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Showing NP-Card for dibromoacetic acid (NP0159959)

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Record Information
Version2.0
Created at2022-09-02 17:48:25 UTC
Updated at2022-09-02 17:48:26 UTC
NP-MRD IDNP0159959
Secondary Accession NumbersNone
Natural Product Identification
Common Namedibromoacetic acid
DescriptionDibromoacetic acid, also known as DBAA or 2,2-dibromoacetate, 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. A monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are replaced by bromo groups. dibromoacetic acid is found in Asparagopsis taxiformis. dibromoacetic acid was first documented in 2013 (PMID: 23348848). Dibromoacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 25556763) (PMID: 25955755) (PMID: 26052022) (PMID: 26188195).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0159959 (dibromoacetic acid)


  Mrv1533004261501352D          

  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 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Br  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
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3D MOL for NP0159959 (dibromoacetic acid)

     RDKit          3D

  8  7  0  0  0  0  0  0  0  0999 V2000
    1.0159   -1.4465   -0.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5777   -0.2977   -0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    0.7392   -0.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8201   -0.0305    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7283    1.1584   -1.0500 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -1.6180    0.4303 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.0950    0.9797    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7895    0.5154    1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  3  7  1  0
  4  8  1  0
M  END
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3D SDF for NP0159959 (dibromoacetic acid)


  Mrv1533004261501352D          

  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 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Br  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>
NP0159959

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C2H2Br2O2/c3-1(4)2(5)6/h1H,(H,5,6)

> <INCHI_KEY>
SIEILFNCEFEENQ-UHFFFAOYSA-N

> <FORMULA>
C2H2Br2O2

> <MOLECULAR_WEIGHT>
217.844

> <EXACT_MASS>
215.842155

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
11.517493543382802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-dibromoacetic acid

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
0.6994413316666667

> <ALOGPS_LOGS>
-1.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6010739005787675

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
28.252699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetic acid, dibromo-

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0159959 (dibromoacetic acid)

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PDB for NP0159959 (dibromoacetic acid)
HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         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 Br   UNK     0       2.310  -1.334   0.000  0.00  0.00          Br+0
HETATM    6 Br   UNK     0       0.000   0.000   0.000  0.00  0.00          Br+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

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3D PDB for NP0159959 (dibromoacetic acid)
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SMILES for NP0159959 (dibromoacetic acid)
OC(=O)C(Br)Br
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INCHI for NP0159959 (dibromoacetic acid)
InChI=1S/C2H2Br2O2/c3-1(4)2(5)6/h1H,(H,5,6)
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View in JSmol
Synonyms
ValueSource
2,2-Dibromoacetic acidChEBI
2,2-Dibromoethanoic acidChEBI
DBAAChEBI
Dibromoethanoic acidChEBI
2,2-DibromoacetateGenerator
2,2-DibromoethanoateGenerator
DibromoethanoateGenerator
DibromoacetateGenerator
Chemical FormulaC2H2Br2O2
Average Mass217.8440 Da
Monoisotopic Mass215.84216 Da
IUPAC Name2,2-dibromoacetic acid
Traditional Nameacetic acid, dibromo-
CAS Registry NumberNot Available
SMILES
OC(=O)C(Br)Br
InChI Identifier
InChI=1S/C2H2Br2O2/c3-1(4)2(5)6/h1H,(H,5,6)
InChI KeySIEILFNCEFEENQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
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
    • 

  • Organobromide
    • 

  • Organohalogen compound
    • 

  • Carbonyl group
    • 

  • Alkyl halide
    • 

  • Alkyl bromide
    • 

  • 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
logP1.35ALOGPS
logP0.7ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.25 m³·mol⁻¹ChemAxon
Polarizability11.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC20123  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12433  
PDB IDNot Available
ChEBI ID90124  
Good Scents IDNot Available
References
General References
  1. Enright BP, Tornesi B, Lorenz H, Whitney K: The inhibin B response to testicular toxicants ethylene glycol monomethyl ether or dibromoacetic acid in male rats. Birth Defects Res B Dev Reprod Toxicol. 2013 Feb;98(1):35-40. doi:  10.1002/bdrb.21039. Epub 2013 Jan 24. [PubMed:23348848  ] 
  2. Baberschke N, Steinberg CE, Saul N: Low concentrations of dibromoacetic acid and N-nitrosodimethylamine induce several stimulatory effects in the invertebrate model Caenorhabditis elegans. Chemosphere. 2015 Apr;124:122-8. doi: 10.1016/j.chemosphere.2014.12.002. Epub  2014 Dec 31. [PubMed:25556763  ] 
  3. Lieke T, Steinberg CE, Ju J, Saul N: Natural Marine and Synthetic Xenobiotics Get on Nematode's Nerves: Neuro-Stimulating and Neurotoxic Findings in Caenorhabditis elegans. Mar Drugs. 2015 May 6;13(5):2785-812. doi: 10.3390/md13052785. [PubMed:25955755  ] 
  4. Michalowicz J, Wroblewski W, Mokra K, Macczak A, Kwiatkowska M: Comparative study of the effect of chloro-, dichloro-, bromo-, and dibromoacetic acid on necrotic, apoptotic and morphological changes in human peripheral blood mononuclear cells (in vitro study). Toxicol In Vitro. 2015 Oct;29(7):1416-24. doi: 10.1016/j.tiv.2015.05.021. Epub  2015 Jun 4. [PubMed:26052022  ] 
  5. Zhang SH, Miao DY, Tan L, Liu AL, Lu WQ: Comparative cytotoxic and genotoxic potential of 13 drinking water disinfection by-products using a microplate-based cytotoxicity assay and a developed SOS/umu assay. Mutagenesis. 2016 Jan;31(1):35-41. doi: 10.1093/mutage/gev053. Epub 2015 Jul 17. [PubMed:26188195  ] 
  6. LOTUS database [Link]