Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Predicted

Creation Date

2021-07-27 23:55:42 UTC

Update Date

2021-10-01 16:48:34 UTC

HMDB ID

HMDB0241956

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Oleoyl Aspartic acid

Description

N-oleoyl aspartic acid, also known as N-oleoyl aspartate 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 an Oleic acid amide of Aspartic acid. 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-Oleoyl Aspartic acid 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-Oleoyl Aspartic acid 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


  Mrv1652307282102052D          

 28 27  0  0  0  0            999 V2000
    4.7586    3.5724    0.0000 O   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
    5.4730    4.8099    0.0000 O   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
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 N   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
    8.3309    4.8099    0.0000 O   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
    9.7599    3.9849    0.0000 C   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
   11.1888    3.9849    0.0000 C   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
   12.6177    3.9849    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
   14.7612    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9046    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9046    7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6190    7.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6190    8.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    5.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    5.2224    0.0000 O   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  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
 14 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  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
  5 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END

HMDB0241956
     RDKit          3D
N-Oleoyl Aspartic acid
 67 66  0  0  0  0  0  0  0  0999 V2000
    9.3717    0.2239    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2008    1.1786    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5258    1.3093    1.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3483    2.2272    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2695    1.7657    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574    0.4054    0.9979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876   -0.0607    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5023    0.8513    0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    0.3514   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -0.7476   -1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7029   -1.2429   -2.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2915   -2.6238   -2.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921   -2.5608   -0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152   -1.6731   -0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5773   -2.1989   -1.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8185   -1.3439   -1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4272   -1.2829   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6331   -0.4312   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9795    0.0890   -1.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3875   -0.2194    0.9125 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5854    0.6025    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3710    1.7206    1.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2148    2.5690    1.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0152    2.2436    1.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4353    3.8204    0.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7325   -0.2603    1.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5758   -1.4797    1.5770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9773    0.3186    1.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2899   -0.5964   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3737   -0.2394    1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3399    0.7477    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4990    0.7466   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5260    2.1523   -0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2537    0.2677    1.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2242    1.6749    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154    3.2083    1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9444    2.4323    2.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7285    1.7357   -0.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4944    2.5408    0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207    0.3490    2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5797   -0.3445    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3685   -1.0913    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1759   -0.1353   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7388    1.9099   -0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0087    0.7954    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472    0.8756   -1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6504   -1.3363   -1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -1.2173   -3.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1461   -0.5393   -2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2449   -3.2250   -2.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3398   -3.1541   -2.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304   -2.1717   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6487   -3.5858   -0.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931   -0.6213   -0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -1.7448    0.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8812   -3.2211   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613   -2.2678   -2.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5958   -1.6873   -2.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4834   -0.2990   -1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7872   -2.3063    0.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6948   -0.9012    0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0703   -0.6703    1.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8227    1.0365   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1371    1.3050    2.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2786    2.3363    2.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0005    3.8867    0.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7199   -0.1965    1.8641 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  2  0
 26 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
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 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
 16 58  1  0
 16 59  1  0
 17 60  1  0
 17 61  1  0
 20 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 25 66  1  0
 28 67  1  0
M  END


  Mrv1652307282102052D          

 28 27  0  0  0  0            999 V2000
    4.7586    3.5724    0.0000 O   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
    5.4730    4.8099    0.0000 O   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
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 N   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
    8.3309    4.8099    0.0000 O   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
    9.7599    3.9849    0.0000 C   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
   11.1888    3.9849    0.0000 C   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
   12.6177    3.9849    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
   14.7612    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4756    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    6.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9046    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9046    7.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6190    7.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6190    8.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    5.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    5.2224    0.0000 O   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  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
 14 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  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
  5 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0241956

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H39NO5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(24)23-19(22(27)28)18-21(25)26/h9-10,19H,2-8,11-18H2,1H3,(H,23,24)(H,25,26)(H,27,28)

> <INCHI_KEY>
XFBKKGFUMFHHHK-UHFFFAOYSA-N

> <FORMULA>
C22H39NO5

> <MOLECULAR_WEIGHT>
397.556

> <EXACT_MASS>
397.28282336

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
48.21619827458062

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(octadec-9-enamido)butanedioic acid

> <ALOGPS_LOGP>
5.29

> <JCHEM_LOGP>
5.605467543666667

> <ALOGPS_LOGS>
-5.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.505595341646542

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7016446935007594

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5516197076919251

> <JCHEM_POLAR_SURFACE_AREA>
103.7

> <JCHEM_REFRACTIVITY>
110.73499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.04e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(octadec-9-enamido)butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241956
     RDKit          3D
N-Oleoyl Aspartic acid
 67 66  0  0  0  0  0  0  0  0999 V2000
    9.3717    0.2239    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2008    1.1786    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5258    1.3093    1.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3483    2.2272    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2695    1.7657    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574    0.4054    0.9979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876   -0.0607    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5023    0.8513    0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    0.3514   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -0.7476   -1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7029   -1.2429   -2.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2915   -2.6238   -2.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921   -2.5608   -0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152   -1.6731   -0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5773   -2.1989   -1.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8185   -1.3439   -1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4272   -1.2829   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6331   -0.4312   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9795    0.0890   -1.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3875   -0.2194    0.9125 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5854    0.6025    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3710    1.7206    1.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2148    2.5690    1.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0152    2.2436    1.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4353    3.8204    0.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7325   -0.2603    1.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5758   -1.4797    1.5770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9773    0.3186    1.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2899   -0.5964   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3737   -0.2394    1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3399    0.7477    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4990    0.7466   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5260    2.1523   -0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2537    0.2677    1.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2242    1.6749    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154    3.2083    1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9444    2.4323    2.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7285    1.7357   -0.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4944    2.5408    0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207    0.3490    2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5797   -0.3445    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3685   -1.0913    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1759   -0.1353   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7388    1.9099   -0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0087    0.7954    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472    0.8756   -1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6504   -1.3363   -1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -1.2173   -3.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1461   -0.5393   -2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2449   -3.2250   -2.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3398   -3.1541   -2.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304   -2.1717   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6487   -3.5858   -0.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931   -0.6213   -0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -1.7448    0.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8812   -3.2211   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613   -2.2678   -2.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5958   -1.6873   -2.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4834   -0.2990   -1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7872   -2.3063    0.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6948   -0.9012    0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0703   -0.6703    1.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8227    1.0365   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1371    1.3050    2.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2786    2.3363    2.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0005    3.8867    0.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7199   -0.1965    1.8641 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  2  0
 26 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
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 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
 16 58  1  0
 16 59  1  0
 17 60  1  0
 17 61  1  0
 20 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 25 66  1  0
 28 67  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       8.883   6.668   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.216   8.978   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      14.217   6.668   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      15.551   8.978   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.220   7.438   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.554   6.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.888   7.438   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.888   8.978   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.222   9.748   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.222  11.288   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.555  12.058   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.555  13.598   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      32.889  14.368   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      32.889  15.908   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.884   8.978   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.217   9.748   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      11.550   9.748   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26    5   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

COMPND    HMDB0241956
HETATM    1  C1  UNL     1       9.372   0.224   0.464  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.201   1.179   0.299  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.526   1.309   1.626  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.348   2.227   1.620  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.270   1.766   0.655  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.757   0.405   0.998  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.688  -0.061   0.036  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.502   0.851   0.034  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.491   0.351  -0.922  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.725  -0.748  -1.611  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.703  -1.243  -2.570  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.292  -2.624  -2.149  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.292  -2.561  -0.766  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.515  -1.673  -0.693  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.577  -2.199  -1.616  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.818  -1.344  -1.581  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.427  -1.283  -0.200  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.633  -0.431  -0.265  1.00  0.00           C  
HETATM   19  O1  UNL     1      -5.980   0.089  -1.331  1.00  0.00           O  
HETATM   20  N1  UNL     1      -6.387  -0.219   0.913  1.00  0.00           N  
HETATM   21  C19 UNL     1      -7.585   0.603   0.935  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.371   1.721   1.927  1.00  0.00           C  
HETATM   23  C21 UNL     1      -6.215   2.569   1.564  1.00  0.00           C  
HETATM   24  O2  UNL     1      -5.015   2.244   1.743  1.00  0.00           O  
HETATM   25  O3  UNL     1      -6.435   3.820   0.981  1.00  0.00           O  
HETATM   26  C22 UNL     1      -8.732  -0.260   1.328  1.00  0.00           C  
HETATM   27  O4  UNL     1      -8.576  -1.480   1.577  1.00  0.00           O  
HETATM   28  O5  UNL     1      -9.977   0.319   1.413  1.00  0.00           O  
HETATM   29  H1  UNL     1       9.290  -0.596  -0.275  1.00  0.00           H  
HETATM   30  H2  UNL     1       9.374  -0.239   1.464  1.00  0.00           H  
HETATM   31  H3  UNL     1      10.340   0.748   0.321  1.00  0.00           H  
HETATM   32  H4  UNL     1       7.499   0.747  -0.440  1.00  0.00           H  
HETATM   33  H5  UNL     1       8.526   2.152  -0.124  1.00  0.00           H  
HETATM   34  H6  UNL     1       7.254   0.268   1.953  1.00  0.00           H  
HETATM   35  H7  UNL     1       8.224   1.675   2.416  1.00  0.00           H  
HETATM   36  H8  UNL     1       6.715   3.208   1.199  1.00  0.00           H  
HETATM   37  H9  UNL     1       5.944   2.432   2.619  1.00  0.00           H  
HETATM   38  H10 UNL     1       5.729   1.736  -0.353  1.00  0.00           H  
HETATM   39  H11 UNL     1       4.494   2.541   0.618  1.00  0.00           H  
HETATM   40  H12 UNL     1       4.321   0.349   2.020  1.00  0.00           H  
HETATM   41  H13 UNL     1       5.580  -0.344   0.950  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.369  -1.091   0.339  1.00  0.00           H  
HETATM   43  H15 UNL     1       4.176  -0.135  -0.959  1.00  0.00           H  
HETATM   44  H16 UNL     1       2.739   1.910  -0.120  1.00  0.00           H  
HETATM   45  H17 UNL     1       2.009   0.795   1.049  1.00  0.00           H  
HETATM   46  H18 UNL     1       0.547   0.876  -1.075  1.00  0.00           H  
HETATM   47  H19 UNL     1       2.650  -1.336  -1.522  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.128  -1.217  -3.596  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.146  -0.539  -2.577  1.00  0.00           H  
HETATM   50  H22 UNL     1       1.245  -3.225  -2.086  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.340  -3.154  -2.864  1.00  0.00           H  
HETATM   52  H24 UNL     1       0.430  -2.172  -0.021  1.00  0.00           H  
HETATM   53  H25 UNL     1      -0.649  -3.586  -0.468  1.00  0.00           H  
HETATM   54  H26 UNL     1      -1.293  -0.621  -0.862  1.00  0.00           H  
HETATM   55  H27 UNL     1      -1.858  -1.745   0.380  1.00  0.00           H  
HETATM   56  H28 UNL     1      -2.881  -3.221  -1.276  1.00  0.00           H  
HETATM   57  H29 UNL     1      -2.161  -2.268  -2.636  1.00  0.00           H  
HETATM   58  H30 UNL     1      -4.596  -1.687  -2.277  1.00  0.00           H  
HETATM   59  H31 UNL     1      -3.483  -0.299  -1.816  1.00  0.00           H  
HETATM   60  H32 UNL     1      -4.787  -2.306   0.115  1.00  0.00           H  
HETATM   61  H33 UNL     1      -3.695  -0.901   0.553  1.00  0.00           H  
HETATM   62  H34 UNL     1      -6.070  -0.670   1.795  1.00  0.00           H  
HETATM   63  H35 UNL     1      -7.823   1.037  -0.036  1.00  0.00           H  
HETATM   64  H36 UNL     1      -7.137   1.305   2.949  1.00  0.00           H  
HETATM   65  H37 UNL     1      -8.279   2.336   2.055  1.00  0.00           H  
HETATM   66  H38 UNL     1      -7.000   3.887   0.141  1.00  0.00           H  
HETATM   67  H39 UNL     1     -10.720  -0.196   1.864  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   40   41
CONECT    7    8   42   43
CONECT    8    9   44   45
CONECT    9   10   10   46
CONECT   10   11   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   58   59
CONECT   17   18   60   61
CONECT   18   19   19   20
CONECT   20   21   62
CONECT   21   22   26   63
CONECT   22   23   64   65
CONECT   23   24   24   25
CONECT   25   66
CONECT   26   27   27   28
CONECT   28   67
END

HMDB0241956
     RDKit          3D
N-Oleoyl Aspartic acid
 67 66  0  0  0  0  0  0  0  0999 V2000
    9.3717    0.2239    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2008    1.1786    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5258    1.3093    1.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3483    2.2272    1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2695    1.7657    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574    0.4054    0.9979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876   -0.0607    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5023    0.8513    0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    0.3514   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -0.7476   -1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7029   -1.2429   -2.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2915   -2.6238   -2.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921   -2.5608   -0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152   -1.6731   -0.6930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5773   -2.1989   -1.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8185   -1.3439   -1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4272   -1.2829   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6331   -0.4312   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9795    0.0890   -1.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3875   -0.2194    0.9125 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5854    0.6025    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3710    1.7206    1.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2148    2.5690    1.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0152    2.2436    1.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4353    3.8204    0.9814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7325   -0.2603    1.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5758   -1.4797    1.5770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9773    0.3186    1.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2899   -0.5964   -0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3737   -0.2394    1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3399    0.7477    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4990    0.7466   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5260    2.1523   -0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2537    0.2677    1.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2242    1.6749    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154    3.2083    1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9444    2.4323    2.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7285    1.7357   -0.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4944    2.5408    0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207    0.3490    2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5797   -0.3445    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3685   -1.0913    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1759   -0.1353   -0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7388    1.9099   -0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0087    0.7954    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472    0.8756   -1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6504   -1.3363   -1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -1.2173   -3.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1461   -0.5393   -2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2449   -3.2250   -2.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3398   -3.1541   -2.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4304   -2.1717   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6487   -3.5858   -0.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931   -0.6213   -0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -1.7448    0.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8812   -3.2211   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613   -2.2678   -2.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5958   -1.6873   -2.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4834   -0.2990   -1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7872   -2.3063    0.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6948   -0.9012    0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0703   -0.6703    1.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8227    1.0365   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1371    1.3050    2.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2786    2.3363    2.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0005    3.8867    0.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7199   -0.1965    1.8641 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 21 26  1  0
 26 27  2  0
 26 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
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 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
 16 58  1  0
 16 59  1  0
 17 60  1  0
 17 61  1  0
 20 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 25 66  1  0
 28 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Oleoyl aspartate	Generator

Chemical Formula

C₂₂H₃₉NO₅

Average Molecular Weight

397.556

Monoisotopic Molecular Weight

397.28282336

IUPAC Name

2-(octadec-9-enamido)butanedioic acid

Traditional Name

2-(octadec-9-enamido)butanedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H39NO5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(24)23-19(22(27)28)18-21(25)26/h9-10,19H,2-8,11-18H2,1H3,(H,23,24)(H,25,26)(H,27,28)

InChI Key

XFBKKGFUMFHHHK-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	5.29	ALOGPS
logP	5.61	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	110.74 m³·mol⁻¹	ChemAxon
Polarizability	48.22 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]+	204.717	30932474
DeepCCS	[M-H]-	202.167	30932474
DeepCCS	[M-2H]-	235.372	30932474
DeepCCS	[M+Na]+	211.332	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Oleoyl Aspartic acid	CCCCCCCCC=CCCCCCCCC(=O)NC(CC(O)=O)C(O)=O	4364.5	Standard polar	33892256
N-Oleoyl Aspartic acid	CCCCCCCCC=CCCCCCCCC(=O)NC(CC(O)=O)C(O)=O	2713.4	Standard non polar	33892256
N-Oleoyl Aspartic acid	CCCCCCCCC=CCCCCCCCC(=O)NC(CC(O)=O)C(O)=O	3073.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Oleoyl Aspartic acid,3TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(C(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3105.7	Semi standard non polar	33892256
N-Oleoyl Aspartic acid,3TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(C(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3044.3	Standard non polar	33892256
N-Oleoyl Aspartic acid,3TMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(C(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3181.6	Standard polar	33892256
N-Oleoyl Aspartic acid,3TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3834.5	Semi standard non polar	33892256
N-Oleoyl Aspartic acid,3TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3522.4	Standard non polar	33892256
N-Oleoyl Aspartic acid,3TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCC(=O)N(C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3429.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Oleoyl Aspartic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxr-6597000000-6f5e7e9bf26239310052	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Oleoyl Aspartic acid 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-Oleoyl Aspartic acid 10V, Positive-QTOF	splash10-00kb-0279000000-bf3fae3ec39e1446ce42	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Aspartic acid 20V, Positive-QTOF	splash10-014i-0972000000-6170e71c098d77adc9d6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Aspartic acid 40V, Positive-QTOF	splash10-053s-9700000000-cdbd963a9ba98f65bc7e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Aspartic acid 10V, Negative-QTOF	splash10-002b-0109000000-9841fd2a2793fbf74f6a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Aspartic acid 20V, Negative-QTOF	splash10-000i-9603000000-01657448cabda8059b07	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Oleoyl Aspartic acid 40V, Negative-QTOF	splash10-000i-9321000000-b47100d4331c1dd6f393	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

76128877

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-Oleoyl Aspartic acid (HMDB0241956)

MOL for HMDB0241956 (N-Oleoyl Aspartic acid)

3D MOL for HMDB0241956 (N-Oleoyl Aspartic acid)

3D SDF for HMDB0241956 (N-Oleoyl Aspartic acid)

3D-SDF for HMDB0241956 (N-Oleoyl Aspartic acid)

PDB for HMDB0241956 (N-Oleoyl Aspartic acid)

3D PDB for HMDB0241956 (N-Oleoyl Aspartic acid)

SMILES for HMDB0241956 (N-Oleoyl Aspartic acid)

INCHI for HMDB0241956 (N-Oleoyl Aspartic acid)

Structure for HMDB0241956 (N-Oleoyl Aspartic acid)

3D Structure for HMDB0241956 (N-Oleoyl Aspartic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra