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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-04-16 17:45:37 UTC

Update Date

2022-10-24 19:44:14 UTC

HMDB ID

HMDB0061677

Secondary Accession Numbers

HMDB61677

Metabolite Identification

Common Name

O-Adipoylcarnitine

Description

O-Adipoylcarnitine is an acylcarnitine. More specifically, it is an adipic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. 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. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. O-Adipoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine O-adipoylcarnitine is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494 ). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).

Structure

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

HMDB0061677
     RDKit          3D
O-Adipoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
   -3.6873   -0.4077    2.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570   -0.2918    0.8504 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.1595    0.8231    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398   -1.5124    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9403   -0.0855    0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148   -0.4555   -0.5416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8817    0.1918   -1.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7977    1.6489   -1.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683    2.2635   -0.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930    2.4101   -2.8184 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -0.2233   -0.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0357   -1.2382   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5981   -2.4045   -0.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5102   -1.0015   -0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8024    0.4694   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2631    0.7715   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9495    0.0634    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4067    0.3668    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9953    1.1189    0.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1465   -0.2399    1.8394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897    0.3697    2.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -1.4032    2.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7942   -0.3710    2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483    1.7973    0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6353    0.6149   -0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0572    0.9486    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4266   -1.3541   -0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -2.3014    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6132   -1.9929    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7486    0.9628    1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -0.7153    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050   -1.5505   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2498   -0.2284   -2.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872   -0.1383   -1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8444    3.2344   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9893   -1.3413   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9573   -1.6183    0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3003    0.8783    0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    0.9809   -1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413    0.5004   -1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203    1.8605   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4909    0.3830    1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548   -1.0408    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0014   -0.7421    1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  6
  7 33  1  0
  7 34  1  0
 10 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 20 44  1  0
M  CHG  1   2   1
M  END


  Mrv1652305221923392D          

 20 19  0  0  0  0            999 V2000
10000.545010002.4198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.259110002.0063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.973510002.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.687410002.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.401310002.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.117310002.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.831210002.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.545210002.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.261210002.4198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.545210001.1814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.973510003.2445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.545010003.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.830610003.6551    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9999.112110003.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.830610004.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.977010004.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.838710001.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.838710001.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.553010000.7577    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 9999.124310000.7577    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
  8 10  2  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>
HMDB0061677

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H23NO6/c1-14(2,3)9-10(8-12(17)18)20-13(19)7-5-4-6-11(15)16/h10H,4-9H2,1-3H3,(H-,15,16,17,18)/t10-/m1/s1

> <INCHI_KEY>
BSVHAXJKBCWVDA-SNVBAGLBSA-N

> <FORMULA>
C13H23NO6

> <MOLECULAR_WEIGHT>
289.328

> <EXACT_MASS>
289.152537465

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
29.80437780597393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(5-carboxypentanoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.84

> <JCHEM_LOGP>
-3.732380560805078

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.391842065487733

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.681365675033958

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057189057238216

> <JCHEM_POLAR_SURFACE_AREA>
103.72999999999999

> <JCHEM_REFRACTIVITY>
92.73209999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(5-carboxypentanoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061677
     RDKit          3D
O-Adipoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
   -3.6873   -0.4077    2.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570   -0.2918    0.8504 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.1595    0.8231    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398   -1.5124    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9403   -0.0855    0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148   -0.4555   -0.5416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8817    0.1918   -1.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7977    1.6489   -1.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683    2.2635   -0.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930    2.4101   -2.8184 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -0.2233   -0.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0357   -1.2382   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5981   -2.4045   -0.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5102   -1.0015   -0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8024    0.4694   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2631    0.7715   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9495    0.0634    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4067    0.3668    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9953    1.1189    0.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1465   -0.2399    1.8394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897    0.3697    2.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -1.4032    2.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7942   -0.3710    2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483    1.7973    0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6353    0.6149   -0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0572    0.9486    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4266   -1.3541   -0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -2.3014    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6132   -1.9929    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7486    0.9628    1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -0.7153    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050   -1.5505   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2498   -0.2284   -2.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872   -0.1383   -1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8444    3.2344   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9893   -1.3413   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9573   -1.6183    0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3003    0.8783    0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    0.9809   -1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413    0.5004   -1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203    1.8605   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4909    0.3830    1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548   -1.0408    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0014   -0.7421    1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  6
  7 33  1  0
  7 34  1  0
 10 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 20 44  1  0
M  CHG  1   2   1
M  END

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0    8667.6848671.184   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8669.0178670.412   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8670.3508671.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8671.6838670.412   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8673.0168671.184   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8674.3528670.412   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8675.6858671.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8677.0188670.412   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8678.3548671.184   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8677.0188668.872   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8670.3508672.723   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8667.6848672.723   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8666.3508673.490   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0    8665.0098672.719   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.3508675.030   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.7578674.410   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8666.3668670.392   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.3668668.853   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8667.6998668.081   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0    8665.0328668.081   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   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
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    HMDB0061677
HETATM    1  C1  UNL     1      -3.687  -0.408   2.300  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.357  -0.292   0.850  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -4.159   0.823   0.393  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.840  -1.512   0.265  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.940  -0.086   0.746  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.315  -0.455  -0.542  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.882   0.192  -1.772  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.798   1.649  -1.773  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.268   2.264  -0.815  1.00  0.00           O  
HETATM   10  O2  UNL     1      -2.293   2.410  -2.818  1.00  0.00           O  
HETATM   11  O3  UNL     1       0.117  -0.223  -0.501  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.036  -1.238  -0.620  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.598  -2.405  -0.769  1.00  0.00           O  
HETATM   14  C9  UNL     1       2.510  -1.001  -0.578  1.00  0.00           C  
HETATM   15  C10 UNL     1       2.802   0.469  -0.390  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.263   0.771  -0.344  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.950   0.063   0.781  1.00  0.00           C  
HETATM   18  C13 UNL     1       6.407   0.367   0.831  1.00  0.00           C  
HETATM   19  O5  UNL     1       6.995   1.119   0.037  1.00  0.00           O  
HETATM   20  O6  UNL     1       7.147  -0.240   1.839  1.00  0.00           O  
HETATM   21  H1  UNL     1      -3.190   0.370   2.879  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.370  -1.403   2.668  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.794  -0.371   2.422  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.648   1.797   0.446  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.635   0.615  -0.599  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.057   0.949   1.075  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.427  -1.354  -0.683  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.068  -2.301   0.155  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.613  -1.993   0.943  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.749   0.963   1.064  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.488  -0.715   1.573  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.405  -1.551  -0.679  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.250  -0.228  -2.622  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.887  -0.138  -1.994  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.844   3.234  -2.631  1.00  0.00           H  
HETATM   36  H16 UNL     1       2.989  -1.341  -1.498  1.00  0.00           H  
HETATM   37  H17 UNL     1       2.957  -1.618   0.253  1.00  0.00           H  
HETATM   38  H18 UNL     1       2.300   0.878   0.515  1.00  0.00           H  
HETATM   39  H19 UNL     1       2.385   0.981  -1.295  1.00  0.00           H  
HETATM   40  H20 UNL     1       4.741   0.500  -1.313  1.00  0.00           H  
HETATM   41  H21 UNL     1       4.420   1.861  -0.229  1.00  0.00           H  
HETATM   42  H22 UNL     1       4.491   0.383   1.728  1.00  0.00           H  
HETATM   43  H23 UNL     1       4.855  -1.041   0.670  1.00  0.00           H  
HETATM   44  H24 UNL     1       8.001  -0.742   1.698  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    5
CONECT    3   24   25   26
CONECT    4   27   28   29
CONECT    5    6   30   31
CONECT    6    7   11   32
CONECT    7    8   33   34
CONECT    8    9    9   10
CONECT   10   35
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   36   37
CONECT   15   16   38   39
CONECT   16   17   40   41
CONECT   17   18   42   43
CONECT   18   19   19   20
CONECT   20   44
END

HMDB0061677
     RDKit          3D
O-Adipoylcarnitine
 44 43  0  0  0  0  0  0  0  0999 V2000
   -3.6873   -0.4077    2.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570   -0.2918    0.8504 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.1595    0.8231    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398   -1.5124    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9403   -0.0855    0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148   -0.4555   -0.5416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8817    0.1918   -1.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7977    1.6489   -1.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683    2.2635   -0.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2930    2.4101   -2.8184 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -0.2233   -0.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0357   -1.2382   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5981   -2.4045   -0.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5102   -1.0015   -0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8024    0.4694   -0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2631    0.7715   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9495    0.0634    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4067    0.3668    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9953    1.1189    0.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1465   -0.2399    1.8394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897    0.3697    2.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3701   -1.4032    2.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7942   -0.3710    2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483    1.7973    0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6353    0.6149   -0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0572    0.9486    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4266   -1.3541   -0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -2.3014    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6132   -1.9929    0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7486    0.9628    1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -0.7153    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4050   -1.5505   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2498   -0.2284   -2.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872   -0.1383   -1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8444    3.2344   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9893   -1.3413   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9573   -1.6183    0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3003    0.8783    0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    0.9809   -1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413    0.5004   -1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203    1.8605   -0.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4909    0.3830    1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548   -1.0408    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0014   -0.7421    1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  6
  7 33  1  0
  7 34  1  0
 10 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 20 44  1  0
M  CHG  1   2   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
O-Adipoyl-L-carnitine	HMDB
O-Adipoylcarnitine	HMDB

Chemical Formula

C₁₃H₂₄NO₆

Average Molecular Weight

290.335

Monoisotopic Molecular Weight

290.159813917

IUPAC Name

(3R)-3-[(5-carboxypentanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-[(5-carboxypentanoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

102636-83-9

SMILES

C[N+](C)(C)C[C@@H](CC(O)=O)OC(=O)CCCCC(O)=O

InChI Identifier

InChI=1S/C13H23NO6/c1-14(2,3)9-10(8-12(17)18)20-13(19)7-5-4-6-11(15)16/h10H,4-9H2,1-3H3,(H-,15,16,17,18)/p+1/t10-/m1/s1

InChI Key

BSVHAXJKBCWVDA-SNVBAGLBSA-O

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
Tricarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organic salt
Organooxygen compound
Organonitrogen compound
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:86507 )
O-adipoylcarnitine (CHEBI:86507 )

Ontology

Physiological effect

Health effect

Cancer

Breast cancer (PMID: 35710135)

Diabetes mellitus type 2 (PMID: 35710135)
Celiac disease (PMID: 35710135)
Inflammatory bowel disease (PMID: 35710135)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (PMID: 35710135)
Heart failure (PMID: 35710135)

Renal system and urinary system

Renal disorder

Renal cell carcinoma (PMID: 35710135)

Urine (PMID: 32966057)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cell

All cells and tissues (PMID: 35710135)

Cellular substructure

cytoplasm (PMID: 35710135)
mitochondrion matrix (PMID: 35710135)

Organelle

peroxisome (PMID: 35710135)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

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
Water Solubility	0.057 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-3.7	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.73 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	92.73 m³·mol⁻¹	ChemAxon
Polarizability	29.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	168.611	30932474
DeepCCS	[M-H]-	166.216	30932474
DeepCCS	[M-2H]-	199.1	30932474
DeepCCS	[M+Na]+	174.524	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Adipoylcarnitine	C[N+](C)(C)C[C@@H](CC(O)=O)OC(=O)CCCCC(O)=O	3346.5	Standard polar	33892256
O-Adipoylcarnitine	C[N+](C)(C)C[C@@H](CC(O)=O)OC(=O)CCCCC(O)=O	1751.1	Standard non polar	33892256
O-Adipoylcarnitine	C[N+](C)(C)C[C@@H](CC(O)=O)OC(=O)CCCCC(O)=O	2133.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Adipoylcarnitine,1TMS,isomer #1	C[N+](C)(C)C[C@@H](CC(=O)O[Si](C)(C)C)OC(=O)CCCCC(=O)O	2141.1	Semi standard non polar	33892256
O-Adipoylcarnitine,1TMS,isomer #2	C[N+](C)(C)C[C@@H](CC(=O)O)OC(=O)CCCCC(=O)O[Si](C)(C)C	2149.2	Semi standard non polar	33892256
O-Adipoylcarnitine,2TMS,isomer #1	C[N+](C)(C)C[C@@H](CC(=O)O[Si](C)(C)C)OC(=O)CCCCC(=O)O[Si](C)(C)C	2182.0	Semi standard non polar	33892256
O-Adipoylcarnitine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C[N+](C)(C)C)OC(=O)CCCCC(=O)O	2378.6	Semi standard non polar	33892256
O-Adipoylcarnitine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(=O)O[C@H](CC(=O)O)C[N+](C)(C)C	2397.7	Semi standard non polar	33892256
O-Adipoylcarnitine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	2630.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O-Adipoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Adipoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Adipoylcarnitine 10V, Positive-QTOF	splash10-0006-0090000000-08d94c016258f3f2a373	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Adipoylcarnitine 20V, Positive-QTOF	splash10-000l-9050000000-42bdebd13e27d1118cb2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Adipoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91826562

PDB ID

Not Available

ChEBI ID

86507

Food Biomarker Ontology

Not Available

VMH ID

C6DC

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ferdinandusse S, Mulders J, IJlst L, Denis S, Dacremont G, Waterham HR, Wanders RJ: Molecular cloning and expression of human carnitine octanoyltransferase: evidence for its role in the peroxisomal beta-oxidation of branched-chain fatty acids. Biochem Biophys Res Commun. 1999 Sep 16;263(1):213-8. [PubMed:10486279 ]
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 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Violante S, Achetib N, van Roermund CWT, Hagen J, Dodatko T, Vaz FM, Waterham HR, Chen H, Baes M, Yu C, Argmann CA, Houten SM: Peroxisomes can oxidize medium- and long-chain fatty acids through a pathway involving ABCD3 and HSD17B4. FASEB J. 2019 Mar;33(3):4355-4364. doi: 10.1096/fj.201801498R. Epub 2018 Dec 12. [PubMed:30540494 ]
Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for O-Adipoylcarnitine (HMDB0061677)

MOL for HMDB0061677 (O-Adipoylcarnitine)

3D MOL for HMDB0061677 (O-Adipoylcarnitine)

3D SDF for HMDB0061677 (O-Adipoylcarnitine)

3D-SDF for HMDB0061677 (O-Adipoylcarnitine)

PDB for HMDB0061677 (O-Adipoylcarnitine)

3D PDB for HMDB0061677 (O-Adipoylcarnitine)

SMILES for HMDB0061677 (O-Adipoylcarnitine)

INCHI for HMDB0061677 (O-Adipoylcarnitine)

Structure for HMDB0061677 (O-Adipoylcarnitine)

3D Structure for HMDB0061677 (O-Adipoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra