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Showing NP-Card for ketopantoic acid (NP0054978)

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Record Information
Version2.0
Created at2022-04-28 01:10:03 UTC
Updated at2022-04-28 01:10:04 UTC
NP-MRD IDNP0054978
Secondary Accession NumbersNone
Natural Product Identification
Common Nameketopantoic acid
Description2-Dehydropantoate, also known as ketopantoic acid or ketopantoate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Dehydropantoate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Dehydropantoate exists in both E. ketopantoic acid is found in Arabidopsis thaliana. ketopantoic acid was first documented in 1975 (PMID: 234966). Coli (prokaryote) and yeast (eukaryote).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0054978 (ketopantoic acid)


  Mrv0541 02231217112D          

 10  9  0  0  0  0            999 V2000
    1.6500    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
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
Download

3D MOL for NP0054978 (ketopantoic acid)

     RDKit          3D

 20 19  0  0  0  0  0  0  0  0999 V2000
   -0.1283   -1.1783   -1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -0.3223   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2634   -1.0251    0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811    0.9703   -0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1824    1.8028    0.5918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9051    0.0207    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0170   -0.3284    1.8804 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0193    0.7488    0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9795    1.1253   -1.1280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1520    1.0505    0.7869 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6084   -1.9767   -1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0947   -0.5208   -2.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -1.6710   -1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6746   -1.6559    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7475   -0.2460    1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0023   -1.6426    0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561    0.6557   -0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3178    1.4509   -1.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    2.2441    0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785    0.4979    0.6423 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
  4  5  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8 10  1  0
  8  9  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
 10 20  1  0
M  END
Download

3D SDF for NP0054978 (ketopantoic acid)


  Mrv0541 02231217112D          

 10  9  0  0  0  0            999 V2000
    1.6500    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
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0054978

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O4/c1-6(2,3-7)4(8)5(9)10/h7H,3H2,1-2H3,(H,9,10)

> <INCHI_KEY>
PKVVTUWHANFMQC-UHFFFAOYSA-N

> <FORMULA>
C6H10O4

> <MOLECULAR_WEIGHT>
146.1412

> <EXACT_MASS>
146.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
13.833096792405735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3,3-dimethyl-2-oxobutanoic acid

> <ALOGPS_LOGP>
-0.35

> <JCHEM_LOGP>
0.5846392240000005

> <ALOGPS_LOGS>
-0.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.980989916536032

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.245393682919492

> <JCHEM_PKA_STRONGEST_BASIC>
-2.820508568337858

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
33.4668

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ketopantoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0054978 (ketopantoic acid)

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PDB for NP0054978 (ketopantoic 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  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976   0.564   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0054978 (ketopantoic acid)
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SMILES for NP0054978 (ketopantoic acid)
CC(C)(CO)C(=O)C(O)=O
Download
INCHI for NP0054978 (ketopantoic acid)
InChI=1S/C6H10O4/c1-6(2,3-7)4(8)5(9)10/h7H,3H2,1-2H3,(H,9,10)
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View in JSmol
Synonyms
ValueSource
Ketopantoic acidChEBI
KetopantoateGenerator
2-Dehydropantoic acidGenerator
2-DehydropantoateChEBI, Generator
Chemical FormulaC6H10O4
Average Mass146.1412 Da
Monoisotopic Mass146.05791 Da
IUPAC Name4-hydroxy-3,3-dimethyl-2-oxobutanoic acid
Traditional Nameketopantoic acid
CAS Registry NumberNot Available
SMILES
CC(C)(CO)C(=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O4/c1-6(2,3-7)4(8)5(9)10/h7H,3H2,1-2H3,(H,9,10)
InChI KeyPKVVTUWHANFMQC-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
Arabidopsis thalianaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassKeto acids and derivatives  
Sub ClassShort-chain keto acids and derivatives  
Direct ParentShort-chain keto acids and derivatives  
Alternative Parents
Substituents
  • Branched fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Short-chain keto acid
    • 

  • Methyl-branched fatty acid
    • 

  • Alpha-keto acid
    • 

  • Beta-hydroxy ketone
    • 

  • Fatty acyl
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • 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-0.35ALOGPS
logP0.58ChemAxon
logS-0.13ALOGPS
pKa (Strongest Acidic)3.25ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.47 m³·mol⁻¹ChemAxon
Polarizability13.83 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB03795  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030332  
KNApSAcK IDC00007477  
Chemspider IDNot Available
KEGG Compound IDC00966  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound38  
PDB IDNot Available
ChEBI ID17094  
Good Scents IDNot Available
References
General References
  1. Wilken DR, King HL Jr, Dyar RE: Ketopantoic acid and ketopantoyl lactone reductases. Stereospecificity of transfer of hydrogen from reduced nicotinamide adenine dinucleotide phosphate. J Biol Chem. 1975 Mar 25;250(6):2311-4. [PubMed:234966  ]