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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:53:21 UTC

Update Date

2021-09-26 23:09:56 UTC

HMDB ID

HMDB0255285

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N(6)-6(R,S)-lipoyl-L-lysine

Description

N(6)-6(R,S)-lipoyl-L-lysine belongs to the class of organic compounds known as lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring. Based on a literature review very few articles have been published on N(6)-6(R,S)-lipoyl-L-lysine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N(6)-6(r,s)-lipoyl-l-lysine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N(6)-6(R,S)-lipoyl-L-lysine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255285
     RDKit          3D
N(6)-6(R,S)-lipoyl-L-lysine
 47 47  0  0  0  0  0  0  0  0999 V2000
    4.0921    1.0424   -1.1119 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3314    0.5083   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2842   -0.3529    0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692    0.2794    1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.7760    1.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885   -0.3224    1.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532    0.2210    1.2248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0265   -0.6273    0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825   -1.8435    0.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942   -0.0913    0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -1.1771    0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7711   -0.7057    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9249    0.3496   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3647    0.8149   -0.8669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2637   -0.2575   -1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4748    0.0651   -1.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2553    1.5106   -2.9814 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022    2.1380   -2.0821 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9159   -0.3169   -1.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3179   -0.4360   -2.8614 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1235   -0.9628   -1.6146 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270    0.3886   -1.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799    1.9933   -1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0420    1.3509   -0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3515   -0.6580    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7264   -1.3054    0.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054    1.1293    2.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7786   -0.4493    2.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    1.1384    2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2848    1.5983    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948   -0.8483    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535   -1.0860    2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952    1.2213    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993    0.6914    0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464    0.3591    1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0567   -1.7641   -0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3395   -1.9151    1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0716   -0.2144    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4018   -1.5931    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870   -0.1002   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2743    1.2198   -0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052    1.2825    0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6981   -1.0669   -1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5700   -0.7874   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3683    0.2399   -1.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7629   -0.7755   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9936   -0.6609   -2.0218 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  1  0
 14 15  1  0
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 16 17  1  0
 17 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 18 14  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
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  4 27  1  0
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  6 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
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 11 36  1  0
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 13 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 21 47  1  0
M  END

  Mrv1652309112116532D          

 21 21  0  0  0  0            999 V2000
    0.9919   -1.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849   -1.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276   -0.5795    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244    0.0336    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7926    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2215    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7939   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5083    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2228   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9373    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6518   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3662    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6518   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9373    0.9355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  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  2  0  0  0  0
 10 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
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255285

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(CCCCNC(=O)CCCCC1CCSS1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H26N2O3S2/c15-12(14(18)19)6-3-4-9-16-13(17)7-2-1-5-11-8-10-20-21-11/h11-12H,1-10,15H2,(H,16,17)(H,18,19)

> <INCHI_KEY>
COTIXRRJLCSLLS-UHFFFAOYSA-N

> <FORMULA>
C14H26N2O3S2

> <MOLECULAR_WEIGHT>
334.49

> <EXACT_MASS>
334.138485053

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.30594074205128

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
-0.8170249658909206

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.876709047638645

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2426573474053453

> <JCHEM_PKA_STRONGEST_BASIC>
9.52653029055576

> <JCHEM_POLAR_SURFACE_AREA>
92.42

> <JCHEM_REFRACTIVITY>
88.98099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255285
     RDKit          3D
N(6)-6(R,S)-lipoyl-L-lysine
 47 47  0  0  0  0  0  0  0  0999 V2000
    4.0921    1.0424   -1.1119 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3314    0.5083   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2842   -0.3529    0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692    0.2794    1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.7760    1.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885   -0.3224    1.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532    0.2210    1.2248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0265   -0.6273    0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825   -1.8435    0.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942   -0.0913    0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -1.1771    0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7711   -0.7057    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9249    0.3496   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3647    0.8149   -0.8669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2637   -0.2575   -1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4748    0.0651   -1.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2553    1.5106   -2.9814 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022    2.1380   -2.0821 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9159   -0.3169   -1.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3179   -0.4360   -2.8614 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1235   -0.9628   -1.6146 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270    0.3886   -1.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799    1.9933   -1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0420    1.3509   -0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3515   -0.6580    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7264   -1.3054    0.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054    1.1293    2.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7786   -0.4493    2.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    1.1384    2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2848    1.5983    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948   -0.8483    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535   -1.0860    2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952    1.2213    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993    0.6914    0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464    0.3591    1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0567   -1.7641   -0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3395   -1.9151    1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0716   -0.2144    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4018   -1.5931    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870   -0.1002   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2743    1.2198   -0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052    1.2825    0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6981   -1.0669   -1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5700   -0.7874   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3683    0.2399   -1.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7629   -0.7755   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9936   -0.6609   -2.0218 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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 18 14  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 21 47  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.851  -2.095   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.345  -2.415   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      -0.425  -1.082   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0       0.606   0.063   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       2.012  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.346   0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.013   0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.347  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.681   0.206   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.681   1.746   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      10.015  -0.564   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      11.348   0.206   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.682  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.016   0.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.349  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.683   0.206   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.017  -0.564   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      19.350   0.206   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      18.017  -2.104   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      16.683   1.746   0.000  0.00  0.00           N+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0255285
HETATM    1  N1  UNL     1       4.092   1.042  -1.112  1.00  0.00           N  
HETATM    2  C1  UNL     1       5.331   0.508  -0.656  1.00  0.00           C  
HETATM    3  C2  UNL     1       5.284  -0.353   0.551  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.769   0.279   1.798  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.367   0.776   1.679  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.388  -0.322   1.325  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.053   0.221   1.225  1.00  0.00           N  
HETATM    8  C6  UNL     1      -0.027  -0.627   0.902  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.183  -1.843   0.704  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.394  -0.091   0.796  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.356  -1.177   0.445  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.771  -0.706   0.322  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.925   0.350  -0.754  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.365   0.815  -0.867  1.00  0.00           C  
HETATM   15  C12 UNL     1      -6.264  -0.258  -1.199  1.00  0.00           C  
HETATM   16  C13 UNL     1      -7.475   0.065  -1.937  1.00  0.00           C  
HETATM   17  S1  UNL     1      -7.255   1.511  -2.981  1.00  0.00           S  
HETATM   18  S2  UNL     1      -5.402   2.138  -2.082  1.00  0.00           S  
HETATM   19  C14 UNL     1       5.916  -0.317  -1.769  1.00  0.00           C  
HETATM   20  O2  UNL     1       5.318  -0.436  -2.861  1.00  0.00           O  
HETATM   21  O3  UNL     1       7.123  -0.963  -1.615  1.00  0.00           O  
HETATM   22  H1  UNL     1       3.527   0.389  -1.690  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.180   1.993  -1.536  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.042   1.351  -0.459  1.00  0.00           H  
HETATM   25  H4  UNL     1       6.352  -0.658   0.778  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.726  -1.305   0.398  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.405   1.129   2.131  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.779  -0.449   2.654  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.056   1.138   2.710  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.285   1.598   0.977  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.695  -0.848   0.409  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.354  -1.086   2.150  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.895   1.221   1.389  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.399   0.691   0.007  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.746   0.359   1.762  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.057  -1.764  -0.445  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.340  -1.915   1.297  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.072  -0.214   1.285  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.402  -1.593   0.112  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.587  -0.100  -1.717  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.274   1.220  -0.571  1.00  0.00           H  
HETATM   42  H21 UNL     1      -5.605   1.283   0.131  1.00  0.00           H  
HETATM   43  H22 UNL     1      -5.698  -1.067  -1.749  1.00  0.00           H  
HETATM   44  H23 UNL     1      -6.570  -0.787  -0.244  1.00  0.00           H  
HETATM   45  H24 UNL     1      -8.368   0.240  -1.300  1.00  0.00           H  
HETATM   46  H25 UNL     1      -7.763  -0.775  -2.620  1.00  0.00           H  
HETATM   47  H26 UNL     1       7.994  -0.661  -2.022  1.00  0.00           H  
CONECT    1    2   22   23
CONECT    2    3   19   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   33
CONECT    8    9    9   10
CONECT   10   11   34   35
CONECT   11   12   36   37
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   18   42
CONECT   15   16   43   44
CONECT   16   17   45   46
CONECT   17   18
CONECT   19   20   20   21
CONECT   21   47
END

HMDB0255285
     RDKit          3D
N(6)-6(R,S)-lipoyl-L-lysine
 47 47  0  0  0  0  0  0  0  0999 V2000
    4.0921    1.0424   -1.1119 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3314    0.5083   -0.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2842   -0.3529    0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7692    0.2794    1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.7760    1.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885   -0.3224    1.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532    0.2210    1.2248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0265   -0.6273    0.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825   -1.8435    0.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3942   -0.0913    0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -1.1771    0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7711   -0.7057    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9249    0.3496   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3647    0.8149   -0.8669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2637   -0.2575   -1.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4748    0.0651   -1.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2553    1.5106   -2.9814 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022    2.1380   -2.0821 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9159   -0.3169   -1.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3179   -0.4360   -2.8614 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1235   -0.9628   -1.6146 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270    0.3886   -1.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799    1.9933   -1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0420    1.3509   -0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3515   -0.6580    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7264   -1.3054    0.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054    1.1293    2.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7786   -0.4493    2.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    1.1384    2.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2848    1.5983    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948   -0.8483    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535   -1.0860    2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952    1.2213    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3993    0.6914    0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464    0.3591    1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0567   -1.7641   -0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3395   -1.9151    1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0716   -0.2144    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4018   -1.5931    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5870   -0.1002   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2743    1.2198   -0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6052    1.2825    0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6981   -1.0669   -1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5700   -0.7874   -0.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3683    0.2399   -1.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7629   -0.7755   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9936   -0.6609   -2.0218 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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 18 14  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 21 47  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₂₆N₂O₃S₂

Average Molecular Weight

334.49

Monoisotopic Molecular Weight

334.138485053

IUPAC Name

2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid

Traditional Name

2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid

CAS Registry Number

Not Available

SMILES

NC(CCCCNC(=O)CCCCC1CCSS1)C(O)=O

InChI Identifier

InChI=1S/C14H26N2O3S2/c15-12(14(18)19)6-3-4-9-16-13(17)7-2-1-5-11-8-10-20-21-11/h11-12H,1-10,15H2,(H,16,17)(H,18,19)

InChI Key

COTIXRRJLCSLLS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dithiolanes

Sub Class

Lipoamides

Direct Parent

Lipoamides

Alternative Parents

Substituents

Lipoamide
Alpha-amino acid
Alpha-amino acid or derivatives
Medium-chain fatty acid
Heterocyclic fatty acid
Fatty amide
N-acyl-amine
Fatty acyl
Fatty acid
1,2-dithiolane
Amino acid or derivatives
Carboxamide group
Amino acid
Organic disulfide
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Primary aliphatic amine
Organic oxygen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	-0.02	ALOGPS
logP	-0.82	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.24	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	88.98 m³·mol⁻¹	ChemAxon
Polarizability	37.31 Å³	ChemAxon
Number of Rings	1	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]+	170.223	30932474
DeepCCS	[M-H]-	166.967	30932474
DeepCCS	[M-2H]-	202.859	30932474
DeepCCS	[M+Na]+	179.038	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N(6)-6(R,S)-lipoyl-L-lysine	NC(CCCCNC(=O)CCCCC1CCSS1)C(O)=O	4166.6	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine	NC(CCCCNC(=O)CCCCC1CCSS1)C(O)=O	2860.3	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine	NC(CCCCNC(=O)CCCCC1CCSS1)C(O)=O	3138.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #1	C[Si](C)(C)NC(CCCCNC(=O)CCCCC1CCSS1)C(=O)O[Si](C)(C)C	3230.9	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #1	C[Si](C)(C)NC(CCCCNC(=O)CCCCC1CCSS1)C(=O)O[Si](C)(C)C	2996.0	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #1	C[Si](C)(C)NC(CCCCNC(=O)CCCCC1CCSS1)C(=O)O[Si](C)(C)C	4332.0	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C	3130.5	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C	2999.5	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(N)CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C	4658.5	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #3	C[Si](C)(C)N(C(CCCCNC(=O)CCCCC1CCSS1)C(=O)O)[Si](C)(C)C	3353.7	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #3	C[Si](C)(C)N(C(CCCCNC(=O)CCCCC1CCSS1)C(=O)O)[Si](C)(C)C	3066.1	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #3	C[Si](C)(C)N(C(CCCCNC(=O)CCCCC1CCSS1)C(=O)O)[Si](C)(C)C	4475.5	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #4	C[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C)C(=O)O	3192.2	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #4	C[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C)C(=O)O	3039.6	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TMS,isomer #4	C[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C)C(=O)O	4495.7	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCNC(=O)CCCCC1CCSS1)N([Si](C)(C)C)[Si](C)(C)C	3340.4	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCNC(=O)CCCCC1CCSS1)N([Si](C)(C)C)[Si](C)(C)C	3119.1	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCNC(=O)CCCCC1CCSS1)N([Si](C)(C)C)[Si](C)(C)C	3929.0	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TMS,isomer #2	C[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3218.3	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TMS,isomer #2	C[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3097.5	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TMS,isomer #2	C[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3904.3	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TMS,isomer #3	C[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)CCCCC1CCSS1	3285.7	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TMS,isomer #3	C[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)CCCCC1CCSS1	3163.2	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TMS,isomer #3	C[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)CCCCC1CCSS1	4080.5	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3284.6	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3209.3	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3620.7	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCCCNC(=O)CCCCC1CCSS1)C(=O)O[Si](C)(C)C(C)(C)C	3689.0	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCCCNC(=O)CCCCC1CCSS1)C(=O)O[Si](C)(C)C(C)(C)C	3458.9	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CCCCNC(=O)CCCCC1CCSS1)C(=O)O[Si](C)(C)C(C)(C)C	4126.7	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C	3571.3	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C	3442.7	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(N)CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C	4465.6	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(CCCCNC(=O)CCCCC1CCSS1)C(=O)O)[Si](C)(C)C(C)(C)C	3796.2	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(CCCCNC(=O)CCCCC1CCSS1)C(=O)O)[Si](C)(C)C(C)(C)C	3470.2	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(CCCCNC(=O)CCCCC1CCSS1)C(=O)O)[Si](C)(C)C(C)(C)C	4303.6	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C)C(=O)O	3664.0	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C)C(=O)O	3472.6	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C)C(=O)O	4291.2	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCNC(=O)CCCCC1CCSS1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3987.6	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCNC(=O)CCCCC1CCSS1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3723.9	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCNC(=O)CCCCC1CCSS1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3901.6	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3827.2	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3715.9	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3899.9	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)CCCCC1CCSS1	3931.7	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)CCCCC1CCSS1	3729.8	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)CCCCC1CCSS1	4013.8	Standard polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4111.0	Semi standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3940.6	Standard non polar	33892256
N(6)-6(R,S)-lipoyl-L-lysine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCN(C(=O)CCCCC1CCSS1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3755.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-6(R,S)-lipoyl-L-lysine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f7x-6940000000-e2852a69a691a0b4e052	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-6(R,S)-lipoyl-L-lysine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-6(R,S)-lipoyl-L-lysine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-6(R,S)-lipoyl-L-lysine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-6(R,S)-lipoyl-L-lysine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-6(R,S)-lipoyl-L-lysine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-6(R,S)-lipoyl-L-lysine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N(6)-6(R,S)-lipoyl-L-lysine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

485486

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

558483

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for N(6)-6(R,S)-lipoyl-L-lysine (HMDB0255285)

MOL for HMDB0255285 (N(6)-6(R,S)-lipoyl-L-lysine)

3D MOL for HMDB0255285 (N(6)-6(R,S)-lipoyl-L-lysine)

3D SDF for HMDB0255285 (N(6)-6(R,S)-lipoyl-L-lysine)

3D-SDF for HMDB0255285 (N(6)-6(R,S)-lipoyl-L-lysine)

PDB for HMDB0255285 (N(6)-6(R,S)-lipoyl-L-lysine)

3D PDB for HMDB0255285 (N(6)-6(R,S)-lipoyl-L-lysine)

SMILES for HMDB0255285 (N(6)-6(R,S)-lipoyl-L-lysine)

INCHI for HMDB0255285 (N(6)-6(R,S)-lipoyl-L-lysine)

Structure for HMDB0255285 (N(6)-6(R,S)-lipoyl-L-lysine)

3D Structure for HMDB0255285 (N(6)-6(R,S)-lipoyl-L-lysine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

NMR Spectra