Hmdb loader

Showing metabocard for (S)-3-Hydroxybutyric acid (HMDB0000442)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:01 UTC
HMDB IDHMDB0000442
Secondary Accession Numbers
  • HMDB0000758
  • HMDB0011597
  • HMDB00442
  • HMDB00758
  • HMDB11597
Metabolite Identification
Common Name(S)-3-Hydroxybutyric acid
Description(S)-3-Hydroxybutyric acid is a normal human metabolite that has been found elevated in geriatric patients remitting from depression (PMID: 17048218 ). 3-Hydroxybutyric acid is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyric acid are raised in ketosis. In humans, 3-hydroxybutyric acid is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low.
Structure
Data?1585155706
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000442 ((S)-3-Hydroxybutyric acid)


  Mrv1652303252017482D          

  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  2  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  6  0  0  0
M  END
Download

3D MOL for HMDB0000442 ((S)-3-Hydroxybutyric acid)

HMDB0000442
     RDKit          3D
(S)-3-Hydroxybutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.7242    0.6862   -0.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6748   -0.3412    0.0035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0187   -0.9020    1.2007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6657    0.3535   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -0.5236    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -1.1485    1.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8613   -0.6931   -0.4972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658    1.4073    0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916    0.1832   -0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372    1.2439   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060   -1.1001   -0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592   -1.2392    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853    1.1907    0.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7818    0.8511   -0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    0.0319   -0.5393 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 HMDB0000442 ((S)-3-Hydroxybutyric acid)


  Mrv1652303252017482D          

  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  2  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  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000442

> <DATABASE_NAME>
hmdb

> <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-/m0/s1

> <INCHI_KEY>
WHBMMWSBFZVSSR-VKHMYHEASA-N

> <FORMULA>
C4H8O3

> <MOLECULAR_WEIGHT>
104.1045

> <EXACT_MASS>
104.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.935816704884763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-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>
23.4641

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.39e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-hydroxybutyrate,l

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000442 ((S)-3-Hydroxybutyric acid)

HMDB0000442
     RDKit          3D
(S)-3-Hydroxybutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.7242    0.6862   -0.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6748   -0.3412    0.0035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0187   -0.9020    1.2007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6657    0.3535   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -0.5236    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -1.1485    1.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8613   -0.6931   -0.4972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658    1.4073    0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916    0.1832   -0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372    1.2439   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060   -1.1001   -0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592   -1.2392    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853    1.1907    0.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7818    0.8511   -0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    0.0319   -0.5393 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 HMDB0000442 ((S)-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 HMDB0000442 ((S)-3-Hydroxybutyric acid)

COMPND    HMDB0000442
HETATM    1  C1  UNL     1      -1.724   0.686  -0.388  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.675  -0.341   0.004  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.019  -0.902   1.201  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.666   0.353  -0.020  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.774  -0.524   0.339  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.749  -1.149   1.423  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.861  -0.693  -0.497  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.866   1.407   0.443  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.692   0.183  -0.614  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.337   1.244  -1.259  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.706  -1.100  -0.819  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.959  -1.239   1.114  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.585   1.191   0.736  1.00  0.00           H  
HETATM   14  H7  UNL     1       0.782   0.851  -0.986  1.00  0.00           H  
HETATM   15  H8  UNL     1       3.560   0.032  -0.539  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 HMDB0000442 ((S)-3-Hydroxybutyric acid)

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

INCHI for HMDB0000442 ((S)-3-Hydroxybutyric acid)

InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(+)-3-Hydroxybutyric acidChEBI
(3S)-3-Hydroxybutyric acidChEBI
(S)-3-Hydroxybutanoic acidChEBI
(S)-3HbChEBI
(S)-beta-Hydroxybutyric acidChEBI
L-(+)-3-Hydroxybutyric acidChEBI
L-3-Hydroxybutyric acidChEBI
(+)-3-HydroxybutyrateGenerator
(3S)-3-HydroxybutyrateGenerator
(S)-3-HydroxybutanoateGenerator
(S)-b-HydroxybutyrateGenerator
(S)-b-Hydroxybutyric acidGenerator
(S)-beta-HydroxybutyrateGenerator
(S)-Β-hydroxybutyrateGenerator
(S)-Β-hydroxybutyric acidGenerator
L-(+)-3-HydroxybutyrateGenerator
L-3-HydroxybutyrateGenerator
(S)-3-HydroxybutyrateGenerator
(+)-3-Hydroxy-N-butyric acidHMDB
(3S)-3-Hydroxy-butanoateHMDB
(3S)-3-Hydroxy-butanoic acidHMDB
(S)-3-Hydroxy-2-methyl-propanoateHMDB
(S)-3-Hydroxy-2-methyl-propanoic acidHMDB
(S)-3-Hydroxy-butanoateHMDB
(S)-3-Hydroxy-butanoic acidHMDB
(S)-b-HydroxyisobutyrateHMDB
(S)-b-Hydroxyisobutyric acidHMDB
(S)-beta-HydroxyisobutyrateHMDB
(S)-beta-Hydroxyisobutyric acidHMDB
L-(+)-2-Methyl-hydracrylateHMDB
L-(+)-2-Methyl-hydracrylic acidHMDB
L-(+)-b-HydroxyisobutyrateHMDB
L-(+)-b-Hydroxyisobutyric acidHMDB
L-(+)-beta-HydroxyisobutyrateHMDB
L-(+)-beta-Hydroxyisobutyric acidHMDB
L-beta-HydroxybutyrateHMDB
(3S)-3-Hydroxybutanoic acidHMDB
(S)-(+)-beta-Hydroxybutyric acidHMDB
(S)-(+)-Β-hydroxybutyric acidHMDB
(S)-beta-Hydroxybutanoic acidHMDB
(S)-Β-hydroxybutanoic acidHMDB
3-Hydroxy-N-butyric acidHMDB
3-Hydroxybutanoic acidHMDB
3-Hydroxybutyric acidHMDB
L-beta-Hydroxybutyric acidHMDB
L-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
(S)-3-Hydroxybutyric acidHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name(3S)-3-hydroxybutanoic acid
Traditional Nameβ-hydroxybutyrate,l
CAS Registry Number6168-83-8
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-/m0/s1
InChI KeyWHBMMWSBFZVSSR-VKHMYHEASA-N
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point45 - 48 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability9.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.4831661259
DarkChem[M-H]-117.27931661259
AllCCS[M+H]+126.73432859911
AllCCS[M-H]-124.25732859911
DeepCCS[M+H]+122.15930932474
DeepCCS[M-H]-119.15930932474
DeepCCS[M-2H]-155.61130932474
DeepCCS[M+Na]+130.7230932474
AllCCS[M+H]+126.732859911
AllCCS[M+H-H2O]+122.432859911
AllCCS[M+NH4]+130.832859911
AllCCS[M+Na]+131.932859911
AllCCS[M-H]-124.332859911
AllCCS[M+Na-2H]-128.132859911
AllCCS[M+HCOO]-132.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.61 minutes32390414
Predicted by Siyang on May 30, 20229.0308 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.05 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid198.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid881.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid340.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid64.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid214.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid52.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid259.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid273.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)207.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid589.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid124.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid811.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid209.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid246.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate621.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA287.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water296.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-3-Hydroxybutyric acidC[C@H](O)CC(O)=O2109.0Standard polar33892256
(S)-3-Hydroxybutyric acidC[C@H](O)CC(O)=O962.0Standard non polar33892256
(S)-3-Hydroxybutyric acidC[C@H](O)CC(O)=O986.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-3-Hydroxybutyric acid,1TMS,isomer #1C[C@@H](CC(=O)O)O[Si](C)(C)C1074.4Semi standard non polar33892256
(S)-3-Hydroxybutyric acid,1TMS,isomer #2C[C@H](O)CC(=O)O[Si](C)(C)C1018.1Semi standard non polar33892256
(S)-3-Hydroxybutyric acid,2TMS,isomer #1C[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1168.2Semi standard non polar33892256
(S)-3-Hydroxybutyric acid,1TBDMS,isomer #1C[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C1313.6Semi standard non polar33892256
(S)-3-Hydroxybutyric acid,1TBDMS,isomer #2C[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C1235.9Semi standard non polar33892256
(S)-3-Hydroxybutyric acid,2TBDMS,isomer #1C[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1603.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxybutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9000000000-5f169537ace358b06fd02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxybutyric acid GC-MS (2 TMS) - 70eV, Positivesplash10-01ei-9710000000-2652bd46b41e50defdb02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxybutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxybutyric acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxybutyric acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxybutyric acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxybutyric acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxybutyric acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0a4i-9200000000-4156904e7472b5e972492012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d7944402012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 10V, Positive-QTOFsplash10-00kr-9100000000-889e2968ad4fd52cdd922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 20V, Positive-QTOFsplash10-05n0-9000000000-6c660170b8f4aa6bcd022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 40V, Positive-QTOFsplash10-0006-9000000000-c39869c905b7e93b7f972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 10V, Negative-QTOFsplash10-0zfr-9800000000-532ea53160d6ca2efcaa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 20V, Negative-QTOFsplash10-0pbi-9200000000-b2c59fd56b1a1d713ea92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 40V, Negative-QTOFsplash10-0a4l-9000000000-29e8d104108ac71cd6402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 10V, Positive-QTOFsplash10-0002-9000000000-de698d113a869245219a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 20V, Positive-QTOFsplash10-0002-9000000000-d964762034ff3766529f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 40V, Positive-QTOFsplash10-0002-9000000000-1c4d36fa24f00e6e9f6e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 10V, Negative-QTOFsplash10-0a4i-9200000000-61512767fe2a2778ee8c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 20V, Negative-QTOFsplash10-0a4i-9000000000-0006bf28af00ac9af39c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxybutyric acid 40V, Negative-QTOFsplash10-052f-9000000000-58f5546067f0f7cf64bb2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Adipose Tissue
  • Brain
  • Neuron
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified20.0 (19.0 - 23.0) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified5.9 umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal details
UrineDetected and Quantified14.0 (1.0-27.0) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified1.4 +/- 1.3 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022048
KNApSAcK IDNot Available
Chemspider ID85121
KEGG Compound IDC03197
BioCyc IDCPD-1843
BiGG IDNot Available
Wikipedia LinkBeta-Hydroxybutyric_acid
METLIN IDNot Available
PubChem Compound94318
PDB IDNot Available
ChEBI ID17290
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceZhao, Jun. Synthesis of (S)-b-hydroxybutanoic acid from L-lactic acid. Hecheng Huaxue (1998), 6(4), 442-444.
Material Safety Data Sheet (MSDS)Download (PDF)
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. Byrne HA, Tieszen KL, Hollis S, Dornan TL, New JP: Evaluation of an electrochemical sensor for measuring blood ketones. Diabetes Care. 2000 Apr;23(4):500-3. [PubMed:10857942 ]
  5. Altorjay A, Juhasz A, Kellner V, Sohar G, Fekete M, Sohar I: Metabolic changes in the lower esophageal sphincter influencing the result of anti-reflux surgical interventions in chronic gastroesophageal reflux disease. World J Gastroenterol. 2005 Mar 21;11(11):1623-8. [PubMed:15786538 ]
  6. Eichler A, Forster H, Heller K, Behne M: [Ketoacidosis in a 14 month old child caused by fasting]. Anaesthesist. 1999 Nov;48(11):813-6. [PubMed:10631441 ]
  7. Soroka SD, Chayaraks S, Cheema-Dhadli S, Myers JA, Rubin S, Sonnenberg H, Halperin ML: Minimum urine flow rate during water deprivation: importance of the nonurea versus total osmolality in the inner medulla. J Am Soc Nephrol. 1997 Jun;8(6):880-6. [PubMed:9189853 ]
  8. Baracos VE, Mackenzie ML: Investigations of branched-chain amino acids and their metabolites in animal models of cancer. J Nutr. 2006 Jan;136(1 Suppl):237S-42S. [PubMed:16365090 ]
  9. Nadgir UM, Silver FL, MacGillivray MH: Unrecognized persistence of beta-hydroxybutyrate in diabetic ketoacidosis. Endocr Res. 2001 Feb-May;27(1-2):41-6. [PubMed:11428720 ]
  10. Oosterheert JJ, van de Wiel A: [Ketoacidosis after cessation of chronic alcohol consumption]. Ned Tijdschr Geneeskd. 2002 May 18;146(20):950-4. [PubMed:12051065 ]
  11. Seyfried TN, Mukherjee P: Targeting energy metabolism in brain cancer: review and hypothesis. Nutr Metab (Lond). 2005 Oct 21;2:30. [PubMed:16242042 ]
  12. Fernqvist-Forbes E, Linde B: Insulin absorption, glucose homeostasis, and lipolysis in IDDM during mental stress. Diabetes Care. 1991 Nov;14(11):1006-12. [PubMed:1797480 ]
  13. Noh HS, Hah YS, Nilufar R, Han J, Bong JH, Kang SS, Cho GJ, Choi WS: Acetoacetate protects neuronal cells from oxidative glutamate toxicity. J Neurosci Res. 2006 Mar;83(4):702-9. [PubMed:16435389 ]
  14. Paige LA, Mitchell MW, Krishnan KR, Kaddurah-Daouk R, Steffens DC: A preliminary metabolomic analysis of older adults with and without depression. Int J Geriatr Psychiatry. 2007 May;22(5):418-23. [PubMed:17048218 ]

Enzymes

Enzyme Details
1. Hydroxyacid-oxoacid transhydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2-hydroxyglutarate (D-2-HG). D,L-3-hydroxyisobutyrate and L-3-hydroxybutyrate (L-3-OHB) are also substrates for HOT with 10-fold lower activities.
Gene Name:
ADHFE1
Uniprot ID:
Q8IWW8
Molecular weight:
50307.42
Reactions
(S)-3-Hydroxybutyric acid + Oxoglutaric acid → Acetoacetic acid + D-2-Hydroxyglutaric aciddetails
Enzyme Details
2. 3-hydroxybutyrate dehydrogenase type 2
General function:
Involved in oxidoreductase activity
Specific function:
Dehydrogenase that mediates the formation of 2,5-dihydroxybenzoic acid (2,5-DHBA), a siderophore that shares structural similarities with bacterial enterobactin and associates with LCN2, thereby playing a key role in iron homeostasis and transport. Also acts as a 3-hydroxybutyrate dehydrogenase (By similarity).
Gene Name:
BDH2
Uniprot ID:
Q9BUT1
Molecular weight:
26723.57