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Showing metabocard for Pivalic acid (HMDB0041992)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:52:01 UTC
Update Date2023-02-21 17:29:05 UTC
HMDB IDHMDB0041992
Secondary Accession Numbers
  • HMDB41992
Metabolite Identification
Common NamePivalic acid
DescriptionPivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. Relative to esters of most carboxylic acids, esters of pivalic acid are unusually resistant to hydrolysis. Some applications result from this thermal stability. Polymers derived from pivalate esters of vinyl alcohol are highly reflective lacquers. The pivaloyl (abbreviated piv or pv) group is a protective group for alcohols in organic synthesis.
Structure
Data?1677000545
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041992 (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 HMDB0041992 (Pivalic acid)

HMDB0041992
     RDKit          3D
Pivalic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.0502    1.2267   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1530    0.0227    0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584   -0.8584    1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042   -0.7550   -1.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404    0.4770    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698    1.7038    0.2919 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3214   -0.3819    0.2513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709    1.8974   -0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099    0.9639   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8893    1.7805    0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984   -1.7465    1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573   -0.2454    2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983   -1.1690    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398   -0.0638   -2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8080   -1.0246   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -1.6521   -1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509   -0.1751   -0.0290 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
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
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3D SDF for HMDB0041992 (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>
HMDB0041992

> <DATABASE_NAME>
hmdb

> <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 HMDB0041992 (Pivalic acid)

HMDB0041992
     RDKit          3D
Pivalic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.0502    1.2267   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1530    0.0227    0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584   -0.8584    1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2042   -0.7550   -1.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404    0.4770    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698    1.7038    0.2919 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3214   -0.3819    0.2513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709    1.8974   -0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099    0.9639   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8893    1.7805    0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984   -1.7465    1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573   -0.2454    2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983   -1.1690    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398   -0.0638   -2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8080   -1.0246   -1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575   -1.6521   -1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509   -0.1751   -0.0290 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
  4 15  1  0
  4 16  1  0
  7 17  1  0
M  END
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PDB for HMDB0041992 (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 HMDB0041992 (Pivalic acid)

COMPND    HMDB0041992
HETATM    1  C1  UNL     1      -1.050   1.227  -0.015  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.153   0.023   0.006  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.558  -0.858   1.176  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.204  -0.755  -1.289  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.240   0.477   0.188  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.470   1.704   0.292  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.321  -0.382   0.251  1.00  0.00           O  
HETATM    8  H1  UNL     1      -0.671   1.897  -0.824  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.110   0.964  -0.184  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.889   1.781   0.931  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.098  -1.747   1.238  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.457  -0.245   2.087  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.598  -1.169   1.075  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.640  -0.064  -2.064  1.00  0.00           H  
HETATM   15  H8  UNL     1       0.808  -1.025  -1.655  1.00  0.00           H  
HETATM   16  H9  UNL     1      -0.857  -1.652  -1.185  1.00  0.00           H  
HETATM   17  H10 UNL     1       3.251  -0.175  -0.029  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4    5
CONECT    3   11   12   13
CONECT    4   14   15   16
CONECT    5    6    6    7
CONECT    7   17
END
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SMILES for HMDB0041992 (Pivalic acid)

CC(C)(C)C(O)=O
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INCHI for HMDB0041992 (Pivalic acid)

InChI=1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7)
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View in JSmolView NMR AssignmentsView Stereo Labels
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 Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Name2,2-dimethylpropanoic acid
Traditional Namepivalic acid
CAS Registry Number75-98-9
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
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
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point35 °CNot Available
Boiling Point164.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility21.7 mg/mL at 20 °CNot Available
LogP1.48Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility56.9 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.0531661259
DarkChem[M-H]-114.27531661259
DeepCCS[M+H]+125.57930932474
DeepCCS[M-H]-122.7830932474
DeepCCS[M-2H]-159.21430932474
DeepCCS[M+Na]+133.93930932474
AllCCS[M+H]+124.232859911
AllCCS[M+H-H2O]+120.132859911
AllCCS[M+NH4]+128.232859911
AllCCS[M+Na]+129.332859911
AllCCS[M-H]-123.532859911
AllCCS[M+Na-2H]-127.632859911
AllCCS[M+HCOO]-132.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.42 minutes32390414
Predicted by Siyang on May 30, 202212.2029 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.54 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid42.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1515.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid424.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid140.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid268.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid88.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid395.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid520.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)145.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid845.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid356.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1072.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid306.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid329.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate493.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA374.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water74.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pivalic acidCC(C)(C)C(O)=O1472.9Standard polar33892256
Pivalic acidCC(C)(C)C(O)=O758.1Standard non polar33892256
Pivalic acidCC(C)(C)C(O)=O782.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pivalic acid,1TMS,isomer #1CC(C)(C)C(=O)O[Si](C)(C)C851.1Semi standard non polar33892256
Pivalic acid,1TBDMS,isomer #1CC(C)(C)C(=O)O[Si](C)(C)C(C)(C)C1090.2Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111687
KNApSAcK IDNot Available
Chemspider ID6177
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPivalic_acid
METLIN IDNot Available
PubChem Compound6417
PDB IDNot Available
ChEBI ID45133
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1293561
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Basso B, Ullrich-Eberius CI: Membrane Potential and Proton Cotransport of Alanine and Phosphate as Affected by Permeant Weak Acids in Lemna gibba. Plant Physiol. 1987 Nov;85(3):674-8. [PubMed:16665758 ]
  2. Deutsch CJ, Holian A, Holian SK, Daniele RP, Wilson DF: Transmembrane electrical and pH gradients across human erythrocytes and human peripheral lymphocytes. J Cell Physiol. 1979 Apr;99(1):79-93. [PubMed:37251 ]
  3. Ovcharenko V, Fursova E, Romanenko G, Eremenko I, Tretyakov E, Ikorskii V: Synthesis, structure, and magnetic properties of (6-9)-nuclear Ni(II) trimethylacetates and their heterospin complexes with nitroxides. Inorg Chem. 2006 Jul 10;45(14):5338-50. [PubMed:16813397 ]
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