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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-02 23:11:25 UTC

Update Date

2021-09-14 15:20:00 UTC

HMDB ID

HMDB0013127

Secondary Accession Numbers

HMDB13127

Metabolite Identification

Common Name

3-Hydroxybutyrylcarnitine

Description

3-Hydroxybutyrylcarnitine is an acylcarnitine. More specifically, it is an 3-hydroxybutyric 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 [Dambrova et al. 2021, Physiological Reviews], 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. 3-Hydroxybutyrylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine 3-hydroxybutyrylcarnitine is a member of the most abundant group of carnitines in the body, comprising more than 50% of all acylcarnitines quantified in tissues and biofluids (PMID: 31920980 ). Some short-chain carnitines have been studied as supplements or treatments for a number of diseases, including neurological disorders and inborn errors of metabolism. In particular 3-hydroxybutyrylcarnitine is elevated in the blood or plasma of individuals with short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency (PMID: 11489939 , PMID: 15870679 ), prediabetes (PMID: 28505362 ), T2DM (PMID: 28505362 ), metallosis (PMID: 30271721 ), mitochondrial acetoacetyl-coa thiolase deficiency (PMID: 20157782 ), and heart failure (PMID: 25881932 ). It is also decreased in the blood or plasma of individuals with psoriasis (PMID: 33391503 ). 3-Hydroxybutyrylcarnitine is elevated in the urine of individuals with renal cell carcinoma (PMID: 29658093 ). Carnitine acetyltransferase (CrAT, EC:2.3.1.7) is responsible for the synthesis of all short-chain and short branched-chain acylcarnitines (PMID: 23485643 ). 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 at [Dambrova et al. 2021, Physiological Reviews].

Structure

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

HMDB0013127
     RDKit          3D
3-Hydroxybutyrylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
    5.3824    0.4962    0.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961    0.5037    0.0116 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8226   -0.8167   -0.3644 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0108    1.0416    0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    1.0531    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836    1.9855   -0.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712    0.0787    0.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528    0.0747   -0.4529 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3985   -1.0880   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2435   -2.3712   -0.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342   -3.4200   -1.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1088   -2.5338    0.6995 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.5454    0.1199    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8771    0.1281    0.1008 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.1377    0.5702   -1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5375   -1.1652    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263    1.0571    0.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7484    1.5488    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1546    0.0918    1.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1321   -0.1220    0.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2274    1.1631   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6464   -1.3780   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793    0.2991    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2884    2.0251    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    1.0031   -1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1982   -1.1144   -2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -0.9631   -1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331    1.0360    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -0.7160    1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0414    1.2503   -1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3193    1.1733   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333   -0.2824   -1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5189   -1.3596    1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6284   -1.0671    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -2.0028   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3377    2.0983    0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993    0.8429    0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4058    0.7597    2.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  CHG  2  12  -1  14   1
M  END


  Mrv1652304202022142D          

 17 16  0  0  1  0            999 V2000
   11.8457   -5.2117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5601   -4.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2746   -5.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2746   -6.0367    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.9891   -4.7992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1312   -4.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1312   -3.9742    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   11.9562   -3.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3062   -3.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1312   -3.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8457   -6.0367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6968   -6.4485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4113   -6.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1257   -6.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1257   -7.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9824   -6.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6969   -7.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  3  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 11 14  1  0  0  0  0
 15 14  2  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  6  0  0  0
  1 11  1  6  0  0  0
M  CHG  2   4  -1   7   1
M  END
> <DATABASE_ID>
HMDB0013127

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21NO5/c1-8(13)5-11(16)17-9(6-10(14)15)7-12(2,3)4/h8-9,13H,5-7H2,1-4H3/t8-,9+/m1/s1

> <INCHI_KEY>
UEFRDQSMQXDWTO-BDAKNGLRSA-N

> <FORMULA>
C11H21NO5

> <MOLECULAR_WEIGHT>
247.291

> <EXACT_MASS>
247.14197278

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
25.514152693911953

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.29

> <JCHEM_LOGP>
-4.610040922805079

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.407211276790267

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.137752211470946

> <JCHEM_PKA_STRONGEST_BASIC>
-2.620686071792176

> <JCHEM_POLAR_SURFACE_AREA>
86.66000000000001

> <JCHEM_REFRACTIVITY>
83.45719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013127
     RDKit          3D
3-Hydroxybutyrylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
    5.3824    0.4962    0.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961    0.5037    0.0116 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8226   -0.8167   -0.3644 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0108    1.0416    0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    1.0531    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836    1.9855   -0.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712    0.0787    0.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528    0.0747   -0.4529 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3985   -1.0880   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2435   -2.3712   -0.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342   -3.4200   -1.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1088   -2.5338    0.6995 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.5454    0.1199    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8771    0.1281    0.1008 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.1377    0.5702   -1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5375   -1.1652    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263    1.0571    0.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7484    1.5488    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1546    0.0918    1.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1321   -0.1220    0.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2274    1.1631   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6464   -1.3780   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793    0.2991    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2884    2.0251    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    1.0031   -1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1982   -1.1144   -2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -0.9631   -1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331    1.0360    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -0.7160    1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0414    1.2503   -1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3193    1.1733   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333   -0.2824   -1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5189   -1.3596    1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6284   -1.0671    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -2.0028   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3377    2.0983    0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993    0.8429    0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4058    0.7597    2.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  CHG  2  12  -1  14   1
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      22.112  -9.729   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.446  -8.959   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.779  -9.729   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      24.779 -11.269   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      26.113  -8.959   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      20.778  -8.959   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      20.778  -7.419   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0      22.318  -7.419   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.238  -7.419   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.778  -5.879   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.112 -11.269   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      18.101 -12.037   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.434 -11.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.768 -12.037   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      20.768 -13.577   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      16.767 -11.267   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      18.101 -13.577   0.000  0.00  0.00           O+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11   14    1                                                       
CONECT   12   13   16   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   11   15                                                  
CONECT   15   14                                                            
CONECT   16   12                                                            
CONECT   17   12                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0013127
HETATM    1  C1  UNL     1       5.382   0.496   0.806  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.096   0.504   0.012  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.823  -0.817  -0.364  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.011   1.042   0.930  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.742   1.053   0.157  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.484   1.985  -0.679  1.00  0.00           O  
HETATM    7  O3  UNL     1       0.771   0.079   0.281  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.453   0.075  -0.453  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.399  -1.088  -1.372  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.244  -2.371  -0.663  1.00  0.00           C  
HETATM   11  O4  UNL     1      -0.234  -3.420  -1.393  1.00  0.00           O  
HETATM   12  O5  UNL     1      -0.109  -2.534   0.699  1.00  0.00           O1-
HETATM   13  C8  UNL     1      -1.545   0.120   0.540  1.00  0.00           C  
HETATM   14  N1  UNL     1      -2.877   0.128   0.101  1.00  0.00           N1+
HETATM   15  C9  UNL     1      -3.138   0.570  -1.241  1.00  0.00           C  
HETATM   16  C10 UNL     1      -3.537  -1.165   0.367  1.00  0.00           C  
HETATM   17  C11 UNL     1      -3.626   1.057   0.976  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.748   1.549   0.824  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.155   0.092   1.806  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.132  -0.122   0.293  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.227   1.163  -0.858  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.646  -1.378  -0.300  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.879   0.299   1.765  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.288   2.025   1.310  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.383   1.003  -1.083  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.198  -1.114  -2.136  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.550  -0.963  -1.978  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.333   1.036   1.176  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.418  -0.716   1.258  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.041   1.250  -1.302  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.319   1.173  -1.675  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.433  -0.282  -1.922  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.519  -1.360   1.457  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.628  -1.067   0.095  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.057  -2.003  -0.132  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.338   2.098   0.758  1.00  0.00           H  
HETATM   37  H20 UNL     1      -4.699   0.843   0.799  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.406   0.760   2.029  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   21
CONECT    3   22
CONECT    4    5   23   24
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   13   25
CONECT    9   10   26   27
CONECT   10   11   11   12
CONECT   13   14   28   29
CONECT   14   15   16   17
CONECT   15   30   31   32
CONECT   16   33   34   35
CONECT   17   36   37   38
END

HMDB0013127
     RDKit          3D
3-Hydroxybutyrylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
    5.3824    0.4962    0.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0961    0.5037    0.0116 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8226   -0.8167   -0.3644 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0108    1.0416    0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    1.0531    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4836    1.9855   -0.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7712    0.0787    0.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4528    0.0747   -0.4529 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3985   -1.0880   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2435   -2.3712   -0.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342   -3.4200   -1.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1088   -2.5338    0.6995 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.5454    0.1199    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8771    0.1281    0.1008 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.1377    0.5702   -1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5375   -1.1652    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263    1.0571    0.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7484    1.5488    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1546    0.0918    1.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1321   -0.1220    0.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2274    1.1631   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6464   -1.3780   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793    0.2991    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2884    2.0251    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    1.0031   -1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1982   -1.1144   -2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5502   -0.9631   -1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331    1.0360    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -0.7160    1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0414    1.2503   -1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3193    1.1733   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333   -0.2824   -1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5189   -1.3596    1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6284   -1.0671    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -2.0028   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3377    2.0983    0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993    0.8429    0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4058    0.7597    2.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  CHG  2  12  -1  14   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylazaniumyl)butanoic acid	HMDB
(3S)-Hydroxybutyrylcarnitine	HMDB
(S)-3-Hydroxybutyrylcarnitine	HMDB
Hydroxybutyrylcarnitine	HMDB
3-Hydroxybutyrylcarnitine	HMDB

Chemical Formula

C₁₁H₂₁NO₅

Average Molecular Weight

247.291

Monoisotopic Molecular Weight

247.14197278

IUPAC Name

(3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylazaniumyl)butanoate

Traditional Name

(3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylammonio)butanoate

CAS Registry Number

1469900-92-2

SMILES

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

InChI Identifier

InChI=1S/C11H21NO5/c1-8(13)5-11(16)17-9(6-10(14)15)7-12(2,3)4/h8-9,13H,5-7H2,1-4H3/t8-,9+/m1/s1

InChI Key

UEFRDQSMQXDWTO-BDAKNGLRSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location

Excreta

Cellular substructure

Macromolecular complex

Blood

Extracellular

Organ

Placenta

Ingestion

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Spectral Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.1 g/L	ALOGPS
logP	10^(-2.3) g/L	ALOGPS
logP	10^(-4.6) g/L	ChemAxon
logS	10^(-2.4) g/L	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.66 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	83.46 m³·mol⁻¹	ChemAxon
Polarizability	25.51 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 Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxybutyrylcarnitine,1TMS,#1	C[C@H](CC(=O)O[C@@H](CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C	1673.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
3-Hydroxybutyrylcarnitine,1TBDMS,#1	C[C@H](CC(=O)O[C@@H](CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1917.6	Semi standard non polar	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxybutyrylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxybutyrylcarnitine 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 - 3-Hydroxybutyrylcarnitine 10V, Positive-QTOF	splash10-0002-0090000000-ced2c98518d1470d08f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyrylcarnitine 20V, Positive-QTOF	splash10-000j-9050000000-1f8bae541c9e0acdc134	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxybutyrylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

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
Blood	Detected and Quantified	0.11 +/- 0.01 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.0960 (0.000-0.360) uM	Infant (0-1 year old)	Not Specified	Normal	11489939	details
Blood	Detected and Quantified	<0.400 uM	Infant (0-1 year old)	Not Specified	Normal	25251209	details
Blood	Detected and Quantified	0.04 +/- 0.02 uM	Adult (>18 years old)	Both	Normal	28278231	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected and Quantified	0.6 +/- 0.36 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.32 +/- 0.2 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.780 (0.920-3.0400) uM	Infant (0-1 year old)	Female	3-Hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)	11489939	details
Blood	Detected and Quantified	0.200 (0.0800-0.500) uM	Infant (0-1 year old)	Not Specified	Ketosis	11489939	details
Blood	Detected and Quantified	0.180 (0.0600-0.360) uM	Infant (0-1 year old)	Not Specified	Short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency	11489939	details
Blood	Detected and Quantified	0.940-1.720 uM	Infant (0-1 year old)	Male	3-Hydroxyacyl-CoA dehydrogenase deficiency (SCHAD)	23430856	details
Blood	Detected and Quantified	0.660-0.810 uM	Infant (0-1 year old)	Male	3-Hydroxyisobutyryl-coa hydrolase deficiency	25251209	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

3-Hydroxyacyl-CoA dehydrogenase deficiency
Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. [PubMed:11489939 ] Popa FI, Perlini S, Teofoli F, Degani D, Funghini S, La Marca G, Rinaldo P, Vincenzi M, Antoniazzi F, Boner A, Camilot M: 3-hydroxyacyl-coenzyme a dehydrogenase deficiency: identification of a new mutation causing hyperinsulinemic hypoketotic hypoglycemia, altered organic acids and acylcarnitines concentrations. JIMD Rep. 2012;2:71-7. doi: 10.1007/8904_2011_50. Epub 2011 Sep 6. [PubMed:23430856 ]
Ketosis
Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. [PubMed:11489939 ]
Short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency
Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. [PubMed:11489939 ]
3-Hydroxyisobutyryl-coa hydrolase deficiency
Reuter MS, Sass JO, Leis T, Kohler J, Mayr JA, Feichtinger RG, Rauh M, Schanze I, Bahr L, Trollmann R, Uebe S, Ekici AB, Reis A: HIBCH deficiency in a patient with phenotypic characteristics of mitochondrial disorders. Am J Med Genet A. 2014 Dec;164A(12):3162-9. doi: 10.1002/ajmg.a.36766. Epub 2014 Sep 23. [PubMed:25251209 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

231530 (3-Hydroxyacyl-CoA dehydrogenase deficiency)
250620 (3-Hydroxyisobutyryl-coa hydrolase deficiency)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112377

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029837

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. [PubMed:11489939 ]
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 ]
Violante S, Ijlst L, Ruiter J, Koster J, van Lenthe H, Duran M, de Almeida IT, Wanders RJ, Houten SM, Ventura FV: Substrate specificity of human carnitine acetyltransferase: Implications for fatty acid and branched-chain amino acid metabolism. Biochim Biophys Acta. 2013 Jun;1832(6):773-9. doi: 10.1016/j.bbadis.2013.02.012. Epub 2013 Feb 24. [PubMed:23485643 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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 ]
Makarova E, Makrecka-Kuka M, Vilks K, Volska K, Sevostjanovs E, Grinberga S, Zarkova-Malkova O, Dambrova M, Liepinsh E: Decreases in Circulating Concentrations of Long-Chain Acylcarnitines and Free Fatty Acids During the Glucose Tolerance Test Represent Tissue-Specific Insulin Sensitivity. Front Endocrinol (Lausanne). 2019 Dec 17;10:870. doi: 10.3389/fendo.2019.00870. eCollection 2019. [PubMed:31920980 ]
Chen C, Hou G, Zeng C, Ren Y, Chen X, Peng C: Metabolomic profiling reveals amino acid and carnitine alterations as metabolic signatures in psoriasis. Theranostics. 2021 Jan 1;11(2):754-767. doi: 10.7150/thno.51154. eCollection 2021. [PubMed:33391503 ]
Hussain K, Clayton PT, Krywawych S, Chatziandreou I, Mills P, Ginbey DW, Geboers AJ, Berger R, van den Berg IE, Eaton S: Hyperinsulinism of infancy associated with a novel splice site mutation in the SCHAD gene. J Pediatr. 2005 May;146(5):706-8. doi: 10.1016/j.jpeds.2005.01.032. [PubMed:15870679 ]
Zhong H, Fang C, Fan Y, Lu Y, Wen B, Ren H, Hou G, Yang F, Xie H, Jie Z, Peng Y, Ye Z, Wu J, Zi J, Zhao G, Chen J, Bao X, Hu Y, Gao Y, Zhang J, Yang H, Wang J, Madsen L, Kristiansen K, Ni C, Li J, Liu S: Lipidomic profiling reveals distinct differences in plasma lipid composition in healthy, prediabetic, and type 2 diabetic individuals. Gigascience. 2017 Jul 1;6(7):1-12. doi: 10.1093/gigascience/gix036. [PubMed:28505362 ]
Stepien KM, Abidin Z, Lee G, Cullen R, Logan P, Pastores GM: Metallosis mimicking a metabolic disorder: a case report. Mol Genet Metab Rep. 2018 Sep 25;17:38-41. doi: 10.1016/j.ymgmr.2018.09.005. eCollection 2018 Dec. [PubMed:30271721 ]
Catanzano F, Ombrone D, Di Stefano C, Rossi A, Nosari N, Scolamiero E, Tandurella I, Frisso G, Parenti G, Ruoppolo M, Andria G, Salvatore F: The first case of mitochondrial acetoacetyl-CoA thiolase deficiency identified by expanded newborn metabolic screening in Italy: the importance of an integrated diagnostic approach. J Inherit Metab Dis. 2010 Dec;33 Suppl 3:S91-4. doi: 10.1007/s10545-009-9028-3. Epub 2010 Feb 16. [PubMed:20157782 ]
Cheng ML, Wang CH, Shiao MS, Liu MH, Huang YY, Huang CY, Mao CT, Lin JF, Ho HY, Yang NI: Metabolic disturbances identified in plasma are associated with outcomes in patients with heart failure: diagnostic and prognostic value of metabolomics. J Am Coll Cardiol. 2015 Apr 21;65(15):1509-20. doi: 10.1016/j.jacc.2015.02.018. [PubMed:25881932 ]
Niziol J, Bonifay V, Ossolinski K, Ossolinski T, Ossolinska A, Sunner J, Beech I, Arendowski A, Ruman T: Metabolomic study of human tissue and urine in clear cell renal carcinoma by LC-HRMS and PLS-DA. Anal Bioanal Chem. 2018 Jun;410(16):3859-3869. doi: 10.1007/s00216-018-1059-x. Epub 2018 Apr 16. [PubMed:29658093 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 3-Hydroxybutyrylcarnitine (HMDB0013127)

MOL for HMDB0013127 (3-Hydroxybutyrylcarnitine)

3D MOL for HMDB0013127 (3-Hydroxybutyrylcarnitine)

3D SDF for HMDB0013127 (3-Hydroxybutyrylcarnitine)

3D-SDF for HMDB0013127 (3-Hydroxybutyrylcarnitine)

PDB for HMDB0013127 (3-Hydroxybutyrylcarnitine)

3D PDB for HMDB0013127 (3-Hydroxybutyrylcarnitine)

SMILES for HMDB0013127 (3-Hydroxybutyrylcarnitine)

INCHI for HMDB0013127 (3-Hydroxybutyrylcarnitine)

Structure for HMDB0013127 (3-Hydroxybutyrylcarnitine)

3D Structure for HMDB0013127 (3-Hydroxybutyrylcarnitine)

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra