NP-MRD: Showing NP-Card for L-Palmitoylcarnitine (NP0000830)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:43:07 UTC

NP-MRD ID

NP0000830

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Palmitoylcarnitine

Description

L-Palmitoylcarnitine or hexadecanoylcarnitine is an acylcarnitine. It is technically a long-chain acyl fatty acid derivative ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids. The general role of acylcarnitines is to transport acyl-groups, organic acids and fatty acids, from the cytoplasm into the mitochondria so that they can be broken down to produce energy. As part of this process, palmitic acid is first transported into the cell via the long-chain fatty acid transport protein 1 (FATP1). Once inside the cell it undergoes a reaction to form an acyl-CoA derivative called palmitoyl-CoA. This reaction is facilitated by the Long-chain fatty-acid CoA ligase 1 protein, which adds a CoA moiety to appropriate acyl groups. Many acyl-CoA groups will then further react with other zwitterionic compounds such as carnitine (to form acylcarnitines) and amino acids (to form acyl amides). The carnitine needed to form acylcarnitines inside the cell is transported into the cell by the organic cation/carnitine transporter 2. In forming an acylcarnitine derivative, palmitoyl-CoA reacts with L-carnitine to form palmitoylcarnitine. This reaction is catalyzed by carnitine O-palmitoyltransferase. This enzyme resides in the mitochondrial outer membrane. While this reaction takes place, the palmitoylcarnitine is moved into the mitochondrial intermembrane space. Following the reaction, the newly synthesized acylcarnitine is transported into the mitochondrial matrix by a mitochondrial carnitine/acylcarnitine carrier protein found in the mitochondrial inner membrane. Once in the matrix, palmitoylcarnitine can react with the carnitine O-palmitoyltransferase 2 enzyme found in the mitochondrial inner membrane to once again form palmitoyl-CoA and L-carnitine. Palmitoyl-CoA then enters into the mitochondrial beta-oxidation pathway to form aceytl-CoA. Acetyl-CoA can go on to enter the TCA cycle, or it can react with L-carnitine to form L-acetylcarnitine in a reaction catalyzed by Carnitine O-acetyltransferase. This reaction can occur in both directions, and L-acetylcarnitine and CoA can react to form acetyl-CoA and L-carnitine in certain circumstances. Finally, acetyl-CoA in the cytosol can be catalyzed by acetyl-CoA carboxylase 1 to form malonyl-CoA, which inhibits the action of carnitine O-palmitoyltransferase 1, thereby preventing palmitoylcarnitine from forming and thereby preventing it from being transported into the mitochondria. L-Palmitoylcarnitine has been also reported to change the activity of certain proteins and to stimulate the activity of caspases 3, 7, and 8. Interestingly, the level of this long-chain acylcarnitine has been shown to increase during apoptosis. Palmitoylcarnitine has also been reported to diminish the binding of phorbol esters (protein kinase C activators) and the autophosphorylation of the enzyme. Some of the physicochemical properties of palmitoylcarnitine may help to explain the need for coenzyme A-carnitine-coenzyme A acyl exchange during mitochondrial fatty acid import. The amphiphilic character of palmitoylcarnitine may also explain its proposed involvement in the pathogenesis of myocardial ischemia. L-Palmitoylcarnitine accumulates in ischemic myocardium and potentially contributes to myocardial damage through alterations in membrane molecular dynamics. This is a mechanism through which could play an important role in ischemic injury (PMID: 2540838 , 15363641 , 8706815 ). Palmitoylcarnitine is characteristically elevated in late-onset carnitine palmitoyltransferase II deficiency (OMIM: 255110 ).

Structure

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

  Mrv1652311191918112D          

 28 27  0  0  0  0            999 V2000
 9998.993110004.0773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.707410003.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.421710004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.136010003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.850310004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.564410003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.278810004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.993110003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.706810004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.422810003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.136710004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.852610003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.566510004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.280410003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.994310004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.710210003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.424110004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.138010003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.421710004.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.993110004.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.278810005.3126    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9997.560410004.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.278810006.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.425210005.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.287010003.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.287010002.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.001110002.4154    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9997.572710002.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  6  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  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
 10 11  1  0  0  0  0
 11 12  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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  CHG  2  21   1  27  -1
M  END

NP0000830
     RDKit          3D

 73 72  0  0  0  0  0  0  0  0999 V2000
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    7.9471    1.4203   -0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4874   -0.1368   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8678    0.9897    3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5215    2.3174    3.5245 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.4188   -0.1445    1.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2648   -0.0891   -0.1435 N   0  0  0  0  0  4  0  0  0  0  0  0
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   -8.6106   -0.4960    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2469   -0.3549    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9943   -0.0436    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6114    1.5773    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6960    0.3857   -1.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556   -0.3816    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937   -1.4421    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7524   -2.7752   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6358   -2.7016    0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4319   -2.3675   -1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3935   -0.9235   -1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599   -1.2351    0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5932    0.2267   -3.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3963   -0.5379   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7282   -1.6345   -1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3046    1.1897   -1.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5418    1.3613   -1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4964    2.0299   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6363   -1.5805    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.8952    0.0531    1.1978 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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 19 60  1  6
 20 61  1  0
 20 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  CHG  2  23  -1  25   1
M  END

  Mrv1652311191918112D          

 28 27  0  0  0  0            999 V2000
 9998.993110004.0773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.707410003.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.421710004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.136010003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.850310004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.564410003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.278810004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.993110003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.706810004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.422810003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.136710004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.852610003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.566510004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.280410003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.994310004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.710210003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.424110004.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.138010003.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.421710004.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.993110004.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.278810005.3126    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9997.560410004.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.278810006.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.425210005.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.287010003.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.287010002.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.001110002.4154    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9997.572710002.4154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  6  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  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
 10 11  1  0  0  0  0
 11 12  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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  CHG  2  21   1  27  -1
M  END
> <DATABASE_ID>
NP0000830

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1

> <INCHI_KEY>
XOMRRQXKHMYMOC-OAQYLSRUSA-N

> <FORMULA>
C23H45NO4

> <MOLECULAR_WEIGHT>
399.6077

> <EXACT_MASS>
399.334858933

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.35273260304272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.77

> <JCHEM_LOGP>
2.033547854194921

> <ALOGPS_LOGS>
-7.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057186892022333

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
137.07670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
palmitoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

NP0000830
     RDKit          3D

 73 72  0  0  0  0  0  0  0  0999 V2000
    9.0112    0.7381    1.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1987    1.2344    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9471    1.4203   -0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0583    0.2798   -0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3832   -0.3819    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4200    0.5120    0.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2980    1.0058    0.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874   -0.1368   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672   -1.0031    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0866   -2.1101   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932   -1.5415   -0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0877   -0.6998   -0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0485   -0.1405   -0.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -1.2029   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0237   -0.4956   -2.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387    0.3185   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    1.5731   -1.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3496   -0.3415   -0.2253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0332    0.3736    0.7818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2198    0.2692    2.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8678    0.9897    3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7549    0.4792    3.9054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5215    2.3174    3.5245 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.4188   -0.1445    1.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2648   -0.0891   -0.1435 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8599   -1.0465   -1.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3674    1.2044   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6106   -0.4960    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2469   -0.3549    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0824    1.0261    1.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8156    1.2599    2.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9747    0.6577   -0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6803    2.2667    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008    2.2331   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1596    1.8933   -1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3027    0.6300   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6017   -0.5515   -1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7252   -1.2376   -0.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0474   -0.8506    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9166    1.4146    1.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9943   -0.0436    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6114    1.5773    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6049    1.6772   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0281   -0.7758   -1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6960    0.3857   -1.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556   -0.3816    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937   -1.4421    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7524   -2.7752   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6358   -2.7016    0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4319   -2.3675   -1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3935   -0.9235   -1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599   -1.2351    0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151    0.1859    0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768    0.5242   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6534    0.4974   -0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4309   -1.7940   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3769   -1.9159   -2.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816   -1.1940   -2.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5932    0.2267   -3.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9916    1.4480    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0105   -0.7758    2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2188    0.7465    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3900   -1.2045    1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8663    0.4282    1.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1274   -1.7632   -0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3963   -0.5379   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7282   -1.6345   -1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3046    1.1897   -1.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5418    1.3613   -1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4964    2.0299   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6363   -1.5805    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3559   -0.3029   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8952    0.0531    1.1978 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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 19 60  1  6
 20 61  1  0
 20 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  CHG  2  23  -1  25   1
M  END

HEADER    PROTEIN                                 19-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-NOV-19         0                                  
HETATM    1  C   UNK     0    8664.7878674.278   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8666.1218673.506   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8667.4548674.278   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8668.7878673.506   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8670.1218674.278   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.4548673.506   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8672.7878674.278   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8674.1208673.506   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8675.4538674.278   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8676.7898673.506   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8678.1228674.278   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8679.4588673.506   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8680.7918674.278   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8682.1238673.506   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8683.4568674.278   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8684.7928673.506   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8686.1258674.278   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8687.4588673.506   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8667.4548675.817   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8664.7878675.817   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0    8663.4548676.584   0.000  0.00  0.00           N+1
HETATM   22  C   UNK     0    8662.1138675.813   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8663.4548678.124   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8661.8608677.504   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8663.4698673.487   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8663.4698671.947   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8664.8028671.175   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0    8662.1368671.175   0.000  0.00  0.00           O+0
CONECT    1    2   20   25                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
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   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    1   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

COMPND    NP0000830
HETATM    1  C1  UNL     1       9.011   0.738   1.479  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.199   1.234   0.103  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.947   1.420  -0.656  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.058   0.280  -0.906  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.383  -0.382   0.235  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.420   0.512   0.983  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.298   1.006   0.114  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.487  -0.137  -0.463  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.867  -1.003   0.597  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.087  -2.110  -0.047  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.993  -1.542  -0.912  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.088  -0.700  -0.077  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.049  -0.140  -0.911  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.905  -1.203  -1.528  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.024  -0.496  -2.305  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.739   0.319  -1.256  1.00  0.00           C  
HETATM   17  O1  UNL     1      -3.789   1.573  -1.297  1.00  0.00           O  
HETATM   18  O2  UNL     1      -4.350  -0.342  -0.225  1.00  0.00           O  
HETATM   19  C17 UNL     1      -5.033   0.374   0.782  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.220   0.269   2.089  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.868   0.990   3.195  1.00  0.00           C  
HETATM   22  O3  UNL     1      -5.755   0.479   3.905  1.00  0.00           O  
HETATM   23  O4  UNL     1      -4.521   2.317   3.525  1.00  0.00           O1-
HETATM   24  C20 UNL     1      -6.419  -0.144   1.016  1.00  0.00           C  
HETATM   25  N1  UNL     1      -7.265  -0.089  -0.144  1.00  0.00           N1+
HETATM   26  C21 UNL     1      -6.860  -1.047  -1.156  1.00  0.00           C  
HETATM   27  C22 UNL     1      -7.367   1.204  -0.747  1.00  0.00           C  
HETATM   28  C23 UNL     1      -8.611  -0.496   0.288  1.00  0.00           C  
HETATM   29  H1  UNL     1       9.247  -0.355   1.536  1.00  0.00           H  
HETATM   30  H2  UNL     1       8.082   1.026   1.987  1.00  0.00           H  
HETATM   31  H3  UNL     1       9.816   1.260   2.113  1.00  0.00           H  
HETATM   32  H4  UNL     1       9.975   0.658  -0.469  1.00  0.00           H  
HETATM   33  H5  UNL     1       9.680   2.267   0.170  1.00  0.00           H  
HETATM   34  H6  UNL     1       7.301   2.233  -0.180  1.00  0.00           H  
HETATM   35  H7  UNL     1       8.160   1.893  -1.674  1.00  0.00           H  
HETATM   36  H8  UNL     1       6.303   0.630  -1.684  1.00  0.00           H  
HETATM   37  H9  UNL     1       7.602  -0.552  -1.466  1.00  0.00           H  
HETATM   38  H10 UNL     1       5.725  -1.238  -0.135  1.00  0.00           H  
HETATM   39  H11 UNL     1       7.047  -0.851   0.955  1.00  0.00           H  
HETATM   40  H12 UNL     1       5.917   1.415   1.393  1.00  0.00           H  
HETATM   41  H13 UNL     1       4.994  -0.044   1.830  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.611   1.577   0.781  1.00  0.00           H  
HETATM   43  H15 UNL     1       4.605   1.677  -0.689  1.00  0.00           H  
HETATM   44  H16 UNL     1       4.028  -0.776  -1.160  1.00  0.00           H  
HETATM   45  H17 UNL     1       2.696   0.386  -1.080  1.00  0.00           H  
HETATM   46  H18 UNL     1       2.256  -0.382   1.282  1.00  0.00           H  
HETATM   47  H19 UNL     1       3.694  -1.442   1.251  1.00  0.00           H  
HETATM   48  H20 UNL     1       2.752  -2.775  -0.646  1.00  0.00           H  
HETATM   49  H21 UNL     1       1.636  -2.702   0.807  1.00  0.00           H  
HETATM   50  H22 UNL     1       0.432  -2.368  -1.432  1.00  0.00           H  
HETATM   51  H23 UNL     1       1.394  -0.924  -1.739  1.00  0.00           H  
HETATM   52  H24 UNL     1      -0.360  -1.235   0.783  1.00  0.00           H  
HETATM   53  H25 UNL     1       0.615   0.186   0.348  1.00  0.00           H  
HETATM   54  H26 UNL     1      -0.577   0.524  -1.666  1.00  0.00           H  
HETATM   55  H27 UNL     1      -1.653   0.497  -0.230  1.00  0.00           H  
HETATM   56  H28 UNL     1      -2.431  -1.794  -0.749  1.00  0.00           H  
HETATM   57  H29 UNL     1      -1.377  -1.916  -2.160  1.00  0.00           H  
HETATM   58  H30 UNL     1      -3.682  -1.194  -2.819  1.00  0.00           H  
HETATM   59  H31 UNL     1      -2.593   0.227  -3.024  1.00  0.00           H  
HETATM   60  H32 UNL     1      -4.992   1.448   0.531  1.00  0.00           H  
HETATM   61  H33 UNL     1      -4.010  -0.776   2.353  1.00  0.00           H  
HETATM   62  H34 UNL     1      -3.219   0.747   1.927  1.00  0.00           H  
HETATM   63  H35 UNL     1      -6.390  -1.205   1.351  1.00  0.00           H  
HETATM   64  H36 UNL     1      -6.866   0.428   1.859  1.00  0.00           H  
HETATM   65  H37 UNL     1      -6.127  -1.763  -0.741  1.00  0.00           H  
HETATM   66  H38 UNL     1      -6.396  -0.538  -2.027  1.00  0.00           H  
HETATM   67  H39 UNL     1      -7.728  -1.634  -1.533  1.00  0.00           H  
HETATM   68  H40 UNL     1      -8.305   1.190  -1.375  1.00  0.00           H  
HETATM   69  H41 UNL     1      -6.542   1.361  -1.464  1.00  0.00           H  
HETATM   70  H42 UNL     1      -7.496   2.030  -0.032  1.00  0.00           H  
HETATM   71  H43 UNL     1      -8.636  -1.581   0.538  1.00  0.00           H  
HETATM   72  H44 UNL     1      -9.356  -0.303  -0.501  1.00  0.00           H  
HETATM   73  H45 UNL     1      -8.895   0.053   1.198  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8   42   43
CONECT    8    9   44   45
CONECT    9   10   46   47
CONECT   10   11   48   49
CONECT   11   12   50   51
CONECT   12   13   52   53
CONECT   13   14   54   55
CONECT   14   15   56   57
CONECT   15   16   58   59
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   24   60
CONECT   20   21   61   62
CONECT   21   22   22   23
CONECT   24   25   63   64
CONECT   25   26   27   28
CONECT   26   65   66   67
CONECT   27   68   69   70
CONECT   28   71   72   73
END

NP0000830
     RDKit          3D

73 72  0  0  0  0  0  0  0  0999 V2000
    9.0112    0.7381    1.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1987    1.2344    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9471    1.4203   -0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0583    0.2798   -0.9062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3832   -0.3819    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4200    0.5120    0.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2980    1.0058    0.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4874   -0.1368   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672   -1.0031    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0866   -2.1101   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932   -1.5415   -0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0877   -0.6998   -0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0485   -0.1405   -0.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -1.2029   -1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0237   -0.4956   -2.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387    0.3185   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    1.5731   -1.2974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3496   -0.3415   -0.2253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0332    0.3736    0.7818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2198    0.2692    2.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8678    0.9897    3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7549    0.4792    3.9054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5215    2.3174    3.5245 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.4188   -0.1445    1.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2648   -0.0891   -0.1435 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.8599   -1.0465   -1.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3674    1.2044   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6106   -0.4960    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2469   -0.3549    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0824    1.0261    1.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8156    1.2599    2.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9747    0.6577   -0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6803    2.2667    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3008    2.2331   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1596    1.8933   -1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3027    0.6300   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6017   -0.5515   -1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7252   -1.2376   -0.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0474   -0.8506    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9166    1.4146    1.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9943   -0.0436    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6114    1.5773    0.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6049    1.6772   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0281   -0.7758   -1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6960    0.3857   -1.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556   -0.3816    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937   -1.4421    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7524   -2.7752   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6358   -2.7016    0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4319   -2.3675   -1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3935   -0.9235   -1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599   -1.2351    0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151    0.1859    0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768    0.5242   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6534    0.4974   -0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4309   -1.7940   -0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3769   -1.9159   -2.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816   -1.1940   -2.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5932    0.2267   -3.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9916    1.4480    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0105   -0.7758    2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2188    0.7465    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3900   -1.2045    1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8663    0.4282    1.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1274   -1.7632   -0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3963   -0.5379   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7282   -1.6345   -1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3046    1.1897   -1.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5418    1.3613   -1.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4964    2.0299   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6363   -1.5805    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3559   -0.3029   -0.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8952    0.0531    1.1978 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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 15 59  1  0
 19 60  1  6
 20 61  1  0
 20 62  1  0
 24 63  1  0
 24 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  CHG  2  23  -1  25   1
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate	ChEBI
(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoate	ChEBI
Hexadecanoyl-L-carnitine	ChEBI
Hexadecanoylcarnitine	ChEBI
Hexadecenoyl carnitine	ChEBI
L-Carnitine palmitoyl ester	ChEBI
L-Palmitoylcarnitine	ChEBI
O-Hexadecanoyl-(R)-carnitine	ChEBI
O-Hexadecanoyl-R-carnitine	ChEBI
Palmitoyl-L-carnitine	ChEBI
(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoic acid	Generator
(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid	Generator
(+)-Palmitoylcarnitine	HMDB
3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-propanaminium	HMDB
L(-)-Palmitylcarnitine	HMDB
L-Palmitoyl-L-carnitine	HMDB
Palmitoyl-(-)-carnitine	HMDB
Palmityl-L-carnitine	HMDB
Palmitylcarnitine	HMDB
(2R)-Palmitoylcarnitine	HMDB
C16 Carnitine	HMDB
Palmitoylcarnitine	ChEBI

Chemical Formula

C₂₃H₄₅NO₄

Average Mass

399.6077 Da

Monoisotopic Mass

399.33486 Da

IUPAC Name

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

Traditional Name

palmitoylcarnitine

CAS Registry Number

2364-67-2

SMILES

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

InChI Identifier

InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1

InChI Key

XOMRRQXKHMYMOC-OAQYLSRUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
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
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
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-acyl-L-carnitine (CHEBI:17490 )
O-palmitoylcarnitine (CHEBI:17490 )
Fatty acyl carnitines (C02990 )
Fatty acyl carnitines (LMFA07070004 )

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	1.2e-05 g/L	ALOGPS
logP	1.77	ALOGPS
logP	2.03	ChemAxon
logS	-7.6	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	20	ChemAxon
Refractivity	137.08 m³·mol⁻¹	ChemAxon
Polarizability	50.35 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

HMDB0000222

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17490

Good Scents ID

Not Available

References

General References

Kamimori H, Hamashima Y, Konishi M: Determination of carnitine and saturated-acyl group carnitines in human urine by high-performance liquid chromatography with fluorescence detection. Anal Biochem. 1994 May 1;218(2):417-24. [PubMed:8074302 ]
Mueller P, Schulze A, Schindler I, Ethofer T, Buehrdel P, Ceglarek U: Validation of an ESI-MS/MS screening method for acylcarnitine profiling in urine specimens of neonates, children, adolescents and adults. Clin Chim Acta. 2003 Jan;327(1-2):47-57. [PubMed:12482618 ]
Moder M, Kiessling A, Loster H, Bruggemann L: The pattern of urinary acylcarnitines determined by electrospray mass spectrometry: a new tool in the diagnosis of diabetes mellitus. Anal Bioanal Chem. 2003 Jan;375(2):200-10. Epub 2003 Jan 4. [PubMed:12560963 ]
Wasant P, Matsumoto I, Naylor E, Liammongkolkul S: Mitochondrial fatty acid oxidation disorders in Thai infants: a report of 3 cases. J Med Assoc Thai. 2002 Aug;85 Suppl 2:S710-9. [PubMed:12403251 ]
Poorthuis BJ, Jille-Vlckova T, Onkenhout W: Determination of acylcarnitines in urine of patients with inborn errors of metabolism using high-performance liquid chromatography after derivatization with 4'-bromophenacylbromide. Clin Chim Acta. 1993 Jul 16;216(1-2):53-61. [PubMed:8222273 ]
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Showing NP-Card for L-Palmitoylcarnitine (NP0000830)

MOL for NP0000830 (L-Palmitoylcarnitine)

3D MOL for NP0000830 (L-Palmitoylcarnitine)

3D SDF for NP0000830 (L-Palmitoylcarnitine)

3D-SDF for NP0000830 (L-Palmitoylcarnitine)

PDB for NP0000830 (L-Palmitoylcarnitine)

3D PDB for NP0000830 (L-Palmitoylcarnitine)

SMILES for NP0000830 (L-Palmitoylcarnitine)

INCHI for NP0000830 (L-Palmitoylcarnitine)

Structure for NP0000830 (L-Palmitoylcarnitine)

3D Structure for NP0000830 (L-Palmitoylcarnitine)