Showing metabocard for 3-Hydroxybutyric acid (MMDBc0030364)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:05:23 UTC
Update Date2024-04-30 19:45:56 UTC
Metabolite IDMMDBc0030364
Metabolite Identification
Common Name3-Hydroxybutyric acid
Description3-Hydroxybutyric acid or beta-hydroxybutyrate belongs to a group of compounds known as ketone bodies. Other ketone bodies include acetoacetate and acetone. 3-hydroxybutyric acid is chiral and so it has 2 enantiomeric forms. (Wikipedia ) In some strains of E. coli, such as E. coli O8 IAI1, the enzyme 3-hydroxybutyrate dehydrogenase (EC:1.1.1.30) catalyzes a reversible redox reaction that converts 3-hydroxybutyric acid to acetoacetate, which can then be converted into acetoacetyl-CoA and participate in fatty acid metabolism. (KEGG). Hydroxybutyrate can also serve as a substrate for short-chain acylCo-A ligase and become a precursor for lipid synthesis.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fe2d6766608>


  Mrv1652305261923572D          

  7  6  0  0  0  0            999 V2000
    9.5122  -10.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3701  -10.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6557  -12.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2267  -11.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9412  -10.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2267  -12.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6557  -11.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  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
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fe2d6766608>

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3D SDF for #<Metabolite:0x00007fe2d6766608>

  Mrv1652305261923572D          

  7  6  0  0  0  0            999 V2000
    9.5122  -10.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3701  -10.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6557  -12.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2267  -11.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9412  -10.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2267  -12.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6557  -11.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  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
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030364

> <DATABASE_NAME>
MIME

> <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_KEY>
WHBMMWSBFZVSSR-UHFFFAOYSA-N

> <FORMULA>
C4H8O3

> <MOLECULAR_WEIGHT>
104.1045

> <EXACT_MASS>
104.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.005337398683004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
3 hydroxybutyrate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fe2d6766608>
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PDB for #<Metabolite:0x00007fe2d6766608>
HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      17.756 -20.292   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      23.091 -20.292   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      21.757 -22.602   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      19.090 -21.062   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.424 -20.292   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.090 -22.602   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.757 -21.062   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    7                                                            
CONECT    3    7                                                            
CONECT    4    1    5    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

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3D PDB for #<Metabolite:0x00007fe2d6766608>
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SMILES for #<Metabolite:0x00007fe2d6766608>
CC(O)CC(O)=O
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INCHI for #<Metabolite:0x00007fe2d6766608>
InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
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Synonyms
ValueSource
(1)-3-Hydroxybutyric acidChEBI
3 HBAChEBI
3-HydroxybuttersaeureChEBI
3-OH-Butyric acidChEBI
beta-Hydroxy-N-butyric acidChEBI
beta-Hydroxybutanoic acidChEBI
beta-HydroxybuttersaeureChEBI
beta-Hydroxybutyric acidChEBI
BHBAChEBI
DL-beta-Hydroxybutyric acidChEBI
(1)-3-HydroxybutyrateGenerator
3-OH-ButyrateGenerator
b-Hydroxy-N-butyrateGenerator
b-Hydroxy-N-butyric acidGenerator
beta-Hydroxy-N-butyrateGenerator
Β-hydroxy-N-butyrateGenerator
Β-hydroxy-N-butyric acidGenerator
b-HydroxybutanoateGenerator
b-Hydroxybutanoic acidGenerator
beta-HydroxybutanoateGenerator
Β-hydroxybutanoateGenerator
Β-hydroxybutanoic acidGenerator
b-HydroxybuttersaeureGenerator
Β-hydroxybuttersaeureGenerator
b-HydroxybutyrateGenerator
b-Hydroxybutyric acidGenerator
beta-HydroxybutyrateGenerator
Β-hydroxybutyrateGenerator
Β-hydroxybutyric acidGenerator
DL-b-HydroxybutyrateGenerator
DL-b-Hydroxybutyric acidGenerator
DL-beta-HydroxybutyrateGenerator
DL-Β-hydroxybutyrateGenerator
DL-Β-hydroxybutyric acidGenerator
3-HydroxybutyrateGenerator
3-Hydroxy-butanoateHMDB
3-Hydroxy-butanoic acidHMDB
3-Hydroxy-butyrateHMDB
3-Hydroxy-butyric acidHMDB
3-HydroxybutanoateHMDB
3-Hydroxybutanoic acidHMDB
BiopolHMDB
DL-3-HydroxybutyrateHMDB
DL-3-Hydroxybutyric acidHMDB
beta Hydroxybutyric acidHMDB
3 Hydroxybutyric acidHMDB
beta HydroxybutyrateHMDB
(+ -)-3-Hydroxybutyric acidHMDB
3 HydroxybutyrateHMDB
Molecular FormulaC4H8O3
Average Mass104.1045
Monoisotopic Mass104.047344122
IUPAC Name3-hydroxybutanoic acid
Traditional Name3 hydroxybutyrate
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