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Showing NP-Card for Pivalic acid (NP0136270)

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Record Information
Version1.0
Created at2022-05-12 15:10:11 UTC
Updated at2022-05-12 15:10:11 UTC
NP-MRD IDNP0136270
Secondary Accession NumbersNone
Natural Product Identification
Common NamePivalic acid
DescriptionPivalic acid, also known as pivalinsaeure or acide pivalique, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Pivalic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. The pivaloyl (abbreviated piv or pv) group is a protective group for alcohols in organic synthesis. This colourless, odiferous organic compound is solid at room temperature. Some applications result from this thermal stability. Polymers derived from Pivalic acid esters of vinyl alcohol are highly reflective lacquers. Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. Pivalic acid is found in Streptomyces avermitilis. It was first documented in 2006 (PMID: 16430936). Relative to esters of most carboxylic acids, esters of pivalic acid are unusually resistant to hydrolysis (PMID: 17724113) (PMID: 21509470) (PMID: 22566287) (PMID: 22790609).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0136270 (Pivalic acid)


  Mrv1652304062013082D          

  7  6  0  0  0  0            999 V2000
    1.6500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    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
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
M  END
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3D MOL for NP0136270 (Pivalic acid)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -0.7582    1.0406   -0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925   -0.0218    0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1425   -0.5544    1.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645   -1.1731   -0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409    0.6033    0.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0832    0.6493    2.1800 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0719    1.1471    0.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512    1.3917   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398    1.8670    0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6945    0.6220   -1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843   -0.2617    2.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1277   -1.6795    1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1709   -0.2089    0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -2.0563   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4097   -1.3079   -1.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3554   -0.8583   -1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0108    0.8007    0.1681 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  7  1  0
  5  6  2  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
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
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3D SDF for NP0136270 (Pivalic acid)


  Mrv1652304062013082D          

  7  6  0  0  0  0            999 V2000
    1.6500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    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
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136270

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7)

> <INCHI_KEY>
IUGYQRQAERSCNH-UHFFFAOYSA-N

> <FORMULA>
C5H10O2

> <MOLECULAR_WEIGHT>
102.1317

> <EXACT_MASS>
102.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
10.926918646601457

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-dimethylpropanoic acid

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
1.5761907130000001

> <ALOGPS_LOGS>
-0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.928208463893052

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
26.346100000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pivalic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0136270 (Pivalic acid)

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PDB for NP0136270 (Pivalic acid)
HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.644   0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    5                                                            
CONECT    4    5    6    7                                                  
CONECT    5    1    2    3    4                                             
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 NP0136270 (Pivalic acid)
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SMILES for NP0136270 (Pivalic acid)
CC(C)(C)C(O)=O
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INCHI for NP0136270 (Pivalic acid)
InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7)
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View in JSmol
Synonyms
ValueSource
2,2-Dimethylpropionic acidChEBI
Acide 2,2-dimethylpropanoiqueChEBI
Acide pivaliqueChEBI
Acido pivalicoChEBI
alpha,alpha-Dimethylpropionic acidChEBI
Dimethylpropionic acidChEBI
Neopentanoic acidChEBI
PivalinsaeureChEBI
Tert-pentanoic acidChEBI
Trimethylacetic acidChEBI
2,2-DimethylpropionateGenerator
a,a-DimethylpropionateGenerator
a,a-Dimethylpropionic acidGenerator
alpha,alpha-DimethylpropionateGenerator
Α,α-dimethylpropionateGenerator
Α,α-dimethylpropionic acidGenerator
DimethylpropionateGenerator
NeopentanoateGenerator
Tert-pentanoateGenerator
TrimethylacetateGenerator
PivalateGenerator
2,2-Dimethyl-propanoic acidHMDB
2,2-Dimethyl-propionic acidHMDB
2,2-Dimethylpropanoic acidHMDB
Kyselina 2,2-dimethylpropionovaHMDB
Kyselina pivalovaHMDB
Neovaleric acidHMDB
Pivalic acid (acd/name 4.0)HMDB
PivalinsaureHMDB
Tert-C4H9COOHHMDB
Trimethyl-acetic acidHMDB
Versatic 5HMDB
Pivalic acid, sodium saltHMDB
Chemical FormulaC5H10O2
Average Mass102.1317 Da
Monoisotopic Mass102.06808 Da
IUPAC Name2,2-dimethylpropanoic acid
Traditional Namepivalic acid
CAS Registry NumberNot Available
SMILES
CC(C)(C)C(O)=O
InChI Identifier
InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7)
InChI KeyIUGYQRQAERSCNH-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
Streptomyces avermitilisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassCarboxylic acids  
Direct ParentCarboxylic acids  
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP1.37ALOGPS
logP1.58ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)4.93ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.35 m³·mol⁻¹ChemAxon
Polarizability10.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041992  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6177  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPivalic_acid  
METLIN IDNot Available
PubChem Compound6417  
PDB IDPIV  
ChEBI ID45133  
Good Scents IDNot Available
References
General References
  1. Yamaguchi T, Nakajima Y, Nakamura Y: Possible mechanism for species difference on the toxicity of pivalic acid between dogs and rats. Toxicol Appl Pharmacol. 2006 Jul 1;214(1):61-8. doi: 10.1016/j.taap.2005.11.013.  Epub 2006 Jan 23. [PubMed:16430936  ] 
  2. Makino Y, Sugiura T, Ito T, Sugiyama N, Koyama N: Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid. Pediatrics. 2007 Sep;120(3):e739-41. doi: 10.1542/peds.2007-0339. Epub 2007 Aug 27. [PubMed:17724113  ] 
  3. Berkovitch-Luria G, Weitman M, Nudelman A, Rephaeli A, Malik Z: Multifunctional 5-aminolevulinic acid prodrugs activating diverse cell-death pathways. Invest New Drugs. 2012 Jun;30(3):1028-38. doi: 10.1007/s10637-011-9669-6. Epub 2011 Apr 21. [PubMed:21509470  ] 
  4. Rasmussen J, Nielsen OW, Lund AM, Kober L, Djurhuus H: Primary carnitine deficiency and pivalic acid exposure causing encephalopathy and fatal cardiac events. J Inherit Metab Dis. 2013 Jan;36(1):35-41. doi: 10.1007/s10545-012-9488-8. Epub 2012 May 8. [PubMed:22566287  ] 
  5. Rezanka T, Kolouchova I, Cejkova A, Sigler K: Biosynthesis and metabolic pathways of pivalic acid. Appl Microbiol Biotechnol. 2012 Sep;95(6):1371-6. doi: 10.1007/s00253-012-4267-x. Epub 2012 Jul 13. [PubMed:22790609  ]