Showing metabocard for (S)-3-hydroxybutanoic acid (MMDBc0054104)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 22:53:04 UTC
Update Date2024-04-30 20:51:17 UTC
Metabolite IDMMDBc0054104
Metabolite Identification
Common Name(S)-3-hydroxybutanoic 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb510bf9a8>


  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
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3D MOL for #<Metabolite:0x00007fdb510bf9a8>

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
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3D SDF for #<Metabolite:0x00007fdb510bf9a8>


  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>
MMDBc0054104

> <DATABASE_NAME>
MIME

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007fdb510bf9a8>

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
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PDB for #<Metabolite:0x00007fdb510bf9a8>

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
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3D PDB for #<Metabolite:0x00007fdb510bf9a8>

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
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SMILES for #<Metabolite:0x00007fdb510bf9a8>

C[C@H](O)CC(O)=O
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INCHI for #<Metabolite:0x00007fdb510bf9a8>

InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
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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
Molecular FormulaC4H8O3
Average Mass104.1045
Monoisotopic Mass104.047344122
IUPAC Name(3S)-3-hydroxybutanoic acid
Traditional Nameβ-hydroxybutyrate,l
CAS Registry NumberNot Available
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