.909   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   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END
Download

3D PDB for HMDB0242093 (N-Nervonoyl Isoleucine)

COMPND    HMDB0242093
HETATM    1  C1  UNL     1      11.215  -2.032   4.193  1.00  0.00           C  
HETATM    2  C2  UNL     1      11.467  -1.074   3.037  1.00  0.00           C  
HETATM    3  C3  UNL     1      10.169  -0.352   2.689  1.00  0.00           C  
HETATM    4  C4  UNL     1       9.104  -1.317   2.292  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.812  -0.625   1.960  1.00  0.00           C  
HETATM    6  C6  UNL     1       8.017   0.317   0.821  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.737   1.032   0.426  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.665   0.038   0.003  1.00  0.00           C  
HETATM    9  C9  UNL     1       6.131  -0.749  -1.142  1.00  0.00           C  
HETATM   10  C10 UNL     1       5.573  -0.805  -2.303  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.357  -0.090  -2.713  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.344  -1.171  -3.111  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.082  -0.514  -3.583  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.476   0.312  -2.514  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.170   1.018  -2.969  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.861   0.028  -3.383  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.153   0.487  -3.877  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.113   1.266  -3.110  1.00  0.00           C  
HETATM   19  C19 UNL     1      -2.807   2.593  -2.582  1.00  0.00           C  
HETATM   20  C20 UNL     1      -4.009   3.208  -1.908  1.00  0.00           C  
HETATM   21  C21 UNL     1      -4.469   2.371  -0.761  1.00  0.00           C  
HETATM   22  C22 UNL     1      -5.650   3.061  -0.084  1.00  0.00           C  
HETATM   23  C23 UNL     1      -6.135   2.256   1.053  1.00  0.00           C  
HETATM   24  C24 UNL     1      -6.684   0.949   0.646  1.00  0.00           C  
HETATM   25  O1  UNL     1      -6.809   0.664  -0.567  1.00  0.00           O  
HETATM   26  N1  UNL     1      -7.069   0.026   1.657  1.00  0.00           N  
HETATM   27  C25 UNL     1      -7.612  -1.252   1.262  1.00  0.00           C  
HETATM   28  C26 UNL     1      -6.824  -2.398   1.773  1.00  0.00           C  
HETATM   29  O2  UNL     1      -5.797  -2.193   2.473  1.00  0.00           O  
HETATM   30  O3  UNL     1      -7.165  -3.715   1.515  1.00  0.00           O  
HETATM   31  C27 UNL     1      -9.089  -1.356   1.582  1.00  0.00           C  
HETATM   32  C28 UNL     1      -9.758  -0.226   0.791  1.00  0.00           C  
HETATM   33  C29 UNL     1      -9.418  -1.122   3.018  1.00  0.00           C  
HETATM   34  C30 UNL     1      -8.780  -2.070   3.980  1.00  0.00           C  
HETATM   35  H1  UNL     1      10.223  -1.882   4.635  1.00  0.00           H  
HETATM   36  H2  UNL     1      11.303  -3.053   3.751  1.00  0.00           H  
HETATM   37  H3  UNL     1      11.994  -1.930   4.962  1.00  0.00           H  
HETATM   38  H4  UNL     1      11.824  -1.566   2.133  1.00  0.00           H  
HETATM   39  H5  UNL     1      12.174  -0.292   3.364  1.00  0.00           H  
HETATM   40  H6  UNL     1       9.808   0.292   3.506  1.00  0.00           H  
HETATM   41  H7  UNL     1      10.412   0.289   1.798  1.00  0.00           H  
HETATM   42  H8  UNL     1       9.431  -1.847   1.370  1.00  0.00           H  
HETATM   43  H9  UNL     1       8.909  -2.092   3.064  1.00  0.00           H  
HETATM   44  H10 UNL     1       7.056  -1.419   1.737  1.00  0.00           H  
HETATM   45  H11 UNL     1       7.507  -0.087   2.901  1.00  0.00           H  
HETATM   46  H12 UNL     1       8.710   1.125   1.185  1.00  0.00           H  
HETATM   47  H13 UNL     1       8.424  -0.212  -0.036  1.00  0.00           H  
HETATM   48  H14 UNL     1       6.326   1.638   1.245  1.00  0.00           H  
HETATM   49  H15 UNL     1       6.934   1.687  -0.443  1.00  0.00           H  
HETATM   50  H16 UNL     1       5.391  -0.627   0.865  1.00  0.00           H  
HETATM   51  H17 UNL     1       4.771   0.629  -0.203  1.00  0.00           H  
HETATM   52  H18 UNL     1       7.056  -1.362  -0.999  1.00  0.00           H  
HETATM   53  H19 UNL     1       6.023  -1.442  -3.102  1.00  0.00           H  
HETATM   54  H20 UNL     1       3.959   0.508  -1.892  1.00  0.00           H  
HETATM   55  H21 UNL     1       4.552   0.545  -3.615  1.00  0.00           H  
HETATM   56  H22 UNL     1       3.097  -1.679  -2.139  1.00  0.00           H  
HETATM   57  H23 UNL     1       3.778  -1.880  -3.835  1.00  0.00           H  
HETATM   58  H24 UNL     1       2.260   0.037  -4.532  1.00  0.00           H  
HETATM   59  H25 UNL     1       1.365  -1.341  -3.839  1.00  0.00           H  
HETATM   60  H26 UNL     1       2.125   1.130  -2.171  1.00  0.00           H  
HETATM   61  H27 UNL     1       1.182  -0.276  -1.646  1.00  0.00           H  
HETATM   62  H28 UNL     1      -0.076   1.639  -2.091  1.00  0.00           H  
HETATM   63  H29 UNL     1       0.386   1.696  -3.825  1.00  0.00           H  
HETATM   64  H30 UNL     1      -0.381  -0.530  -4.265  1.00  0.00           H  
HETATM   65  H31 UNL     1      -0.943  -0.822  -2.635  1.00  0.00           H  
HETATM   66  H32 UNL     1      -2.698  -0.451  -4.262  1.00  0.00           H  
HETATM   67  H33 UNL     1      -1.940   1.001  -4.888  1.00  0.00           H  
HETATM   68  H34 UNL     1      -4.050   1.371  -3.750  1.00  0.00           H  
HETATM   69  H35 UNL     1      -3.516   0.612  -2.258  1.00  0.00           H  
HETATM   70  H36 UNL     1      -2.004   2.667  -1.814  1.00  0.00           H  
HETATM   71  H37 UNL     1      -2.580   3.300  -3.443  1.00  0.00           H  
HETATM   72  H38 UNL     1      -3.727   4.208  -1.484  1.00  0.00           H  
HETATM   73  H39 UNL     1      -4.831   3.359  -2.641  1.00  0.00           H  
HETATM   74  H40 UNL     1      -4.788   1.367  -1.051  1.00  0.00           H  
HETATM   75  H41 UNL     1      -3.652   2.216   0.001  1.00  0.00           H  
HETATM   76  H42 UNL     1      -5.320   4.077   0.264  1.00  0.00           H  
HETATM   77  H43 UNL     1      -6.413   3.222  -0.873  1.00  0.00           H  
HETATM   78  H44 UNL     1      -6.864   2.841   1.667  1.00  0.00           H  
HETATM   79  H45 UNL     1      -5.303   2.034   1.781  1.00  0.00           H  
HETATM   80  H46 UNL     1      -6.942   0.314   2.647  1.00  0.00           H  
HETATM   81  H47 UNL     1      -7.576  -1.339   0.134  1.00  0.00           H  
HETATM   82  H48 UNL     1      -7.573  -3.884   0.583  1.00  0.00           H  
HETATM   83  H49 UNL     1      -9.480  -2.293   1.196  1.00  0.00           H  
HETATM   84  H50 UNL     1     -10.820  -0.114   1.026  1.00  0.00           H  
HETATM   85  H51 UNL     1      -9.521  -0.412  -0.266  1.00  0.00           H  
HETATM   86  H52 UNL     1      -9.227   0.719   1.110  1.00  0.00           H  
HETATM   87  H53 UNL     1      -9.232  -0.049   3.290  1.00  0.00           H  
HETATM   88  H54 UNL     1     -10.528  -1.242   3.112  1.00  0.00           H  
HETATM   89  H55 UNL     1      -8.889  -3.094   3.568  1.00  0.00           H  
HETATM   90  H56 UNL     1      -7.784  -1.807   4.327  1.00  0.00           H  
HETATM   91  H57 UNL     1      -9.436  -2.069   4.901  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3   38   39
CONECT    3    4   40   41
CONECT    4    5   42   43
CONECT    5    6   44   45
CONECT    6    7   46   47
CONECT    7    8   48   49
CONECT    8    9   50   51
CONECT    9   10   10   52
CONECT   10   11   53
CONECT   11   12   54   55
CONECT   12   13   56   57
CONECT   13   14   58   59
CONECT   14   15   60   61
CONECT   15   16   62   63
CONECT   16   17   64   65
CONECT   17   18   66   67
CONECT   18   19   68   69
CONECT   19   20   70   71
CONECT   20   21   72   73
CONECT   21   22   74   75
CONECT   22   23   76   77
CONECT   23   24   78   79
CONECT   24   25   25   26
CONECT   26   27   80
CONECT   27   28   31   81
CONECT   28   29   29   30
CONECT   30   82
CONECT   31   32   33   83
CONECT   32   84   85   86
CONECT   33   34   87   88
CONECT   34   89   90   91
END
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SMILES for HMDB0242093 (N-Nervonoyl Isoleucine)

CCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O
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INCHI for HMDB0242093 (N-Nervonoyl Isoleucine)

InChI=1S/C30H57NO3/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-28(32)31-29(30(33)34)27(3)5-2/h12-13,27,29H,4-11,14-26H2,1-3H3,(H,31,32)(H,33,34)
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC30H57NO3
Average Molecular Weight479.79
Monoisotopic Molecular Weight479.433844699
IUPAC Name3-methyl-2-(tetracos-15-enamido)pentanoic acid
Traditional Name3-methyl-2-(tetracos-15-enamido)pentanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O
InChI Identifier
InChI=1S/C30H57NO3/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-28(32)31-29(30(33)34)27(3)5-2/h12-13,27,29H,4-11,14-26H2,1-3H3,(H,31,32)(H,33,34)
InChI KeyMBNAEHFLAWUAIS-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP9.37ALOGPS
logP10.25ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity145.9 m³·mol⁻¹ChemAxon
Polarizability63.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+230.10630932474
DeepCCS[M-H]-227.55530932474
DeepCCS[M-2H]-260.9330932474
DeepCCS[M+Na]+237.03230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Nervonoyl IsoleucineCCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O3932.2Standard polar33892256
N-Nervonoyl IsoleucineCCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O3275.6Standard non polar33892256
N-Nervonoyl IsoleucineCCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(C(C)CC)C(O)=O3492.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Nervonoyl Isoleucine,2TMS,isomer #1CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)CC)[Si](C)(C)C3534.4Semi standard non polar33892256
N-Nervonoyl Isoleucine,2TMS,isomer #1CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)CC)[Si](C)(C)C3370.5Standard non polar33892256
N-Nervonoyl Isoleucine,2TMS,isomer #1CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)CC)[Si](C)(C)C3446.1Standard polar33892256
N-Nervonoyl Isoleucine,2TBDMS,isomer #1CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)CC)[Si](C)(C)C(C)(C)C4020.7Semi standard non polar33892256
N-Nervonoyl Isoleucine,2TBDMS,isomer #1CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)CC)[Si](C)(C)C(C)(C)C3660.2Standard non polar33892256
N-Nervonoyl Isoleucine,2TBDMS,isomer #1CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)CC)[Si](C)(C)C(C)(C)C3623.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Nervonoyl Isoleucine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uea-6797700000-e73932c21bc89ced699f2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Nervonoyl Isoleucine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nervonoyl Isoleucine 10V, Positive-QTOFsplash10-001i-0102900000-8bc77c1798088b8195e82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nervonoyl Isoleucine 20V, Positive-QTOFsplash10-01q9-5309800000-925d971a1ed4a31a734b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nervonoyl Isoleucine 40V, Positive-QTOFsplash10-05we-9400000000-87911d6256e2a793b40c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nervonoyl Isoleucine 10V, Negative-QTOFsplash10-004i-0000900000-a2c4ee4114c6ad18834a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nervonoyl Isoleucine 20V, Negative-QTOFsplash10-001i-0900300000-7ef0a388cc80e6fde23f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nervonoyl Isoleucine 40V, Negative-QTOFsplash10-01po-9804000000-44abe8b394d50854933d2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]