NP-MRD: Showing NP-Card for L-Octanoylcarnitine (NP0000302)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:14:26 UTC

NP-MRD ID

NP0000302

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Octanoylcarnitine

Description

L-Octanoylcarnitine is the physiologically active form of octanoylcarnitine (PMID 11274033 ). Octanoylcarnitine is detected in medium-chain acyl-CoA dehydrogenase (MCAD) deficiency. MCAD is characterized by intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels (OMIM 201450 ). L-Octanoylcarnitine is also found to be associated with celiac disease and glutaric aciduria II, which are inborn errors of metabolism.

Structure

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

NP0000302
     RDKit          3D

 49 48  0  0  0  0  0  0  0  0999 V2000
    6.4321   -0.3657    0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2326   -1.4230   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -2.0864   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7301   -1.3582   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249   -0.3087    0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471    0.4021   -0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774   -0.5119   -0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792    0.3393   -0.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3010    0.7443   -1.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    0.6885    0.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768    1.5118   -0.3194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1552    2.8659    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511    3.8186   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9190    3.5700   -1.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2819    5.0884    0.4802 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.6949    0.9890    0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0596   -0.3241   -0.2590 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.2718   -0.2550   -1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4817   -1.0787    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0967   -1.1300   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5192   -0.4178    1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3740    0.6728    0.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8700   -0.4689    1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0122   -2.2308    0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100   -1.0072   -1.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947   -2.9251   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978   -2.6916    0.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8764   -2.1108   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6961   -0.9779   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0637   -0.8395    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    0.4451    0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291    0.9391   -1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7969    1.1460    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222   -1.2225   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -1.0820    0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190    1.6981   -1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    2.7512    1.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261    3.2472    0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812    1.0816    1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4947    1.6936   -0.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9498   -0.1189   -2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8527    0.6284   -0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8933   -1.1524   -0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966   -0.4272    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049   -1.8415    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -1.6479    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3598   -1.5485   -0.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678   -2.0548   -1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -0.7137   -1.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 11 36  1  6
 12 37  1  0
 12 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
M  CHG  2  15  -1  17   1
M  END


  Mrv1652303062019112D          

 20 19  0  0  0  0            999 V2000
 9999.133810001.3705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.847810000.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.562110001.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.276510000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.990110001.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.706010000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.419910001.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.135810000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.849610001.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.563510000.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.562110002.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.133810002.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.419510002.6057    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9997.701110002.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.419510003.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.566010003.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.427610000.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.427610000.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1418 9999.7086    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9997.7133 9999.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  6  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  CHG  2  13   1  19  -1
M  END
> <DATABASE_ID>
NP0000302

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H29NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h13H,5-12H2,1-4H3/t13-/m1/s1

> <INCHI_KEY>
CXTATJFJDMJMIY-CYBMUJFWSA-N

> <FORMULA>
C15H29NO4

> <MOLECULAR_WEIGHT>
287.3951

> <EXACT_MASS>
287.209658421

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
33.279951202307146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-(octanoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.22

> <JCHEM_LOGP>
-1.5230014658050801

> <ALOGPS_LOGS>
-5.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.05718689202227

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
100.2687

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-octanoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

NP0000302
     RDKit          3D

 49 48  0  0  0  0  0  0  0  0999 V2000
    6.4321   -0.3657    0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2326   -1.4230   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -2.0864   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7301   -1.3582   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249   -0.3087    0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471    0.4021   -0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774   -0.5119   -0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792    0.3393   -0.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3010    0.7443   -1.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    0.6885    0.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768    1.5118   -0.3194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1552    2.8659    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511    3.8186   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9190    3.5700   -1.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2819    5.0884    0.4802 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.6949    0.9890    0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0596   -0.3241   -0.2590 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.2718   -0.2550   -1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4817   -1.0787    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0967   -1.1300   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5192   -0.4178    1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3740    0.6728    0.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8700   -0.4689    1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0122   -2.2308    0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100   -1.0072   -1.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947   -2.9251   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978   -2.6916    0.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8764   -2.1108   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6961   -0.9779   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0637   -0.8395    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    0.4451    0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291    0.9391   -1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7969    1.1460    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222   -1.2225   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -1.0820    0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190    1.6981   -1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    2.7512    1.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261    3.2472    0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812    1.0816    1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4947    1.6936   -0.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9498   -0.1189   -2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8527    0.6284   -0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8933   -1.1524   -0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966   -0.4272    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049   -1.8415    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -1.6479    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3598   -1.5485   -0.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678   -2.0548   -1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -0.7137   -1.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 11 36  1  6
 12 37  1  0
 12 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
M  CHG  2  15  -1  17   1
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.0508669.225   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8666.3838668.453   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8667.7168669.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.0498668.453   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8670.3828669.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.7188668.453   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8673.0508669.225   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8674.3878668.453   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8675.7198669.225   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8677.0528668.453   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8667.7168670.764   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8665.0508670.764   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8663.7168671.531   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0    8662.3758670.760   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.7168673.071   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.1238672.451   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.7328668.434   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.7328666.894   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8665.0658666.123   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0    8662.3988666.123   0.000  0.00  0.00           O+0
CONECT    1    2   12   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    3                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    1   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    NP0000302
HETATM    1  C1  UNL     1       6.432  -0.366   0.865  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.233  -1.423  -0.138  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.943  -2.086  -0.291  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.730  -1.358  -0.655  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.325  -0.309   0.341  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.047   0.402  -0.096  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.877  -0.512  -0.246  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.279   0.339  -0.668  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.301   0.744  -1.858  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.310   0.688   0.198  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.377   1.512  -0.319  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.155   2.866   0.375  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.151   3.819  -0.121  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.919   3.570  -1.075  1.00  0.00           O  
HETATM   15  O4  UNL     1      -3.282   5.088   0.480  1.00  0.00           O1-
HETATM   16  C12 UNL     1      -3.695   0.989   0.131  1.00  0.00           C  
HETATM   17  N1  UNL     1      -4.060  -0.324  -0.259  1.00  0.00           N1+
HETATM   18  C13 UNL     1      -5.272  -0.255  -1.105  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.482  -1.079   0.937  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.097  -1.130  -0.920  1.00  0.00           C  
HETATM   21  H1  UNL     1       7.519  -0.418   1.211  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.374   0.673   0.470  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.870  -0.469   1.814  1.00  0.00           H  
HETATM   24  H4  UNL     1       7.012  -2.231   0.063  1.00  0.00           H  
HETATM   25  H5  UNL     1       6.610  -1.007  -1.130  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.095  -2.925  -1.051  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.698  -2.692   0.642  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.876  -2.111  -0.640  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.696  -0.978  -1.702  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.064  -0.840   1.303  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.072   0.445   0.575  1.00  0.00           H  
HETATM   32  H12 UNL     1       2.229   0.939  -1.032  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.797   1.146   0.689  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.122  -1.223  -1.090  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.631  -1.082   0.660  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.219   1.698  -1.367  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.277   2.751   1.477  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.126   3.247   0.171  1.00  0.00           H  
HETATM   39  H19 UNL     1      -3.681   1.082   1.265  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.495   1.694  -0.164  1.00  0.00           H  
HETATM   41  H21 UNL     1      -4.950  -0.119  -2.164  1.00  0.00           H  
HETATM   42  H22 UNL     1      -5.853   0.628  -0.740  1.00  0.00           H  
HETATM   43  H23 UNL     1      -5.893  -1.152  -0.960  1.00  0.00           H  
HETATM   44  H24 UNL     1      -4.897  -0.427   1.706  1.00  0.00           H  
HETATM   45  H25 UNL     1      -5.205  -1.842   0.587  1.00  0.00           H  
HETATM   46  H26 UNL     1      -3.587  -1.648   1.290  1.00  0.00           H  
HETATM   47  H27 UNL     1      -2.360  -1.549  -0.212  1.00  0.00           H  
HETATM   48  H28 UNL     1      -3.668  -2.055  -1.269  1.00  0.00           H  
HETATM   49  H29 UNL     1      -2.664  -0.714  -1.824  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   16   36
CONECT   12   13   37   38
CONECT   13   14   14   15
CONECT   16   17   39   40
CONECT   17   18   19   20
CONECT   18   41   42   43
CONECT   19   44   45   46
CONECT   20   47   48   49
END

NP0000302
     RDKit          3D

49 48  0  0  0  0  0  0  0  0999 V2000
    6.4321   -0.3657    0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2326   -1.4230   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -2.0864   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7301   -1.3582   -0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249   -0.3087    0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0471    0.4021   -0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774   -0.5119   -0.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792    0.3393   -0.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3010    0.7443   -1.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    0.6885    0.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768    1.5118   -0.3194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1552    2.8659    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511    3.8186   -0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9190    3.5700   -1.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2819    5.0884    0.4802 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.6949    0.9890    0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0596   -0.3241   -0.2590 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.2718   -0.2550   -1.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4817   -1.0787    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0967   -1.1300   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5192   -0.4178    1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3740    0.6728    0.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8700   -0.4689    1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0122   -2.2308    0.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100   -1.0072   -1.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947   -2.9251   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978   -2.6916    0.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8764   -2.1108   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6961   -0.9779   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0637   -0.8395    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    0.4451    0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291    0.9391   -1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7969    1.1460    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222   -1.2225   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -1.0820    0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190    1.6981   -1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    2.7512    1.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261    3.2472    0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6812    1.0816    1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4947    1.6936   -0.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9498   -0.1189   -2.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8527    0.6284   -0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8933   -1.1524   -0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966   -0.4272    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2049   -1.8415    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -1.6479    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3598   -1.5485   -0.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678   -2.0548   -1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -0.7137   -1.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 11 36  1  6
 12 37  1  0
 12 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
M  CHG  2  15  -1  17   1
M  END

View in JSmol

Synonyms

Value	Source
L-Octanoyl-L-carnitine	ChEBI
L-Octanoylcarnitine	ChEBI
O-Octanoyl-(R)-carnitine	ChEBI
O-Octanoyl-R-carnitine	ChEBI
(-)-Octanoylcarnitine	HMDB
L-Carnitine octanoyl ester	HMDB
L-O-Octanoylcarnitine	HMDB
Octanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt	HMDB
Octanoyl-L-carnitine	HMDB
Octanoylcarnitine chloride, (R)-isomer	HMDB
Octanoylcarnitine, (R)-isomer	HMDB
Octanoylcarnitine chloride	HMDB
Octanoylcarnitine chloride, (+-)-isomer	HMDB
Octanoylcarnitine, (+-)-isomer	HMDB
C8-Carnitine	HMDB
Octanoylcarnitine	HMDB

Chemical Formula

C₁₅H₂₉NO₄

Average Mass

287.3951 Da

Monoisotopic Mass

287.20966 Da

IUPAC Name

(3R)-3-(octanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

L-octanoylcarnitine

CAS Registry Number

25243-95-2

SMILES

CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C15H29NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h13H,5-12H2,1-4H3/t13-/m1/s1

InChI Key

CXTATJFJDMJMIY-CYBMUJFWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-octanoylcarnitine (CHEBI:18102 )
O-acyl-L-carnitine (CHEBI:18102 )
Fatty acyl carnitines (C02838 )
Fatty acyl carnitines (LMFA07070002 )

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
Water Solubility	0.00085 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.5	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.22	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	12	ChemAxon
Refractivity	100.27 m³·mol⁻¹	ChemAxon
Polarizability	33.28 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

External Links

HMDB ID

HMDB0000791

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11953814

PDB ID

Not Available

ChEBI ID

18102

Good Scents ID

Not Available

References

General References

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
Chace DH, DiPerna JC, Adam BW, Hannon WH: Errors caused by the use of D,L-octanoylcarnitine for blood-spot calibrators. Clin Chem. 2001 Apr;47(4):758-60. [PubMed:11274033 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
Xiao JF, Varghese RS, Zhou B, Nezami Ranjbar MR, Zhao Y, Tsai TH, Di Poto C, Wang J, Goerlitz D, Luo Y, Cheema AK, Sarhan N, Soliman H, Tadesse MG, Ziada DH, Ressom HW: LC-MS based serum metabolomics for identification of hepatocellular carcinoma biomarkers in Egyptian cohort. J Proteome Res. 2012 Dec 7;11(12):5914-23. doi: 10.1021/pr300673x. Epub 2012 Nov 1. [PubMed:23078175 ]

Showing NP-Card for L-Octanoylcarnitine (NP0000302)

MOL for NP0000302 (L-Octanoylcarnitine)

3D MOL for NP0000302 (L-Octanoylcarnitine)

3D SDF for NP0000302 (L-Octanoylcarnitine)

3D-SDF for NP0000302 (L-Octanoylcarnitine)

PDB for NP0000302 (L-Octanoylcarnitine)

3D PDB for NP0000302 (L-Octanoylcarnitine)

SMILES for NP0000302 (L-Octanoylcarnitine)

INCHI for NP0000302 (L-Octanoylcarnitine)

Structure for NP0000302 (L-Octanoylcarnitine)

3D Structure for NP0000302 (L-Octanoylcarnitine)