Np mrd loader

Showing NP-Card for 3-Hydroxybutyric acid (NP0000718)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-09 16:31:25 UTC
NP-MRD IDNP0000718
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxybutyric acid
Description3-Hydroxybutyric acid (or beta-hydroxybutyrate) is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyrate in blood and urine are raised in ketosis. In humans, 3-hydroxybutyrate is synthesized in the liver from acetyl-CoA and can be used as an energy source by the brain when blood glucose is low. Blood levels of 3-hydroxybutyric acid levels may be monitored in diabetic patients to look for diabetic ketoacidosis. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing mammals. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for the synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies is utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmitoylphosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life (PMID: 3884391 ). 3-Hydroxybutyric acid is found to be associated with fumarase deficiency and medium-chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000718 (3-Hydroxybutyric acid)


  Mrv1652303252017492D          

  7  6  0  0  0  0            999 V2000
   12.3700  -12.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5121  -12.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2266  -10.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6556  -11.6956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9411  -12.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6556  -10.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2266  -11.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
  1  4  1  0  0  0  0
  4  6  1  1  0  0  0
M  END
Download

3D MOL for NP0000718 (3-Hydroxybutyric acid)

HMDB0000011
     RDKit          3D
3-Hydroxybutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.7425   -0.4236    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7444    0.6456    0.0230 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4149    1.3086    1.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104    0.2340   -0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3087   -0.7914   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7814   -1.8855    0.3046 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6465   -0.5912    0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6225    0.0533    0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0681   -0.8741   -0.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3154   -1.2104    0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441    1.4129   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665    0.8920    1.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1227    1.1704   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2318   -0.1403   -1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1839    0.1997   -0.0514 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
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  6
  3 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
Download

3D SDF for NP0000718 (3-Hydroxybutyric acid)


  Mrv1652303252017492D          

  7  6  0  0  0  0            999 V2000
   12.3700  -12.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5121  -12.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2266  -10.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6556  -11.6956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9411  -12.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6556  -10.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2266  -11.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
  1  4  1  0  0  0  0
  4  6  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0000718

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1

> <INCHI_KEY>
WHBMMWSBFZVSSR-GSVOUGTGSA-N

> <FORMULA>
C4H8O3

> <MOLECULAR_WEIGHT>
104.1045

> <EXACT_MASS>
104.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.959788970081753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-hydroxybutanoic acid

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-0.38700599933333335

> <ALOGPS_LOGS>
0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.695695082377142

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.406291419798768

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6205133689113183

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
23.464100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.39e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-3-hydroxybutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000718 (3-Hydroxybutyric acid)

HMDB0000011
     RDKit          3D
3-Hydroxybutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.7425   -0.4236    0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7444    0.6456    0.0230 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4149    1.3086    1.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104    0.2340   -0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3087   -0.7914   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7814   -1.8855    0.3046 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6465   -0.5912    0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6225    0.0533    0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0681   -0.8741   -0.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3154   -1.2104    0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441    1.4129   -0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665    0.8920    1.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1227    1.1704   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2318   -0.1403   -1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1839    0.1997   -0.0514 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
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  6
  3 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
Download

PDB for NP0000718 (3-Hydroxybutyric acid)

HEADER    PROTEIN                                 25-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAR-20         0                                  
HETATM    1  O   UNK     0      23.091 -22.602   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      17.756 -22.602   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      19.090 -20.292   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      21.757 -21.832   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.423 -22.602   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.757 -20.292   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.090 -21.832   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    7                                                            
CONECT    3    7                                                            
CONECT    4    5    1    6                                                  
CONECT    5    4    7                                                       
CONECT    6    4                                                            
CONECT    7    2    3    5                                                  
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
Download

3D PDB for NP0000718 (3-Hydroxybutyric acid)

COMPND    HMDB0000011
HETATM    1  C1  UNL     1      -1.743  -0.424   0.266  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.744   0.646   0.023  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.415   1.309   1.219  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.510   0.234  -0.676  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.309  -0.791  -0.002  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.781  -1.886   0.305  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.647  -0.591   0.313  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.623   0.053   0.770  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.068  -0.874  -0.678  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.315  -1.210   0.917  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.244   1.413  -0.651  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.366   0.892   1.669  1.00  0.00           H  
HETATM   13  H6  UNL     1       1.123   1.170  -0.816  1.00  0.00           H  
HETATM   14  H7  UNL     1       0.232  -0.140  -1.705  1.00  0.00           H  
HETATM   15  H8  UNL     1       3.184   0.200  -0.051  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4   11
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6    6    7
CONECT    7   15
END
Download

SMILES for NP0000718 (3-Hydroxybutyric acid)

C[C@@H](O)CC(O)=O
Download

INCHI for NP0000718 (3-Hydroxybutyric acid)

InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(R)-(-)-beta-Hydroxybutyric acidChEBI
(R)-3-Hydroxybutanoic acidChEBI
3-D-Hydroxybutyric acidChEBI
D-3-Hydroxybutyric acidChEBI
(R)-3-Hydroxybutyric acidKegg
D-beta-Hydroxybutyric acidKegg
(R)-(-)-b-HydroxybutyrateGenerator
(R)-(-)-b-Hydroxybutyric acidGenerator
(R)-(-)-beta-HydroxybutyrateGenerator
(R)-(-)-Β-hydroxybutyrateGenerator
(R)-(-)-Β-hydroxybutyric acidGenerator
(R)-3-HydroxybutanoateGenerator
3-D-HydroxybutyrateGenerator
D-3-HydroxybutyrateGenerator
(R)-3-HydroxybutyrateGenerator
D-b-HydroxybutyrateGenerator
D-b-Hydroxybutyric acidGenerator
D-beta-HydroxybutyrateGenerator
D-Β-hydroxybutyrateGenerator
D-Β-hydroxybutyric acidGenerator
3-HydroxybutyrateGenerator
3-delta-HydroxybutyrateHMDB
3-delta-Hydroxybutyric acidHMDB
BHIBHMDB
D-(-)-3-HydroxybutyrateHMDB
delta-(-)-3-HydroxybutyrateHMDB
delta-3-HydroxybutyrateHMDB
delta-3-Hydroxybutyric acidHMDB
delta-beta-HydroxybutyrateHMDB
3R-Hydroxy-butanoateHMDB
(-)-3-Hydroxy-N-butyric acidHMDB
(-)-3-Hydroxybutyric acidHMDB
(3R)-3-Hydroxybutanoic acidHMDB
(3R)-3-Hydroxybutyric acidHMDB
(3R)-HydroxybutyrateHMDB
(R)-(-)-3-Hydroxybutyric acidHMDB
(R)-beta-Hydroxybutanoic acidHMDB
(R)-beta-Hydroxybutyric acidHMDB
(R)-Β-hydroxybutanoic acidHMDB
(R)-Β-hydroxybutyric acidHMDB
3-Hydroxy-N-butyric acidHMDB
3-Hydroxybutanoic acidHMDB
3R-Hydroxybutanoic acidHMDB
D-(-)-3-Hydroxybutanoic acidHMDB
D-(-)-3-Hydroxybutyric acidHMDB
D-(-)-beta-Hydroxybutyric acidHMDB
D-(-)-Β-hydroxybutyric acidHMDB
beta-Hydroxy-N-butyric acidHMDB
beta-Hydroxybutanoic acidHMDB
beta-Hydroxybutyric acidHMDB
Β-hydroxy-N-butyric acidHMDB
Β-hydroxybutanoic acidHMDB
Β-hydroxybutyric acidHMDB
3-Hydroxybutyric acidHMDB
Chemical FormulaC4H8O3
Average Mass104.1045 Da
Monoisotopic Mass104.04734 Da
IUPAC Name(3R)-3-hydroxybutanoic acid
Traditional Name(-)-3-hydroxybutyric acid
CAS Registry Number300-85-6
SMILES
CC(O)CC(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
InChI KeyWHBMMWSBFZVSSR-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-09View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-02-09View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Annulohypoxylon truncatumLOTUS Database
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Cyphomandra betaceaLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Homo sapiens (Serum)Animalia
Hydroclathrus clathratusLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Salmonella entericaLOTUS Database
Secale cerealeLOTUS Database
Spondias mombinLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Triticum aestivumPlant
Vitis rotundifoliaLOTUS Database
Vitis viniferaLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point46 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility444 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility539 g/LALOGPS
logP-0.5ALOGPS
logP-0.39ChemAxon
logS0.71ALOGPS
pKa (Strongest Acidic)4.41ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.46 m³·mol⁻¹ChemAxon
Polarizability9.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000011
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021869
KNApSAcK IDC00052123
Chemspider ID83181
KEGG Compound IDC01089
BioCyc IDCPD-335
BiGG ID36784
Wikipedia LinkBeta-Hydroxybutyric_acid
METLIN IDNot Available
PubChem Compound92135
PDB IDNot Available
ChEBI ID17066
Good Scents IDNot Available
References
General References
  1. Pan JW, Rothman TL, Behar KL, Stein DT, Hetherington HP: Human brain beta-hydroxybutyrate and lactate increase in fasting-induced ketosis. J Cereb Blood Flow Metab. 2000 Oct;20(10):1502-7. [PubMed:11043913 ]
  2. Pan JW, Telang FW, Lee JH, de Graaf RA, Rothman DL, Stein DT, Hetherington HP: Measurement of beta-hydroxybutyrate in acute hyperketonemia in human brain. J Neurochem. 2001 Nov;79(3):539-44. [PubMed:11701757 ]
  3. Plecko B, Stoeckler-Ipsiroglu S, Schober E, Harrer G, Mlynarik V, Gruber S, Moser E, Moeslinger D, Silgoner H, Ipsiroglu O: Oral beta-hydroxybutyrate supplementation in two patients with hyperinsulinemic hypoglycemia: monitoring of beta-hydroxybutyrate levels in blood and cerebrospinal fluid, and in the brain by in vivo magnetic resonance spectroscopy. Pediatr Res. 2002 Aug;52(2):301-6. [PubMed:12149510 ]
  4. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
  5. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  6. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. [PubMed:8579834 ]
  7. Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. [PubMed:9693263 ]
  8. Frenkel G, Peterson RN, Freund M: Oxidative and glycolytic metabolism of semen components by washed guinea pig spermatozoa. Fertil Steril. 1975 Feb;26(2):144-7. [PubMed:1126459 ]
  9. Abrahamsson K, Eriksson BO, Holme E, Jodal U, Jonsson A, Lindstedt S: Pivalic acid-induced carnitine deficiency and physical exercise in humans. Metabolism. 1996 Dec;45(12):1501-7. [PubMed:8969283 ]
  10. Teresinski G, Buszewicz G, Madro R: The influence of ethanol on the level of ketone bodies in hypothermia. Forensic Sci Int. 2002 Jun 25;127(1-2):88-96. [PubMed:12098531 ]
  11. Nalecz KA, Miecz D, Berezowski V, Cecchelli R: Carnitine: transport and physiological functions in the brain. Mol Aspects Med. 2004 Oct-Dec;25(5-6):551-67. [PubMed:15363641 ]
  12. Blomqvist G, Alvarsson M, Grill V, Von Heijne G, Ingvar M, Thorell JO, Stone-Elander S, Widen L, Ekberg K: Effect of acute hyperketonemia on the cerebral uptake of ketone bodies in nondiabetic subjects and IDDM patients. Am J Physiol Endocrinol Metab. 2002 Jul;283(1):E20-8. [PubMed:12067838 ]
  13. Krotkiewski M: Value of VLCD supplementation with medium chain triglycerides. Int J Obes Relat Metab Disord. 2001 Sep;25(9):1393-400. [PubMed:11571605 ]
  14. Kamijo T, Indo Y, Souri M, Aoyama T, Hara T, Yamamoto S, Ushikubo S, Rinaldo P, Matsuda I, Komiyama A, Hashimoto T: Medium chain 3-ketoacyl-coenzyme A thiolase deficiency: a new disorder of mitochondrial fatty acid beta-oxidation. Pediatr Res. 1997 Nov;42(5):569-76. [PubMed:9357925 ]
  15. Geary N, Grotschel H, Scharrer E: Blood metabolites and feeding during postinsulin hypophagia. Am J Physiol. 1982 Sep;243(3):R304-11. [PubMed:7051864 ]
  16. Yeh YY, Sheehan PM: Preferential utilization of ketone bodies in the brain and lung of newborn rats. Fed Proc. 1985 Apr;44(7):2352-8. [PubMed:3884391 ]
  17. Shi D, Yan R, Lv L, Jiang H, Lu Y, Sheng J, Xie J, Wu W, Xia J, Xu K, Gu S, Chen Y, Huang C, Guo J, Du Y, Li L: The serum metabolome of COVID-19 patients is distinctive and predictive. Metabolism. 2021 May;118:154739. doi: 10.1016/j.metabol.2021.154739. Epub 2021 Mar 2. [PubMed:33662365 ]