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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:50 UTC

Update Date

2021-10-13 04:39:06 UTC

HMDB ID

HMDB0002368

Secondary Accession Numbers

HMDB02368

Metabolite 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>
HMDB0002368

> <DATABASE_NAME>
hmdb

> <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 Stereo Labels

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 Molecular Weight

366.6208

Monoisotopic Molecular Weight

366.349780716

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

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 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Inborn errors of metabolism

Organic acidemia

Isovaleric acidemia - Elevated in human blood (PMID: 27329611 ).

Disposition

Biological location

Excreta

Feces

Cellular substructure

Macromolecular complex

Blood

Organ

Placenta

Ingestion

Physical Properties

State

Liquid

Experimental Molecular 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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	196.321	30932474
[M-H]-	Not Available	196.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000264

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.8e-05 g/L	ALOGPS
logP	10^(9.45) g/L	ALOGPS
logP	10^(9.45) g/L	ChemAxon
logS	10^(-7.3) g/L	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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	200.739	31661259
DarkChem	[M-H]-	201.353	31661259

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nervonic acid	CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O	3700.0	Standard polar	33892256
Nervonic acid	CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O	2673.3	Standard non polar	33892256
Nervonic acid	CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O	2750.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nervonic acid,1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)O[Si](C)(C)C	2822.4	Semi standard non polar	33892256
Nervonic acid,1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	3117.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Nervonic acid GC-MS (1 TMS)	splash10-00nb-5900000000-969f119cba8683e5cc50	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Nervonic acid GC-MS (Non-derivatized)	splash10-00nb-5900000000-969f119cba8683e5cc50	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nervonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9782000000-97d131b02e4a98acfe12	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nervonic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9551000000-d11282fde9bc72e71510	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nervonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nervonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nervonic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014i-0009000000-77254b7f9e0c5adec2c5	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nervonic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-05ur-9300000000-c24f47c8ec64393d34b0	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nervonic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0api-9000000000-f9dc5919bdde58922d07	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nervonic acid 35V, Negative-QTOF	splash10-014i-0009000000-b5ce223be566232389ce	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 10V, Positive-QTOF	splash10-0002-0009000000-23437c970e4496314dc2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 20V, Positive-QTOF	splash10-0601-4529000000-0a095c0f2e7f69a7046c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 40V, Positive-QTOF	splash10-0a4l-9873000000-0479aea7f81e735a49b4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 10V, Negative-QTOF	splash10-014i-0009000000-6bdffa41d37f32273117	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 20V, Negative-QTOF	splash10-01ba-0009000000-f28d20de75190fe2dfd6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 40V, Negative-QTOF	splash10-0a4l-9113000000-2bdab238903303f33f49	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 10V, Negative-QTOF	splash10-014i-0009000000-340806f152b23d48ad56	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 20V, Negative-QTOF	splash10-014j-1009000000-ecb8e3e7292d693c5e2d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 40V, Negative-QTOF	splash10-0006-9011000000-3a65628878739cc356f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 10V, Positive-QTOF	splash10-014j-2009000000-966c9a99f927842d86e9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 20V, Positive-QTOF	splash10-00l2-8349000000-44259b5853a420e306d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nervonic acid 40V, Positive-QTOF	splash10-0aou-9100000000-3338b5c4d18e533bf611	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	34.532 +/- 23.730 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	0.070 +/- 0.006 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.900 +/- 0.974 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	68.5 +/- 18.2 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	77.5 +/- 21.6 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details

Associated Disorders and Diseases

Disease References

Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

NRVNC

MarkerDB ID

MDB00000392

Good Scents ID

rw1268611

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Nervonic acid (HMDB0002368)

MOL for HMDB0002368 (Nervonic acid)

3D MOL for HMDB0002368 (Nervonic acid)

3D SDF for HMDB0002368 (Nervonic acid)

3D-SDF for HMDB0002368 (Nervonic acid)

PDB for HMDB0002368 (Nervonic acid)

3D PDB for HMDB0002368 (Nervonic acid)

SMILES for HMDB0002368 (Nervonic acid)

INCHI for HMDB0002368 (Nervonic acid)

Structure for HMDB0002368 (Nervonic acid)

3D Structure for HMDB0002368 (Nervonic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra