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Showing NP-Card for 4-hydroxybutanoate (NP0334334)

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Record Information
Version2.0
Created at2024-09-09 23:12:45 UTC
Updated at2024-09-09 23:12:45 UTC
NP-MRD IDNP0334334
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxybutanoate
DescriptionGamma hydroxybutyric acid, also known as 4-hydroxybutanoic acid or ghb, is a member of the class of compounds known as hydroxy fatty acids. Hydroxy fatty acids are fatty acids in which the chain bears a hydroxyl group. Gamma hydroxybutyric acid is soluble (in water) and a weakly acidic compound (based on its pKa). Gamma hydroxybutyric acid can be found in a number of food items such as cauliflower, burdock, acorn, and mountain yam, which makes gamma hydroxybutyric acid a potential biomarker for the consumption of these food products. Gamma hydroxybutyric acid can be found primarily in blood and urine. Gamma hydroxybutyric acid is a drug which is used as a general anesthetic, to treat conditions such as insomnia, clinical depression, narcolepsy, and alcoholism, and to improve athletic performance. At higher doses, GHB may induce nausea, dizziness, drowsiness, agitation, visual disturbances, depressed breathing, amnesia, unconsciousness, and death (DrugBank).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334334 (4-hydroxybutanoate)


  Mrv1652306251823462D          

  7  6  0  0  0  0            999 V2000
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
M  CHG  1   7  -1
M  END
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3D MOL for NP0334334 (4-hydroxybutanoate)

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3D SDF for NP0334334 (4-hydroxybutanoate)

  Mrv1652306251823462D          

  7  6  0  0  0  0            999 V2000
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
M  CHG  1   7  -1
M  END
> <DATABASE_ID>
NP0334334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCCC([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)/p-1

> <INCHI_KEY>
SJZRECIVHVDYJC-UHFFFAOYSA-M

> <FORMULA>
C4H7O3

> <MOLECULAR_WEIGHT>
103.0966

> <EXACT_MASS>
103.03951909

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.73296833303153

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxybutanoate

> <ALOGPS_LOGP>
-0.60

> <JCHEM_LOGP>
-0.5149198190000002

> <ALOGPS_LOGS>
0.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.98255965448772

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.440873954984472

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3817124873466886

> <JCHEM_POLAR_SURFACE_AREA>
60.36

> <JCHEM_REFRACTIVITY>
34.6374

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.11e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-hydroxybutyrate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334334 (4-hydroxybutanoate)
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PDB for NP0334334 (4-hydroxybutanoate)
HEADER    PROTEIN                                 25-JUN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JUN-18         0                                  
HETATM    1  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.207  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.541   0.770   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.127   0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O-1
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6    7                                                  
CONECT    5    3                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0334334 (4-hydroxybutanoate)
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SMILES for NP0334334 (4-hydroxybutanoate)
OCCCC([O-])=O
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INCHI for NP0334334 (4-hydroxybutanoate)
InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)/p-1
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Synonyms
ValueSource
4-HydroxybutanoateChEBI
gamma-HydroxybutyrateChEBI
GHBChEBI
4-Hydroxybutanoic acidGenerator
g-HydroxybutyrateGenerator
g-Hydroxybutyric acidGenerator
Γ-hydroxybutyrateGenerator
Γ-hydroxybutyric acidGenerator
g HydroxybutyrateGenerator
g Hydroxybutyric acidGenerator
gamma HydroxybutyrateGenerator, MeSH
γ hydroxybutyrateGenerator
γ hydroxybutyric acidGenerator
gamma-Hydroxybutyric acidGenerator
4-Hydroxy-butanoic acidHMDB
4-Hydroxybutyric acidHMDB
JuiceHMDB
Liquid ecstasyHMDB
Sodium oxybateHMDB, MeSH
4 Hydroxybutyrate sodiumMeSH
Sodium gamma hydroxybutyrateMeSH
Sodium gamma-hydroxybutyrateMeSH
Oxybutyrate, sodiumMeSH
Sodium oxybutyrateMeSH
SomsanitMeSH
4-Hydroxybutyrate sodiumMeSH
Oxybate sodiumMeSH
Oxybate, sodiumMeSH
XyremMeSH
Chemical FormulaC4H7O3
Average Mass103.0966 Da
Monoisotopic Mass103.03952 Da
IUPAC Name4-hydroxybutanoate
Traditional Namegamma-hydroxybutyrate
CAS Registry NumberNot Available
SMILES
OCCCC([O-])=O
InChI Identifier
InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)/p-1
InChI KeySJZRECIVHVDYJC-UHFFFAOYSA-M
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentHydroxy fatty acids  
Alternative Parents
Substituents
  • Short-chain hydroxy acid
    • 

  • Hydroxy fatty acid
    • 

  • Straight chain fatty acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Organic anion
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.6ALOGPS
logP-0.51ChemAxon
logS0.77ALOGPS
pKa (Strongest Acidic)4.44ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.64 m³·mol⁻¹ChemAxon
Polarizability9.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0015507  
DrugBank IDDB01440  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030502  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGamma-Hydroxybutyric acid  
METLIN IDNot Available
PubChem Compound3037032  
PDB IDNot Available
ChEBI ID16724  
Good Scents IDNot Available
References
General References