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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-07-28 19:19:37 UTC

Update Date

2021-09-16 22:46:37 UTC

HMDB ID

HMDB0242020

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Docosahexaenoyl Proline

Description

N-docosahexaenoyl proline 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 Docosahexaenoyl amide of Proline. 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-Docosahexaenoyl Proline 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-Docosahexaenoyl Proline 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

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


  Mrv1652307282121292D          

 31 31  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1475    2.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321    3.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1036    3.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883    4.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5014    3.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2860    3.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4575    4.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2421    4.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4137    5.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8006    6.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9721    7.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3590    7.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5744    7.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9613    7.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1767    7.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0051    6.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2205    6.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0490    5.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644    5.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
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 27 28  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  4 31  1  0  0  0  0
M  END

HMDB0242020
     RDKit          3D
N-Docosahexaenoyl Proline
 70 70  0  0  0  0  0  0  0  0999 V2000
  -11.7181    0.7210   -1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2492    0.6389   -1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5342   -0.2784   -1.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9172   -1.3561   -1.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8368   -1.8326   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3835   -1.8705    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8940   -1.1627    1.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4300   -1.2224    1.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8485    0.1311    1.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8930    0.4991    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2082   -0.4095   -0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -0.3805    0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8564    0.0172   -0.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5794    0.0574   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208   -0.4050    0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130    0.3325    1.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949    1.7041    1.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1539    1.7265    2.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0357    2.1060    1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5076    2.1514    1.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1766    1.2174    0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6579    1.1851    0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1489    1.8767    1.6124 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5059    0.3953   -0.1103 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9415    0.3015    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4300   -0.3945   -1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2438   -0.6975   -2.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0474   -0.4429   -1.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5079   -1.7260   -0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0697   -2.5584   -1.5024 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.2129    0.3389   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5198   -0.0307   -3.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4028   -1.9797   -2.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4521   -1.3196    0.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2049   -2.9075   -0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7559   -2.5133   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5078   -0.5248    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9762   -1.9342    0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3206   -1.5417    2.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2942    0.9185    1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815    1.5762    0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -0.0918   -1.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5035   -1.4576   -0.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428   -0.7021    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1531    0.3181   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    0.9906   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -0.7076   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3977   -1.4253    1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2897   -0.0821    2.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1202    2.3354    2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325    2.1395    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205    1.4286    3.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6838    2.3983    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311    1.8309    2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8229    3.2009    1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8094    0.1936    0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9568    1.5534   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3578    1.3332    0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2033   -0.2381    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9838   -1.3145   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1328    0.3080   -1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2387    0.0243   -2.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2246   -1.7484   -2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2262    0.0441   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9003   -2.6455    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  2  3
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 22 24  1  0
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 29 30  2  0
 29 31  1  0
 28 24  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 11 47  1  0
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 21 62  1  0
 25 63  1  0
 25 64  1  0
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 26 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 31 70  1  0
M  END


  Mrv1652307282121292D          

 31 31  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1475    2.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321    3.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1036    3.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883    4.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5014    3.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2860    3.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4575    4.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2421    4.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4137    5.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8006    6.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9721    7.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3590    7.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5744    7.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9613    7.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1767    7.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0051    6.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2205    6.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
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 13 12  1  4  0  0  0
 13 14  2  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
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 22 23  2  0  0  0  0
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  5 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  4 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242020

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)N1CCCC1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23-26(29)28-24-21-22-25(28)27(30)31/h3-4,6-7,9-10,12-13,15-16,18-19,25H,2,5,8,11,14,17,20-24H2,1H3,(H,30,31)

> <INCHI_KEY>
PMYCLCQAGGZCSW-UHFFFAOYSA-N

> <FORMULA>
C27H39NO3

> <MOLECULAR_WEIGHT>
425.613

> <EXACT_MASS>
425.29299412

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.97126949226316

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(docosa-4,7,10,13,16,19-hexaenoyl)pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
6.62

> <JCHEM_LOGP>
6.488611408000001

> <ALOGPS_LOGS>
-5.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.057754802709056

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1211952753128918

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
136.3757

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(docosa-4,7,10,13,16,19-hexaenoyl)pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242020
     RDKit          3D
N-Docosahexaenoyl Proline
 70 70  0  0  0  0  0  0  0  0999 V2000
  -11.7181    0.7210   -1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2492    0.6389   -1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5342   -0.2784   -1.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9172   -1.3561   -1.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8368   -1.8326   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3835   -1.8705    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8940   -1.1627    1.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4300   -1.2224    1.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8485    0.1311    1.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8930    0.4991    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2082   -0.4095   -0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -0.3805    0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8564    0.0172   -0.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5794    0.0574   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208   -0.4050    0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130    0.3325    1.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949    1.7041    1.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1539    1.7265    2.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0357    2.1060    1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5076    2.1514    1.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1766    1.2174    0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6579    1.1851    0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1489    1.8767    1.6124 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5059    0.3953   -0.1103 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9415    0.3015    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4300   -0.3945   -1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2438   -0.6975   -2.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0474   -0.4429   -1.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5079   -1.7260   -0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0697   -2.5584   -1.5024 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4980   -1.9766    0.7027 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7998    0.5389   -2.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2824   -0.0638   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0624    1.7411   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8124    1.6679   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2129    0.3389   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5198   -0.0307   -3.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4028   -1.9797   -2.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4521   -1.3196    0.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2049   -2.9075   -0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7559   -2.5133   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5078   -0.5248    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9762   -1.9342    0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3206   -1.5417    2.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2942    0.9185    1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815    1.5762    0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -0.0918   -1.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5035   -1.4576   -0.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428   -0.7021    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1531    0.3181   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    0.9906   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -0.7076   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3977   -1.4253    1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2897   -0.0821    2.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1202    2.3354    2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325    2.1395    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205    1.4286    3.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6838    2.3983    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311    1.8309    2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8229    3.2009    1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8094    0.1936    0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9568    1.5534   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3578    1.3332    0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2033   -0.2381    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9838   -1.3145   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1328    0.3080   -1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2387    0.0243   -2.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2246   -1.7484   -2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2262    0.0441   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9003   -2.6455    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 28 24  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 31 70  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      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.306   1.175   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.915   0.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.091   3.157   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.555   3.633   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.875   5.139   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.340   5.615   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.660   7.122   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.125   7.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.269   6.567   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.734   7.043   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.054   8.549   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.519   9.025   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.839  10.531   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.694  11.562   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.015  13.068   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.870  14.099   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.405  13.623   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.261  14.653   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.796  14.177   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.476  12.671   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.012  12.195   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.691  10.689   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.227  10.213   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   31                                                  
CONECT    5    4    6   29                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29    5   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    4                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

COMPND    HMDB0242020
HETATM    1  C1  UNL     1     -11.718   0.721  -1.514  1.00  0.00           C  
HETATM    2  C2  UNL     1     -10.249   0.639  -1.110  1.00  0.00           C  
HETATM    3  C3  UNL     1      -9.534  -0.278  -1.996  1.00  0.00           C  
HETATM    4  C4  UNL     1      -8.917  -1.356  -1.609  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.837  -1.833  -0.210  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.383  -1.870   0.144  1.00  0.00           C  
HETATM    7  C7  UNL     1      -6.894  -1.163   1.132  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.430  -1.222   1.462  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.849   0.131   1.331  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.893   0.499   0.539  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.208  -0.410  -0.391  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.748  -0.380   0.012  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.856   0.017  -0.859  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.579   0.057  -0.497  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.721  -0.405   0.902  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.213   0.333   1.840  1.00  0.00           C  
HETATM   17  C17 UNL     1       1.695   1.704   1.678  1.00  0.00           C  
HETATM   18  C18 UNL     1       3.154   1.727   2.049  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.036   2.106   1.148  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.508   2.151   1.453  1.00  0.00           C  
HETATM   21  C21 UNL     1       6.177   1.217   0.486  1.00  0.00           C  
HETATM   22  C22 UNL     1       7.658   1.185   0.697  1.00  0.00           C  
HETATM   23  O1  UNL     1       8.149   1.877   1.612  1.00  0.00           O  
HETATM   24  N1  UNL     1       8.506   0.395  -0.110  1.00  0.00           N  
HETATM   25  C23 UNL     1       9.942   0.301   0.019  1.00  0.00           C  
HETATM   26  C24 UNL     1      10.430  -0.394  -1.208  1.00  0.00           C  
HETATM   27  C25 UNL     1       9.244  -0.697  -2.066  1.00  0.00           C  
HETATM   28  C26 UNL     1       8.047  -0.443  -1.200  1.00  0.00           C  
HETATM   29  C27 UNL     1       7.508  -1.726  -0.670  1.00  0.00           C  
HETATM   30  O2  UNL     1       7.070  -2.558  -1.502  1.00  0.00           O  
HETATM   31  O3  UNL     1       7.498  -1.977   0.703  1.00  0.00           O  
HETATM   32  H1  UNL     1     -11.800   0.539  -2.606  1.00  0.00           H  
HETATM   33  H2  UNL     1     -12.282  -0.064  -1.006  1.00  0.00           H  
HETATM   34  H3  UNL     1     -12.062   1.741  -1.279  1.00  0.00           H  
HETATM   35  H4  UNL     1      -9.812   1.668  -1.182  1.00  0.00           H  
HETATM   36  H5  UNL     1     -10.213   0.339  -0.058  1.00  0.00           H  
HETATM   37  H6  UNL     1      -9.520  -0.031  -3.080  1.00  0.00           H  
HETATM   38  H7  UNL     1      -8.403  -1.980  -2.395  1.00  0.00           H  
HETATM   39  H8  UNL     1      -9.452  -1.320   0.503  1.00  0.00           H  
HETATM   40  H9  UNL     1      -9.205  -2.907  -0.243  1.00  0.00           H  
HETATM   41  H10 UNL     1      -6.756  -2.513  -0.458  1.00  0.00           H  
HETATM   42  H11 UNL     1      -7.508  -0.525   1.732  1.00  0.00           H  
HETATM   43  H12 UNL     1      -4.976  -1.934   0.779  1.00  0.00           H  
HETATM   44  H13 UNL     1      -5.321  -1.542   2.528  1.00  0.00           H  
HETATM   45  H14 UNL     1      -5.294   0.919   1.997  1.00  0.00           H  
HETATM   46  H15 UNL     1      -3.581   1.576   0.578  1.00  0.00           H  
HETATM   47  H16 UNL     1      -3.307  -0.092  -1.454  1.00  0.00           H  
HETATM   48  H17 UNL     1      -3.503  -1.458  -0.331  1.00  0.00           H  
HETATM   49  H18 UNL     1      -1.543  -0.702   1.026  1.00  0.00           H  
HETATM   50  H19 UNL     1      -1.153   0.318  -1.842  1.00  0.00           H  
HETATM   51  H20 UNL     1       1.068   0.991  -0.748  1.00  0.00           H  
HETATM   52  H21 UNL     1       1.075  -0.708  -1.198  1.00  0.00           H  
HETATM   53  H22 UNL     1       0.398  -1.425   1.183  1.00  0.00           H  
HETATM   54  H23 UNL     1       1.290  -0.082   2.864  1.00  0.00           H  
HETATM   55  H24 UNL     1       1.120   2.335   2.415  1.00  0.00           H  
HETATM   56  H25 UNL     1       1.533   2.139   0.700  1.00  0.00           H  
HETATM   57  H26 UNL     1       3.421   1.429   3.045  1.00  0.00           H  
HETATM   58  H27 UNL     1       3.684   2.398   0.143  1.00  0.00           H  
HETATM   59  H28 UNL     1       5.631   1.831   2.504  1.00  0.00           H  
HETATM   60  H29 UNL     1       5.823   3.201   1.343  1.00  0.00           H  
HETATM   61  H30 UNL     1       5.809   0.194   0.715  1.00  0.00           H  
HETATM   62  H31 UNL     1       5.957   1.553  -0.533  1.00  0.00           H  
HETATM   63  H32 UNL     1      10.358   1.333   0.144  1.00  0.00           H  
HETATM   64  H33 UNL     1      10.203  -0.238   0.960  1.00  0.00           H  
HETATM   65  H34 UNL     1      10.984  -1.314  -0.909  1.00  0.00           H  
HETATM   66  H35 UNL     1      11.133   0.308  -1.730  1.00  0.00           H  
HETATM   67  H36 UNL     1       9.239   0.024  -2.916  1.00  0.00           H  
HETATM   68  H37 UNL     1       9.225  -1.748  -2.417  1.00  0.00           H  
HETATM   69  H38 UNL     1       7.226   0.044  -1.770  1.00  0.00           H  
HETATM   70  H39 UNL     1       6.900  -2.645   1.134  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4    4   37
CONECT    4    5   38
CONECT    5    6   39   40
CONECT    6    7    7   41
CONECT    7    8   42
CONECT    8    9   43   44
CONECT    9   10   10   45
CONECT   10   11   46
CONECT   11   12   47   48
CONECT   12   13   13   49
CONECT   13   14   50
CONECT   14   15   51   52
CONECT   15   16   16   53
CONECT   16   17   54
CONECT   17   18   55   56
CONECT   18   19   19   57
CONECT   19   20   58
CONECT   20   21   59   60
CONECT   21   22   61   62
CONECT   22   23   23   24
CONECT   24   25   28
CONECT   25   26   63   64
CONECT   26   27   65   66
CONECT   27   28   67   68
CONECT   28   29   69
CONECT   29   30   30   31
CONECT   31   70
END

HMDB0242020
     RDKit          3D
N-Docosahexaenoyl Proline
 70 70  0  0  0  0  0  0  0  0999 V2000
  -11.7181    0.7210   -1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2492    0.6389   -1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5342   -0.2784   -1.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9172   -1.3561   -1.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8368   -1.8326   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3835   -1.8705    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8940   -1.1627    1.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4300   -1.2224    1.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8485    0.1311    1.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8930    0.4991    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2082   -0.4095   -0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -0.3805    0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8564    0.0172   -0.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5794    0.0574   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208   -0.4050    0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130    0.3325    1.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949    1.7041    1.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1539    1.7265    2.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0357    2.1060    1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5076    2.1514    1.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1766    1.2174    0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6579    1.1851    0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1489    1.8767    1.6124 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5059    0.3953   -0.1103 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9415    0.3015    0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4300   -0.3945   -1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2438   -0.6975   -2.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0474   -0.4429   -1.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5079   -1.7260   -0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0697   -2.5584   -1.5024 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4980   -1.9766    0.7027 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7998    0.5389   -2.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2824   -0.0638   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0624    1.7411   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8124    1.6679   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2129    0.3389   -0.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5198   -0.0307   -3.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4028   -1.9797   -2.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4521   -1.3196    0.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2049   -2.9075   -0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7559   -2.5133   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5078   -0.5248    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9762   -1.9342    0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3206   -1.5417    2.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2942    0.9185    1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815    1.5762    0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3066   -0.0918   -1.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5035   -1.4576   -0.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428   -0.7021    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1531    0.3181   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    0.9906   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -0.7076   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3977   -1.4253    1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2897   -0.0821    2.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1202    2.3354    2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5325    2.1395    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205    1.4286    3.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6838    2.3983    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311    1.8309    2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8229    3.2009    1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8094    0.1936    0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9568    1.5534   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3578    1.3332    0.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2033   -0.2381    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9838   -1.3145   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1328    0.3080   -1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2387    0.0243   -2.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2246   -1.7484   -2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2262    0.0441   -1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9003   -2.6455    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 28 24  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 25 63  1  0
 25 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 31 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(Docosa-4,7,10,13,16,19-hexaenoyl)pyrrolidine-2-carboxylate	Generator

Chemical Formula

C₂₇H₃₉NO₃

Average Molecular Weight

425.613

Monoisotopic Molecular Weight

425.29299412

IUPAC Name

1-(docosa-4,7,10,13,16,19-hexaenoyl)pyrrolidine-2-carboxylic acid

Traditional Name

1-(docosa-4,7,10,13,16,19-hexaenoyl)pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)N1CCCC1C(O)=O

InChI Identifier

InChI=1S/C27H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23-26(29)28-24-21-22-25(28)27(30)31/h3-4,6-7,9-10,12-13,15-16,18-19,25H,2,5,8,11,14,17,20-24H2,1H3,(H,30,31)

InChI Key

PMYCLCQAGGZCSW-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	6.62	ALOGPS
logP	6.49	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.06	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	136.38 m³·mol⁻¹	ChemAxon
Polarizability	49.97 Å³	ChemAxon
Number of Rings	1	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]+	202.452	30932474
DeepCCS	[M-H]-	200.094	30932474
DeepCCS	[M-2H]-	232.98	30932474
DeepCCS	[M+Na]+	208.545	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Docosahexaenoyl Proline	CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)N1CCCC1C(O)=O	4667.0	Standard polar	33892256
N-Docosahexaenoyl Proline	CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)N1CCCC1C(O)=O	3098.1	Standard non polar	33892256
N-Docosahexaenoyl Proline	CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)N1CCCC1C(O)=O	3404.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Docosahexaenoyl Proline GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q9-2339000000-22fd465a9b811527bd40	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Docosahexaenoyl Proline 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-Docosahexaenoyl Proline 10V, Negative-QTOF	splash10-00di-0200900000-02f1b63de93ca9d4a6ca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Docosahexaenoyl Proline 20V, Negative-QTOF	splash10-03di-4900000000-13a25f6609f8c18f1848	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Docosahexaenoyl Proline 40V, Negative-QTOF	splash10-03dj-9500000000-2c883f67b1a3741e6d81	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Docosahexaenoyl Proline 10V, Positive-QTOF	splash10-014i-5901300000-217d2e66f8dabafced7b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Docosahexaenoyl Proline 20V, Positive-QTOF	splash10-01ba-9603100000-4cf67cf08f2800931e6f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Docosahexaenoyl Proline 40V, Positive-QTOF	splash10-00xr-9200000000-990d2627c6c895b03d9c	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for N-Docosahexaenoyl Proline (HMDB0242020)

MOL for HMDB0242020 (N-Docosahexaenoyl Proline)

3D MOL for HMDB0242020 (N-Docosahexaenoyl Proline)

3D SDF for HMDB0242020 (N-Docosahexaenoyl Proline)

3D-SDF for HMDB0242020 (N-Docosahexaenoyl Proline)

PDB for HMDB0242020 (N-Docosahexaenoyl Proline)

3D PDB for HMDB0242020 (N-Docosahexaenoyl Proline)

SMILES for HMDB0242020 (N-Docosahexaenoyl Proline)

INCHI for HMDB0242020 (N-Docosahexaenoyl Proline)

Structure for HMDB0242020 (N-Docosahexaenoyl Proline)

3D Structure for HMDB0242020 (N-Docosahexaenoyl Proline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra