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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 17:43:44 UTC

HMDB ID

HMDB0000801

Secondary Accession Numbers

HMDB00801

Metabolite Identification

Common Name

Phytanic acid

Description

Phytanic acid (or 3,7,11,15-tetramethylhexadecanoic acid) is a 20-carbon branched-chain fatty acid that humans can obtain through the consumption of dairy products, ruminant animal fats, and certain fish. It is primarily formed by bacterial degradation of chlorophyll in the intestinal tract of ruminants. Unlike most fatty acids, phytanic acid cannot be metabolized by beta-oxidation (because of a methyl group in the beta position). Instead, it undergoes alpha-oxidation in the peroxisome, where it is converted into pristanic acid by the removal of one carbon. Pristanic acid can undergo several rounds of beta-oxidation in the peroxisome to form medium-chain fatty acids that can be converted into carbon dioxide and water in mitochondria. Refsum disease, an autosomal recessive neurological disorder caused by mutations in the PHYH gene, is characterized by having impaired alpha-oxidation activity. Individuals with Refsum disease accumulate large stores of phytanic acid in their blood and tissues. This frequently leads to peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss. Therefore, chronically high levels of phytanic acid can be neurotoxic. Phytanic acid's neurotoxicity appears to lie in its ability to initiate astrocyte/neural cell death by activating the mitochondrial route of apoptosis. In particular, phytanic acid can induce the substantial generation of reactive oxygen species in isolated mitochondria as well as in intact cells. It also induces the release of cytochrome c from mitochondria.

Structure

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

HMDB0000801
     RDKit          3D
Phytanic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
   -7.3370   -1.2705   -1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5422   -0.9456   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3195   -2.2280    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2736   -0.2763   -0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4009    0.0928    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331    0.7656    0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131    1.1075    1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443   -0.1241    2.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    1.9430    0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.3053    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166    2.3041   -0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731    1.8042   -1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4756    1.5558   -2.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    0.5567   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603    0.8586    0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1839   -0.2371    1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998   -0.9156    0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4069   -0.0170    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419   -1.9605   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1359   -2.5918   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0209   -3.4323   -1.8540 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838   -2.2206   -0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0261   -2.2843   -1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4021   -1.2833   -1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1508   -0.5008   -2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1588   -0.2889    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3249   -2.6004    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7263   -2.1307    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9098   -3.0248   -0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4964    0.6536   -1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7467   -0.9479   -1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781   -0.8580    1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9450    0.7337    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4178    1.7083   -0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6400    0.0487   -0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745    1.7163    1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0803    0.1499    2.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371   -0.9672    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733   -0.3994    2.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5769    2.1014    1.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    2.9524    0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266    0.4090    0.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    1.0067   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860    2.5785    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406    3.1905   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425    2.5892   -1.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8040    2.4127   -2.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8650    0.6308   -2.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2722    1.5742   -3.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097   -0.3526   -0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475    0.4675   -1.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    1.7952    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416    1.1752    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280    0.0649    2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -1.0467    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7927   -1.5463    1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6191   -0.0592   -0.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3454   -0.2951    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2098    1.0347    0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505   -1.6711   -1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4493   -2.8038    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2304   -2.7271   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 22 62  1  0
M  END

  Mrv1652305231920272D          

 22 21  0  0  0  0            999 V2000
 9995.4926 9996.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2072 9996.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9219 9996.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6375 9996.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3510 9996.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0664 9996.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7800 9996.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4955 9996.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2110 9996.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9244 9996.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.6401 9996.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9244 9997.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0664 9997.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2072 9997.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.7776 9996.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.0629 9996.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3482 9996.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.6335 9996.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9186 9996.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.2039 9996.3084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9186 9997.5455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.3482 9997.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  2 14  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
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000801

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)

> <INCHI_KEY>
RLCKHJSFHOZMDR-UHFFFAOYSA-N

> <FORMULA>
C20H40O2

> <MOLECULAR_WEIGHT>
312.5304

> <EXACT_MASS>
312.302830524

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
41.09002581606026

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,7,11,15-tetramethylhexadecanoic acid

> <ALOGPS_LOGP>
7.28

> <JCHEM_LOGP>
7.404659163

> <ALOGPS_LOGS>
-6.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.040832283720321

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
95.27799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.17e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phytanic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000801
     RDKit          3D
Phytanic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
   -7.3370   -1.2705   -1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5422   -0.9456   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3195   -2.2280    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2736   -0.2763   -0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4009    0.0928    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331    0.7656    0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131    1.1075    1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443   -0.1241    2.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    1.9430    0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.3053    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166    2.3041   -0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731    1.8042   -1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4756    1.5558   -2.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    0.5567   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603    0.8586    0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1839   -0.2371    1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998   -0.9156    0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4069   -0.0170    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419   -1.9605   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1359   -2.5918   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0209   -3.4323   -1.8540 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838   -2.2206   -0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0261   -2.2843   -1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4021   -1.2833   -1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1508   -0.5008   -2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1588   -0.2889    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3249   -2.6004    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7263   -2.1307    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9098   -3.0248   -0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4964    0.6536   -1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7467   -0.9479   -1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781   -0.8580    1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9450    0.7337    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4178    1.7083   -0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6400    0.0487   -0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745    1.7163    1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0803    0.1499    2.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371   -0.9672    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733   -0.3994    2.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5769    2.1014    1.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    2.9524    0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266    0.4090    0.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    1.0067   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860    2.5785    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406    3.1905   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425    2.5892   -1.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8040    2.4127   -2.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8650    0.6308   -2.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2722    1.5742   -3.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097   -0.3526   -0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475    0.4675   -1.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    1.7952    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416    1.1752    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280    0.0649    2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -1.0467    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7927   -1.5463    1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6191   -0.0592   -0.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3454   -0.2951    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2098    1.0347    0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505   -1.6711   -1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4493   -2.8038    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2304   -2.7271   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 22 62  1  0
M  END

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  C   UNK     0    8658.2538659.776   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8659.5878660.544   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8660.9218659.776   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8662.2578660.544   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.5888659.776   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8664.9248660.544   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.2568659.776   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.5928660.544   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.9278659.776   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8670.2598660.544   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8671.5958659.776   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.2598662.085   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.9248662.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8659.5878662.085   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8656.9188660.544   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8655.5848659.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8654.2508660.544   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8652.9168659.776   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8651.5818660.544   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8650.2478659.776   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0    8651.5818662.085   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0    8654.2508662.085   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    6                                                            
CONECT   14    2                                                            
CONECT   15    1   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0000801
HETATM    1  C1  UNL     1      -7.337  -1.270  -1.485  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.542  -0.946  -0.226  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.319  -2.228   0.506  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.274  -0.276  -0.662  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.401   0.093   0.524  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.133   0.766   0.030  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.313   1.108   1.236  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.944  -0.124   2.048  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.112   1.943   0.950  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.131   1.305   0.004  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.017   2.304  -0.160  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.073   1.804  -1.077  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.476   1.556  -2.457  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.798   0.557  -0.591  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.460   0.859   0.716  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.184  -0.237   1.386  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.300  -0.916   0.690  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.407  -0.017   0.261  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.942  -1.960  -0.303  1.00  0.00           C  
HETATM   20  C20 UNL     1       6.136  -2.592  -0.946  1.00  0.00           C  
HETATM   21  O1  UNL     1       6.021  -3.432  -1.854  1.00  0.00           O  
HETATM   22  O2  UNL     1       7.384  -2.221  -0.508  1.00  0.00           O  
HETATM   23  H1  UNL     1      -7.026  -2.284  -1.813  1.00  0.00           H  
HETATM   24  H2  UNL     1      -8.402  -1.283  -1.175  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.151  -0.501  -2.262  1.00  0.00           H  
HETATM   26  H4  UNL     1      -7.159  -0.289   0.434  1.00  0.00           H  
HETATM   27  H5  UNL     1      -7.325  -2.600   0.830  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.726  -2.131   1.430  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.910  -3.025  -0.167  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.496   0.654  -1.199  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.747  -0.948  -1.346  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.178  -0.858   1.056  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.945   0.734   1.230  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.418   1.708  -0.463  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.640   0.049  -0.650  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.975   1.716   1.910  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.080   0.150   2.689  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.637  -0.967   1.415  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.773  -0.399   2.759  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.577   2.101   1.911  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.417   2.952   0.605  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.327   0.409   0.472  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.549   1.007  -0.954  1.00  0.00           H  
HETATM   44  H22 UNL     1       1.386   2.578   0.838  1.00  0.00           H  
HETATM   45  H23 UNL     1       0.541   3.190  -0.651  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.842   2.589  -1.203  1.00  0.00           H  
HETATM   47  H25 UNL     1       0.804   2.413  -2.675  1.00  0.00           H  
HETATM   48  H26 UNL     1       0.865   0.631  -2.475  1.00  0.00           H  
HETATM   49  H27 UNL     1       2.272   1.574  -3.215  1.00  0.00           H  
HETATM   50  H28 UNL     1       2.210  -0.353  -0.631  1.00  0.00           H  
HETATM   51  H29 UNL     1       3.647   0.468  -1.353  1.00  0.00           H  
HETATM   52  H30 UNL     1       4.059   1.795   0.605  1.00  0.00           H  
HETATM   53  H31 UNL     1       2.642   1.175   1.442  1.00  0.00           H  
HETATM   54  H32 UNL     1       4.528   0.065   2.424  1.00  0.00           H  
HETATM   55  H33 UNL     1       3.421  -1.047   1.631  1.00  0.00           H  
HETATM   56  H34 UNL     1       5.793  -1.546   1.552  1.00  0.00           H  
HETATM   57  H35 UNL     1       6.619  -0.059  -0.842  1.00  0.00           H  
HETATM   58  H36 UNL     1       7.345  -0.295   0.767  1.00  0.00           H  
HETATM   59  H37 UNL     1       6.210   1.035   0.575  1.00  0.00           H  
HETATM   60  H38 UNL     1       4.251  -1.671  -1.081  1.00  0.00           H  
HETATM   61  H39 UNL     1       4.449  -2.804   0.268  1.00  0.00           H  
HETATM   62  H40 UNL     1       8.230  -2.727  -0.769  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4   26
CONECT    3   27   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8    9   36
CONECT    8   37   38   39
CONECT    9   10   40   41
CONECT   10   11   42   43
CONECT   11   12   44   45
CONECT   12   13   14   46
CONECT   13   47   48   49
CONECT   14   15   50   51
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18   19   56
CONECT   18   57   58   59
CONECT   19   20   60   61
CONECT   20   21   21   22
CONECT   22   62
END

HMDB0000801
     RDKit          3D
Phytanic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
   -7.3370   -1.2705   -1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5422   -0.9456   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3195   -2.2280    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2736   -0.2763   -0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4009    0.0928    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331    0.7656    0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131    1.1075    1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443   -0.1241    2.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    1.9430    0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.3053    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166    2.3041   -0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731    1.8042   -1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4756    1.5558   -2.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    0.5567   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603    0.8586    0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1839   -0.2371    1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2998   -0.9156    0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4069   -0.0170    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419   -1.9605   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1359   -2.5918   -0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0209   -3.4323   -1.8540 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838   -2.2206   -0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0261   -2.2843   -1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4021   -1.2833   -1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1508   -0.5008   -2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1588   -0.2889    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3249   -2.6004    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7263   -2.1307    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9098   -3.0248   -0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4964    0.6536   -1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7467   -0.9479   -1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781   -0.8580    1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9450    0.7337    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4178    1.7083   -0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6400    0.0487   -0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745    1.7163    1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0803    0.1499    2.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371   -0.9672    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7733   -0.3994    2.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5769    2.1014    1.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    2.9524    0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266    0.4090    0.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    1.0067   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860    2.5785    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406    3.1905   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425    2.5892   -1.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8040    2.4127   -2.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8650    0.6308   -2.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2722    1.5742   -3.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097   -0.3526   -0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475    0.4675   -1.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    1.7952    0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416    1.1752    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280    0.0649    2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -1.0467    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7927   -1.5463    1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6191   -0.0592   -0.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3454   -0.2951    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2098    1.0347    0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2505   -1.6711   -1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4493   -2.8038    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2304   -2.7271   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 22 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,7,11,15-Tetramethyl hexadecanoic acid	ChEBI
3,7,11,15-Tetramethyl-hexadecanoic acid	ChEBI
3,7,11,15-Tetramethyl-hexadecansaeure	ChEBI
3,7,11,15-Tetramethylhexadecanoic acid	Kegg
3,7,11,15-Tetramethyl hexadecanoate	Generator
3,7,11,15-Tetramethyl-hexadecanoate	Generator
3,7,11,15-Tetramethylhexadecanoate	Generator
Phytanate	Generator
3,7,11,15-Tetramethylhexadecoanoate	HMDB
3,7,11,15-Tetramethylhexadecoanoic acid	HMDB
Phytanoate	HMDB
Phytanoic acid	HMDB
Acid, phytanic	HMDB

Chemical Formula

C₂₀H₄₀O₂

Average Molecular Weight

312.5304

Monoisotopic Molecular Weight

312.302830524

IUPAC Name

3,7,11,15-tetramethylhexadecanoic acid

Traditional Name

phytanic acid

CAS Registry Number

14721-66-5

SMILES

CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O

InChI Identifier

InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)

InChI Key

RLCKHJSFHOZMDR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Long-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Fatty acyl
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

long-chain fatty acid (CHEBI:16285 )
branched-chain saturated fatty acid (CHEBI:16285 )
methyl-branched fatty acid (CHEBI:16285 )
Acyclic diterpenoids (C01607 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0011 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	183.172	30932474
[M-H]-	Not Available	183.172	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000217

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.2e-05 g/L	ALOGPS
logP	7.28	ALOGPS
logP	7.4	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	5.04	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	14	ChemAxon
Refractivity	95.28 m³·mol⁻¹	ChemAxon
Polarizability	41.09 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]+	180.224	31661259
DarkChem	[M-H]-	177.327	31661259
AllCCS	[M+H]+	191.794	32859911
AllCCS	[M-H]-	186.413	32859911
DeepCCS	[M+H]+	185.693	30932474
DeepCCS	[M-H]-	183.335	30932474
DeepCCS	[M-2H]-	217.007	30932474
DeepCCS	[M+Na]+	192.589	30932474
AllCCS	[M+H]+	191.8	32859911
AllCCS	[M+H-H2O]+	189.1	32859911
AllCCS	[M+NH4]+	194.3	32859911
AllCCS	[M+Na]+	195.0	32859911
AllCCS	[M-H]-	186.4	32859911
AllCCS	[M+Na-2H]-	188.4	32859911
AllCCS	[M+HCOO]-	190.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phytanic acid	CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O	3118.3	Standard polar	33892256
Phytanic acid	CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O	2069.9	Standard non polar	33892256
Phytanic acid	CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O	2151.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phytanic acid,1TMS,isomer #1	CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)O[Si](C)(C)C	2180.9	Semi standard non polar	33892256
Phytanic acid,1TBDMS,isomer #1	CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)O[Si](C)(C)C(C)(C)C	2406.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phytanic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9780000000-d08f456f5acb304b7ea2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phytanic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00y0-9443000000-5bbc79ddca11ee15c346	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phytanic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phytanic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phytanic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-03di-0009000000-1344b5ce122597753d72	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phytanic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00e9-9000000000-d058ed1cd7bf2496d801	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phytanic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-01b9-9000000000-b91cf96bf3e1ed9907c9	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 10V, Positive-QTOF	splash10-0002-0192000000-404c7c552fbd445291f4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 20V, Positive-QTOF	splash10-00mk-4790000000-c4c72f2a0388e83c4d50	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 40V, Positive-QTOF	splash10-0a4i-9720000000-e2429e81001f3469126a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 10V, Negative-QTOF	splash10-03xr-0089000000-e67aa3a53cb223588ace	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 20V, Negative-QTOF	splash10-02tc-1094000000-c8ba97412b0185f5a5b3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 40V, Negative-QTOF	splash10-0a4l-8590000000-02e2e52e9c0e6f20a064	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 10V, Negative-QTOF	splash10-03di-0009000000-849ba1e3311607445182	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 20V, Negative-QTOF	splash10-03di-0029000000-1d86a3df25ae3d6f62b5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 40V, Negative-QTOF	splash10-06r6-8393000000-8564c0781362b5ca2da4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 10V, Positive-QTOF	splash10-03di-4569000000-0ae84af33d4a6cee1563	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 20V, Positive-QTOF	splash10-06y9-9720000000-8d0e05ef1818d392c4fb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytanic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-19bc307031b7da7b3414	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Peroxisome

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Fibroblasts
Liver
Neuron
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Oxidation of Branched Chain Fatty Acids		Not Available
Phytanic Acid Peroxisomal Oxidation		Not Available
Refsum Disease		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	4.8 (0.0-9.6) uM	Adult (>18 years old)	Both	Normal	2427795	details
Blood	Detected and Quantified	2.7 (2.0-4.0) uM	Adult (>18 years old)	Both	Normal	12700346	details
Blood	Detected and Quantified	<12.800 uM	Adult (>18 years old)	Male	Normal	11861706	details
Blood	Detected and Quantified	0-12.799 uM	Children (1-13 years old)	Both	Normal	7931872	details
Blood	Detected and Quantified	1.600-11.199 uM	Not Specified	Not Specified	Normal	16445943	details
Blood	Detected and Quantified	3.93 uM	Adult (>18 years old)	Female	Normal	17868488	details
Blood	Detected and Quantified	5.77 uM	Adult (>18 years old)	Female	Normal	17868488	details
Blood	Detected and Quantified	0.86 uM	Adult (>18 years old)	Female	Normal	17868488	details
Blood	Detected and Quantified	6.719 uM	Not Specified	Not Specified	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	<10 uM	Children (1-13 years old)	Not Specified	Normal	2894756	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	40.3 (27.5-53.0) uM	Adult (>18 years old)	Both	Infantile Refsum disease	2427795	details
Blood	Detected and Quantified	72.0 (64.0-80.0) uM	Children (1-13 years old)	Both	Adrenoleukodystrophy (ALD)	MetaGene: Metabol...	details
Blood	Detected and Quantified	410.0 (46.0-1127.0) uM	Adult (>18 years old)	Both	Refsum's Disease	12700346	details
Blood	Detected and Quantified	20 uM	Adult (>18 years old)	Male	Alpha-Methylacyl-CoA racemase deficiency	11861706	details
Blood	Detected and Quantified	5.46 uM	Newborn (0-30 days old)	Not Specified	Zellweger syndrome	9818927	details
Blood	Detected and Quantified	9.75 uM	Infant (0-1 year old)	Male	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	197 uM	Newborn (0-30 days old)	Female	Rhizomelic chondrodysplasia punctata	9818927	details
Blood	Detected and Quantified	1439.86 uM	Infant (0-1 year old)	Not Specified	Refsum disease, classic, adult-onset	2408988	details
Blood	Detected and Quantified	6335.384 uM	Infant (0-1 year old)	Not Specified	Refsum disease, classic, early-onset	2408988	details
Blood	Detected and Quantified	0-2335.773 uM	Adult (>18 years old)	Not Specified	Classicle Refsum's disease	2433405	details
Blood	Detected and Quantified	0-50.300 uM	Newborn (0-30 days old)	Not Specified	Neonatal adrenoleukodystrophy	9818927	details
Blood	Detected and Quantified	26.557-30.717 uM	Children (1-13 years old)	Male	Peroxisomal disorders, new type, liver	7931872	details
Blood	Detected and Quantified	3.200-1391.865 uM	Children (1-13 years old)	Both	Zellweger syndrome	7931872	details
Blood	Detected and Quantified	3.200-15.998 uM	Children (1-13 years old)	Not Specified	Adrenoleukodystrophy, X-linked	2408988	details
Blood	Detected and Quantified	34.800-274 uM	Children (1-13 years old)	Female	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	399.961-479.953 uM	Children (1-13 years old)	Not Specified	Refsum disease, infantile	2408988	details
Blood	Detected and Quantified	6.400-34.800 uM	Newborn (0-30 days old)	Female	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	9.599-28.797 uM	Newborn (0-30 days old)	Both	Neonatal adrenoleukodystrophy	2408988	details
Blood	Detected and Quantified	9.599-67.193 uM	Children (1-13 years old)	Not Specified	Refsum disease, juvenile	2408988	details
Blood	Detected and Quantified	9.599-86.392 uM	Infant (0-1 year old)	Both	Zellweger syndrome	2418187	details
Blood	Detected and Quantified	8.639 uM	Adult (>18 years old)	Male	27-hydroxylase deficiency	16445943	details
Blood	Detected and Quantified	0-6.4 uM	Children (1-13 years old)	Both	Pseudoneonatal adrenoleukodystrophy	2894756	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Refsum's disease
Wierzbicki AS, Mayne PD, Lloyd MD, Burston D, Mei G, Sidey MC, Feher MD, Gibberd FB: Metabolism of phytanic acid and 3-methyl-adipic acid excretion in patients with adult Refsum disease. J Lipid Res. 2003 Aug;44(8):1481-8. Epub 2003 Apr 16. [PubMed:12700346 ] Poulos A, Sharp P, Fellenberg AJ, Danks DM: Cerebro-hepato-renal (Zellweger) syndrome, adrenoleukodystrophy, and Refsum's disease: plasma changes and skin fibroblast phytanic acid oxidase. Hum Genet. 1985;70(2):172-7. [PubMed:2408988 ] Skjeldal OH, Stokke O, Refsum S, Norseth J, Petit H: Clinical and biochemical heterogeneity in conditions with phytanic acid accumulation. J Neurol Sci. 1987 Jan;77(1):87-96. [PubMed:2433405 ]
Infantile Refsum's disease
Poll-The BT, Saudubray JM, Ogier H, Schutgens RB, Wanders RJ, Schrakamp G, van den Bosch H, Trijbels JM, Poulos A, Moser HW, et al.: Infantile Refsum's disease: biochemical findings suggesting multiple peroxisomal dysfunction. J Inherit Metab Dis. 1986;9(2):169-74. [PubMed:2427795 ] Poulos A, Sharp P, Fellenberg AJ, Danks DM: Cerebro-hepato-renal (Zellweger) syndrome, adrenoleukodystrophy, and Refsum's disease: plasma changes and skin fibroblast phytanic acid oxidase. Hum Genet. 1985;70(2):172-7. [PubMed:2408988 ]
Adrenoleukodystrophy
Poulos A, Sharp P, Fellenberg AJ, Danks DM: Cerebro-hepato-renal (Zellweger) syndrome, adrenoleukodystrophy, and Refsum's disease: plasma changes and skin fibroblast phytanic acid oxidase. Hum Genet. 1985;70(2):172-7. [PubMed:2408988 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Peroxisomal biogenesis defect
Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ] Mandel H, Espeel M, Roels F, Sofer N, Luder A, Iancu TC, Aizin A, Berant M, Wanders RJ, Schutgens RB: A new type of peroxisomal disorder with variable expression in liver and fibroblasts. J Pediatr. 1994 Oct;125(4):549-55. [PubMed:7931872 ] Budden SS, Kennaway NG, Buist NR, Poulos A, Weleber RG: Dysmorphic syndrome with phytanic acid oxidase deficiency, abnormal very long chain fatty acids, and pipecolic acidemia: studies in four children. J Pediatr. 1986 Jan;108(1):33-9. [PubMed:2418187 ]
Rhizomelic chondrodysplasia punctata
Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ]
Peroxisomal disorders, new type, liver
Mandel H, Espeel M, Roels F, Sofer N, Luder A, Iancu TC, Aizin A, Berant M, Wanders RJ, Schutgens RB: A new type of peroxisomal disorder with variable expression in liver and fibroblasts. J Pediatr. 1994 Oct;125(4):549-55. [PubMed:7931872 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Alpha-Methylacyl-CoA racemase deficiency
McLean BN, Allen J, Ferdinandusse S, Wanders RJ: A new defect of peroxisomal function involving pristanic acid: a case report. J Neurol Neurosurg Psychiatry. 2002 Mar;72(3):396-9. [PubMed:11861706 ]
Cerebrotendinous xanthomatosis
Siman-Tov T, Meiner V, Gadoth N: Could steroids mask the diagnosis of cerebrotendinous xanthomatosis? J Neurol Sci. 2006 Apr 15;243(1-2):83-6. Epub 2006 Jan 30. [PubMed:16445943 ]
Pseudoneonatal adrenoleukodystrophy
Poll-The BT, Roels F, Ogier H, Scotto J, Vamecq J, Schutgens RB, Wanders RJ, van Roermund CW, van Wijland MJ, Schram AW, et al.: A new peroxisomal disorder with enlarged peroxisomes and a specific deficiency of acyl-CoA oxidase (pseudo-neonatal adrenoleukodystrophy). Am J Hum Genet. 1988 Mar;42(3):422-34. [PubMed:2894756 ]
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 ] 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

266500 (Refsum's disease)
266510 (Infantile Refsum's disease)
300100 (Adrenoleukodystrophy)
214100 (Peroxisomal biogenesis defect)
215100 (Rhizomelic chondrodysplasia punctata)
614307 (Alpha-Methylacyl-CoA racemase deficiency)
213700 (Cerebrotendinous xanthomatosis)
264470 (Pseudoneonatal adrenoleukodystrophy)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022252

KNApSAcK ID

Not Available

Chemspider ID

25001

KEGG Compound ID

C01607

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16285

Food Biomarker Ontology

Not Available

VMH ID

CE2414

MarkerDB ID

MDB00000257

Good Scents ID

rw1438851

References

Synthesis Reference

Karrer, P.; Epprecht, A.; Konig, Hans. General method of preparation for 2-methyl-3-alkylnaphthoquinones. Constitution and vitamin K activity. Helvetica Chimica Acta (1940), 23 272-83.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Zomer AW, van Der Burg B, Jansen GA, Wanders RJ, Poll-The BT, van Der Saag PT: Pristanic acid and phytanic acid: naturally occurring ligands for the nuclear receptor peroxisome proliferator-activated receptor alpha. J Lipid Res. 2000 Nov;41(11):1801-7. [PubMed:11060349 ]
Komen JC, Duran M, Wanders RJ: Characterization of phytanic acid omega-hydroxylation in human liver microsomes. Mol Genet Metab. 2005 Jul;85(3):190-5. Epub 2005 Mar 17. [PubMed:15979030 ]
Schonfeld P, Struy H: Refsum disease diagnostic marker phytanic acid alters the physical state of membrane proteins of liver mitochondria. FEBS Lett. 1999 Aug 27;457(2):179-83. [PubMed:10471774 ]
Xu J, Thornburg T, Turner AR, Vitolins M, Case D, Shadle J, Hinson L, Sun J, Liu W, Chang B, Adams TS, Zheng SL, Torti FM: Serum levels of phytanic acid are associated with prostate cancer risk. Prostate. 2005 May 15;63(3):209-14. [PubMed:15712232 ]
Molzer B, Kainz-Korschinsky M, Sundt-Heller R, Bernheimer H: Phytanic acid and very long chain fatty acids in genetic peroxisomal disorders. J Clin Chem Clin Biochem. 1989 May;27(5):309-14. [PubMed:2474624 ]
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Showing metabocard for Phytanic acid (HMDB0000801)

MOL for HMDB0000801 (Phytanic acid)

3D MOL for HMDB0000801 (Phytanic acid)

3D SDF for HMDB0000801 (Phytanic acid)

3D-SDF for HMDB0000801 (Phytanic acid)

PDB for HMDB0000801 (Phytanic acid)

3D PDB for HMDB0000801 (Phytanic acid)

SMILES for HMDB0000801 (Phytanic acid)

INCHI for HMDB0000801 (Phytanic acid)

Structure for HMDB0000801 (Phytanic acid)

3D Structure for HMDB0000801 (Phytanic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra