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Showing NP-Card for Fluoroacetate (NP0012911)

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Record Information
Version1.0
Created at2021-01-05 22:26:57 UTC
Updated at2021-07-15 17:13:04 UTC
NP-MRD IDNP0012911
Secondary Accession NumbersNone
Natural Product Identification
Common NameFluoroacetate
Provided ByNPAtlasNPAtlas Logo
DescriptionFluoroacetic acid, also known as monofluoroacetate or cymonic acid, 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. Fluoroacetic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Fluoroacetate is found in Streptomyces. It was first documented in 2007 (PMID: 17141253). Based on a literature review a significant number of articles have been published on Fluoroacetic acid (PMID: 24903341) (PMID: 17425556) (PMID: 18803668) (PMID: 19069133).
Structure
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MOL3D MOLSDF3D SDFPDBSMILESInChI

MOL for NP0012911 (Fluoroacetate)


  Mrv1652306242119313D          

  8  7  0  0  0  0            999 V2000
    0.6612    1.4584   -0.9690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277    0.5207   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -0.0212    0.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9254   -0.1421   -0.0591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1672   -0.2140    1.2993 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.7407    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383   -1.2080   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952    0.3470   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
M  END
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3D MOL for NP0012911 (Fluoroacetate)

     RDKit          3D

  8  7  0  0  0  0  0  0  0  0999 V2000
    0.6612    1.4584   -0.9690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277    0.5207   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -0.0212    0.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9254   -0.1421   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1672   -0.2140    1.2993 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.7407    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383   -1.2080   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952    0.3470   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  3  6  1  0
  4  7  1  0
  4  8  1  0
M  END
Download

3D SDF for NP0012911 (Fluoroacetate)


  Mrv1652306242119313D          

  8  7  0  0  0  0            999 V2000
    0.6612    1.4584   -0.9690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277    0.5207   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -0.0212    0.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9254   -0.1421   -0.0591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1672   -0.2140    1.2993 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.7407    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383   -1.2080   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952    0.3470   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0012911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])F

> <INCHI_IDENTIFIER>
InChI=1S/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)

> <INCHI_KEY>
QEWYKACRFQMRMB-UHFFFAOYSA-N

> <FORMULA>
C2H3FO2

> <MOLECULAR_WEIGHT>
78.0424

> <EXACT_MASS>
78.011707545

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
5.4193454359261795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-fluoroacetic acid

> <ALOGPS_LOGP>
-0.31

> <JCHEM_LOGP>
-0.14950198633333325

> <ALOGPS_LOGS>
0.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.128982033101654

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
12.6538

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fluoroacetic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0012911 (Fluoroacetate)

     RDKit          3D

  8  7  0  0  0  0  0  0  0  0999 V2000
    0.6612    1.4584   -0.9690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4277    0.5207   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -0.0212    0.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9254   -0.1421   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1672   -0.2140    1.2993 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.7407    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383   -1.2080   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952    0.3470   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  3  6  1  0
  4  7  1  0
  4  8  1  0
M  END
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PDB for NP0012911 (Fluoroacetate)

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       0.661   1.458  -0.969  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.428   0.521  -0.204  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.418  -0.021   0.651  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.925  -0.142  -0.059  0.00  0.00           C+0
HETATM    5  F   UNK     0      -1.167  -0.214   1.299  0.00  0.00           F+0
HETATM    6  H   UNK     0       2.019  -0.741   0.288  0.00  0.00           H+0
HETATM    7  H   UNK     0      -0.738  -1.208  -0.374  0.00  0.00           H+0
HETATM    8  H   UNK     0      -1.695   0.347  -0.632  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    6                                                       
CONECT    4    2    5    7    8                                             
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for NP0012911 (Fluoroacetate)

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SMILES for NP0012911 (Fluoroacetate)
[H]OC(=O)C([H])([H])F
Download
INCHI for NP0012911 (Fluoroacetate)
InChI=1S/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)
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View in JSmolView NMR Assignments
Synonyms
ValueSource
Acide-monofluoracetiqueChEBI
Cymonic acidChEBI
Gifblaar poisonChEBI
HFAChEBI
MonofluoressigsaureChEBI
Monofluoroacetic acidChEBI
UN 2642ChEBI
CymonateGenerator
MonofluoroacetateGenerator
FluoroacetateGenerator
Fluoroacetic acid, calcium saltHMDB
Fluoroacetic acid, potassium saltHMDB
Fluoroacetic acid, sodium saltHMDB
Fluoroacetic acid, aluminum saltHMDB
Fluoroacetic acid, mercury (2+) saltHMDB
Fluoroacetic acid, 18F-labeledHMDB
Fluoroacetic acid, ammonium saltHMDB
Fluoroacetic acid, ammonium salt, 2-(14)C-labeledHMDB
Fluoroacetic acid, lead (+4) saltHMDB
Sodium (18F)fluoroacetateHMDB
Sodium fluoroacetateHMDB
Compound 1080HMDB
Fluoroacetic acid, barium saltHMDB
Fluoroacetic acid, cadmium saltHMDB
Fluoroacetic acid, copper (2+) saltHMDB
Fluoroacetic acid, magnesium saltHMDB
Fluoroacetic acid, terbium (+3) saltHMDB
Chemical FormulaC2H3FO2
Average Mass78.0424 Da
Monoisotopic Mass78.01171 Da
IUPAC Name2-fluoroacetic acid
Traditional Namefluoroacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CF
InChI Identifier
InChI=1S/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)
InChI KeyQEWYKACRFQMRMB-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
Dichapetalum cymosumKNApSAcK Database
Gastrolobium spp.KNApSAcK Database
Oxylobium spp.KNApSAcK Database
StreptomycesNPAtlas
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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-0.31ALOGPS
logP-0.15ChemAxon
logS0.05ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity12.65 m³·mol⁻¹ChemAxon
Polarizability5.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA003759  
HMDB IDHMDB0252369  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001196  
Chemspider ID10205670  
KEGG Compound IDC06108  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluoroacetic_acid  
METLIN IDNot Available
PubChem Compound5237  
PDB IDNot Available
ChEBI ID30775  
Good Scents IDNot Available
References
General References
  1. Huang S, Ma L, Tong MH, Yu Y, O'Hagan D, Deng H: Fluoroacetate biosynthesis from the marine-derived bacterium Streptomyces xinghaiensis NRRL B-24674. Org Biomol Chem. 2014 Jul 21;12(27):4828-31. doi: 10.1039/c4ob00970c. [PubMed:24903341  ] 
  2. Noonan GO, Begley TH, Diachenko GW: Rapid quantitative and qualitative confirmatory method for the determination of monofluoroacetic acid in foods by liquid chromatography-mass spectrometry. J Chromatogr A. 2007 Jan 19;1139(2):271-8. doi: 10.1016/j.chroma.2006.11.034. Epub 2006 Dec 1. [PubMed:17141253  ] 
  3. Ikeda H, Tsuda M, Inoue K, Murase K: Long-term potentiation of neuronal excitation by neuron-glia interactions in the rat spinal dorsal horn. Eur J Neurosci. 2007 Mar;25(5):1297-306. doi: 10.1111/j.1460-9568.2007.05386.x. [PubMed:17425556  ] 
  4. Lemaire S, Trinh TT, Le HT, Tang SC, Hincke M, Wellman-Labadie O, Ziai S: Antimicrobial effects of H4-(86-100), histogranin and related compounds--possible involvement of DNA gyrase. FEBS J. 2008 Nov;275(21):5286-97. doi: 10.1111/j.1742-4658.2008.06659.x. Epub 2008 Sep 18. [PubMed:18803668  ] 
  5. Fukushima H: [Case of sodium monofluoroacetic acid intoxication]. Chudoku Kenkyu. 2008 Oct;21(4):391-2. [PubMed:19069133  ]