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Showing NP-Card for 2-Hydroxy-2-methylbutyric acid (NP0000921)

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Record Information
Version2.0
Created at2006-05-22 14:17:30 UTC
Updated at2021-06-29 00:47:18 UTC
NP-MRD IDNP0000921
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Hydroxy-2-methylbutyric acid
Description2-Hydroxy-2-methylbutyric acid, also known as (+/-)-2-hydroxy-2-methylbutanoate or 2-methyl-2-hydroxybutyric acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Hydroxy-2-methylbutyric acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000921 (2-Hydroxy-2-methylbutyric acid)


  Mrv1652305261923542D          

  8  7  0  0  0  0            999 V2000
   15.6916  -13.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4061  -13.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1206  -13.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4061  -12.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9772  -13.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2627  -13.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6916  -14.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6916  -12.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
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3D MOL for NP0000921 (2-Hydroxy-2-methylbutyric acid)

HMDB0001987
     RDKit          3D
2-Hydroxy-2-methylbutyric acid
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.9167   -0.3728    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    0.0106   -0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820    0.1473   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5733    1.2248    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2481    0.6350   -1.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730   -1.0873    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -1.7213    1.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163   -1.5781   -0.3593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041    0.0638   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027    0.0552    1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -1.4747    0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9224   -0.7622   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158    0.9660   -1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495    2.0632    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291    1.5601    0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357    0.8312    1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6734    1.2865   -1.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398   -1.8473    0.1433 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
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
M  END
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3D SDF for NP0000921 (2-Hydroxy-2-methylbutyric acid)


  Mrv1652305261923542D          

  8  7  0  0  0  0            999 V2000
   15.6916  -13.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4061  -13.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1206  -13.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4061  -12.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9772  -13.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2627  -13.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6916  -14.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6916  -12.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O3/c1-3-5(2,8)4(6)7/h8H,3H2,1-2H3,(H,6,7)

> <INCHI_KEY>
MBIQENSCDNJOIY-UHFFFAOYSA-N

> <FORMULA>
C5H10O3

> <MOLECULAR_WEIGHT>
118.1311

> <EXACT_MASS>
118.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
11.730470416866911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-methylbutanoic acid

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
0.483458763

> <ALOGPS_LOGS>
0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.140030807663564

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.096793172378484

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8451698490140247

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
28.0771

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2-methylbutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000921 (2-Hydroxy-2-methylbutyric acid)

HMDB0001987
     RDKit          3D
2-Hydroxy-2-methylbutyric acid
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.9167   -0.3728    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    0.0106   -0.7677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820    0.1473   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5733    1.2248    0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2481    0.6350   -1.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730   -1.0873    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -1.7213    1.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163   -1.5781   -0.3593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041    0.0638   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027    0.0552    1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -1.4747    0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9224   -0.7622   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158    0.9660   -1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495    2.0632    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291    1.5601    0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2357    0.8312    1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6734    1.2865   -1.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398   -1.8473    0.1433 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
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  4 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
M  END
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PDB for NP0000921 (2-Hydroxy-2-methylbutyric acid)

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  C   UNK     0      29.291 -25.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.625 -24.320   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      31.958 -25.090   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      30.625 -22.780   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      27.957 -24.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.624 -25.090   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      29.291 -26.630   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      29.291 -23.550   0.000  0.00  0.00           C+0
CONECT    1    2    5    7    8                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1    6                                                       
CONECT    6    5                                                            
CONECT    7    1                                                            
CONECT    8    1                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for NP0000921 (2-Hydroxy-2-methylbutyric acid)

COMPND    HMDB0001987
HETATM    1  C1  UNL     1      -1.917  -0.373   0.273  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.923   0.011  -0.768  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.482   0.147  -0.263  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.573   1.225   0.829  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.248   0.635  -1.319  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.073  -1.087   0.228  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.567  -1.721   1.178  1.00  0.00           O  
HETATM    8  O3  UNL     1       2.216  -1.578  -0.359  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.904   0.064  -0.041  1.00  0.00           H  
HETATM   10  H2  UNL     1      -1.703   0.055   1.283  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.104  -1.475   0.324  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.922  -0.762  -1.552  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.216   0.966  -1.232  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.050   2.063   0.461  1.00  0.00           H  
HETATM   15  H7  UNL     1       1.629   1.560   0.833  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.236   0.831   1.808  1.00  0.00           H  
HETATM   17  H9  UNL     1       0.673   1.286  -1.827  1.00  0.00           H  
HETATM   18  H10 UNL     1       3.040  -1.847   0.143  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4    5    6
CONECT    4   14   15   16
CONECT    5   17
CONECT    6    7    7    8
CONECT    8   18
END
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SMILES for NP0000921 (2-Hydroxy-2-methylbutyric acid)

CCC(C)(O)C(O)=O
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INCHI for NP0000921 (2-Hydroxy-2-methylbutyric acid)

InChI=1S/C5H10O3/c1-3-5(2,8)4(6)7/h8H,3H2,1-2H3,(H,6,7)
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View in JSmol
Synonyms
ValueSource
2-Hydroxy-2-methylbutyrateGenerator
(+/-)-2-hydroxy-2-methylbutanoateHMDB
(+/-)-2-hydroxy-2-methylbutanoic acidHMDB
(+/-)-2-hydroxy-2-methylbutyric acidHMDB
(+/-)-a-hydroxy-a-methylbutyric acidHMDB
(+/-)-alpha-hydroxy-alpha-methylbutyric acidHMDB
2-Hydroxy-2-methyl butyrateHMDB
2-Hydroxy-2-methyl butyric acidHMDB
2-Hydroxy-2-methyl-butanoateHMDB
2-Hydroxy-2-methyl-butanoic acidHMDB
2-Hydroxy-2-methyl-butyrateHMDB
2-Hydroxy-2-methyl-butyric acidHMDB
2-Hydroxy-2-methyl-N-butyrateHMDB
2-Hydroxy-2-methyl-N-butyric acidHMDB
2-Hydroxy-2-methylbutanoateHMDB
2-Hydroxy-2-methylbutanoic acidHMDB
2-Methyl-2-hydroxybutyric acidHMDB
a-Hydroxy-a-methyl-butyric acidHMDB
a-Hydroxy-a-methylbutyric acidHMDB
alpha-Hydroxy-alpha-methyl-butyric acidHMDB
alpha-Hydroxy-alpha-methylbutyric acidHMDB
2-Hydroxy-2-methylbutyric acidMeSH
Chemical FormulaC5H10O3
Average Mass118.1311 Da
Monoisotopic Mass118.06299 Da
IUPAC Name2-hydroxy-2-methylbutanoic acid
Traditional Name2-hydroxy-2-methylbutyric acid
CAS Registry Number3739-30-8
SMILES
CCC(C)(O)C(O)=O
InChI Identifier
InChI=1S/C5H10O3/c1-3-5(2,8)4(6)7/h8H,3H2,1-2H3,(H,6,7)
InChI KeyMBIQENSCDNJOIY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 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
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
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point74 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility349 g/LALOGPS
logP0.13ALOGPS
logP0.48ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.08 m³·mol⁻¹ChemAxon
Polarizability11.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001987
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022784
KNApSAcK IDC00052118
Chemspider ID86129
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6416
PubChem Compound95433
PDB IDNot Available
ChEBI ID68454
Good Scents IDNot Available
References
General References
  1. Amberg A, Rosner E, Dekant W: Biotransformation and kinetics of excretion of tert-amyl-methyl ether in humans and rats after inhalation exposure. Toxicol Sci. 2000 Jun;55(2):274-83. [PubMed:10828258 ]
  2. Dekant W, Bernauer U, Rosner E, Amberg A: Biotransformation of MTBE, ETBE, and TAME after inhalation or ingestion in rats and humans. Res Rep Health Eff Inst. 2001 May;(102):29-71; discussion 95-109. [PubMed:11504147 ]