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Showing NP-Card for Hexachloroacetone (NP0086330)

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Record Information
Version2.0
Created at2022-04-29 06:38:36 UTC
Updated at2022-04-29 06:38:36 UTC
NP-MRD IDNP0086330
Secondary Accession NumbersNone
Natural Product Identification
Common NameHexachloroacetone
Description1,1,1,3,3,3-Hexachloro-2-propanone, also known as Hca or bis(trichloromethyl) ketone, belongs to the class of organic compounds known as alpha-chloroketones. These are organic compounds contaning a chlorine atom attached to the alpha carbon atom relative to C=O group. 1,1,1,3,3,3-Hexachloro-2-propanone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1,1,1,3,3,3-Hexachloro-2-propanone has been detected, but not quantified in, herbs and spices. Hexachloroacetone is found in Osmanthus fragrans . Hexachloroacetone was first documented in 1970 (PMID: 5432860). This could make 1,1,1,3,3,3-hexachloro-2-propanone a potential biomarker for the consumption of these foods (PMID: 6614489) (PMID: 18844418) (PMID: 7027027) (PMID: 18007406).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0086330 (Hexachloroacetone)


  Mrv0541 05061305582D          

 10  9  0  0  0  0            999 V2000
    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 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
    1.6500    1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  2  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  3  1  0  0  0  0
  9  3  1  0  0  0  0
 10  1  2  0  0  0  0
M  END
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3D MOL for NP0086330 (Hexachloroacetone)

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3D SDF for NP0086330 (Hexachloroacetone)

  Mrv0541 05061305582D          

 10  9  0  0  0  0            999 V2000
    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 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
    1.6500    1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  2  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  3  1  0  0  0  0
  9  3  1  0  0  0  0
 10  1  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086330

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9

> <INCHI_KEY>
DOJXGHGHTWFZHK-UHFFFAOYSA-N

> <FORMULA>
C3Cl6O

> <MOLECULAR_WEIGHT>
264.75

> <EXACT_MASS>
261.808030864

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.293917118017827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexachloropropan-2-one

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
3.611056659

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.495720709598888

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
47.224000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexachloroacetone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0086330 (Hexachloroacetone)
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PDB for NP0086330 (Hexachloroacetone)
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       1.540   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       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       3.080   2.667   0.000  0.00  0.00          Cl+0
HETATM    5 Cl   UNK     0       0.976   2.104   0.000  0.00  0.00          Cl+0
HETATM    6 Cl   UNK     0       3.644   0.564   0.000  0.00  0.00          Cl+0
HETATM    7 Cl   UNK     0       3.080  -2.667   0.000  0.00  0.00          Cl+0
HETATM    8 Cl   UNK     0       0.976  -2.104   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0       3.644  -0.564   0.000  0.00  0.00          Cl+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3   10                                                  
CONECT    2    1    4    5    6                                             
CONECT    3    1    7    8    9                                             
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
CONECT    8    3                                                            
CONECT    9    3                                                            
CONECT   10    1                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0086330 (Hexachloroacetone)
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SMILES for NP0086330 (Hexachloroacetone)
ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl
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INCHI for NP0086330 (Hexachloroacetone)
InChI=1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9
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View in JSmol
Synonyms
ValueSource
1,1, 1,3,3,3-Hexachloro-2-propanoneHMDB
1,1,1,3,3,3-HexachloroacetoneHMDB
1,1,1,3,3,3-HexachloropropanoneHMDB
Bis(trichloromethyl) ketoneHMDB
HcaHMDB
Hca weedkillerHMDB
HCA, wssaHMDB
Hexachloro-2-propanoneHMDB
Hexachloro-acetoneHMDB
HexachloroacetoneHMDB
Hexachloroacetone, practHMDB
HexachloropropanoneHMDB
Kureha hcaHMDB
Perchloro-2-propanoneHMDB
PerchloroacetoneHMDB
Chemical FormulaC3Cl6O
Average Mass264.7500 Da
Monoisotopic Mass261.80803 Da
IUPAC Namehexachloropropan-2-one
Traditional Namehexachloroacetone
CAS Registry NumberNot Available
SMILES
ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl
InChI Identifier
InChI=1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9
InChI KeyDOJXGHGHTWFZHK-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Osmanthus fragransPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-chloroketones. These are organic compounds contaning a chlorine atom attached to the alpha carbon atom relative to C=O group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAlpha-chloroketones  
Alternative Parents
Substituents
  • Alpha-chloroketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • 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
logP3.66ALOGPS
logP3.61ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)-9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.22 m³·mol⁻¹ChemAxon
Polarizability18.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031489  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008067  
KNApSAcK IDNot Available
Chemspider ID13873693  
KEGG Compound IDC19122  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8303  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kissa E: Determination of hexachloroacetone in air. Anal Chem. 1983 Jul;55(8):1222-5. doi: 10.1021/ac00259a010. [PubMed:6614489  ] 
  2. Butini S, Gabellieri E, Huleatt PB, Campiani G, Franceschini S, Brindisi M, Ros S, Coccone SS, Fiorini I, Novellino E, Giorgi G, Gemma S: An efficient approach to chiral C8/C9-piperazino-substituted 1,4-benzodiazepin-2-ones as peptidomimetic scaffolds. J Org Chem. 2008 Nov 7;73(21):8458-68. doi: 10.1021/jo8015456. Epub 2008 Oct 10. [PubMed:18844418  ] 
  3. Zochlinski H, Mower H: The mutagenic properties of hexachloroacetone in short-term bacterial mutagen assay systems. Mutat Res. 1981 Jun;89(2):137-44. doi: 10.1016/0165-1218(81)90119-1. [PubMed:7027027  ] 
  4. Panetta CA, Casanova TG: Trichloroacetylation of dipeptides by hexachloroacetone in dimethyl sulfoxide under neutral conditions. J Org Chem. 1970 Jul;35(7):2423-5. doi: 10.1021/jo00832a076. [PubMed:5432860  ] 
  5. Fohlisch B, Reiner S: Hexachloroacetone as a precursor for a tetrachloro-substituted oxyallyl intermediate: [4+3] cycloaddition to cyclic 1,3-dienes. Molecules. 2004 Jan 31;9(1):1-10. doi: 10.3390/90100001. [PubMed:18007406  ]