NP-MRD: Showing NP-Card for Nervonic acid (NP0000682)

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Record Information

Version

1.0

Created at

2006-05-22 14:17:50 UTC

Updated at

2024-05-05 00:32:34 UTC

NP-MRD ID

NP0000682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nervonic acid

Description

Nervonic acid is a long chain unsaturated fatty acid that is enriched in sphingomyelin. It consists of choline, sphingosine, phosphoric acid, and fatty acid. Nervonic acid may enhance the brain functions and prevent demyelination (Chemical Land21). Research shows that there is negative relationship between nervonic acid and obesity-related risk factors (PMID: 16394593 ). Demyelination in adrenoleukodystrophy (ALD) is associated with an accumulation of very long chain saturated fatty acids stemming from a genetic defect in the peroxisomal beta oxidation system responsible for the chain shortening of these fatty acids. Sphingolipids from post mortem ALD brain have decreased levels of nervonic acid, 24:1(N-9), and increased levels of stearic acid, 18:0. (PMID: 8072429 ).

Structure

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


  Mrv1652311181918372D          

 26 25  0  0  0  0            999 V2000
 9994.7043 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4191 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1338 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8488 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5635 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2787 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9922 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7078 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5326 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2483 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9638 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6773 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3930 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.1085 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.8241 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.5397 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.2532 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9895 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.2746 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5598 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.8451 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.1283 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.4134 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.6985 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9838 9997.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.6985 9998.2571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END

HMDB0002368
     RDKit          3D
Nervonic acid
 72 71  0  0  0  0  0  0  0  0999 V2000
  -10.6475    0.4072    0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1068   -0.3621   -1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5990   -0.6089   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8495    0.6772   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3419    0.4955   -0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7333   -0.2318   -1.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003   -0.4977   -1.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7385   -1.4670   -0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9597   -1.2252    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -0.9590    1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878   -0.8765    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.4954    1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614    0.5315    0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2970   -0.4728    1.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -0.4184    1.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423   -0.6861   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3265   -0.6772   -0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389    0.5355   -0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843    1.2819    0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868    0.5331    1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5161   -0.0609    1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5179    0.9556    0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8137    0.2829    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6642   -0.6500   -0.8274 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5718   -0.7593   -1.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7916   -1.3870   -1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0026    1.4049   -0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5534   -0.1101    0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8825    0.5108    0.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5679   -1.3779   -1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3394    0.1319   -2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3205   -1.1081   -1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4809   -1.2642   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9848    1.3158   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1802    1.2554    0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0743    0.2748    0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9645    1.5899   -0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0131    0.3814   -2.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3214   -1.1866   -2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    0.5145   -1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0046   -0.8592   -2.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2798   -2.4757   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -1.7176   -1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9968   -1.3385    0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -0.7944    2.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0297   -1.5603    1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2718   -1.2051    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115    1.2952    0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0752    0.7628    2.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838    0.2910   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493    1.5611    1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2845   -0.3741    2.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799   -1.5091    1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700    0.4394    1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172   -1.3388    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636    0.0816   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092   -1.6577   -0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2564   -1.0452   -1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9408   -1.5242   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5647    1.2952   -1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0788    0.3910   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6553    1.8680    0.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2178    2.1057    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5791   -0.2718    1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3941    1.2611    2.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9386   -0.4738    2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3486   -0.9111    0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6649    1.6526    1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1517    1.6046   -0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2660   -0.2394    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5434    1.0978    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4491   -0.9188   -1.8054 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  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  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
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 18 60  1  0
 18 61  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 22 68  1  0
 22 69  1  0
 23 70  1  0
 23 71  1  0
 26 72  1  0
M  END


  Mrv1652311181918372D          

 26 25  0  0  0  0            999 V2000
 9994.7043 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4191 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1338 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8488 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5635 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2787 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9922 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7078 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5326 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2483 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9638 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6773 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3930 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.1085 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.8241 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.5397 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.2532 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9895 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.2746 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.5598 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.8451 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.1283 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.4134 9997.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.6985 9997.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9838 9997.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.6985 9998.2571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9-

> <INCHI_KEY>
GWHCXVQVJPWHRF-KTKRTIGZSA-N

> <FORMULA>
C24H46O2

> <MOLECULAR_WEIGHT>
366.6208

> <EXACT_MASS>
366.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
49.832609595717976

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(15Z)-tetracos-15-enoic acid

> <ALOGPS_LOGP>
9.45

> <JCHEM_LOGP>
9.451210441

> <ALOGPS_LOGS>
-7.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
115.00819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.77e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nervonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002368
     RDKit          3D
Nervonic acid
 72 71  0  0  0  0  0  0  0  0999 V2000
  -10.6475    0.4072    0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1068   -0.3621   -1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5990   -0.6089   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8495    0.6772   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3419    0.4955   -0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7333   -0.2318   -1.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003   -0.4977   -1.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7385   -1.4670   -0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9597   -1.2252    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -0.9590    1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878   -0.8765    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.4954    1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614    0.5315    0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2970   -0.4728    1.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -0.4184    1.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423   -0.6861   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3265   -0.6772   -0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389    0.5355   -0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843    1.2819    0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868    0.5331    1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5161   -0.0609    1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5179    0.9556    0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8137    0.2829    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6642   -0.6500   -0.8274 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5718   -0.7593   -1.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7916   -1.3870   -1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0026    1.4049   -0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5534   -0.1101    0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8825    0.5108    0.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5679   -1.3779   -1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3394    0.1319   -2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3205   -1.1081   -1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4809   -1.2642   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9848    1.3158   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1802    1.2554    0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0743    0.2748    0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9645    1.5899   -0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0131    0.3814   -2.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3214   -1.1866   -2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    0.5145   -1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0046   -0.8592   -2.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2798   -2.4757   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -1.7176   -1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9968   -1.3385    0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -0.7944    2.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0297   -1.5603    1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2718   -1.2051    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115    1.2952    0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0752    0.7628    2.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838    0.2910   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493    1.5611    1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2845   -0.3741    2.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799   -1.5091    1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700    0.4394    1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172   -1.3388    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636    0.0816   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092   -1.6577   -0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2564   -1.0452   -1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9408   -1.5242   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5647    1.2952   -1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0788    0.3910   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6553    1.8680    0.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2178    2.1057    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5791   -0.2718    1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3941    1.2611    2.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9386   -0.4738    2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3486   -0.9111    0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6649    1.6526    1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1517    1.6046   -0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2660   -0.2394    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5434    1.0978    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4491   -0.9188   -1.8054 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  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  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
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 18 60  1  0
 18 61  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 22 68  1  0
 22 69  1  0
 23 70  1  0
 23 71  1  0
 26 72  1  0
M  END

HEADER    PROTEIN                                 18-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-NOV-19         0                                  
HETATM    1  C   UNK     0    8656.7818661.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8658.1168661.872   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8659.4508661.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8660.7848661.872   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8662.1198661.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8663.4548661.872   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.7858661.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.1218661.872   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.6618661.872   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.9978661.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8670.3328661.872   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8671.6648661.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8673.0008661.872   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8674.3368661.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8675.6728661.872   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8677.0078661.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8678.3398661.872   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8655.4478661.872   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8654.1138661.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8652.7788661.872   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8651.4448661.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8650.1068661.872   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8648.7728661.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8647.4378661.872   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0    8646.1038661.104   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0    8647.4378663.413   0.000  0.00  0.00           O+0
CONECT    1    2   18                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    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                                                            
CONECT   18    1   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   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0002368
HETATM    1  C1  UNL     1     -10.648   0.407   0.074  1.00  0.00           C  
HETATM    2  C2  UNL     1     -10.107  -0.362  -1.113  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.599  -0.609  -0.957  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.849   0.677  -0.861  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.342   0.495  -0.691  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.733  -0.232  -1.821  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.300  -0.498  -1.806  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.738  -1.467  -0.853  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.960  -1.225   0.554  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.986  -0.959   1.403  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.588  -0.876   1.031  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.985   0.495   1.321  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.461   0.531   0.918  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.297  -0.473   1.637  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.779  -0.418   1.228  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.942  -0.686  -0.229  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.327  -0.677  -0.755  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.139   0.535  -0.777  1.00  0.00           C  
HETATM   19  C19 UNL     1       5.484   1.282   0.442  1.00  0.00           C  
HETATM   20  C20 UNL     1       6.187   0.533   1.519  1.00  0.00           C  
HETATM   21  C21 UNL     1       7.516  -0.061   1.118  1.00  0.00           C  
HETATM   22  C22 UNL     1       8.518   0.956   0.669  1.00  0.00           C  
HETATM   23  C23 UNL     1       9.814   0.283   0.298  1.00  0.00           C  
HETATM   24  C24 UNL     1       9.664  -0.650  -0.827  1.00  0.00           C  
HETATM   25  O1  UNL     1       8.572  -0.759  -1.418  1.00  0.00           O  
HETATM   26  O2  UNL     1      10.792  -1.387  -1.185  1.00  0.00           O  
HETATM   27  H1  UNL     1     -11.003   1.405  -0.300  1.00  0.00           H  
HETATM   28  H2  UNL     1     -11.553  -0.110   0.500  1.00  0.00           H  
HETATM   29  H3  UNL     1      -9.883   0.511   0.867  1.00  0.00           H  
HETATM   30  H4  UNL     1     -10.568  -1.378  -1.137  1.00  0.00           H  
HETATM   31  H5  UNL     1     -10.339   0.132  -2.069  1.00  0.00           H  
HETATM   32  H6  UNL     1      -8.320  -1.108  -1.931  1.00  0.00           H  
HETATM   33  H7  UNL     1      -8.481  -1.264  -0.088  1.00  0.00           H  
HETATM   34  H8  UNL     1      -7.985   1.316  -1.758  1.00  0.00           H  
HETATM   35  H9  UNL     1      -8.180   1.255   0.029  1.00  0.00           H  
HETATM   36  H10 UNL     1      -6.074   0.275   0.328  1.00  0.00           H  
HETATM   37  H11 UNL     1      -5.965   1.590  -0.814  1.00  0.00           H  
HETATM   38  H12 UNL     1      -6.013   0.381  -2.756  1.00  0.00           H  
HETATM   39  H13 UNL     1      -6.321  -1.187  -2.029  1.00  0.00           H  
HETATM   40  H14 UNL     1      -3.747   0.515  -1.680  1.00  0.00           H  
HETATM   41  H15 UNL     1      -4.005  -0.859  -2.850  1.00  0.00           H  
HETATM   42  H16 UNL     1      -4.280  -2.476  -1.119  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.661  -1.718  -1.097  1.00  0.00           H  
HETATM   44  H18 UNL     1      -4.997  -1.339   0.940  1.00  0.00           H  
HETATM   45  H19 UNL     1      -3.299  -0.794   2.462  1.00  0.00           H  
HETATM   46  H20 UNL     1      -1.030  -1.560   1.759  1.00  0.00           H  
HETATM   47  H21 UNL     1      -1.272  -1.205   0.057  1.00  0.00           H  
HETATM   48  H22 UNL     1      -1.511   1.295   0.755  1.00  0.00           H  
HETATM   49  H23 UNL     1      -1.075   0.763   2.394  1.00  0.00           H  
HETATM   50  H24 UNL     1       0.484   0.291  -0.185  1.00  0.00           H  
HETATM   51  H25 UNL     1       0.849   1.561   1.009  1.00  0.00           H  
HETATM   52  H26 UNL     1       1.285  -0.374   2.723  1.00  0.00           H  
HETATM   53  H27 UNL     1       0.980  -1.509   1.400  1.00  0.00           H  
HETATM   54  H28 UNL     1       3.270   0.439   1.647  1.00  0.00           H  
HETATM   55  H29 UNL     1       3.217  -1.339   1.748  1.00  0.00           H  
HETATM   56  H30 UNL     1       2.364   0.082  -0.850  1.00  0.00           H  
HETATM   57  H31 UNL     1       2.409  -1.658  -0.497  1.00  0.00           H  
HETATM   58  H32 UNL     1       4.256  -1.045  -1.846  1.00  0.00           H  
HETATM   59  H33 UNL     1       4.941  -1.524  -0.296  1.00  0.00           H  
HETATM   60  H34 UNL     1       4.565   1.295  -1.431  1.00  0.00           H  
HETATM   61  H35 UNL     1       6.079   0.391  -1.399  1.00  0.00           H  
HETATM   62  H36 UNL     1       4.655   1.868   0.851  1.00  0.00           H  
HETATM   63  H37 UNL     1       6.218   2.106   0.065  1.00  0.00           H  
HETATM   64  H38 UNL     1       5.579  -0.272   1.928  1.00  0.00           H  
HETATM   65  H39 UNL     1       6.394   1.261   2.346  1.00  0.00           H  
HETATM   66  H40 UNL     1       7.939  -0.474   2.091  1.00  0.00           H  
HETATM   67  H41 UNL     1       7.349  -0.911   0.463  1.00  0.00           H  
HETATM   68  H42 UNL     1       8.665   1.653   1.545  1.00  0.00           H  
HETATM   69  H43 UNL     1       8.152   1.605  -0.164  1.00  0.00           H  
HETATM   70  H44 UNL     1      10.266  -0.239   1.194  1.00  0.00           H  
HETATM   71  H45 UNL     1      10.543   1.098   0.081  1.00  0.00           H  
HETATM   72  H46 UNL     1      11.449  -0.919  -1.805  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7   38   39
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   10   44
CONECT   10   11   45
CONECT   11   12   46   47
CONECT   12   13   48   49
CONECT   13   14   50   51
CONECT   14   15   52   53
CONECT   15   16   54   55
CONECT   16   17   56   57
CONECT   17   18   58   59
CONECT   18   19   60   61
CONECT   19   20   62   63
CONECT   20   21   64   65
CONECT   21   22   66   67
CONECT   22   23   68   69
CONECT   23   24   70   71
CONECT   24   25   25   26
CONECT   26   72
END

HMDB0002368
     RDKit          3D
Nervonic acid
 72 71  0  0  0  0  0  0  0  0999 V2000
  -10.6475    0.4072    0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1068   -0.3621   -1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5990   -0.6089   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8495    0.6772   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3419    0.4955   -0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7333   -0.2318   -1.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003   -0.4977   -1.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7385   -1.4670   -0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9597   -1.2252    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -0.9590    1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878   -0.8765    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.4954    1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614    0.5315    0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2970   -0.4728    1.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -0.4184    1.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423   -0.6861   -0.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3265   -0.6772   -0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389    0.5355   -0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843    1.2819    0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868    0.5331    1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5161   -0.0609    1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5179    0.9556    0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8137    0.2829    0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6642   -0.6500   -0.8274 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5718   -0.7593   -1.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7916   -1.3870   -1.1851 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0026    1.4049   -0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5534   -0.1101    0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8825    0.5108    0.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5679   -1.3779   -1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3394    0.1319   -2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3205   -1.1081   -1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4809   -1.2642   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9848    1.3158   -1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1802    1.2554    0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0743    0.2748    0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9645    1.5899   -0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0131    0.3814   -2.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3214   -1.1866   -2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    0.5145   -1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0046   -0.8592   -2.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2798   -2.4757   -1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -1.7176   -1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9968   -1.3385    0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994   -0.7944    2.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0297   -1.5603    1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2718   -1.2051    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115    1.2952    0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0752    0.7628    2.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838    0.2910   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493    1.5611    1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2845   -0.3741    2.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799   -1.5091    1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700    0.4394    1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172   -1.3388    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636    0.0816   -0.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4092   -1.6577   -0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2564   -1.0452   -1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9408   -1.5242   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5647    1.2952   -1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0788    0.3910   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6553    1.8680    0.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2178    2.1057    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5791   -0.2718    1.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3941    1.2611    2.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9386   -0.4738    2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3486   -0.9111    0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6649    1.6526    1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1517    1.6046   -0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2660   -0.2394    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5434    1.0978    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4491   -0.9188   -1.8054 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  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  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
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 18 60  1  0
 18 61  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 22 68  1  0
 22 69  1  0
 23 70  1  0
 23 71  1  0
 26 72  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(Z)-15-Tetracosenoic acid	ChEBI
(Z)-Tetracos-15-enoic acid	ChEBI
15cis-Tetracosenoic acid	ChEBI
cis-15-Tetracosenoic acid	ChEBI
cis-Delta(15)-Tetracosenoic acid	ChEBI
Nervonsaeure	ChEBI
Selacholeic acid	ChEBI
(Z)-15-Tetracosenoate	Generator
(Z)-Tetracos-15-enoate	Generator
15cis-Tetracosenoate	Generator
cis-15-Tetracosenoate	Generator
cis-delta(15)-Tetracosenoate	Generator
cis-Δ(15)-tetracosenoate	Generator
cis-Δ(15)-tetracosenoic acid	Generator
Selacholeate	Generator
Nervonate	Generator
(15Z)-Tetracos-15-enoate	HMDB
(15Z)-Tetracos-15-enoic acid	HMDB
(15Z)-Tetracosenoate	HMDB
(15Z)-Tetracosenoic acid	HMDB
15-Tetracosenoate	HMDB
15-Tetracosenoic acid	HMDB
15Z-Tetracosenoate	HMDB
15Z-Tetracosenoic acid	HMDB
cis-15-Teracosenoate	HMDB
cis-15-Teracosenoic acid	HMDB
cis-15-Tetracosenate	HMDB
cis-15-Tetracosenic acid	HMDB
cis-Selacholeate	HMDB
cis-Selacholeic acid	HMDB
trans-Tetracos-15-enoic acid	HMDB
(15Z)-15-Tetracosenoic acid	HMDB
FA(24:1(15Z))	HMDB
FA(24:1n9)	HMDB
Nevonic acid	HMDB
Nervonic acid	ChEBI

Chemical Formula

C₂₄H₄₆O₂

Average Mass

366.6208 Da

Monoisotopic Mass

366.34978 Da

IUPAC Name

(15Z)-tetracos-15-enoic acid

Traditional Name

nervonic acid

CAS Registry Number

506-37-6

SMILES

CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C24H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9-

InChI Key

GWHCXVQVJPWHRF-KTKRTIGZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	DTU Food
Abramis brama	FooDB	DTU Food
Acipenseridae	FooDB	DTU Food
Actinidia chinensis	FooDB	DTU Food
Agaricus bisporus	FooDB	DTU Food
Allium cepa L.	FooDB	DTU Food
Allium sativum	FooDB	DTU Food
Allium schoenoprasum	FooDB	DTU Food
Anacardium occidentale	FooDB	DTU Food
Ananas comosus	FooDB	DTU Food
Anarhichas lupus	FooDB	DTU Food
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	DTU Food
Anethum graveolens	FooDB	DTU Food
Anguilliformes	FooDB	DTU Food
Annona cherimola	FooDB	DTU Food
Anser anser	FooDB	FooDB
Anthriscus cerefolium	FooDB	DTU Food
Apium graveolens	FooDB	DTU Food
Apium graveolens var. rapaceum	FooDB	DTU Food
Apium graveolens var. secalinum	FooDB	DTU Food
Arachis hypogaea	FooDB	DTU Food
Armoracia rusticana	FooDB	DTU Food
Asparagus officinalis	FooDB	DTU Food
Astacidea	FooDB	DTU Food
Avena sativa L.	FooDB	DTU Food
Averrhoa carambola	FooDB	DTU Food
Belone belone	FooDB	DTU Food
Bertholletia excelsa	FooDB	DTU Food
Beta vulgaris ssp. cicla	FooDB	DTU Food
Bison bison	FooDB	FooDB
Bos taurus	FooDB	DTU Food
Bos taurus X Bison bison	FooDB	FooDB
Brachyura	FooDB	DTU Food
Brassica napus	KNApSAcK Database	22123792
Brassica napus var. napus	FooDB	DTU Food
Brassica oleracea	FooDB	DTU Food
Brassica oleracea var. botrytis	FooDB	DTU Food
Brassica oleracea var. gemmifera	FooDB	DTU Food
Brassica oleracea var. gongylodes	FooDB	DTU Food
Brassica oleracea var. italica	FooDB	DTU Food
Brassica oleracea var. sabauda	FooDB	DTU Food
Brassica rapa	FooDB	DTU Food
Brassica rapa ssp. chinensis	FooDB	DTU Food
Brassica rapa var. rapa	FooDB	DTU Food
Bubalus bubalis	FooDB	FooDB
Calophyllum calaba	KNApSAcK Database	22123792
Calophyllum inophyllum	KNApSAcK Database	22123792
Cantharellus cibarius	FooDB	DTU Food
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	DTU Food
Carica papaya L.	FooDB	DTU Food
Caridea	FooDB	DTU Food
Carthamus tinctorius	KNApSAcK Database	22123792
Carya illinoinensis	FooDB	DTU Food
Castanea	FooDB	DTU Food
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Cicer arietinum	FooDB	DTU Food
Cichorium endivia	FooDB	DTU Food
Cichorium intybus	FooDB	DTU Food
Cinnamomum	FooDB	DTU Food
Cirsium	FooDB	DTU Food
Citrullus lanatus	FooDB	DTU Food
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	DTU Food
Citrus aurantiifolia	FooDB	DTU Food
Citrus limon	FooDB	DTU Food
Citrus paradisi	FooDB	DTU Food
Citrus reticulata	FooDB	DTU Food
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	DTU Food
Clupeinae	FooDB	DTU Food
Cocos nucifera	FooDB	DTU Food
Coffea arabica L.	FooDB	DTU Food
Coffea canephora	FooDB	DTU Food
Columba	FooDB	FooDB
Columbidae	FooDB	DTU Food
Coregonus	FooDB	DTU Food
Coriandrum sativum L.	FooDB	DTU Food
Corylus	FooDB	DTU Food
Cucumis melo	FooDB	DTU Food
Cucumis sativus L.	FooDB	DTU Food
Cucurbita	FooDB	DTU Food
Cyclopteridae	FooDB	DTU Food
Cydonia oblonga	FooDB	DTU Food
Cynara scolymus	FooDB	DTU Food
Daucus carota ssp. sativus	FooDB	DTU Food
Dioscorea	FooDB	DTU Food
Diospyros	FooDB	DTU Food
Dromaius novaehollandiae	FooDB	FooDB
Elaeis	FooDB	DTU Food
Engraulidae	FooDB	DTU Food
Equus caballus	FooDB	FooDB
Eriobotrya japonica	FooDB	DTU Food
Esox lucius	FooDB	DTU Food
Eucheuma	FooDB	DTU Food
Fagopyrum esculentum	FooDB	DTU Food
Ficus carica	FooDB	DTU Food
Foeniculum vulgare	FooDB	DTU Food
Fragaria x ananassa	FooDB	DTU Food
Gadiformes	FooDB	DTU Food
Gadus	FooDB	DTU Food
Gallus gallus	FooDB	DTU Food
Gastropoda	FooDB	DTU Food
Glycine max	FooDB	DTU Food
Gossypium	FooDB	DTU Food
Helianthus annuus L.	FooDB	DTU Food
Helianthus tuberosus	FooDB	DTU Food
Hippoglossus hippoglossus	FooDB	DTU Food
Hordeum vulgare	FooDB	DTU Food
Ipomoea batatas	FooDB	DTU Food
Juglans	FooDB	DTU Food
Juglans nigra L.	FooDB	DTU Food
Lactuca sativa	FooDB	DTU Food
Lagopus muta	FooDB	DTU Food
Lens culinaris	FooDB	DTU Food
Lepidium sativum	FooDB	DTU Food
Leporidae	FooDB	DTU Food
Lepus timidus	FooDB	DTU Food
Limanda limanda	FooDB	DTU Food
Linum usitatissimum	FooDB	DTU Food
Litchi chinensis	FooDB	DTU Food
Lota lota	FooDB	DTU Food
Lunaria biennis	KNApSAcK Database	22123792
Malus	FooDB	DTU Food
Malus pumila	FooDB	DTU Food
Mangifera indica	FooDB	DTU Food
Manihot esculenta	FooDB	DTU Food
Medicago sativa	FooDB	DTU Food
Melanitta fusca	FooDB	FooDB
Melanogrammus aeglefinus	FooDB	DTU Food
Meleagris gallopavo	FooDB	DTU Food
Merlangius merlangus	FooDB	DTU Food
Micromesistius poutassou	FooDB	DTU Food
Microstomus kitt	FooDB	DTU Food
Molva molva	FooDB	DTU Food
Musa x paradisiaca	FooDB	DTU Food
Myristica fragrans	FooDB	DTU Food
Mytilidae	FooDB	DTU Food
Nephropidae	FooDB	DTU Food
Nephrops norvegicus	FooDB	DTU Food
Numida meleagris	FooDB	FooDB
Octopus vulgaris	FooDB	DTU Food
Odocoileus	FooDB	FooDB
Olea europaea	FooDB	DTU Food
Oncorhynchus mykiss	FooDB	DTU Food
Opuntia	FooDB	DTU Food
Oryctolagus	FooDB	FooDB
Oryza sativa	FooDB	DTU Food
Ovis aries	FooDB	DTU Food
Panicum miliaceum	FooDB	DTU Food
Papaver	FooDB	DTU Food
Passiflora edulis	FooDB	DTU Food
Pastinaca sativa	FooDB	DTU Food
Perciformes	FooDB	DTU Food
Persea americana	FooDB	DTU Food
Petroselinum crispum	FooDB	DTU Food
Phaseolus vulgaris	FooDB	DTU Food
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phoenix dactylifera	FooDB	DTU Food
Phyllostachys edulis	FooDB	DTU Food
Physalis	FooDB	DTU Food
Pinus	FooDB	DTU Food
Piper nigrum L.	FooDB	DTU Food
Pistacia vera	FooDB	DTU Food
Pisum sativum	FooDB	DTU Food
Pleuronectidae	FooDB	DTU Food
Pleuronectiformes	FooDB	DTU Food
Pleurotus ostreatus	FooDB	DTU Food
Pollachius	FooDB	DTU Food
Prunus armeniaca	FooDB	DTU Food
Prunus avium L.	FooDB	DTU Food
Prunus domestica	FooDB	DTU Food
Prunus dulcis	FooDB	DTU Food
Prunus persica	FooDB	DTU Food
Prunus persica var. nucipersica	FooDB	DTU Food
Psidium guajava	FooDB	DTU Food
Punica granatum	KNApSAcK Database	22123792
Pyrus communis	FooDB	DTU Food
Ranidae	FooDB	DTU Food
Raphanus sativus var. longipinnatus	FooDB	DTU Food
Reinhardtius hippoglossoides	FooDB	DTU Food
Rheum rhabarbarum	FooDB	DTU Food
Ribes nigrum	FooDB	DTU Food
Ribes rubrum	FooDB	DTU Food
Ribes uva-crispa	FooDB	DTU Food
Rosa	FooDB	DTU Food
Rumex acetosa	FooDB	DTU Food
Saccharina japonica	FooDB	DTU Food
Salmonidae	FooDB	DTU Food
Salvelinus	FooDB	DTU Food
Salvelinus namaycush	FooDB	DTU Food
Sambucus nigra L.	FooDB	DTU Food
Sander lucioperca	FooDB	DTU Food
Scombridae	FooDB	DTU Food
Scophthalmus maximus	FooDB	DTU Food
Scorzonera hispanica	FooDB	DTU Food
Sebastes alutus	FooDB	DTU Food
Sebastes viviparus	FooDB	DTU Food
Secale cereale	FooDB	DTU Food
Sechium edule	FooDB	DTU Food
Sesamum indicum	FooDB	DTU Food
Siluriformes	FooDB	DTU Food
Solanum lycopersicum	FooDB	DTU Food
Solanum melongena	FooDB	DTU Food
Solanum tuberosum	FooDB	DTU Food
Spinacia oleracea	FooDB	DTU Food
Squalus acanthias	FooDB	DTU Food
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	DTU Food
Tamarindus indica	FooDB	DTU Food
Taraxacum officinale	FooDB	DTU Food
Thunnus	FooDB	DTU Food
Trisopterus esmarkii	FooDB	DTU Food
Triticum	FooDB	DTU Food
Triticum durum	FooDB	DTU Food
Tropaeolum speciosum	LOTUS Database	35616633
Vaccinium	FooDB	DTU Food
Vaccinium myrtillus	FooDB	DTU Food
Vaccinium vitis-idaea	FooDB	DTU Food
Vigna angularis	FooDB	DTU Food
Vigna radiata	FooDB	DTU Food
Vitis	FooDB	DTU Food
Zea mays L.	FooDB	DTU Food
Zingiber officinale	FooDB	DTU Food

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tetracosenoic acid (CHEBI:44247 )
Unsaturated fatty acids (C08323 )
Monounsaturated fatty acids (C08323 )
Unsaturated fatty acids (LMFA01030092 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	479.20 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	9.3e-06 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	10.890 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	1.8e-05 g/L	ALOGPS
logP	9.45	ALOGPS
logP	9.45	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	115.01 m³·mol⁻¹	ChemAxon
Polarizability	49.83 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

External Links

HMDB ID

HMDB0002368

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

44247

Good Scents ID

rw1268611

References

General References

Bitsanis D, Crawford MA, Moodley T, Holmsen H, Ghebremeskel K, Djahanbakhch O: Arachidonic acid predominates in the membrane phosphoglycerides of the early and term human placenta. J Nutr. 2005 Nov;135(11):2566-71. [PubMed:16251612 ]
Laasonen M, Erkkila AT, Isotalo E, Maenpaa PK, Pulkkinen JJ, Virsu V, Haapanen ML: Serum lipid fatty acids and temporal processing acuity in children with oral clefts. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):263-70. Epub 2006 Mar 20. [PubMed:16545557 ]
Karlsson M, Marild S, Brandberg J, Lonn L, Friberg P, Strandvik B: Serum phospholipid fatty acids, adipose tissue, and metabolic markers in obese adolescents. Obesity (Silver Spring). 2006 Nov;14(11):1931-9. [PubMed:17135608 ]
Oda E, Hatada K, Kimura J, Aizawa Y, Thanikachalam PV, Watanabe K: Relationships between serum unsaturated fatty acids and coronary risk factors: negative relations between nervonic acid and obesity-related risk factors. Int Heart J. 2005 Nov;46(6):975-85. [PubMed:16394593 ]
Sargent JR, Coupland K, Wilson R: Nervonic acid and demyelinating disease. Med Hypotheses. 1994 Apr;42(4):237-42. [PubMed:8072429 ]

Showing NP-Card for Nervonic acid (NP0000682)

MOL for NP0000682 (Nervonic acid)

3D MOL for NP0000682 (Nervonic acid)

3D SDF for NP0000682 (Nervonic acid)

3D-SDF for NP0000682 (Nervonic acid)

PDB for NP0000682 (Nervonic acid)

3D PDB for NP0000682 (Nervonic acid)

SMILES for NP0000682 (Nervonic acid)

INCHI for NP0000682 (Nervonic acid)

Structure for NP0000682 (Nervonic acid)

3D Structure for NP0000682 (Nervonic acid)