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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 16:35:51 UTC

Update Date

2022-03-07 02:49:30 UTC

HMDB ID

HMDB0006202

Secondary Accession Numbers

HMDB06202

Metabolite Identification

Common Name

4,8 Dimethylnonanoyl carnitine

Description

4,8 dimethylnonanoyl carnitine is an intermediate in phytanic and pristanic acid metabolism. Both phytanic acid and pristanic acid are initially oxidized in peroxisomes to 4,8-dimethylnonanoyl-CoA, which is then converted to to 4,8-dimethylnonanoyl carnitine (presumably by peroxisomal carnitine octanoyltransferase), and exported to the mitochondrion. After transport across the mitochondrial membrane and transfer of the acylgroup to coenzyme A, further oxidation to 2,6-dimethylheptanoyl-CoA occurs (PMID: 9469587 ). 4,8 dimethylnonanoyl carnitine is not a substrate for carnitine acetyltransferase, another acyltransferase localized in peroxisomes, which catalyzes the formation of carnitine esters of the other products of pristanic acid beta-oxidation, namely acetyl-CoA and propionyl-CoA. (PMID: 10486279 ). Earlier studies have shown that pristanic acid undergoes three cycles of beta-oxidation in peroxisomes to produce 4,8-dimethylnonanoyl-CoA (DMN-CoA) which is then transported to the mitochondria for full oxidation to CO(2) and H(2)O. In principle, this can be done via two different mechanisms in which DMN-CoA is either converted into the corresponding carnitine ester or hydrolyzed to 4,8-dimethylnonanoic acid plus CoASH.(PMID: 11785945 ). Phytanic acid (3,7,11,15-tetramethylhexadecanoic acid) and pristanic acid (2,6,10,14-tetramethylpentadecanoic acid) are branched-chain fatty acids that are constituents of the human diet. As phytanic acid possesses a beta-methyl group, it cannot be degraded by beta-oxidation. Instead, phytanic acid is first degraded by alpha-oxidation, yielding pristanic acid, which is subsequently degraded by beta-oxidation. Phytanic acid alpha-oxidation is thought to occur partly, and pristanic acid beta-oxidation exclusively, in peroxisomes. Accumulation of phytanic acid and pristanic acid is found in blood and tissues of patients affected with generalized peroxisomal disorders.

Structure

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

HMDB0006202
     RDKit          3D
4,8 Dimethylnonanoyl carnitine
 58 57  0  0  0  0  0  0  0  0999 V2000
    7.8291    0.4824   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6732   -0.2869   -0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8871   -0.0012    0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4094    0.3053   -1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1205   -0.2687   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8281   -0.2178    0.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.8368    1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2499   -0.7531    2.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3270   -0.1193    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0689   -0.8678    0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -0.2574    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    0.7453   -0.5621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105   -0.7230    0.3758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702   -0.1102   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1536   -1.1144   -1.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5650   -2.3690   -0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4511   -2.5938    0.6821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1148   -3.3684   -1.3381 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.5142    0.3634    0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7042    1.0110    0.3776 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.7864    0.1632   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1804    1.8015    1.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4198    1.9815   -0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7321   -0.1216   -1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4961    0.6086   -2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9553    1.4307   -0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7737   -1.3484   -0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1995    0.7595    1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9626    0.3241    1.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8269   -0.9556    1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4110    0.2316   -2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4345    1.4366   -0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538   -1.3484   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2517    0.2007   -1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.8262    1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5436   -0.8822    1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4737   -1.8962    0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6259   -1.5756    2.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585    0.2527    2.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2349   -0.8379    3.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566    0.9273    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3861   -0.1364   -0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0483   -0.7703    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -1.9277    0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1782    0.7335   -0.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2631   -1.4097   -1.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690   -0.7059   -1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282   -0.4381    1.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9466    1.1305    1.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9494    0.0797   -1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7374   -0.7985    0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7455    0.6372    0.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5071    2.6905    1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0458    1.1247    2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2348    2.0687    1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1352    2.8458   -0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3778    2.3469   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6267    1.5312   -1.6524 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
M  CHG  2  18  -1  20   1
M  END

Untitled Document-2
  Mrv0541 02231220332D          

 23 22  0  0  0  0            999 V2000
    2.1434   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8563    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4289    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.2062    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 21  2  0  0  0  0
 19 22  1  0  0  0  0
 15 23  1  0  0  0  0
  1 12  1  0  0  0  0
M  CHG  2   2  -1   8   1
M  END
> <DATABASE_ID>
HMDB0006202

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCCC(C)CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C18H35NO4/c1-14(2)8-7-9-15(3)10-11-18(22)23-16(12-17(20)21)13-19(4,5)6/h14-16H,7-13H2,1-6H3

> <INCHI_KEY>
DDTDJDZHDFMZED-UHFFFAOYSA-N

> <FORMULA>
C18H35NO4

> <MOLECULAR_WEIGHT>
329.4748

> <EXACT_MASS>
329.256608613

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.58102570614146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4,8-dimethylnonanoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
-0.5043946081384132

> <ALOGPS_LOGS>
-6.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.285634865646305

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057294180424632

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
113.96689999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dimethylnonanoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006202
     RDKit          3D
4,8 Dimethylnonanoyl carnitine
 58 57  0  0  0  0  0  0  0  0999 V2000
    7.8291    0.4824   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6732   -0.2869   -0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8871   -0.0012    0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4094    0.3053   -1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1205   -0.2687   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8281   -0.2178    0.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.8368    1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2499   -0.7531    2.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3270   -0.1193    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0689   -0.8678    0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -0.2574    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    0.7453   -0.5621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105   -0.7230    0.3758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702   -0.1102   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1536   -1.1144   -1.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5650   -2.3690   -0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4511   -2.5938    0.6821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1148   -3.3684   -1.3381 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.5142    0.3634    0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7042    1.0110    0.3776 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.7864    0.1632   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1804    1.8015    1.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4198    1.9815   -0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7321   -0.1216   -1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4961    0.6086   -2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9553    1.4307   -0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7737   -1.3484   -0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1995    0.7595    1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9626    0.3241    1.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8269   -0.9556    1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4110    0.2316   -2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4345    1.4366   -0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538   -1.3484   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2517    0.2007   -1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.8262    1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5436   -0.8822    1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4737   -1.8962    0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6259   -1.5756    2.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585    0.2527    2.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2349   -0.8379    3.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566    0.9273    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3861   -0.1364   -0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0483   -0.7703    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -1.9277    0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1782    0.7335   -0.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2631   -1.4097   -1.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690   -0.7059   -1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282   -0.4381    1.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9466    1.1305    1.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9494    0.0797   -1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7374   -0.7985    0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7455    0.6372    0.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5071    2.6905    1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0458    1.1247    2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2348    2.0687    1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1352    2.8458   -0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3778    2.3469   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6267    1.5312   -1.6524 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
M  CHG  2  18  -1  20   1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-2                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.001  -1.155   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       1.334   3.465   0.000  0.00  0.00           O-1
HETATM    3  C   UNK     0       2.667   2.695   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001   3.465   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.155   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.668   0.385   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0       8.002  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.898  -0.949   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.438   1.719   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001  -1.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335  -1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668  -1.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.002  -1.925   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -3.465   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.668   0.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   0.385   0.000  0.00  0.00           C+0
CONECT    1    6   12                                                       
CONECT    2    3                                                            
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13   21    1                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19                                                            
CONECT   21   12                                                            
CONECT   22   19                                                            
CONECT   23   15                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0006202
HETATM    1  C1  UNL     1       7.829   0.482  -1.321  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.673  -0.287  -0.625  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.887  -0.001   0.836  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.409   0.305  -1.131  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.121  -0.269  -0.676  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.828  -0.218   0.784  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.464  -0.837   1.070  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.250  -0.753   2.573  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.327  -0.119   0.383  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.069  -0.868   0.795  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.141  -0.257   0.180  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.980   0.745  -0.562  1.00  0.00           O  
HETATM   13  O2  UNL     1      -2.410  -0.723   0.376  1.00  0.00           O  
HETATM   14  C12 UNL     1      -3.570  -0.110  -0.235  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.154  -1.114  -1.212  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.565  -2.369  -0.549  1.00  0.00           C  
HETATM   17  O3  UNL     1      -4.451  -2.594   0.682  1.00  0.00           O  
HETATM   18  O4  UNL     1      -5.115  -3.368  -1.338  1.00  0.00           O1-
HETATM   19  C15 UNL     1      -4.514   0.363   0.811  1.00  0.00           C  
HETATM   20  N1  UNL     1      -5.704   1.011   0.378  1.00  0.00           N1+
HETATM   21  C16 UNL     1      -6.786   0.163  -0.009  1.00  0.00           C  
HETATM   22  C17 UNL     1      -6.180   1.802   1.540  1.00  0.00           C  
HETATM   23  C18 UNL     1      -5.420   1.982  -0.684  1.00  0.00           C  
HETATM   24  H1  UNL     1       8.732  -0.122  -1.200  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.496   0.609  -2.370  1.00  0.00           H  
HETATM   26  H3  UNL     1       7.955   1.431  -0.796  1.00  0.00           H  
HETATM   27  H4  UNL     1       6.774  -1.348  -0.863  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.199   0.759   1.182  1.00  0.00           H  
HETATM   29  H6  UNL     1       7.963   0.324   1.023  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.827  -0.956   1.396  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.411   0.232  -2.272  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.434   1.437  -0.968  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.054  -1.348  -1.043  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.252   0.201  -1.221  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.859   0.826   1.164  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.544  -0.882   1.322  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.474  -1.896   0.769  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.626  -1.576   2.955  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.859   0.253   2.797  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.235  -0.838   3.088  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.257   0.927   0.705  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.386  -0.136  -0.719  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.048  -0.770   1.896  1.00  0.00           H  
HETATM   44  H21 UNL     1       0.192  -1.928   0.539  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.178   0.734  -0.828  1.00  0.00           H  
HETATM   46  H23 UNL     1      -3.263  -1.410  -1.854  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.869  -0.706  -1.920  1.00  0.00           H  
HETATM   48  H25 UNL     1      -4.728  -0.438   1.579  1.00  0.00           H  
HETATM   49  H26 UNL     1      -3.947   1.130   1.420  1.00  0.00           H  
HETATM   50  H27 UNL     1      -6.949   0.080  -1.104  1.00  0.00           H  
HETATM   51  H28 UNL     1      -6.737  -0.798   0.521  1.00  0.00           H  
HETATM   52  H29 UNL     1      -7.746   0.637   0.360  1.00  0.00           H  
HETATM   53  H30 UNL     1      -5.507   2.690   1.668  1.00  0.00           H  
HETATM   54  H31 UNL     1      -6.046   1.125   2.409  1.00  0.00           H  
HETATM   55  H32 UNL     1      -7.235   2.069   1.435  1.00  0.00           H  
HETATM   56  H33 UNL     1      -6.135   2.846  -0.546  1.00  0.00           H  
HETATM   57  H34 UNL     1      -4.378   2.347  -0.598  1.00  0.00           H  
HETATM   58  H35 UNL     1      -5.627   1.531  -1.652  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   27
CONECT    3   28   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8    9   37
CONECT    8   38   39   40
CONECT    9   10   41   42
CONECT   10   11   43   44
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   19   45
CONECT   15   16   46   47
CONECT   16   17   17   18
CONECT   19   20   48   49
CONECT   20   21   22   23
CONECT   21   50   51   52
CONECT   22   53   54   55
CONECT   23   56   57   58
END

HMDB0006202
     RDKit          3D
4,8 Dimethylnonanoyl carnitine
 58 57  0  0  0  0  0  0  0  0999 V2000
    7.8291    0.4824   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6732   -0.2869   -0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8871   -0.0012    0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4094    0.3053   -1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1205   -0.2687   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8281   -0.2178    0.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.8368    1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2499   -0.7531    2.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3270   -0.1193    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0689   -0.8678    0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -0.2574    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    0.7453   -0.5621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4105   -0.7230    0.3758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702   -0.1102   -0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1536   -1.1144   -1.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5650   -2.3690   -0.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4511   -2.5938    0.6821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1148   -3.3684   -1.3381 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.5142    0.3634    0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7042    1.0110    0.3776 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.7864    0.1632   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1804    1.8015    1.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4198    1.9815   -0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7321   -0.1216   -1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4961    0.6086   -2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9553    1.4307   -0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7737   -1.3484   -0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1995    0.7595    1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9626    0.3241    1.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8269   -0.9556    1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4110    0.2316   -2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4345    1.4366   -0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538   -1.3484   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2517    0.2007   -1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.8262    1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5436   -0.8822    1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4737   -1.8962    0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6259   -1.5756    2.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585    0.2527    2.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2349   -0.8379    3.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566    0.9273    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3861   -0.1364   -0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0483   -0.7703    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -1.9277    0.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1782    0.7335   -0.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2631   -1.4097   -1.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8690   -0.7059   -1.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282   -0.4381    1.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9466    1.1305    1.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9494    0.0797   -1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7374   -0.7985    0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7455    0.6372    0.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5071    2.6905    1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0458    1.1247    2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2348    2.0687    1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1352    2.8458   -0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3778    2.3469   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6267    1.5312   -1.6524 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 23 58  1  0
M  CHG  2  18  -1  20   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4,8-Dimethylnonanoylcarnitine	ChEBI

Chemical Formula

C₁₈H₃₅NO₄

Average Molecular Weight

329.4748

Monoisotopic Molecular Weight

329.256608613

IUPAC Name

3-[(4,8-dimethylnonanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

4,8-dimethylnonanoylcarnitine

CAS Registry Number

Not Available

SMILES

CC(C)CCCC(C)CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C18H35NO4/c1-14(2)8-7-9-15(3)10-11-18(22)23-16(12-17(20)21)13-19(4,5)6/h14-16H,7-13H2,1-6H3

InChI Key

DDTDJDZHDFMZED-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Branched fatty acid
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Organooxygen compound
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxylic ester (CHEBI:63874 )
O-acylcarnitine (CHEBI:63874 )
ammonium betaine (CHEBI:63874 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006202)
Peroxisome (HMDB: HMDB0006202)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006202)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006202)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006202)

Source

Endogenous

Endogenous (HMDB: HMDB0006202)

Animal

Animal (HMDB: HMDB0006202)

Exogenous

Food

Food (HMDB: HMDB0006202)

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: HMDB0006202)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006202)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006202)
Oxidation of Branched-Chain Fatty Acids (PathBank: SMP0087255)

Lipid metabolism pathway (HMDB: HMDB0006202)

Cellular process

Cell signaling (HMDB: HMDB0006202)

Biochemical process

Lipid transport (HMDB: HMDB0006202)

Role

Biological role

Energy source (HMDB: HMDB0006202)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006202)

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	0.00024 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	-0.5	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	113.97 m³·mol⁻¹	ChemAxon
Polarizability	38.58 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DeepCCS	[M+H]+	188.535	30932474
DeepCCS	[M-H]-	184.516	30932474
DeepCCS	[M-2H]-	221.059	30932474
DeepCCS	[M+Na]+	197.351	30932474
AllCCS	[M+H]+	190.9	32859911
AllCCS	[M+H-H2O]+	188.5	32859911
AllCCS	[M+NH4]+	193.1	32859911
AllCCS	[M+Na]+	193.7	32859911
AllCCS	[M-H]-	187.0	32859911
AllCCS	[M+Na-2H]-	188.4	32859911
AllCCS	[M+HCOO]-	190.1	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.	5.22 minutes	32390414
Predicted by Siyang on May 30, 2022	15.4701 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.29 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	58.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2123.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	202.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	728.5 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	647.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	222.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1610.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	485.0 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	1927.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	430.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	205.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	90.8 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	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,8 Dimethylnonanoyl carnitine	CC(C)CCCC(C)CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2389.6	Standard polar	33892256
4,8 Dimethylnonanoyl carnitine	CC(C)CCCC(C)CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	1750.4	Standard non polar	33892256
4,8 Dimethylnonanoyl carnitine	CC(C)CCCC(C)CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C	2041.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4,8 Dimethylnonanoyl carnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9300000000-7404eec33724333cbe3b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,8 Dimethylnonanoyl carnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,8 Dimethylnonanoyl carnitine 10V, Positive-QTOF	splash10-01qc-0925000000-45565d6ef3b2d942da8c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,8 Dimethylnonanoyl carnitine 20V, Positive-QTOF	splash10-0006-2900000000-d0e0f6f815e417182179	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,8 Dimethylnonanoyl carnitine 40V, Positive-QTOF	splash10-0abc-9600000000-d22566bfbdfdf194d9e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,8 Dimethylnonanoyl carnitine 10V, Negative-QTOF	splash10-004i-1319000000-298fff1a97503d7e7ca0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,8 Dimethylnonanoyl carnitine 20V, Negative-QTOF	splash10-0170-1973000000-b1cfe17300810f8c9ed5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,8 Dimethylnonanoyl carnitine 40V, Negative-QTOF	splash10-0673-4900000000-0babf4d8840191a63c64	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,8 Dimethylnonanoyl carnitine 10V, Positive-QTOF	splash10-001i-0009000000-298104349b7d0b2a8ba8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,8 Dimethylnonanoyl carnitine 20V, Positive-QTOF	splash10-0019-9005000000-651a44cad152195d72f6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,8 Dimethylnonanoyl carnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Oxidation of Branched Chain Fatty Acids		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023834

KNApSAcK ID

Not Available

Chemspider ID

21233922

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2365396

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477801

PDB ID

Not Available

ChEBI ID

63874

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ferdinandusse S, Mulders J, IJlst L, Denis S, Dacremont G, Waterham HR, Wanders RJ: Molecular cloning and expression of human carnitine octanoyltransferase: evidence for its role in the peroxisomal beta-oxidation of branched-chain fatty acids. Biochem Biophys Res Commun. 1999 Sep 16;263(1):213-8. [PubMed:10486279 ]
Verhoeven NM, Roe DS, Kok RM, Wanders RJ, Jakobs C, Roe CR: Phytanic acid and pristanic acid are oxidized by sequential peroxisomal and mitochondrial reactions in cultured fibroblasts. J Lipid Res. 1998 Jan;39(1):66-74. [PubMed:9469587 ]
Ofman R, el Mrabet L, Dacremont G, Spijer D, Wanders RJ: Demonstration of dimethylnonanoyl-CoA thioesterase activity in rat liver peroxisomes followed by purification and molecular cloning of the thioesterase involved. Biochem Biophys Res Commun. 2002 Jan 18;290(2):629-34. [PubMed:11785945 ]

Enzymes

Enzyme Details

1. Peroxisomal carnitine O-octanoyltransferase

General function:: Involved in acyltransferase activity
Specific function:: Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate. Converts the end product of pristanic acid beta oxidation, 4,8-dimethylnonanoyl-CoA, to its corresponding carnitine ester.
Gene Name:: CROT
Uniprot ID:: Q9UKG9
Molecular weight:: 10213.63

Enzyme Details

2. Carnitine O-palmitoyltransferase 2, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: CPT2
Uniprot ID:: P23786
Molecular weight:: 73776.335

Enzyme Details

3. Mitochondrial carnitine/acylcarnitine carrier protein

General function:: Involved in transporter activity
Specific function:: Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:: SLC25A20
Uniprot ID:: O43772
Molecular weight:: 32943.46

Showing metabocard for 4,8 Dimethylnonanoyl carnitine (HMDB0006202)

MOL for HMDB0006202 (4,8 Dimethylnonanoyl carnitine)

3D MOL for HMDB0006202 (4,8 Dimethylnonanoyl carnitine)

3D SDF for HMDB0006202 (4,8 Dimethylnonanoyl carnitine)

3D-SDF for HMDB0006202 (4,8 Dimethylnonanoyl carnitine)

PDB for HMDB0006202 (4,8 Dimethylnonanoyl carnitine)

3D PDB for HMDB0006202 (4,8 Dimethylnonanoyl carnitine)

SMILES for HMDB0006202 (4,8 Dimethylnonanoyl carnitine)

INCHI for HMDB0006202 (4,8 Dimethylnonanoyl carnitine)

Structure for HMDB0006202 (4,8 Dimethylnonanoyl carnitine)

3D Structure for HMDB0006202 (4,8 Dimethylnonanoyl carnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes