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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-07-27 20:06:36 UTC

Update Date

2021-10-01 16:48:37 UTC

HMDB ID

HMDB0241915

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Nervonoyl Valine

Description

N-nervonoyl valine, also known as beta-citrylglutamate or b-citrylglutamic acid belongs to the class of compounds known as N-acylamides. These are molecules characterized by a fatty acyl group linked to a primary amine by an amide bond. More specifically, it is a Nervonic acid amide of Valine. It is believed that there are more than 800 types of N-acylamides in the human body. N-acylamides fall into several categories: amino acid conjugates (e.g., those acyl amides conjugated with amino acids), neurotransmitter conjugates (e.g., those acylamides conjugated with neurotransmitters), ethanolamine conjugates (e.g., those acylamides conjugated to ethanolamine), and taurine conjugates (e.g., those acyamides conjugated to taurine). N-Nervonoyl Valine is an amino acid conjugate. N-acylamides can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain N-acylamides; 2) medium-chain N-acylamides; 3) long-chain N-acylamides; and 4) very long-chain N-acylamides; 5) hydroxy N-acylamides; 6) branched chain N-acylamides; 7) unsaturated N-acylamides; 8) dicarboxylic N-acylamides and 9) miscellaneous N-acylamides. N-Nervonoyl Valine 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

HMDB0241915
     RDKit          3D
N-Nervonoyl Valine
 88 87  0  0  0  0  0  0  0  0999 V2000
   11.6827   -0.9408   -3.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2410   -1.3619   -2.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8613   -0.9411   -1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4250   -1.3667   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377   -0.9895    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9732    0.4767    0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1611    1.3212   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6775    1.0841   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0616    1.2976    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3915    0.3742    1.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1355   -0.9851    1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471   -1.2911    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0026   -1.1107    2.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -1.4565    2.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1646   -0.5704    1.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6675   -0.8967    1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -0.7284    2.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    0.5341    3.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777    1.7741    2.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720    2.6136    1.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4094    2.1522    0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153    1.8489    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950    1.3883   -0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9333    1.1029   -0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4662    1.2147    0.4763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7405    0.7058   -1.7415 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1540    0.4216   -1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8967    1.3308   -2.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2882    2.1703   -3.2095 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2690    1.2739   -2.5593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4498   -1.0288   -1.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6657   -1.9198   -1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9387   -1.2425   -1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6845    0.1578   -3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1399   -1.4608   -3.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2267   -1.0697   -2.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1603   -2.4271   -2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5655   -0.7799   -3.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5659   -1.4620   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0420    0.1274   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3769   -2.4568   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8277   -0.8504   -1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9409   -1.4136    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6166   -1.5273    0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5768    0.6296    1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0024    0.8948    0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4715    1.2554   -1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3420    2.3894   -0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3654    0.1754   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    1.9241   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1457    2.2947    1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9790    0.6492    2.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116   -1.2447    0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5833   -1.6842    1.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224   -2.2986    0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454   -0.5569    0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349   -0.0333    2.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701   -1.7490    3.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259   -2.4991    1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606   -1.3192    3.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0622    0.4956    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -0.7132    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -2.0547    0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0587   -0.4945    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -1.5220    3.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4231   -1.1556    2.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6993    0.2794    4.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260    0.7605    3.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1277    1.6608    3.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7544    2.4756    3.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8187    3.0492    1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504    3.5823    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3794    3.0551   -0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9413    1.3412   -0.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4453    2.7086    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0102    1.0106    1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0130    0.4255   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3019    2.1681   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3063    0.6118   -2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4175    0.5720   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7982    1.6223   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1242   -1.2349   -2.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5911   -1.8878   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8986   -1.7007    0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0273   -2.9626   -1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5485   -1.0317   -2.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3242   -0.6588   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0907   -2.3226   -1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 27 31  1  0
 31 32  1  0
 31 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 18 67  1  0
 18 68  1  0
 19 69  1  0
 19 70  1  0
 20 71  1  0
 20 72  1  0
 21 73  1  0
 21 74  1  0
 22 75  1  0
 22 76  1  0
 23 77  1  0
 23 78  1  0
 26 79  1  0
 27 80  1  0
 30 81  1  0
 31 82  1  0
 32 83  1  0
 32 84  1  0
 32 85  1  0
 33 86  1  0
 33 87  1  0
 33 88  1  0
M  END


  Mrv1652308272120412D          

 23 22  0  0  1  0            999 V2000
    2.4750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    3.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.0934    3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    5.1118    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.5211    5.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    5.9368    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  1  0  0  0  0
  5 12  1  1  0  0  0
 12 10  2  0  0  0  0
 13  6  2  0  0  0  0
 14  6  1  0  0  0  0
 15  7  2  0  0  0  0
 16  7  1  0  0  0  0
 17  8  2  0  0  0  0
 18  8  1  0  0  0  0
 19  9  2  0  0  0  0
 20  9  1  0  0  0  0
 10 21  1  4  0  0  0
 22 11  1  0  0  0  0
  5 23  1  1  0  0  0
M  CHG  4  14  -1  16  -1  18  -1  20  -1
M  END
> <DATABASE_ID>
HMDB0241915

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](CCC([O-])=O)(N=C(O)C(O)(CC([O-])=O)CC([O-])=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H15NO10/c13-6(14)2-1-5(9(19)20)12-10(21)11(22,3-7(15)16)4-8(17)18/h5,22H,1-4H2,(H,12,21)(H,13,14)(H,15,16)(H,17,18)(H,19,20)/p-4/t5-/m0/s1

> <INCHI_KEY>
GAQNUGISBQJMKO-YFKPBYRVSA-J

> <FORMULA>
C11H11NO10

> <MOLECULAR_WEIGHT>
317.208

> <EXACT_MASS>
317.040489878

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.998184312610093

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[3-carboxy-2-(carboxymethyl)-1,2-dihydroxypropylidene]amino}pentanedioate

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-1.392753027333334

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.170348807171705

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.556821018931162

> <JCHEM_PKA_STRONGEST_BASIC>
-0.25305809665978296

> <JCHEM_POLAR_SURFACE_AREA>
213.33999999999997

> <JCHEM_REFRACTIVITY>
107.58180000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[3-carboxy-2-(carboxymethyl)-1,2-dihydroxypropylidene]amino}pentanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241915
     RDKit          3D
N-Nervonoyl Valine
 88 87  0  0  0  0  0  0  0  0999 V2000
   11.6827   -0.9408   -3.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2410   -1.3619   -2.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8613   -0.9411   -1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4250   -1.3667   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377   -0.9895    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9732    0.4767    0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1611    1.3212   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6775    1.0841   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0616    1.2976    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3915    0.3742    1.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1355   -0.9851    1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471   -1.2911    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0026   -1.1107    2.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -1.4565    2.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1646   -0.5704    1.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6675   -0.8967    1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -0.7284    2.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    0.5341    3.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777    1.7741    2.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720    2.6136    1.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4094    2.1522    0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153    1.8489    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950    1.3883   -0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9333    1.1029   -0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4662    1.2147    0.4763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7405    0.7058   -1.7415 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1540    0.4216   -1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8967    1.3308   -2.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2882    2.1703   -3.2095 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2690    1.2739   -2.5593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4498   -1.0288   -1.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6657   -1.9198   -1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9387   -1.2425   -1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6845    0.1578   -3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1399   -1.4608   -3.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2267   -1.0697   -2.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1603   -2.4271   -2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5655   -0.7799   -3.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5659   -1.4620   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0420    0.1274   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3769   -2.4568   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8277   -0.8504   -1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9409   -1.4136    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6166   -1.5273    0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5768    0.6296    1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0024    0.8948    0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4715    1.2554   -1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3420    2.3894   -0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3654    0.1754   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    1.9241   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1457    2.2947    1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9790    0.6492    2.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116   -1.2447    0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5833   -1.6842    1.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224   -2.2986    0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454   -0.5569    0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349   -0.0333    2.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701   -1.7490    3.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259   -2.4991    1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606   -1.3192    3.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0622    0.4956    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -0.7132    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -2.0547    0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0587   -0.4945    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -1.5220    3.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4231   -1.1556    2.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6993    0.2794    4.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260    0.7605    3.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1277    1.6608    3.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7544    2.4756    3.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8187    3.0492    1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504    3.5823    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3794    3.0551   -0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9413    1.3412   -0.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4453    2.7086    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0102    1.0106    1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0130    0.4255   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3019    2.1681   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3063    0.6118   -2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4175    0.5720   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7982    1.6223   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1242   -1.2349   -2.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5911   -1.8878   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8986   -1.7007    0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0273   -2.9626   -1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5485   -1.0317   -2.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3242   -0.6588   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0907   -2.3226   -1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 27 31  1  0
 31 32  1  0
 31 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 18 67  1  0
 18 68  1  0
 19 69  1  0
 19 70  1  0
 20 71  1  0
 20 72  1  0
 21 73  1  0
 21 74  1  0
 22 75  1  0
 22 76  1  0
 23 77  1  0
 23 78  1  0
 26 79  1  0
 27 80  1  0
 30 81  1  0
 31 82  1  0
 32 83  1  0
 32 84  1  0
 32 85  1  0
 33 86  1  0
 33 87  1  0
 33 88  1  0
M  END

HEADER    PROTEIN                                 27-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-AUG-21         0                                  
HETATM    1  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.574   7.232   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.906   8.772   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.907   8.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.906  10.312   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.470   6.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.240   8.002   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.930   6.668   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.540   5.335   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0      13.241   7.232   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      11.907   9.542   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0       6.573  11.082   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.240  11.082   0.000  0.00  0.00           O-1
HETATM   19  O   UNK     0       8.470   4.001   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0       9.240   5.335   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.010   9.336   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       5.390   4.001   0.000  0.00  0.00           H+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    7   11                                                       
CONECT    4    8   11                                                       
CONECT    5    1    9   12   23                                             
CONECT    6    2   13   14                                                  
CONECT    7    3   15   16                                                  
CONECT    8    4   17   18                                                  
CONECT    9    5   19   20                                                  
CONECT   10   11   12   21                                                  
CONECT   11    3    4   10   22                                             
CONECT   12    5   10                                                       
CONECT   13    6                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20    9                                                            
CONECT   21   10                                                            
CONECT   22   11                                                            
CONECT   23    5                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0241915
HETATM    1  C1  UNL     1      11.683  -0.941  -3.041  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.241  -1.362  -2.805  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.861  -0.941  -1.396  1.00  0.00           C  
HETATM    4  C4  UNL     1       8.425  -1.367  -1.173  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.938  -0.990   0.207  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.973   0.477   0.458  1.00  0.00           C  
HETATM    7  C7  UNL     1       7.161   1.321  -0.440  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.677   1.084  -0.437  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.062   1.298   0.872  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.392   0.374   1.512  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.135  -0.985   1.072  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.647  -1.291   0.959  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.003  -1.111   2.286  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.540  -1.457   2.235  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.165  -0.570   1.259  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.667  -0.897   1.184  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.340  -0.728   2.484  1.00  0.00           C  
HETATM   18  C18 UNL     1      -2.336   0.534   3.201  1.00  0.00           C  
HETATM   19  C19 UNL     1      -2.978   1.774   2.883  1.00  0.00           C  
HETATM   20  C20 UNL     1      -2.872   2.614   1.705  1.00  0.00           C  
HETATM   21  C21 UNL     1      -3.409   2.152   0.398  1.00  0.00           C  
HETATM   22  C22 UNL     1      -4.915   1.849   0.518  1.00  0.00           C  
HETATM   23  C23 UNL     1      -5.495   1.388  -0.804  1.00  0.00           C  
HETATM   24  C24 UNL     1      -6.933   1.103  -0.651  1.00  0.00           C  
HETATM   25  O1  UNL     1      -7.466   1.215   0.476  1.00  0.00           O  
HETATM   26  N1  UNL     1      -7.741   0.706  -1.741  1.00  0.00           N  
HETATM   27  C25 UNL     1      -9.154   0.422  -1.613  1.00  0.00           C  
HETATM   28  C26 UNL     1      -9.897   1.331  -2.498  1.00  0.00           C  
HETATM   29  O2  UNL     1      -9.288   2.170  -3.210  1.00  0.00           O  
HETATM   30  O3  UNL     1     -11.269   1.274  -2.559  1.00  0.00           O  
HETATM   31  C27 UNL     1      -9.450  -1.029  -1.962  1.00  0.00           C  
HETATM   32  C28 UNL     1      -8.666  -1.920  -1.019  1.00  0.00           C  
HETATM   33  C29 UNL     1     -10.939  -1.242  -1.753  1.00  0.00           C  
HETATM   34  H1  UNL     1      11.684   0.158  -3.288  1.00  0.00           H  
HETATM   35  H2  UNL     1      12.140  -1.461  -3.903  1.00  0.00           H  
HETATM   36  H3  UNL     1      12.227  -1.070  -2.105  1.00  0.00           H  
HETATM   37  H4  UNL     1      10.160  -2.427  -2.985  1.00  0.00           H  
HETATM   38  H5  UNL     1       9.565  -0.780  -3.498  1.00  0.00           H  
HETATM   39  H6  UNL     1      10.566  -1.462  -0.688  1.00  0.00           H  
HETATM   40  H7  UNL     1      10.042   0.127  -1.313  1.00  0.00           H  
HETATM   41  H8  UNL     1       8.377  -2.457  -1.341  1.00  0.00           H  
HETATM   42  H9  UNL     1       7.828  -0.850  -1.953  1.00  0.00           H  
HETATM   43  H10 UNL     1       6.941  -1.414   0.382  1.00  0.00           H  
HETATM   44  H11 UNL     1       8.617  -1.527   0.925  1.00  0.00           H  
HETATM   45  H12 UNL     1       7.577   0.630   1.506  1.00  0.00           H  
HETATM   46  H13 UNL     1       9.002   0.895   0.504  1.00  0.00           H  
HETATM   47  H14 UNL     1       7.472   1.255  -1.518  1.00  0.00           H  
HETATM   48  H15 UNL     1       7.342   2.389  -0.171  1.00  0.00           H  
HETATM   49  H16 UNL     1       5.365   0.175  -0.953  1.00  0.00           H  
HETATM   50  H17 UNL     1       5.263   1.924  -1.098  1.00  0.00           H  
HETATM   51  H18 UNL     1       5.146   2.295   1.373  1.00  0.00           H  
HETATM   52  H19 UNL     1       3.979   0.649   2.510  1.00  0.00           H  
HETATM   53  H20 UNL     1       4.612  -1.245   0.120  1.00  0.00           H  
HETATM   54  H21 UNL     1       4.583  -1.684   1.826  1.00  0.00           H  
HETATM   55  H22 UNL     1       2.522  -2.299   0.542  1.00  0.00           H  
HETATM   56  H23 UNL     1       2.245  -0.557   0.223  1.00  0.00           H  
HETATM   57  H24 UNL     1       2.135  -0.033   2.594  1.00  0.00           H  
HETATM   58  H25 UNL     1       2.470  -1.749   3.063  1.00  0.00           H  
HETATM   59  H26 UNL     1       0.426  -2.499   1.878  1.00  0.00           H  
HETATM   60  H27 UNL     1       0.061  -1.319   3.236  1.00  0.00           H  
HETATM   61  H28 UNL     1      -0.062   0.496   1.473  1.00  0.00           H  
HETATM   62  H29 UNL     1       0.246  -0.713   0.219  1.00  0.00           H  
HETATM   63  H30 UNL     1      -1.617  -2.055   0.998  1.00  0.00           H  
HETATM   64  H31 UNL     1      -2.059  -0.494   0.287  1.00  0.00           H  
HETATM   65  H32 UNL     1      -1.896  -1.522   3.179  1.00  0.00           H  
HETATM   66  H33 UNL     1      -3.423  -1.156   2.415  1.00  0.00           H  
HETATM   67  H34 UNL     1      -2.699   0.279   4.299  1.00  0.00           H  
HETATM   68  H35 UNL     1      -1.226   0.761   3.494  1.00  0.00           H  
HETATM   69  H36 UNL     1      -4.128   1.661   3.079  1.00  0.00           H  
HETATM   70  H37 UNL     1      -2.754   2.476   3.804  1.00  0.00           H  
HETATM   71  H38 UNL     1      -1.819   3.049   1.566  1.00  0.00           H  
HETATM   72  H39 UNL     1      -3.450   3.582   1.933  1.00  0.00           H  
HETATM   73  H40 UNL     1      -3.379   3.055  -0.331  1.00  0.00           H  
HETATM   74  H41 UNL     1      -2.941   1.341  -0.116  1.00  0.00           H  
HETATM   75  H42 UNL     1      -5.445   2.709   0.923  1.00  0.00           H  
HETATM   76  H43 UNL     1      -5.010   1.011   1.223  1.00  0.00           H  
HETATM   77  H44 UNL     1      -5.013   0.426  -1.109  1.00  0.00           H  
HETATM   78  H45 UNL     1      -5.302   2.168  -1.591  1.00  0.00           H  
HETATM   79  H46 UNL     1      -7.306   0.612  -2.672  1.00  0.00           H  
HETATM   80  H47 UNL     1      -9.417   0.572  -0.536  1.00  0.00           H  
HETATM   81  H48 UNL     1     -11.798   1.622  -1.762  1.00  0.00           H  
HETATM   82  H49 UNL     1      -9.124  -1.235  -2.990  1.00  0.00           H  
HETATM   83  H50 UNL     1      -7.591  -1.888  -1.219  1.00  0.00           H  
HETATM   84  H51 UNL     1      -8.899  -1.701   0.044  1.00  0.00           H  
HETATM   85  H52 UNL     1      -9.027  -2.963  -1.189  1.00  0.00           H  
HETATM   86  H53 UNL     1     -11.549  -1.032  -2.634  1.00  0.00           H  
HETATM   87  H54 UNL     1     -11.324  -0.659  -0.890  1.00  0.00           H  
HETATM   88  H55 UNL     1     -11.091  -2.323  -1.480  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   37   38
CONECT    3    4   39   40
CONECT    4    5   41   42
CONECT    5    6   43   44
CONECT    6    7   45   46
CONECT    7    8   47   48
CONECT    8    9   49   50
CONECT    9   10   10   51
CONECT   10   11   52
CONECT   11   12   53   54
CONECT   12   13   55   56
CONECT   13   14   57   58
CONECT   14   15   59   60
CONECT   15   16   61   62
CONECT   16   17   63   64
CONECT   17   18   65   66
CONECT   18   19   67   68
CONECT   19   20   69   70
CONECT   20   21   71   72
CONECT   21   22   73   74
CONECT   22   23   75   76
CONECT   23   24   77   78
CONECT   24   25   25   26
CONECT   26   27   79
CONECT   27   28   31   80
CONECT   28   29   29   30
CONECT   30   81
CONECT   31   32   33   82
CONECT   32   83   84   85
CONECT   33   86   87   88
END

HMDB0241915
     RDKit          3D
N-Nervonoyl Valine
 88 87  0  0  0  0  0  0  0  0999 V2000
   11.6827   -0.9408   -3.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2410   -1.3619   -2.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8613   -0.9411   -1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4250   -1.3667   -1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9377   -0.9895    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9732    0.4767    0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1611    1.3212   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6775    1.0841   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0616    1.2976    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3915    0.3742    1.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1355   -0.9851    1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471   -1.2911    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0026   -1.1107    2.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -1.4565    2.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1646   -0.5704    1.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6675   -0.8967    1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -0.7284    2.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    0.5341    3.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777    1.7741    2.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720    2.6136    1.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4094    2.1522    0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153    1.8489    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950    1.3883   -0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9333    1.1029   -0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4662    1.2147    0.4763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7405    0.7058   -1.7415 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1540    0.4216   -1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8967    1.3308   -2.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2882    2.1703   -3.2095 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2690    1.2739   -2.5593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4498   -1.0288   -1.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6657   -1.9198   -1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9387   -1.2425   -1.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6845    0.1578   -3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1399   -1.4608   -3.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2267   -1.0697   -2.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1603   -2.4271   -2.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5655   -0.7799   -3.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5659   -1.4620   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0420    0.1274   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3769   -2.4568   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8277   -0.8504   -1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9409   -1.4136    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6166   -1.5273    0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5768    0.6296    1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0024    0.8948    0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4715    1.2554   -1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3420    2.3894   -0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3654    0.1754   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    1.9241   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1457    2.2947    1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9790    0.6492    2.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116   -1.2447    0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5833   -1.6842    1.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224   -2.2986    0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454   -0.5569    0.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349   -0.0333    2.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4701   -1.7490    3.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259   -2.4991    1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606   -1.3192    3.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0622    0.4956    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -0.7132    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -2.0547    0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0587   -0.4945    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -1.5220    3.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4231   -1.1556    2.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6993    0.2794    4.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260    0.7605    3.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1277    1.6608    3.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7544    2.4756    3.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8187    3.0492    1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504    3.5823    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3794    3.0551   -0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9413    1.3412   -0.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4453    2.7086    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0102    1.0106    1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0130    0.4255   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3019    2.1681   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3063    0.6118   -2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4175    0.5720   -0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7982    1.6223   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1242   -1.2349   -2.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5911   -1.8878   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8986   -1.7007    0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0273   -2.9626   -1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5485   -1.0317   -2.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3242   -0.6588   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0907   -2.3226   -1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 27 31  1  0
 31 32  1  0
 31 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 14 60  1  0
 15 61  1  0
 15 62  1  0
 16 63  1  0
 16 64  1  0
 17 65  1  0
 17 66  1  0
 18 67  1  0
 18 68  1  0
 19 69  1  0
 19 70  1  0
 20 71  1  0
 20 72  1  0
 21 73  1  0
 21 74  1  0
 22 75  1  0
 22 76  1  0
 23 77  1  0
 23 78  1  0
 26 79  1  0
 27 80  1  0
 30 81  1  0
 31 82  1  0
 32 83  1  0
 32 84  1  0
 32 85  1  0
 33 86  1  0
 33 87  1  0
 33 88  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
beta-Citrylglutamate	ChEBI
b-Citrylglutamate	Generator
b-Citrylglutamic acid	Generator
beta-Citrylglutamic acid	Generator
Β-citrylglutamate	Generator
Β-citrylglutamic acid	Generator
b-Citrylglutamate(4-)	Generator
b-Citrylglutamic acid(4-)	Generator
beta-Citrylglutamic acid(4-)	Generator
Β-citrylglutamate(4-)	Generator
Β-citrylglutamic acid(4-)	Generator
beta-Citryl-L-glutamate	MeSH
beta-Citrylglutamic acid, (S)-isomer	MeSH
beta-Citryl-L-glutamic acid	MeSH

Chemical Formula

C₂₉H₅₅NO₃

Average Molecular Weight

465.763

Monoisotopic Molecular Weight

465.418194635

IUPAC Name

(2S)-2-{[3-carboxy-2-(carboxymethyl)-1,2-dihydroxypropylidene]amino}pentanedioate

Traditional Name

(2S)-2-{[3-carboxy-2-(carboxymethyl)-1,2-dihydroxypropylidene]amino}pentanedioate

CAS Registry Number

Not Available

SMILES

CCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(C(C)C)C(O)=O

InChI Identifier

InChI=1S/C29H55NO3/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-27(31)30-28(26(2)3)29(32)33/h11-12,26,28H,4-10,13-25H2,1-3H3,(H,30,31)(H,32,33)

InChI Key

XPTYCUVCGKYPRD-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Tetracarboxylic acid or derivatives
N-acyl-l-alpha-amino acid
Fatty amide
N-acyl-amine
Fatty acyl
Tertiary alcohol
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-amino-acid anion (CHEBI:76942 )
tetracarboxylic acid anion (CHEBI:76942 )

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	-0.64	ALOGPS
logP	-1.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.56	ChemAxon
pKa (Strongest Basic)	-0.25	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	213.34 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	107.58 m³·mol⁻¹	ChemAxon
Polarizability	26 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]+	226.583	30932474
DeepCCS	[M-H]-	224.032	30932474
DeepCCS	[M-2H]-	257.235	30932474
DeepCCS	[M+Na]+	233.505	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Nervonoyl Valine	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(C(C)C)C(O)=O	3940.9	Standard polar	33892256
N-Nervonoyl Valine	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(C(C)C)C(O)=O	3199.0	Standard non polar	33892256
N-Nervonoyl Valine	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)NC(C(C)C)C(O)=O	3410.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Nervonoyl Valine,1TMS,isomer #2	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O)C(C)C)[Si](C)(C)C	3494.7	Semi standard non polar	33892256
N-Nervonoyl Valine,1TMS,isomer #2	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O)C(C)C)[Si](C)(C)C	3299.2	Standard non polar	33892256
N-Nervonoyl Valine,1TMS,isomer #2	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O)C(C)C)[Si](C)(C)C	3756.1	Standard polar	33892256
N-Nervonoyl Valine,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)C)[Si](C)(C)C	3471.2	Semi standard non polar	33892256
N-Nervonoyl Valine,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)C)[Si](C)(C)C	3317.7	Standard non polar	33892256
N-Nervonoyl Valine,2TMS,isomer #1	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)C)[Si](C)(C)C	3358.4	Standard polar	33892256
N-Nervonoyl Valine,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)C)[Si](C)(C)C(C)(C)C	3956.0	Semi standard non polar	33892256
N-Nervonoyl Valine,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)C)[Si](C)(C)C(C)(C)C	3605.9	Standard non polar	33892256
N-Nervonoyl Valine,2TBDMS,isomer #1	CCCCCCCCC=CCCCCCCCCCCCCCC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)C)[Si](C)(C)C(C)(C)C	3536.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nervonoyl Valine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g4j-6897500000-4f7bc3c9b509aa3c4521	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Nervonoyl Valine 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-Nervonoyl Valine 10V, Positive-QTOF	splash10-01b9-0101900000-ddcd1781998f34b7dd89	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nervonoyl Valine 20V, Positive-QTOF	splash10-00dj-3207900000-5dbc1833248d61cd9c8d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nervonoyl Valine 40V, Positive-QTOF	splash10-05u5-9500000000-36a40866b46482445b02	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nervonoyl Valine 10V, Negative-QTOF	splash10-01ot-0000900000-a36740f23ccef7d85542	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nervonoyl Valine 20V, Negative-QTOF	splash10-014i-1900300000-d686bc1ef567f21bdf89	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Nervonoyl Valine 40V, Negative-QTOF	splash10-00ke-9413000000-fbd573a568e57018da15	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

30786116

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

76942

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-Nervonoyl Valine (HMDB0241915)

MOL for HMDB0241915 (N-Nervonoyl Valine)

3D MOL for HMDB0241915 (N-Nervonoyl Valine)

3D SDF for HMDB0241915 (N-Nervonoyl Valine)

3D-SDF for HMDB0241915 (N-Nervonoyl Valine)

PDB for HMDB0241915 (N-Nervonoyl Valine)

3D PDB for HMDB0241915 (N-Nervonoyl Valine)

SMILES for HMDB0241915 (N-Nervonoyl Valine)

INCHI for HMDB0241915 (N-Nervonoyl Valine)

Structure for HMDB0241915 (N-Nervonoyl Valine)

3D Structure for HMDB0241915 (N-Nervonoyl Valine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra