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Showing NP-Card for 4-Hydroxyisovaleric acid (NP0086838)

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Record Information
Version2.0
Created at2022-05-11 16:32:25 UTC
Updated at2022-05-11 16:32:25 UTC
NP-MRD IDNP0086838
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxyisovaleric acid
Description4-Hydroxyisovaleric acid, also known as 4-hydroxyisopentanoate, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 4-Hydroxyisovaleric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Hydroxyisovaleric acid, with regard to humans, has been linked to the inborn metabolic disorder isovaleric acidemia. The effects of HMB on human skeletal muscle were first discovered by Steven L. 4-Hydroxyisovaleric acid was first documented in 1981 (PMID: 6452974). Nissen at Iowa State University in the mid-1990s.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086838 (4-Hydroxyisovaleric acid)


  Mrv0541 02231219192D          

  8  7  0  0  0  0            999 V2000
   15.7468   -3.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3193   -3.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6047   -4.5513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1758   -3.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4613   -3.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8903   -3.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1758   -4.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6047   -3.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for NP0086838 (4-Hydroxyisovaleric acid)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.2330   -1.5139   -0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5162   -0.1953   -0.7205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2107    0.8472    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7624    2.1264   -0.0250 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9187   -0.4215   -0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8384    0.6805   -0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129    1.7574   -1.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1733    0.5561   -0.2768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3431   -1.4804    0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430   -1.5507   -0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000   -2.3827   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7066   -0.0688   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1526    0.5330    1.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2841    0.8258   -0.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435    2.6500    0.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198   -1.3609   -0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9251   -0.7272    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068   -0.2749    0.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  6
  3 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  8 18  1  0
M  END
Download

3D SDF for NP0086838 (4-Hydroxyisovaleric acid)


  Mrv0541 02231219192D          

  8  7  0  0  0  0            999 V2000
   15.7468   -3.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3193   -3.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6047   -4.5513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1758   -3.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4613   -3.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8903   -3.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1758   -4.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6047   -3.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  8  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O3/c1-4(3-6)2-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)

> <INCHI_KEY>
ZGYGEPZZMAXSKH-UHFFFAOYSA-N

> <FORMULA>
C5H10O3

> <MOLECULAR_WEIGHT>
118.1311

> <EXACT_MASS>
118.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
11.912681109086346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3-methylbutanoic acid

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
-0.1499469926666665

> <ALOGPS_LOGS>
0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.487778583149005

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.589412306262043

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5977380607571785

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
28.2719

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxyisopentanoate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0086838 (4-Hydroxyisovaleric acid)

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PDB for NP0086838 (4-Hydroxyisovaleric acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      29.394  -6.956   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      36.063  -6.186   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.729  -8.496   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      32.061  -6.956   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.728  -6.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.395  -6.186   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.061  -8.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.729  -6.956   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4    5    6    7                                                  
CONECT    5    1    4                                                       
CONECT    6    4    8                                                       
CONECT    7    4                                                            
CONECT    8    2    3    6                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0086838 (4-Hydroxyisovaleric acid)
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SMILES for NP0086838 (4-Hydroxyisovaleric acid)
CC(CO)CC(O)=O
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INCHI for NP0086838 (4-Hydroxyisovaleric acid)
InChI=1S/C5H10O3/c1-4(3-6)2-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)
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View in JSmol
Synonyms
ValueSource
4-HydroxyisovalerateGenerator
4-HydroxyisopentanoateHMDB
4-Hydroxyisopentanoic acidHMDB
4-Hydroxy-isovalerateHMDB
4-Hydroxyisovaleric acidMeSH
Chemical FormulaC5H10O3
Average Mass118.1311 Da
Monoisotopic Mass118.06299 Da
IUPAC Name4-hydroxy-3-methylbutanoic acid
Traditional Name4-hydroxyisopentanoate
CAS Registry NumberNot Available
SMILES
CC(CO)CC(O)=O
InChI Identifier
InChI=1S/C5H10O3/c1-4(3-6)2-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)
InChI KeyZGYGEPZZMAXSKH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
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 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
  • Methyl-branched fatty acid
    • 

  • Short-chain hydroxy acid
    • 

  • Hydroxy fatty acid
    • 

  • Branched 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
    • 

  • 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-0.09ALOGPS
logP-0.15ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)4.59ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.27 m³·mol⁻¹ChemAxon
Polarizability11.91 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002011  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022793  
KNApSAcK IDNot Available
Chemspider ID116413  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBeta-Hydroxy beta-methylbutyric acid  
METLIN ID6434  
PubChem Compound131760  
PDB IDNot Available
ChEBI ID384411  
Good Scents IDNot Available
References
General References
  1. Truscott RJ, Malegan D, McCairns E, Burke D, Hick L, Sims P, Halpern B, Tanaka K, Sweetman L, Nyhan WL, Hammond J, Bumack C, Haan EA, Danks DM: New metabolites in isovaleric acidemia. Clin Chim Acta. 1981 Mar 5;110(2-3):187-203. [PubMed:6452974  ]