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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:03 UTC

HMDB ID

HMDB0000553

Secondary Accession Numbers

HMDB00553

Metabolite Identification

Common Name

3L,7D,11D-Phytanic acid

Description

3L,7D,11D-Phytanic acid is an isomer of Phytanic acid, an unusual 20-carbon branched-chain fatty acid; Phytanic acid accumulates in blood and tissues of patients with Refsum disease (RD, an inborn error of lipid metabolism inherited as an autosomal recessive trait (OMIM 266500 )), and is a reliably identifier of RD from a large number of other neurological disorders. Phytanic acid also accumulates in a number of other disorders with a very different clinical course: disorders of peroxisome biogenesis (Zellweger syndrome (OMIM 214100 ), neonatal adrenoleukodystrophy (OMIM 202370 ), infantile Refsum disease (OMIM 266510 )) and rhizomelic chondrodysplasia punctata, type 1 (OMIM 215100 ). Phytanic acid is a 3-methyl fatty acid that cannot be beta-oxidized directly, and first undergoes an alpha-oxidation a reaction catalyzed by the enzyme phytanoyl-CoA hydroxylase, which is deficient in RD, the only true disorder of phytanic acid alpha-oxidation. (The Metabolic and Molecular Bases of Inherited Disease).

Structure

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

HMDB0000553
     RDKit          3D
3L,7D,11D-Phytanic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
   -3.1209    2.0437    0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2517    1.4132    1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    1.0819    2.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9600    0.3467    0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207   -0.8408   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -1.6837    0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140   -2.8710    0.3992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9395   -3.7799   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7984   -2.7159   -0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673   -2.0016   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652   -0.5588    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    0.0541    0.4929 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3060   -0.5648    1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802    0.0342   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9045    0.6689   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879    0.6934   -1.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1633    1.3272   -0.9122 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8233    2.7228   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2836    1.2916   -1.8942 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0012    1.9933   -3.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244    2.5838   -3.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921    1.9859   -4.1309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163    1.5122   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3862    3.0857    0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1733    2.0736    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0356    2.2403    1.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    0.9632    2.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0019    1.9975    3.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946    0.2900    2.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4440    0.8469   -0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8362    0.0372    0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4647   -0.6387   -0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708   -1.5081   -0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5399   -2.0794    1.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0384   -1.2228    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006   -3.5157    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1895   -3.3756   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7786   -3.9690    0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3986   -4.7367   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -3.7537   -0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687   -2.2534   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -2.1749   -1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0699   -2.5508    0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224   -0.2047    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.0503   -0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    1.1190    0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8539   -1.4965    1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -0.8278    2.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9374    0.1872    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1290    0.7040   -1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -0.9642   -1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610    1.6653    0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838    0.0316    0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3932    1.2996   -2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559   -0.3249   -1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4655    0.7578   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3876    2.6438    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7166    3.3715   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    3.1794   -1.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792    0.2242   -2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1894    1.6781   -1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8453    2.5149   -3.9770 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  1
  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  1
 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  1
 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


  Mrv1652305231918072D          

 22 21  0  0  1  0            999 V2000
    4.0125    3.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250    2.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500    2.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125    1.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875    1.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500    1.1042    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5375    1.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375    0.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125    0.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3000   -0.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250   -0.3248    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9375    0.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375   -1.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -1.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750   -1.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000   -1.7537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4125   -1.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4125   -2.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2375   -2.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6500   -1.7537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6500   -3.1826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000553

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](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)/t17-,18-,19+/m1/s1

> <INCHI_KEY>
RLCKHJSFHOZMDR-QRVBRYPASA-N

> <FORMULA>
C20H40O2

> <MOLECULAR_WEIGHT>
312.5304

> <EXACT_MASS>
312.302830524

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
41.000985921298806

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,7R,11R)-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>
3L,7D,11D-phytanate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000553
     RDKit          3D
3L,7D,11D-Phytanic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
   -3.1209    2.0437    0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2517    1.4132    1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    1.0819    2.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9600    0.3467    0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207   -0.8408   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -1.6837    0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140   -2.8710    0.3992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9395   -3.7799   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7984   -2.7159   -0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673   -2.0016   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652   -0.5588    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    0.0541    0.4929 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3060   -0.5648    1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802    0.0342   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9045    0.6689   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879    0.6934   -1.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1633    1.3272   -0.9122 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8233    2.7228   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2836    1.2916   -1.8942 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0012    1.9933   -3.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244    2.5838   -3.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921    1.9859   -4.1309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163    1.5122   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3862    3.0857    0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1733    2.0736    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0356    2.2403    1.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    0.9632    2.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0019    1.9975    3.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946    0.2900    2.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4440    0.8469   -0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8362    0.0372    0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4647   -0.6387   -0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708   -1.5081   -0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5399   -2.0794    1.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0384   -1.2228    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006   -3.5157    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1895   -3.3756   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7786   -3.9690    0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3986   -4.7367   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -3.7537   -0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687   -2.2534   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -2.1749   -1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0699   -2.5508    0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224   -0.2047    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.0503   -0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    1.1190    0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8539   -1.4965    1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -0.8278    2.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9374    0.1872    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1290    0.7040   -1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -0.9642   -1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610    1.6653    0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838    0.0316    0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3932    1.2996   -2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559   -0.3249   -1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4655    0.7578   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3876    2.6438    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7166    3.3715   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    3.1794   -1.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792    0.2242   -2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1894    1.6781   -1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8453    2.5149   -3.9770 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  1
  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  1
 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  1
 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       7.490   6.062   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.260   4.728   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.800   4.728   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.490   3.395   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.950   3.395   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.180   2.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.640   2.061   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.870   3.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.870   0.727   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.330   0.727   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.560  -0.606   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.980  -0.606   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.750   0.727   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.750  -1.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.290  -1.940   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.060  -3.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.600  -3.274   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.370  -1.940   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.370  -4.607   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.910  -4.607   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.680  -3.274   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -8.680  -5.941   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0000553
HETATM    1  C1  UNL     1      -3.121   2.044   0.341  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.252   1.413   1.096  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.814   1.082   2.484  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.960   0.347   0.351  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.221  -0.841  -0.100  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.601  -1.684   0.952  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.914  -2.871   0.399  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.940  -3.780  -0.338  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.798  -2.716  -0.552  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.567  -2.002  -0.170  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.665  -0.559   0.122  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.684   0.054   0.493  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.306  -0.565   1.696  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.580   0.034  -0.714  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.904   0.669  -0.259  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.888   0.693  -1.420  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.163   1.327  -0.912  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.823   2.723  -0.449  1.00  0.00           C  
HETATM   19  C19 UNL     1       6.284   1.292  -1.894  1.00  0.00           C  
HETATM   20  C20 UNL     1       6.001   1.993  -3.150  1.00  0.00           C  
HETATM   21  O1  UNL     1       4.924   2.584  -3.362  1.00  0.00           O  
HETATM   22  O2  UNL     1       6.992   1.986  -4.131  1.00  0.00           O  
HETATM   23  H1  UNL     1      -3.016   1.512  -0.628  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.386   3.086   0.094  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.173   2.074   0.912  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.036   2.240   1.227  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.708   0.963   2.544  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.002   1.997   3.129  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.395   0.290   2.959  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.444   0.847  -0.546  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.836   0.037   0.980  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.465  -0.639  -0.894  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.971  -1.508  -0.632  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.540  -2.079   1.549  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.038  -1.223   1.744  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.601  -3.516   1.272  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.190  -3.376  -1.317  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.779  -3.969   0.340  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.399  -4.737  -0.485  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.452  -3.754  -0.929  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.169  -2.253  -1.530  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.162  -2.175  -1.040  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.070  -2.551   0.696  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.422  -0.205   0.805  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.909  -0.050  -0.869  1.00  0.00           H  
HETATM   46  H24 UNL     1       0.466   1.119   0.727  1.00  0.00           H  
HETATM   47  H25 UNL     1       1.854  -1.496   1.493  1.00  0.00           H  
HETATM   48  H26 UNL     1       0.478  -0.828   2.407  1.00  0.00           H  
HETATM   49  H27 UNL     1       1.937   0.187   2.241  1.00  0.00           H  
HETATM   50  H28 UNL     1       1.129   0.704  -1.470  1.00  0.00           H  
HETATM   51  H29 UNL     1       1.753  -0.964  -1.129  1.00  0.00           H  
HETATM   52  H30 UNL     1       2.661   1.665   0.104  1.00  0.00           H  
HETATM   53  H31 UNL     1       3.284   0.032   0.564  1.00  0.00           H  
HETATM   54  H32 UNL     1       3.393   1.300  -2.205  1.00  0.00           H  
HETATM   55  H33 UNL     1       4.056  -0.325  -1.814  1.00  0.00           H  
HETATM   56  H34 UNL     1       5.466   0.758  -0.003  1.00  0.00           H  
HETATM   57  H35 UNL     1       4.388   2.644   0.565  1.00  0.00           H  
HETATM   58  H36 UNL     1       5.717   3.372  -0.368  1.00  0.00           H  
HETATM   59  H37 UNL     1       4.044   3.179  -1.099  1.00  0.00           H  
HETATM   60  H38 UNL     1       6.479   0.224  -2.141  1.00  0.00           H  
HETATM   61  H39 UNL     1       7.189   1.678  -1.374  1.00  0.00           H  
HETATM   62  H40 UNL     1       7.845   2.515  -3.977  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

HMDB0000553
     RDKit          3D
3L,7D,11D-Phytanic acid
 62 61  0  0  0  0  0  0  0  0999 V2000
   -3.1209    2.0437    0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2517    1.4132    1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    1.0819    2.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9600    0.3467    0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207   -0.8408   -0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -1.6837    0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140   -2.8710    0.3992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9395   -3.7799   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7984   -2.7159   -0.5517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5673   -2.0016   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6652   -0.5588    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839    0.0541    0.4929 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3060   -0.5648    1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802    0.0342   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9045    0.6689   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879    0.6934   -1.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1633    1.3272   -0.9122 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8233    2.7228   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2836    1.2916   -1.8942 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0012    1.9933   -3.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244    2.5838   -3.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9921    1.9859   -4.1309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163    1.5122   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3862    3.0857    0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1733    2.0736    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0356    2.2403    1.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    0.9632    2.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0019    1.9975    3.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946    0.2900    2.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4440    0.8469   -0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8362    0.0372    0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4647   -0.6387   -0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708   -1.5081   -0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5399   -2.0794    1.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0384   -1.2228    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006   -3.5157    1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1895   -3.3756   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7786   -3.9690    0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3986   -4.7367   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -3.7537   -0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687   -2.2534   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -2.1749   -1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0699   -2.5508    0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224   -0.2047    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.0503   -0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    1.1190    0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8539   -1.4965    1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -0.8278    2.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9374    0.1872    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1290    0.7040   -1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -0.9642   -1.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610    1.6653    0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838    0.0316    0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3932    1.2996   -2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559   -0.3249   -1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4655    0.7578   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3876    2.6438    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7166    3.3715   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    3.1794   -1.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792    0.2242   -2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1894    1.6781   -1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8453    2.5149   -3.9770 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  1
  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  1
 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  1
 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
3l,7D,11D-Phytanate	Generator
3,7,11,15-Tetramethyl-[3S-(3R,7S,11S*)]-hexadecanoate	HMDB
3,7,11,15-Tetramethyl-[3S-(3R,7S,11S*)]-hexadecanoic acid	HMDB
(3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoate	HMDB

Chemical Formula

C₂₀H₄₀O₂

Average Molecular Weight

312.5304

Monoisotopic Molecular Weight

312.302830524

IUPAC Name

(3S,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid

Traditional Name

3L,7D,11D-phytanate

CAS Registry Number

31653-05-1

SMILES

CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](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)/t17-,18-,19+/m1/s1

InChI Key

RLCKHJSFHOZMDR-QRVBRYPASA-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

Branched fatty acids (LMFA01020287 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000553)

Source

Endogenous

Endogenous (HMDB: HMDB0000553)

Animal

Animal (HMDB: HMDB0000553)

Exogenous

Food

Food (HMDB: HMDB0000553)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000553)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000553)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000553)

Lipid metabolism pathway (HMDB: HMDB0000553)

Cellular process

Cell signaling (HMDB: HMDB0000553)

Biochemical process

Lipid transport (HMDB: HMDB0000553)

Role

Biological role

Energy source (HMDB: HMDB0000553)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000553)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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 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]+	178.369	31661259
DarkChem	[M-H]-	177.284	31661259
AllCCS	[M+H]+	191.794	32859911
AllCCS	[M-H]-	186.413	32859911
DeepCCS	[M+H]+	194.081	30932474
DeepCCS	[M-H]-	191.723	30932474
DeepCCS	[M-2H]-	224.609	30932474
DeepCCS	[M+Na]+	200.174	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 Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	10.47 minutes	32390414
Predicted by Siyang on May 30, 2022	28.1771 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.03 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	41.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3465.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	919.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	339.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	507.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	685.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1405.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1235.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	193.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2428.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	859.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2447.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	895.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	633.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	916.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	743.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3L,7D,11D-Phytanic acid	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)CC(O)=O	3150.8	Standard polar	33892256
3L,7D,11D-Phytanic acid	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)CC(O)=O	2108.5	Standard non polar	33892256
3L,7D,11D-Phytanic acid	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)CC(O)=O	2174.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3L,7D,11D-Phytanic acid,1TMS,isomer #1	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)CC(=O)O[Si](C)(C)C	2194.7	Semi standard non polar	33892256
3L,7D,11D-Phytanic acid,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)CC(=O)O[Si](C)(C)C(C)(C)C	2411.5	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 - 3L,7D,11D-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 - 3L,7D,11D-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 - 3L,7D,11D-Phytanic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3L,7D,11D-Phytanic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3L,7D,11D-Phytanic acid 10V, Positive-QTOF	splash10-0002-0192000000-34f7c55e3580ca5fc625	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3L,7D,11D-Phytanic acid 20V, Positive-QTOF	splash10-05mk-4790000000-5828bc7866f5845eb77b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3L,7D,11D-Phytanic acid 40V, Positive-QTOF	splash10-0a4i-9710000000-5f784ee3e3419af622fc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3L,7D,11D-Phytanic acid 10V, Negative-QTOF	splash10-03xr-0079000000-7dee3469c9da4c2717db	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3L,7D,11D-Phytanic acid 20V, Negative-QTOF	splash10-02tc-0094000000-6a9da9098072c0f2e5c2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3L,7D,11D-Phytanic acid 40V, Negative-QTOF	splash10-0a4l-8490000000-566e2d4f44ddcc36f2ad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3L,7D,11D-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 - 3L,7D,11D-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 - 3L,7D,11D-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 - 3L,7D,11D-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 - 3L,7D,11D-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 - 3L,7D,11D-Phytanic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-19bc307031b7da7b3414	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

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 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022113

KNApSAcK ID

Not Available

Chemspider ID

8148435

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5537

PubChem Compound

9972843

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Burns, Christopher J.; Field, Leslie D.; Hashimoto, Kikuko; Petteys, Brian J.; Ridley, Damon D.; Rose, Michael. Synthesis of stereoisomerically pure monoether lipids. Australian Journal of Chemistry (1999), 52(5), 387-394.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3L,7D,11D-Phytanic acid (HMDB0000553)

MOL for HMDB0000553 (3L,7D,11D-Phytanic acid)

3D MOL for HMDB0000553 (3L,7D,11D-Phytanic acid)

3D SDF for HMDB0000553 (3L,7D,11D-Phytanic acid)

3D-SDF for HMDB0000553 (3L,7D,11D-Phytanic acid)

PDB for HMDB0000553 (3L,7D,11D-Phytanic acid)

3D PDB for HMDB0000553 (3L,7D,11D-Phytanic acid)

SMILES for HMDB0000553 (3L,7D,11D-Phytanic acid)

INCHI for HMDB0000553 (3L,7D,11D-Phytanic acid)

Structure for HMDB0000553 (3L,7D,11D-Phytanic acid)

3D Structure for HMDB0000553 (3L,7D,11D-Phytanic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra