Np mrd loader

Showing NP-Card for Sodium Dichloroacetate (NP0137526)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-05-30 16:55:06 UTC
Updated at2022-05-30 16:55:06 UTC
NP-MRD IDNP0137526
Secondary Accession NumbersNone
Natural Product Identification
Common NameSodium Dichloroacetate
DescriptionDichloroacetic acid, also known as dichloroacetate or dichloressigsaeure, belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom. The salts and esters of dichloroacetic acid are called dichloroacetates. Dichloroacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dichloroacetic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Dichloroacetic acid, often abbreviated DCA, is an acid analogue of acetic acid in which two of the three hydrogen atoms of the methyl group have been replaced by chlorine atoms. There is an extensive and consistent data base demonstrating the reproductive toxicity of DCA in males and females. A phase 1 study in 5 patients concluded that DCA was safe, but wasn't designed to establish effectiveness. Early reports of its activity against brain cancer cells led patients to treat themselves with DCA, which is commercially available in non-pharmaceutical grade. Multiple independent studies demonstrate that DCA has the ability to alter normal carbohydrate metabolism. Sodium Dichloroacetate is found in Apis cerana and Asparagopsis taxiformis. Sodium Dichloroacetate was first documented in 2014 (PMID: 24112699). Thus, it decreases lactate production by shifting the metabolism of pyruvate from fermentation towards oxidation in the mitochondria.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0137526 (Sodium Dichloroacetate)


  Mrv0541 02241205512D          

  6  5  0  0  0  0            999 V2000
    0.8250    1.4289    0.0000 O   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
    2.0625    0.7145    0.0000 O   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 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
M  END
Download

3D MOL for NP0137526 (Sodium Dichloroacetate)

Download
3D SDF for NP0137526 (Sodium Dichloroacetate)

  Mrv0541 02241205512D          

  6  5  0  0  0  0            999 V2000
    0.8250    1.4289    0.0000 O   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
    2.0625    0.7145    0.0000 O   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 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137526

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)

> <INCHI_KEY>
JXTHNDFMNIQAHM-UHFFFAOYSA-N

> <FORMULA>
C2H2Cl2O2

> <MOLECULAR_WEIGHT>
128.942

> <EXACT_MASS>
127.943184722

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.32308517760299

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-dichloroacetic acid

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
1.0581826133333334

> <ALOGPS_LOGS>
-0.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2969741576208516

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
22.6195

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dichloroacetic acid

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0137526 (Sodium Dichloroacetate)
Download
PDB for NP0137526 (Sodium Dichloroacetate)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5 Cl   UNK     0       2.310  -1.334   0.000  0.00  0.00          Cl+0
HETATM    6 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

Download
3D PDB for NP0137526 (Sodium Dichloroacetate)
Download
SMILES for NP0137526 (Sodium Dichloroacetate)
OC(=O)C(Cl)Cl
Download
INCHI for NP0137526 (Sodium Dichloroacetate)
InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)
Download
View in JSmol
Synonyms
ValueSource
2,2-Dichloroacetic acidChEBI
Bichloracetic acidChEBI
Dichloracetic acidChEBI
DichloressigsaeureChEBI
DICHLORO-acetIC ACIDChEBI
DichloroacetateChEBI
2,2-DichloroacetateGenerator
BichloracetateGenerator
DichloracetateGenerator
DICHLORO-acetateGenerator
Bichloroacetic acidMeSH
Dichloroacetate, potassiumMeSH
Dichloroacetate, sodiumMeSH
Acid, bichloroaceticMeSH
Acid, dichloroaceticMeSH
Potassium dichloroacetateMeSH
Sodium dichloroacetateMeSH
Chemical FormulaC2H2Cl2O2
Average Mass128.9420 Da
Monoisotopic Mass127.94318 Da
IUPAC Name2,2-dichloroacetic acid
Traditional Namedichloroacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(Cl)Cl
InChI Identifier
InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)
InChI KeyJXTHNDFMNIQAHM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Asparagopsis taxiformisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAlpha-halocarboxylic acids and derivatives  
Direct ParentAlpha-halocarboxylic acids  
Alternative Parents
Substituents
  • Alpha-halocarboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Carbonyl group
    • 

  • Alkyl halide
    • 

  • Alkyl chloride
    • 

  • 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
logP0.99ALOGPS
logP1.06ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)2.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.62 m³·mol⁻¹ChemAxon
Polarizability9.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB08809  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11149  
BioCyc IDCPD-9674  
BiGG IDNot Available
Wikipedia LinkDichloroacetic_acid  
METLIN IDNot Available
PubChem Compound6597  
PDB IDNot Available
ChEBI ID36386  
Good Scents IDNot Available
References
General References
  1. Berthiaume C, Gilbert Y, Fournier-Larente J, Pluchon C, Filion G, Jubinville E, Serodes JB, Rodriguez M, Duchaine C, Charette SJ: Identification of dichloroacetic acid degrading Cupriavidus bacteria in a drinking water distribution network model. J Appl Microbiol. 2014 Jan;116(1):208-21. doi: 10.1111/jam.12353. Epub 2013 Oct 17. [PubMed:24112699  ]