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Showing NP-Card for (S)-3-Hydroxybutyric acid (NP0001137)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:21:05 UTC
NP-MRD IDNP0001137
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001137 ((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 NP0001137 ((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
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3D SDF for NP0001137 ((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>
NP0001137

> <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-/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 NP0001137 ((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
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PDB for NP0001137 ((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
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3D PDB for NP0001137 ((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
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SMILES for NP0001137 ((S)-3-Hydroxybutyric acid)

C[C@H](O)CC(O)=O
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INCHI for NP0001137 ((S)-3-Hydroxybutyric acid)

InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
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View in JSmol
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 Mass104.1045 Da
Monoisotopic Mass104.04734 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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 Point45 - 48 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
Polarizability9.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000442
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. 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 ]