Np mrd loader

Showing NP-Card for Alpha-Hydroxyisobutyric acid (NP0000707)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-04-19 09:55:09 UTC
NP-MRD IDNP0000707
Secondary Accession NumbersNone
Natural Product Identification
Common NameAlpha-Hydroxyisobutyric acid
DescriptionAlpha-Hydroxyisobutyric acid is a metabolite of methyl tert-butyl ether (MTBE). MTBE may be obtained through environmental exposure. MTBE is rapidly eliminated from the body, mainly through expired air as the unchanged compound. MTBE is to some extent metabolised to t-butyl alcohol (TBA) and formaldehyde and oxidised to 2-methyl-1,2-propanediol and a-hydroxy isobuturic acid. Alpha-Hydroxyisobutyric acid has been used as an arial bactericide.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000707 (Alpha-Hydroxyisobutyric acid)


  Mrv1652305271900022D          

  7  6  0  0  0  0            999 V2000
   -1.7435    0.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580   -0.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096   -1.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518   -1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489   -0.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -0.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  7  3  1  0  0  0  0
M  END
Download

3D MOL for NP0000707 (Alpha-Hydroxyisobutyric acid)

HMDB0000729
     RDKit          3D
alpha-Hydroxyisobutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.2535    1.4434    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765   -0.0224    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9877   -0.7766   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586   -0.1556    1.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951   -0.5442    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -1.0199    1.4050 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -0.5077   -0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460    2.0958    0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    1.7310   -0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    1.6634   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -0.2726   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450   -1.8514   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559   -0.5829   -0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.1098    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560   -0.0904   -0.8888 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  7 15  1  0
M  END
Download

3D SDF for NP0000707 (Alpha-Hydroxyisobutyric acid)


  Mrv1652305271900022D          

  7  6  0  0  0  0            999 V2000
   -1.7435    0.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580   -0.4930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096   -1.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518   -1.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489   -0.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -0.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -0.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  7  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000707

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)

> <INCHI_KEY>
BWLBGMIXKSTLSX-UHFFFAOYSA-N

> <FORMULA>
C4H8O3

> <MOLECULAR_WEIGHT>
104.1045

> <EXACT_MASS>
104.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.872501504091092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-methylpropanoic acid

> <ALOGPS_LOGP>
-0.37

> <JCHEM_LOGP>
-0.039063632000000056

> <ALOGPS_LOGS>
0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.40275140597527

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.948421773706818

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7355605250234243

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
23.5531

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetonate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000707 (Alpha-Hydroxyisobutyric acid)

HMDB0000729
     RDKit          3D
alpha-Hydroxyisobutyric acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.2535    1.4434    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765   -0.0224    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9877   -0.7766   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586   -0.1556    1.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951   -0.5442    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -1.0199    1.4050 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -0.5077   -0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460    2.0958    0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    1.7310   -0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    1.6634   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -0.2726   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450   -1.8514   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559   -0.5829   -0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.1098    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560   -0.0904   -0.8888 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  7 15  1  0
M  END
Download

PDB for NP0000707 (Alpha-Hydroxyisobutyric acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      -3.255   1.390   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -4.588  -0.920   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -0.951  -2.123   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.897  -2.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.265  -0.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.582  -0.148   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.916  -0.918   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    7                                                            
CONECT    4    7                                                            
CONECT    5    7    1    2                                                  
CONECT    6    7                                                            
CONECT    7    6    4    5    3                                             
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
Download

3D PDB for NP0000707 (Alpha-Hydroxyisobutyric acid)

COMPND    HMDB0000729
HETATM    1  C1  UNL     1      -0.254   1.443   0.001  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.176  -0.022   0.363  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.988  -0.777  -0.685  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.759  -0.156   1.633  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.195  -0.544   0.356  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.672  -1.020   1.405  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.944  -0.508  -0.796  1.00  0.00           O  
HETATM    8  H1  UNL     1      -0.246   2.096   0.916  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.539   1.731  -0.721  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.215   1.663  -0.513  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.760  -0.273  -1.656  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.745  -1.851  -0.709  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.056  -0.583  -0.437  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.009  -1.110   1.731  1.00  0.00           H  
HETATM   15  H8  UNL     1       2.856  -0.090  -0.889  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4    5
CONECT    3   11   12   13
CONECT    4   14
CONECT    5    6    6    7
CONECT    7   15
END
Download

SMILES for NP0000707 (Alpha-Hydroxyisobutyric acid)

CC(C)(O)C(O)=O
Download

INCHI for NP0000707 (Alpha-Hydroxyisobutyric acid)

InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)
Download
View in JSmol
Synonyms
ValueSource
2-Hydroxy-2-methylpropionic acidChEBI
2-Hydroxy-2-methylpropionsaeureChEBI
2-Methyl-2-hydroxypropanoic acidChEBI
2-Methyl-2-hydroxypropionsaeureChEBI
2-Methyllactic acidChEBI
Acetonic acidChEBI
Acide 2-hydroxy-2-methylpropanoiqueChEBI
Acido 2-hidroxi-2-metilpropionicoChEBI
alpha-Hydroxy-alpha-methylpropanoic acidChEBI
alpha-Hydroxy-alpha-methylpropionic acidChEBI
alpha-Hydroxyisobutanoic acidChEBI
HIBAChEBI
Hydroxydimethylacetic acidChEBI
2-Hydroxy-2-methylpropionateGenerator
2-Methyl-2-hydroxypropanoateGenerator
2-MethyllactateGenerator
AcetonateGenerator
a-Hydroxy-a-methylpropanoateGenerator
a-Hydroxy-a-methylpropanoic acidGenerator
alpha-Hydroxy-alpha-methylpropanoateGenerator
Α-hydroxy-α-methylpropanoateGenerator
Α-hydroxy-α-methylpropanoic acidGenerator
a-Hydroxy-a-methylpropionateGenerator
a-Hydroxy-a-methylpropionic acidGenerator
alpha-Hydroxy-alpha-methylpropionateGenerator
Α-hydroxy-α-methylpropionateGenerator
Α-hydroxy-α-methylpropionic acidGenerator
a-HydroxyisobutanoateGenerator
a-Hydroxyisobutanoic acidGenerator
alpha-HydroxyisobutanoateGenerator
Α-hydroxyisobutanoateGenerator
Α-hydroxyisobutanoic acidGenerator
HydroxydimethylacetateGenerator
a-HydroxyisobutyrateGenerator
a-Hydroxyisobutyric acidGenerator
alpha-HydroxyisobutyrateGenerator
Α-hydroxyisobutyrateGenerator
Α-hydroxyisobutyric acidGenerator
a-Hydroxy-isobutyrateHMDB
a-Hydroxy-isobutyric acidHMDB
alpha-Hydroxy-isobutyrateHMDB
Α-hydroxy-isobutyrateHMDB
Α-hydroxy-isobutyric acidHMDB
(CH3)2cohcoohHMDB
2-Hydroxy-2-methylpropanoateHMDB
2-Hydroxy-2-methylpropanoic acidHMDB
2-HydroxyisobutyrateHMDB
2-Hydroxyisobutyric acidHMDB
a-HIBHMDB
alpha-HIBHMDB
HydroxyisobutyrateHMDB
L-2-MethyllactateHMDB
L-2-Methyllactic acidHMDB
2-Hydroxyisobutyric acid, lead saltHMDB
Lead 2-hydroxyisobutyric acidHMDB
alpha-Hydroxyisobutyric acidChEBI
Chemical FormulaC4H8O3
Average Mass104.1045 Da
Monoisotopic Mass104.04734 Da
IUPAC Name2-hydroxy-2-methylpropanoic acid
Traditional Nameacetonate
CAS Registry Number594-61-6
SMILES
CC(C)(O)C(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)
InChI KeyBWLBGMIXKSTLSX-UHFFFAOYSA-N
Experimental Spectra
truetrue
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-02View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-02View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-02View Spectrum
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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-07View Spectrum
Species
Species of Origin
Species NameSourceReference
Homo sapiensLOTUS Database
Hyacinthoides non-scriptaLOTUS Database
Salmonella entericaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Tertiary 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 Point82.5 °CNot Available
Boiling Point212.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.36Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility378 g/LALOGPS
logP-0.37ALOGPS
logP-0.039ChemAxon
logS0.56ALOGPS
pKa (Strongest Acidic)3.95ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.55 m³·mol⁻¹ChemAxon
Polarizability9.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000729
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022207
KNApSAcK IDNot Available
Chemspider ID11181
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3750
PubChem Compound11671
PDB IDNot Available
ChEBI ID50129
Good Scents IDrw1176881
References
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Benson JM, Barr EB, Krone JR: MTBE inhaled alone and in combination with gasoline vapor: uptake, distribution, metabolism, and excretion in rats. Res Rep Health Eff Inst. 2001 May;(102):73-94; discussion 95-109. [PubMed:11504149 ]
  3. Authors unspecified: NTP Toxicology and Carcinogenesis Studies of Isobutene (CAS No. 115-11-7) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser. 1998 Dec;487:1-230. [PubMed:12563344 ]
  4. Shigematsu Y, Sudo M, Momoi T, Inoue Y, Suzuki Y, Kameyama J: Changing plasma and urinary organic acid levels in a patient with isovaleric acidemia during an attack. Pediatr Res. 1982 Sep;16(9):771-5. [PubMed:7133811 ]
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]