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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2017-03-23 05:57:16 UTC

Update Date

2022-10-24 19:44:14 UTC

HMDB ID

HMDB0062735

Secondary Accession Numbers

HMDB62735

Metabolite Identification

Common Name

(R)-3-hydroxybutyrylcarnitine

Description

(R)-3-Hydroxybutyrylcarnitine is an acylcarnitine. More specifically, it is an 3-hydroxybutanoic 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. (R)-3-Hydroxybutyrylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine (R)-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 (R)-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 ). (R)-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 (PMID: 35710135 ).

Structure

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

HMDB0062735
     RDKit          3D
(R)-3-hydroxybutyrylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
    2.6750    1.3355   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    0.0165   -0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733    0.3246   -1.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3165   -0.6726    0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640   -1.0095    0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415   -1.5622    1.9713 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806   -0.7973    0.1744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008   -1.1460    0.6513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1020   -2.3242   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196   -2.6082    0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4569   -2.4935   -0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4900   -3.0013    1.8421 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4016   -0.0283    0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7587    0.9180    0.0044 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.2681    2.0859    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7219    1.4497   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8969    0.5630   -0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0746    1.3705    0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    1.4959   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3874    2.1967   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0920   -0.6008   -1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3778   -0.3804   -0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879   -1.6412    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8903   -0.0693    1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670   -1.6054    1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4563   -3.2053    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518   -2.1676   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422    0.5268    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340   -0.4604    1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0331    2.6363    0.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4566    2.7511    1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695    1.7202    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663    0.6530   -1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395    2.0074   -1.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1121    2.2215   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454    0.2381   -0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050   -0.1873   -1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571    1.4502   -1.4011 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  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  1
  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

  Mrv1652303231706572D          

 19 18  0  0  1  0            999 V2000
   -0.1914   -1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.5230    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.3809    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -2.3645    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.6829   -3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -2.7770    0.0000 C   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
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
M  CHG  2  13  -1  16   1
M  END
> <DATABASE_ID>
HMDB0062735

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(C)(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-YGPZHTELSA-N

> <FORMULA>
C11H21NO5

> <MOLECULAR_WEIGHT>
247.291

> <EXACT_MASS>
247.14197278

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
25.706733142672874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(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>
86.66

> <JCHEM_REFRACTIVITY>
83.4572

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062735
     RDKit          3D
(R)-3-hydroxybutyrylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
    2.6750    1.3355   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    0.0165   -0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733    0.3246   -1.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3165   -0.6726    0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640   -1.0095    0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415   -1.5622    1.9713 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806   -0.7973    0.1744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008   -1.1460    0.6513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1020   -2.3242   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196   -2.6082    0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4569   -2.4935   -0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4900   -3.0013    1.8421 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4016   -0.0283    0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7587    0.9180    0.0044 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.2681    2.0859    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7219    1.4497   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8969    0.5630   -0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0746    1.3705    0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    1.4959   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3874    2.1967   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0920   -0.6008   -1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3778   -0.3804   -0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879   -1.6412    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8903   -0.0693    1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670   -1.6054    1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4563   -3.2053    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518   -2.1676   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422    0.5268    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340   -0.4604    1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0331    2.6363    0.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4566    2.7511    1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695    1.7202    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663    0.6530   -1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395    2.0074   -1.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1121    2.2215   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454    0.2381   -0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050   -0.1873   -1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571    1.4502   -1.4011 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  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  1
  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                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  H   UNK     0      -0.357  -2.874   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.357  -1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.976  -3.644   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.644  -3.644   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.977  -1.334   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.311  -2.104   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       6.311  -0.564   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       7.645  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.645   0.206   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.978   0.976   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0       6.311   0.976   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.311  -3.644   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       7.645  -4.414   0.000  0.00  0.00           N+1
HETATM   17  C   UNK     0       6.875  -5.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.978  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   15                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0062735
HETATM    1  C1  UNL     1       2.675   1.336  -0.869  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.426   0.016  -0.922  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.773   0.325  -1.149  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.316  -0.673   0.391  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.964  -1.010   0.840  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.841  -1.562   1.971  1.00  0.00           O  
HETATM    7  O3  UNL     1       0.781  -0.797   0.174  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.501  -1.146   0.651  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.102  -2.324  -0.069  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.420  -2.608   0.527  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.457  -2.494  -0.148  1.00  0.00           O  
HETATM   12  O5  UNL     1      -2.490  -3.001   1.842  1.00  0.00           O1-
HETATM   13  C8  UNL     1      -1.402  -0.028   0.976  1.00  0.00           C  
HETATM   14  N1  UNL     1      -1.759   0.918   0.004  1.00  0.00           N1+
HETATM   15  C9  UNL     1      -2.268   2.086   0.771  1.00  0.00           C  
HETATM   16  C10 UNL     1      -0.722   1.450  -0.828  1.00  0.00           C  
HETATM   17  C11 UNL     1      -2.897   0.563  -0.844  1.00  0.00           C  
HETATM   18  H1  UNL     1       2.075   1.370   0.076  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.066   1.496  -1.775  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.387   2.197  -0.777  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.092  -0.601  -1.786  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.378  -0.380  -0.838  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.888  -1.641   0.302  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.890  -0.069   1.127  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.267  -1.605   1.681  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.456  -3.205   0.142  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.152  -2.168  -1.167  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.942   0.527   1.845  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.334  -0.460   1.406  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.033   2.636   0.214  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.457   2.751   1.071  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.769   1.720   1.712  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.166   0.653  -1.337  1.00  0.00           H  
HETATM   34  H17 UNL     1      -1.239   2.007  -1.666  1.00  0.00           H  
HETATM   35  H18 UNL     1      -0.112   2.221  -0.332  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.745   0.238  -0.209  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.605  -0.187  -1.608  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.257   1.450  -1.401  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

HMDB0062735
     RDKit          3D
(R)-3-hydroxybutyrylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
    2.6750    1.3355   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    0.0165   -0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733    0.3246   -1.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3165   -0.6726    0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640   -1.0095    0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415   -1.5622    1.9713 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806   -0.7973    0.1744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008   -1.1460    0.6513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1020   -2.3242   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196   -2.6082    0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4569   -2.4935   -0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4900   -3.0013    1.8421 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4016   -0.0283    0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7587    0.9180    0.0044 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.2681    2.0859    0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7219    1.4497   -0.8281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8969    0.5630   -0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0746    1.3705    0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    1.4959   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3874    2.1967   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0920   -0.6008   -1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3778   -0.3804   -0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879   -1.6412    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8903   -0.0693    1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670   -1.6054    1.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4563   -3.2053    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518   -2.1676   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422    0.5268    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340   -0.4604    1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0331    2.6363    0.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4566    2.7511    1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695    1.7202    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663    0.6530   -1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395    2.0074   -1.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1121    2.2215   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7454    0.2381   -0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050   -0.1873   -1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571    1.4502   -1.4011 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  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  1
  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 NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Hydroxybutyryl-L-carnitine	ChEBI
3-Hydroxybutyrylcarnitine	ChEBI
Hydroxybutyrylcarnitine	ChEBI
O-3-Hydroxybutanoyl-(R)-carnitine	ChEBI

Chemical Formula

C₁₁H₂₁NO₅

Average Molecular Weight

247.291

Monoisotopic Molecular Weight

247.14197278

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]C(C)(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-YGPZHTELSA-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
Dicarboxylic acid or derivatives
Hydroxy acid
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic zwitterion
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-hydroxybutyryl-L-carnitine (CHEBI:84842 )

Ontology

Urine (PMID: 32340350)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0062735)

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	1.1 g/l	ALOGPS
LogP	-2.29	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2.3	ALOGPS
logP	-4.6	ChemAxon
logS	-2.4	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	25.71 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]+	154.234	30932474
DeepCCS	[M-H]-	151.304	30932474
DeepCCS	[M-2H]-	186.776	30932474
DeepCCS	[M+Na]+	162.796	30932474
AllCCS	[M+H]+	158.4	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	161.3	32859911
AllCCS	[M+Na]+	162.1	32859911
AllCCS	[M-H]-	163.3	32859911
AllCCS	[M+Na-2H]-	164.3	32859911
AllCCS	[M+HCOO]-	165.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-3-hydroxybutyrylcarnitine	[H]C(C)(O)CC(=O)O[C@]([H])(CC([O-])=O)C[N+](C)(C)C	2421.4	Standard polar	33892256
(R)-3-hydroxybutyrylcarnitine	[H]C(C)(O)CC(=O)O[C@]([H])(CC([O-])=O)C[N+](C)(C)C	1382.6	Standard non polar	33892256
(R)-3-hydroxybutyrylcarnitine	[H]C(C)(O)CC(=O)O[C@]([H])(CC([O-])=O)C[N+](C)(C)C	1699.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-3-hydroxybutyrylcarnitine,1TMS,isomer #1	CC(CC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C	1692.1	Semi standard non polar	33892256
(R)-3-hydroxybutyrylcarnitine,1TBDMS,isomer #1	CC(CC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1929.8	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 - (R)-3-hydroxybutyrylcarnitine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9100000000-4477b542f5098992f775	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-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 - (R)-3-hydroxybutyrylcarnitine 10V, Positive-QTOF	splash10-0002-0090000000-ced2c98518d1470d08f7	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-hydroxybutyrylcarnitine 20V, Positive-QTOF	splash10-000j-9050000000-1f8bae541c9e0acdc134	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-3-hydroxybutyrylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-21	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

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
Urine	Detected and Quantified	0.01-0.08 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.04 +/- 0.02 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.04 +/- 0.02 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

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

90659885

PDB ID

Not Available

ChEBI ID

84842

Food Biomarker Ontology

Not Available

VMH ID

3BCRN

MarkerDB ID

Not Available

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 ]
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 ]
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Showing metabocard for (R)-3-hydroxybutyrylcarnitine (HMDB0062735)

MOL for HMDB0062735 ((R)-3-hydroxybutyrylcarnitine)

3D MOL for HMDB0062735 ((R)-3-hydroxybutyrylcarnitine)

3D SDF for HMDB0062735 ((R)-3-hydroxybutyrylcarnitine)

3D-SDF for HMDB0062735 ((R)-3-hydroxybutyrylcarnitine)

PDB for HMDB0062735 ((R)-3-hydroxybutyrylcarnitine)

3D PDB for HMDB0062735 ((R)-3-hydroxybutyrylcarnitine)

SMILES for HMDB0062735 ((R)-3-hydroxybutyrylcarnitine)

INCHI for HMDB0062735 ((R)-3-hydroxybutyrylcarnitine)

Structure for HMDB0062735 ((R)-3-hydroxybutyrylcarnitine)

3D Structure for HMDB0062735 ((R)-3-hydroxybutyrylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra