MiMeDB: Showing metabocard for Phytanic acid (MMDBc0000369)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:17 UTC

Update Date

2024-04-30 19:31:56 UTC

Metabolite ID

MMDBc0000369

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>
MMDBc0000369

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₂₀H₄₀O₂

Average Mass

312.5304

Monoisotopic Mass

312.302830524

IUPAC Name

3,7,11,15-tetramethylhexadecanoic acid

Traditional Name

phytanic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9780000000-d08f456f5acb304b7ea2	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00y0-9443000000-5bbc79ddca11ee15c346	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0009000000-1344b5ce122597753d72	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00e9-9000000000-d058ed1cd7bf2496d801	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01b9-9000000000-b91cf96bf3e1ed9907c9	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0192000000-404c7c552fbd445291f4	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00mk-4790000000-c4c72f2a0388e83c4d50	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9720000000-e2429e81001f3469126a	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-0089000000-e67aa3a53cb223588ace	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02tc-1094000000-c8ba97412b0185f5a5b3	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-8590000000-02e2e52e9c0e6f20a064	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-849ba1e3311607445182	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0029000000-1d86a3df25ae3d6f62b5	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06r6-8393000000-8564c0781362b5ca2da4	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-4569000000-0ae84af33d4a6cee1563	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06y9-9720000000-8d0e05ef1818d392c4fb	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-19bc307031b7da7b3414	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Peroxisome

Biospecimen Locations

Blood
Feces
Fibroblasts
Liver
Neuron
Prostate

Tissue Locations

Fibroblasts
Liver
Neuron
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001118	Adenosine triphosphate	Adenosine monophosphate	Solute carrier family 27 (fatty acid transporter), member 2	Fatty-Acid- Coenzyme A Ligase	VMH	30371894
MMDBr0001939	Phytanic acid	Phytanic acid	Not Available	Fatty Acid Transport via Diffusion	VMH	30371894
MMDBr0002030	Water	Coenzyme A	Acyl-coa thioesterase 2	Peroxisomal Acyl Coenzyme A Thioesterase	VMH	10944470
MMDBr0004486	Adenosine triphosphate	Adenosine monophosphate	Not Available	Phytanate- Coenzyme A Ligase	VMH	11356164
MMDBr0004487	Adenosine triphosphate	Adenosine monophosphate	Solute carrier family 27 (fatty acid transporter), member 2	Phytanate- Coenzyme A Ligase	VMH	11356164
MMDBr0005249	Adenosine triphosphate	Adenosine monophosphate	Solute carrier family 27 (fatty acid transporter), member 2	Fatty Acid Activation (C16Br), Peroxisomal	VMH	11591435
MMDBr0010196	Phytanic acid	Phytanic acid	Not Available	HMR_3478	VMH	30371894
MMDBr0038935	Phytanic acid	N-(2-hydroxyeicosanoyl)-4R-hydroxysphinganine	Alkaline ceramidase YPC1	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Adrenoleukodystrophy	Slight Increase	Association	Human Blood	HMDB	2408988
Cerebrotendinous xanthomatosis		Association	Human Blood	HMDB	16445943
Infantile refsum's disease	Increased	Association	Human Blood	HMDB	2408988
Infantile refsum's disease	Increased	Association	Human Blood	HMDB	2427795
Refsum's disease		Association	Human Blood	HMDB	2408988
Refsum's disease		Association	Human Blood	HMDB	2433405
Refsum's disease	Increased	Association	Human Blood	HMDB	12700346
Adrenoleukodystrophy	Increased	Association	Human Blood	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1		Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human Blood	Detected and Quantified		3.200	15.998	uM	Children (1-13 years old)	Not Specified	Adrenoleukodystrophy, X-linked	HMDB	2408988
Human Blood	Detected and Quantified	20			uM	Adult (>18 years old)	Male	Alpha-Methylacyl-CoA racemase deficiency	HMDB	11861706
Human Blood	Detected and Quantified	8.639			uM	Adult (>18 years old)	Male	27-hydroxylase deficiency	HMDB	16445943
Human Blood	Detected and Quantified		399.961	479.953	uM	Children (1-13 years old)	Not Specified	Refsum disease, infantile	HMDB	2408988
Human Blood	Detected and Quantified	40.3	27.5	53.0	uM	Adult (>18 years old)	Both	Infantile Refsum disease	HMDB	2427795
Human Blood	Detected and Quantified	5.46			uM	Newborn (0-30 days old)	Not Specified	Zellweger syndrome	HMDB	9818927
Human Blood	Detected and Quantified		3.200	1391.865	uM	Children (1-13 years old)	Both	Zellweger syndrome	HMDB	7931872
Human Blood	Detected and Quantified		9.599	86.392	uM	Infant (0-1 year old)	Both	Zellweger syndrome	HMDB	2418187
Human Blood	Detected and Quantified		26.557	30.717	uM	Children (1-13 years old)	Male	Peroxisomal disorders, new type, liver	HMDB	7931872
Human Blood	Detected and Quantified		0	6.4	uM	Children (1-13 years old)	Both	Pseudoneonatal adrenoleukodystrophy	HMDB	2894756
Human Blood	Detected and Quantified	1439.86			uM	Infant (0-1 year old)	Not Specified	Refsum disease, classic, adult-onset	HMDB	2408988
Human Blood	Detected and Quantified	6335.384			uM	Infant (0-1 year old)	Not Specified	Refsum disease, classic, early-onset	HMDB	2408988
Human Blood	Detected and Quantified		0	2335.773	uM	Adult (>18 years old)	Not Specified	Classicle Refsum's disease	HMDB	2433405
Human Blood	Detected and Quantified	410.0	46.0	1127.0	uM	Adult (>18 years old)	Both	Refsum's Disease	HMDB	12700346
Human Blood	Detected and Quantified	197			uM	Newborn (0-30 days old)	Female	Rhizomelic chondrodysplasia punctata	HMDB	9818927
Human Blood	Detected and Quantified	0.86			uM	Adult (>18 years old)	Female	Normal	HMDB	17868488
Human Blood	Detected and Quantified	3.93			uM	Adult (>18 years old)	Female	Normal	HMDB	17868488
Human Blood	Detected and Quantified	5.77			uM	Adult (>18 years old)	Female	Normal	HMDB	17868488
Human Blood	Detected and Quantified	<10			uM	Children (1-13 years old)	Not Specified	Normal	HMDB	2894756
Human Blood	Detected and Quantified	<12.800			uM	Adult (>18 years old)	Male	Normal	HMDB	11861706
Human Blood	Detected and Quantified		0	12.799	uM	Children (1-13 years old)	Both	Normal	HMDB	7931872
Human Blood	Detected and Quantified		1.600	11.199	uM	Not Specified	Not Specified	Normal	HMDB	16445943
Human Blood	Detected and Quantified	2.7	2.0	4.0	uM	Adult (>18 years old)	Both	Normal	HMDB	12700346
Human Blood	Detected and Quantified	4.8	0.0	9.6	uM	Adult (>18 years old)	Both	Normal	HMDB	2427795
Human Blood	Detected and Quantified	72.0	64.0	80.0	uM	Children (1-13 years old)	Both	Adrenoleukodystrophy (ALD)	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Blood	Detected and Quantified	6.719			uM	Not Specified	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Fibroblasts	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000801

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

References

Synthesis Reference

Not Available

General References

Yao JK, Dyck PJ: Tissue distribution of phytanic acid and its analogues in a kinship with Refsum's disease. Lipids. 1987 Feb;22(2):69-75. doi: 10.1007/BF02534855. [PubMed:2436023 ]
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 ]
Pahan K, Singh I: Intraorganellar localization of CoASH-independent phytanic acid oxidation in human liver peroxisomes. FEBS Lett. 1993 Oct 25;333(1-2):154-8. doi: 10.1016/0014-5793(93)80395-b. [PubMed:8224157 ]
Poggi-Travert F, Fournier B, Poll-The BT, Saudubray JM: Clinical approach to inherited peroxisomal disorders. J Inherit Metab Dis. 1995;18 Suppl 1:1-18. doi: 10.1007/BF00711425. [PubMed:9053544 ]
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. doi: 10.1016/s0014-5793(99)01009-1. [PubMed:10471774 ]
Bernscherer G, Berenyi E, Karabelyos C, Laszlo A, David Z, Hollody K, Toth EZ: [Refsum disease]. Orv Hetil. 2000 Jan 2;141(1):31-4. [PubMed:10673856 ]
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 ]
Young SP, Johnson AW, Muller DP: Effects of phytanic acid on the vitamin E status, lipid composition and physical properties of retinal cell membranes: implications for adult Refsum disease. Clin Sci (Lond). 2001 Dec;101(6):697-705. [PubMed:11724659 ]
Heim M, Johnson J, Boess F, Bendik I, Weber P, Hunziker W, Fluhmann B: Phytanic acid, a natural peroxisome proliferator-activated receptor (PPAR) agonist, regulates glucose metabolism in rat primary hepatocytes. FASEB J. 2002 May;16(7):718-20. doi: 10.1096/fj.01-0816fje. Epub 2002 Mar 26. [PubMed:11923221 ]
Cakirer S, Savas MR: Infantile Refsum disease: serial evaluation with MRI. Pediatr Radiol. 2005 Feb;35(2):212-5. doi: 10.1007/s00247-004-1332-3. Epub 2004 Oct 6. [PubMed:15480616 ]
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. doi: 10.1002/pros.20233. [PubMed:15712232 ]
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. doi: 10.1016/j.ymgme.2005.02.005. Epub 2005 Mar 17. [PubMed:15979030 ]

Showing metabocard for Phytanic acid (MMDBc0000369)

MOL for #<Metabolite:0x000055e8c8cc6f08>

3D MOL for #<Metabolite:0x000055e8c8cc6f08>

3D SDF for #<Metabolite:0x000055e8c8cc6f08>

3D-SDF for #<Metabolite:0x000055e8c8cc6f08>

PDB for #<Metabolite:0x000055e8c8cc6f08>

3D PDB for #<Metabolite:0x000055e8c8cc6f08>

SMILES for #<Metabolite:0x000055e8c8cc6f08>

INCHI for #<Metabolite:0x000055e8c8cc6f08>

Structure for #<Metabolite:0x000055e8c8cc6f08>

3D Structure for #<Metabolite:0x000055e8c8cc6f08>