Np mrd loader

Showing NP-Card for Chloroacetic Acid (NP0002714)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2020-11-23 19:38:36 UTC
Updated at2021-08-19 23:59:17 UTC
NP-MRD IDNP0002714
Secondary Accession NumbersNone
Natural Product Identification
Common NameChloroacetic Acid
Provided ByBMRBBMRB logo
DescriptionChloroacetic acid, also known as acide chloracetique or 2-chloro-acetate, 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. Chloroacetic acid exists in all living organisms, ranging from bacteria to humans. Chloroacetic 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. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on Chloroacetic acid (PMID: 22139456) (PMID: 22864241) (PMID: 22426733) (PMID: 21442555).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002714 (Chloroacetic Acid)


     RDKit          2D

  8  7  0  0  0  0  0  0  0  0999 V2000
   -0.7517   -1.7482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4030   -0.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4922    0.7422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0348    0.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726    0.5658    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9299    0.3147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    1.5761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4623   -1.2995    0.0000 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  6
  4  8  1  0
M  END
Download

3D MOL for NP0002714 (Chloroacetic Acid)

NP0002714
     RDKit          3D

  8  7  0  0  0  0  0  0  0  0999 V2000
    0.9151   -1.7207    0.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568   -0.5076    0.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.4679    0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609   -0.0921    0.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9258    1.6746    0.1487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5222    1.1857   -0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -0.4750   -0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3659   -0.5328    0.9497 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 NP0002714 (Chloroacetic Acid)


     RDKit          2D

  8  7  0  0  0  0  0  0  0  0999 V2000
   -0.7517   -1.7482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4030   -0.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4922    0.7422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0348    0.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726    0.5658    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9299    0.3147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    1.5761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4623   -1.2995    0.0000 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  6
  4  8  1  0
M  END
> <DATABASE_ID>
NP0002714

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCl

> <INCHI_IDENTIFIER>
InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)

> <INCHI_KEY>
FOCAUTSVDIKZOP-UHFFFAOYSA-N

> <FORMULA>
C2H3ClO2

> <MOLECULAR_WEIGHT>
94.497

> <EXACT_MASS>
93.982157047

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
7.327140146836344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-chloroacetic acid

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
0.3139980956666667

> <ALOGPS_LOGS>
0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.05571004281989

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
17.3969

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chloroacetic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002714 (Chloroacetic Acid)

NP0002714
     RDKit          3D

  8  7  0  0  0  0  0  0  0  0999 V2000
    0.9151   -1.7207    0.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5568   -0.5076    0.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.4679    0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609   -0.0921    0.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9258    1.6746    0.1487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5222    1.1857   -0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -0.4750   -0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3659   -0.5328    0.9497 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

PDB for NP0002714 (Chloroacetic Acid)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3 Cl   UNK     0       1.540   2.667   0.000  0.00  0.00          Cl+0
HETATM    4  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5                                                  
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
Download

3D PDB for NP0002714 (Chloroacetic Acid)

COMPND    NP0002714
HETATM    1  O1  UNL     1       0.915  -1.721   0.017  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.557  -0.508   0.077  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.535   0.468   0.179  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.861  -0.092   0.042  1.00  0.00           C  
HETATM    5 CL1  UNL     1      -0.926   1.675   0.149  1.00  0.00          CL  
HETATM    6  H1  UNL     1       1.522   1.186  -0.549  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.377  -0.475  -0.864  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.366  -0.533   0.950  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    6
CONECT    4    5    7    8
END
Download

SMILES for NP0002714 (Chloroacetic Acid)

OC(=O)CCl
Download

INCHI for NP0002714 (Chloroacetic Acid)

InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
Download
View in JSmol
Synonyms
ValueSource
2-Chloro-acetic acidChEBI
2-Chloro-ethanoic acidChEBI
2-Chloroacetic acidChEBI
Acide chloracetiqueChEBI
Acide chloroacetiqueChEBI
Acide monochloracetiqueChEBI
alpha-Chloro-acetic acidChEBI
CAAChEBI
Chloracetic acidChEBI
Chloroethanoic acidChEBI
MonochloressigsaeureChEBI
Monochloroacetic acidChEBI
Monochloroethanoic acidChEBI
AcetocaustinKegg
2-Chloro-acetateGenerator
2-Chloro-ethanoateGenerator
2-ChloroacetateGenerator
a-Chloro-acetateGenerator
a-Chloro-acetic acidGenerator
alpha-Chloro-acetateGenerator
Α-chloro-acetateGenerator
Α-chloro-acetic acidGenerator
ChloracetateGenerator
ChloroethanoateGenerator
MonochloroacetateGenerator
MonochloroethanoateGenerator
ChloroacetateGenerator
AcidomonocloroaceticoHMDB
alpha-Chloroacetic acidHMDB
CH2ClCOOHHMDB
Chloro-acetic acidHMDB
ChloroaceticHMDB
Chloroacetic acid (80% or less)HMDB
Chloroacetic acid crystallineHMDB
Chloroacetic acid, acsHMDB
Chloroacetic acid, liquidHMDB
Chloroacetic acid, moltenHMDB
Chloroacetic acid, solidHMDB
Chloroacetic acid, solid (dot)HMDB
Chloroacetic-acidHMDB
MCAHMDB
MonochloorazijnzuurHMDB
Monochloracetic acidHMDB
Monochloracetic acidacide monochloracetiqueHMDB
Sjphlqdiktp@HMDB
Chloroacetic acid, calcium saltHMDB
Chloroacetic acid, sodium (2:1) saltHMDB
Chloroacetic acid, sodium (5:2) saltHMDB
Chloroacetic acid, ammonium (2:1) saltHMDB
Chloroacetic acid, aluminum saltHMDB
Chloroacetic acid, ammonium saltHMDB
Chloroacetic acid, potassium (2:1) saltHMDB
Chloroacetic acid, silver saltHMDB
Chloroacetic acid, sodium saltHMDB
SODIUM chloroacetATEHMDB
Chloroacetic acid, calcium (3:1) saltHMDB
Chloroacetic acid, potassium saltHMDB
Chloroacetic acidMeSH
Chemical FormulaC2H3ClO2
Average Mass94.4970 Da
Monoisotopic Mass93.98216 Da
IUPAC Name2-chloroacetic acid
Traditional Namechloroacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCl
InChI Identifier
InChI=1S/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)
InChI KeyFOCAUTSVDIKZOP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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 Point61.00 to 63.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point187.00 to 190.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility858000 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP0.220The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP0.18ALOGPS
logP0.31ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.4 m³·mol⁻¹ChemAxon
Polarizability7.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031331
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003394
KNApSAcK IDNot Available
Chemspider ID10772140
KEGG Compound IDC06755
BioCyc IDCHLOROACETIC-ACID
BiGG IDNot Available
Wikipedia LinkChloroacetic acid
METLIN IDNot Available
PubChem Compound300
PDB IDNot Available
ChEBI ID27869
Good Scents IDrw1228311
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Horisaki T, Yoshida E, Sumiya K, Takemura T, Yamane H, Nojiri H: Isolation and characterization of monochloroacetic acid-degrading bacteria. J Gen Appl Microbiol. 2011;57(5):277-84. doi: 10.2323/jgam.57.277. [PubMed:22139456 ]
  3. Gomha SM, Khalil KD: A convenient ultrasound-promoted synthesis of some new thiazole derivatives bearing a coumarin nucleus and their cytotoxic activity. Molecules. 2012 Aug 3;17(8):9335-47. doi: 10.3390/molecules17089335. [PubMed:22864241 ]
  4. Baldessari A: Lipases as catalysts in synthesis of fine chemicals. Methods Mol Biol. 2012;861:445-56. doi: 10.1007/978-1-61779-600-5_25. [PubMed:22426733 ]
  5. Zhang YK, Li W, Wu KY, Chen GG, Liang ZQ: Purification and characterization of an intracellular alpha-glucosidase with high transglycosylation activity from A. niger M-1. Prep Biochem Biotechnol. 2011;41(2):201-17. doi: 10.1080/10826068.2011.547384. [PubMed:21442555 ]