MiMeDB: Showing metabocard for Pristanic acid (MMDBc0000548)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:16 UTC

Update Date

2024-04-30 19:32:57 UTC

Metabolite ID

MMDBc0000548

Metabolite Identification

Common Name

Pristanic acid

Description

Pristanic acid (2,6,10,14-tetramethylpentadecanoic acid) is a terpenoid acid present at micromolar concentrations in the plasma of healthy individuals. It is also found in the lipids from many sources such as freshwater sponges, krill, earthworms, whales, human milk fat, bovine depot fat, butterfat or Californian petroleum. It is usually present in combination with phytanic acid. In humans, pristanic acid is obtained from two sources: either directly from the diet or as the alpha oxidation product of phytanic acid. At physiological concentrations pristanic acid is a natural ligand for PPARalpha. In liver, pristanic acid is degraded by peroxisomal beta oxidation to propionyl-CoA. Together with phytanic acid, pristanic acid accumulates in several inherited disorders such as Zellweger syndrome. Pristanic acid is a branched chain fatty acid that arises from the breakdown of phytanic acid. It is present at micromolar concentrations in the plasma of healthy individuals. Pristanic acid is normally degraded by peroxisomal beta-oxidation. In patients affected with generalized peroxisomal disorders, degradation of both phytanic acid and pristanic acid is impaired owing to absence of functional peroxisomes. Pristanic acid has been found to activate the peroxisome proliferator-activated receptor {alpha} (PPAR{alpha}) in a concentration dependent manner.

Structure

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

HMDB0000795
     RDKit          3D
Pristanic acid
 59 58  0  0  0  0  0  0  0  0999 V2000
   -6.5866   -2.4689   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4576   -1.3029   -1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3329   -0.1718   -0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0330   -0.8605   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3626   -0.4466   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613   -0.0338   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008    0.4076    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0275   -0.6123    1.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    0.9679    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1534    1.3901    1.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751    1.9768    1.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.0046    0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3294   -0.1663    1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2971    1.7869    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3683    1.1718   -0.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0434    0.0236    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1811   -0.5355   -0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2505    0.4521   -1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6706   -1.1622   -2.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4346   -1.2333   -2.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5592   -1.6556   -2.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2653   -3.2638   -0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6376   -2.9453   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0757   -2.1732    0.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8488   -1.6097   -2.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3974   -0.4951   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0967    0.7175   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1860    0.0174    0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0486    0.0258   -2.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4198   -1.6385   -1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3011   -1.2876    0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680    0.4469    0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981   -0.8723   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519    0.7994   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    1.2905    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7566   -1.4217    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230   -1.1200    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -0.0948    2.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2537    0.1930   -0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0035    1.8063   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943    0.5542    2.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8248    2.1667    2.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7101    2.2866    2.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9969    2.8875    0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6141    0.6678   -0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158   -1.1561    1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -0.1089    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5853   -0.1377    2.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8930    2.6793   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7169    2.2739    1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    1.9602   -0.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0813    0.9675   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4226    0.2327    1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3383   -0.8530    0.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5708   -1.3999   -0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2721   -0.0046   -0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2108    1.2565   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1578    0.9496   -2.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4183   -2.1289   -2.7585 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  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 21 59  1  0
M  END


  Mrv1652305231920232D          

 21 20  0  0  0  0            999 V2000
    5.9961    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    3.4618    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  0  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  0  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  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000548

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H38O2/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19(20)21/h15-18H,6-14H2,1-5H3,(H,20,21)

> <INCHI_KEY>
PAHGJZDQXIOYTH-UHFFFAOYSA-N

> <FORMULA>
C19H38O2

> <MOLECULAR_WEIGHT>
298.511

> <EXACT_MASS>
298.287180464

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
38.822272987812994

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6,10,14-tetramethylpentadecanoic acid

> <ALOGPS_LOGP>
6.90

> <JCHEM_LOGP>
7.2160576800000005

> <ALOGPS_LOGS>
-6.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.999793865317857

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
90.70289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.36e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pristanic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000795
     RDKit          3D
Pristanic acid
 59 58  0  0  0  0  0  0  0  0999 V2000
   -6.5866   -2.4689   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4576   -1.3029   -1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3329   -0.1718   -0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0330   -0.8605   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3626   -0.4466   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613   -0.0338   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008    0.4076    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0275   -0.6123    1.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    0.9679    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1534    1.3901    1.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751    1.9768    1.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.0046    0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3294   -0.1663    1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2971    1.7869    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3683    1.1718   -0.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0434    0.0236    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1811   -0.5355   -0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2505    0.4521   -1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6706   -1.1622   -2.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4346   -1.2333   -2.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5592   -1.6556   -2.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2653   -3.2638   -0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6376   -2.9453   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0757   -2.1732    0.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8488   -1.6097   -2.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3974   -0.4951   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0967    0.7175   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1860    0.0174    0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0486    0.0258   -2.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4198   -1.6385   -1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3011   -1.2876    0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680    0.4469    0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981   -0.8723   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519    0.7994   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    1.2905    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7566   -1.4217    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230   -1.1200    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -0.0948    2.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2537    0.1930   -0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0035    1.8063   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943    0.5542    2.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8248    2.1667    2.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7101    2.2866    2.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9969    2.8875    0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6141    0.6678   -0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158   -1.1561    1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -0.1089    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5853   -0.1377    2.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8930    2.6793   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7169    2.2739    1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    1.9602   -0.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0813    0.9675   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4226    0.2327    1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3383   -0.8530    0.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5708   -1.3999   -0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2721   -0.0046   -0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2108    1.2565   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1578    0.9496   -2.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4183   -2.1289   -2.7585 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  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 21 59  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      11.193   8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.526  10.312   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.194   8.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.861  10.312   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.196  10.312   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.197   8.002   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.531   8.772   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.531  10.312   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.864   8.002   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      31.198   8.772   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      29.864   6.462   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   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0000795
HETATM    1  C1  UNL     1      -6.587  -2.469  -0.294  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.458  -1.303  -1.213  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.333  -0.172  -0.736  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.033  -0.861  -1.432  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.363  -0.447  -0.134  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.961  -0.034  -0.501  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.201   0.408   0.697  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.027  -0.612   1.770  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.832   0.968   0.318  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.153   1.390   1.614  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.175   1.977   1.313  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.093   1.005   0.594  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.329  -0.166   1.478  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.297   1.787   0.185  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.368   1.172  -0.593  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.043   0.024   0.046  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.181  -0.536  -0.808  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.251   0.452  -1.107  1.00  0.00           C  
HETATM   19  C19 UNL     1       5.671  -1.162  -2.038  1.00  0.00           C  
HETATM   20  O1  UNL     1       4.435  -1.233  -2.222  1.00  0.00           O  
HETATM   21  O2  UNL     1       6.559  -1.656  -2.956  1.00  0.00           O  
HETATM   22  H1  UNL     1      -7.265  -3.264  -0.713  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.638  -2.945  -0.018  1.00  0.00           H  
HETATM   24  H3  UNL     1      -7.076  -2.173   0.676  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.849  -1.610  -2.210  1.00  0.00           H  
HETATM   26  H5  UNL     1      -8.397  -0.495  -0.845  1.00  0.00           H  
HETATM   27  H6  UNL     1      -7.097   0.717  -1.346  1.00  0.00           H  
HETATM   28  H7  UNL     1      -7.186   0.017   0.361  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.049   0.026  -2.086  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.420  -1.638  -1.897  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.301  -1.288   0.574  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.868   0.447   0.280  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.398  -0.872  -0.988  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.952   0.799  -1.241  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.756   1.291   1.123  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.757  -1.422   1.804  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.023  -1.120   1.651  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.956  -0.095   2.773  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.254   0.193  -0.198  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.004   1.806  -0.368  1.00  0.00           H  
HETATM   41  H20 UNL     1      -0.094   0.554   2.299  1.00  0.00           H  
HETATM   42  H21 UNL     1      -0.825   2.167   2.124  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.710   2.287   2.268  1.00  0.00           H  
HETATM   44  H23 UNL     1       0.997   2.887   0.689  1.00  0.00           H  
HETATM   45  H24 UNL     1       1.614   0.668  -0.378  1.00  0.00           H  
HETATM   46  H25 UNL     1       2.216  -1.156   1.024  1.00  0.00           H  
HETATM   47  H26 UNL     1       3.313  -0.109   2.022  1.00  0.00           H  
HETATM   48  H27 UNL     1       1.585  -0.138   2.331  1.00  0.00           H  
HETATM   49  H28 UNL     1       2.893   2.679  -0.402  1.00  0.00           H  
HETATM   50  H29 UNL     1       3.717   2.274   1.107  1.00  0.00           H  
HETATM   51  H30 UNL     1       5.192   1.960  -0.739  1.00  0.00           H  
HETATM   52  H31 UNL     1       4.081   0.967  -1.663  1.00  0.00           H  
HETATM   53  H32 UNL     1       5.423   0.233   1.057  1.00  0.00           H  
HETATM   54  H33 UNL     1       4.338  -0.853   0.136  1.00  0.00           H  
HETATM   55  H34 UNL     1       6.571  -1.400  -0.182  1.00  0.00           H  
HETATM   56  H35 UNL     1       8.272  -0.005  -0.993  1.00  0.00           H  
HETATM   57  H36 UNL     1       7.211   1.256  -0.328  1.00  0.00           H  
HETATM   58  H37 UNL     1       7.158   0.950  -2.080  1.00  0.00           H  
HETATM   59  H38 UNL     1       7.418  -2.129  -2.758  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4   25
CONECT    3   26   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8    9   35
CONECT    8   36   37   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   43   44
CONECT   12   13   14   45
CONECT   13   46   47   48
CONECT   14   15   49   50
CONECT   15   16   51   52
CONECT   16   17   53   54
CONECT   17   18   19   55
CONECT   18   56   57   58
CONECT   19   20   20   21
CONECT   21   59
END

HMDB0000795
     RDKit          3D
Pristanic acid
 59 58  0  0  0  0  0  0  0  0999 V2000
   -6.5866   -2.4689   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4576   -1.3029   -1.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3329   -0.1718   -0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0330   -0.8605   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3626   -0.4466   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613   -0.0338   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008    0.4076    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0275   -0.6123    1.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    0.9679    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1534    1.3901    1.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751    1.9768    1.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.0046    0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3294   -0.1663    1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2971    1.7869    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3683    1.1718   -0.5930 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0434    0.0236    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1811   -0.5355   -0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2505    0.4521   -1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6706   -1.1622   -2.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4346   -1.2333   -2.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5592   -1.6556   -2.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2653   -3.2638   -0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6376   -2.9453   -0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0757   -2.1732    0.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8488   -1.6097   -2.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3974   -0.4951   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0967    0.7175   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1860    0.0174    0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0486    0.0258   -2.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4198   -1.6385   -1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3011   -1.2876    0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680    0.4469    0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981   -0.8723   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519    0.7994   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    1.2905    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7566   -1.4217    1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230   -1.1200    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -0.0948    2.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2537    0.1930   -0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0035    1.8063   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943    0.5542    2.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8248    2.1667    2.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7101    2.2866    2.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9969    2.8875    0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6141    0.6678   -0.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158   -1.1561    1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -0.1089    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5853   -0.1377    2.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8930    2.6793   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7169    2.2739    1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    1.9602   -0.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0813    0.9675   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4226    0.2327    1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3383   -0.8530    0.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5708   -1.3999   -0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2721   -0.0046   -0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2108    1.2565   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1578    0.9496   -2.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4183   -2.1289   -2.7585 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  2  0
 19 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 21 59  1  0
M  END

Synonyms

Value	Source
2,6,10,14-Tetramethyl-pentadecansaeure	ChEBI
2,6,10,14-Tetramethylpentadecylic acid	ChEBI
Acide pristanique	ChEBI
Acido pristanico	ChEBI
Pristaninsaeure	ChEBI
2,6,10,14-Tetramethylpentadecylate	Generator
Pristanate	Generator
(2S)-Pristanic acid	HMDB
(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanoate	HMDB
(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanoic acid	HMDB
(2S,6R,10R)-Pristanic acid	HMDB
2,6,10,14-Tetramethylpentadecanoate	HMDB
2,6,10,14-Tetramethylpentadecanoic acid	HMDB
Pristanate:(2S,6R,10R)-pristanate	HMDB

Molecular Formula

C₁₉H₃₈O₂

Average Mass

298.511

Monoisotopic Mass

298.287180464

IUPAC Name

2,6,10,14-tetramethylpentadecanoic acid

Traditional Name

pristanic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H38O2/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19(20)21/h15-18H,6-14H2,1-5H3,(H,20,21)

InChI Key

PAHGJZDQXIOYTH-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:51340 )
branched-chain saturated fatty acid (CHEBI:51340 )
methyl-branched fatty acid (CHEBI:51340 )
Acyclic diterpenoids (LMPR0104010022 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00014 g/L	ALOGPS
logP	6.9	ALOGPS
logP	7.22	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	5	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	13	ChemAxon
Refractivity	90.7 m³·mol⁻¹	ChemAxon
Polarizability	38.82 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

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Peroxisome

Biospecimen Locations

Blood
Feces
Fibroblasts
Neuron
Prostate

Tissue Locations

Fibroblasts
Neuron
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192221	Long-chain-fatty-acid--CoA ligase 1	Unknown	P33121	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0038947	Pristanic acid	N-(2,6,10,14-Tetramethylpentadecanoyl)-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

Microbial Sources

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

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

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	105			uM	Adult (>18 years old)	Male	Alpha-Methylacyl-CoA racemase deficiency	HMDB	11861706
Human Blood	Detected and Quantified	27.6			uM	Newborn (0-30 days old)	Not Specified	Zellweger syndrome	HMDB	9818927
Human Blood	Detected and Quantified	0.61			uM	Newborn (0-30 days old)	Female	Rhizomelic chondrodysplasia punctata	HMDB	9818927
Human Blood	Detected and Quantified	<3.000			uM	Adult (>18 years old)	Male	Normal	HMDB	11861706
Human Blood	Detected and Quantified		0	3.350	uM	Children (1-13 years old)	Both	Normal	HMDB	7931872
Human Blood	Detected and Quantified	1.5	0.0	3.0	uM	Newborn (0-30 days old)	Both	Adrenoleukodystrophy, neonatal	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Fibroblasts	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	29808030

External Links

HMDB ID

HMDB0000795

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012993

KNApSAcK ID

Not Available

Chemspider ID

110458

KEGG Compound ID

Not Available

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

51340

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wanders RJ, Barth PG, Schutgens RB, Tager JM: Clinical and biochemical characteristics of peroxisomal disorders: an update. Eur J Pediatr. 1994;153(7 Suppl 1):S44-8. doi: 10.1007/BF02138777. [PubMed:7957386 ]
Verhoeven NM, Kulik W, van den Heuvel CM, Jakobs C: Pre- and postnatal diagnosis of peroxisomal disorders using stable-isotope dilution gas chromatography--mass spectrometry. J Inherit Metab Dis. 1995;18 Suppl 1:45-60. doi: 10.1007/BF00711428. [PubMed:9053555 ]
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 ]
Ferdinandusse S, Denis S, IJlst L, Dacremont G, Waterham HR, Wanders RJ: Subcellular localization and physiological role of alpha-methylacyl-CoA racemase. J Lipid Res. 2000 Nov;41(11):1890-6. [PubMed:11060359 ]
Gootjes J, Mooijer PA, Dekker C, Barth PG, Poll-The BT, Waterham HR, Wanders RJ: Biochemical markers predicting survival in peroxisome biogenesis disorders. Neurology. 2002 Dec 10;59(11):1746-9. doi: 10.1212/01.wnl.0000036609.14203.70. [PubMed:12473763 ]
Straube R, Gackler D, Thiele A, Muselmann L, Kingreen H, Klingel R: Membrane differential filtration is safe and effective for the long-term treatment of Refsum syndrome--an update of treatment modalities and pathophysiological cognition. Transfus Apher Sci. 2003 Aug;29(1):85-91. doi: 10.1016/S1473-0502(03)00102-2. [PubMed:12877898 ]
Mobley JA, Leav I, Zielie P, Wotkowitz C, Evans J, Lam YW, L'Esperance BS, Jiang Z, Ho SM: Branched fatty acids in dairy and beef products markedly enhance alpha-methylacyl-CoA racemase expression in prostate cancer cells in vitro. Cancer Epidemiol Biomarkers Prev. 2003 Aug;12(8):775-83. [PubMed:12917210 ]
Ferdinandusse S, Kostopoulos P, Denis S, Rusch H, Overmars H, Dillmann U, Reith W, Haas D, Wanders RJ, Duran M, Marziniak M: Mutations in the gene encoding peroxisomal sterol carrier protein X (SCPx) cause leukencephalopathy with dystonia and motor neuropathy. Am J Hum Genet. 2006 Jun;78(6):1046-52. doi: 10.1086/503921. Epub 2006 Mar 29. [PubMed:16685654 ]

Showing metabocard for Pristanic acid (MMDBc0000548)

MOL for #<Metabolite:0x00007f923edb0b78>

3D MOL for #<Metabolite:0x00007f923edb0b78>

3D SDF for #<Metabolite:0x00007f923edb0b78>

3D-SDF for #<Metabolite:0x00007f923edb0b78>

PDB for #<Metabolite:0x00007f923edb0b78>

3D PDB for #<Metabolite:0x00007f923edb0b78>

SMILES for #<Metabolite:0x00007f923edb0b78>

INCHI for #<Metabolite:0x00007f923edb0b78>

Structure for #<Metabolite:0x00007f923edb0b78>

3D Structure for #<Metabolite:0x00007f923edb0b78>