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Showing metabocard for 1,1,1-Trichloroacetone (HMDB0244030)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 21:13:49 UTC
Update Date2021-09-26 22:51:29 UTC
HMDB IDHMDB0244030
Secondary Accession NumbersNone
Metabolite Identification
Common Name1,1,1-Trichloroacetone
Description1,1,1-Trichloroacetone, also known as 1,1,1-TCP, 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. Based on a literature review very few articles have been published on 1,1,1-Trichloroacetone. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,1,1-trichloroacetone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,1,1-Trichloroacetone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0244030 (1,1,1-Trichloroacetone)


  Mrv1572004221603092D          

  7  6  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   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 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
    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  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  2  0  0  0  0
M  END
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3D MOL for HMDB0244030 (1,1,1-Trichloroacetone)

HMDB0244030
     RDKit          3D
1,1,1-Trichloroacetone
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.3116   -0.2561   -0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0630    0.5873   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029    1.7263   -0.5622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -0.0296    0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784   -0.5509    1.9309 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4877    1.1997    0.1260 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5967   -1.4130   -0.8103 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -1.3177   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921   -0.0637    0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9304    0.1177   -1.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  4  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
M  END
Download

3D SDF for HMDB0244030 (1,1,1-Trichloroacetone)


  Mrv1572004221603092D          

  7  6  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   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 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
    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  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244030

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H3Cl3O/c1-2(7)3(4,5)6/h1H3

> <INCHI_KEY>
SMZHKGXSEAGRTI-UHFFFAOYSA-N

> <FORMULA>
C3H3Cl3O

> <MOLECULAR_WEIGHT>
161.41

> <EXACT_MASS>
159.9249478

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
12.349980617884563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,1,1-trichloropropan-2-one

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
1.8586682336666667

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.2198039933417

> <JCHEM_PKA_STRONGEST_BASIC>
-8.34662348030962

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
31.709400000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,1,1-trichloroacetone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0244030 (1,1,1-Trichloroacetone)

HMDB0244030
     RDKit          3D
1,1,1-Trichloroacetone
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.3116   -0.2561   -0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0630    0.5873   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029    1.7263   -0.5622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2144   -0.0296    0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784   -0.5509    1.9309 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4877    1.1997    0.1260 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5967   -1.4130   -0.8103 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772   -1.3177   -0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7921   -0.0637    0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9304    0.1177   -1.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  4  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
M  END
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PDB for HMDB0244030 (1,1,1-Trichloroacetone)

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         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  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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    2                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0244030 (1,1,1-Trichloroacetone)

COMPND    HMDB0244030
HETATM    1  C1  UNL     1      -1.312  -0.256  -0.185  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.063   0.587  -0.202  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.103   1.726  -0.562  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.214  -0.030   0.238  1.00  0.00           C  
HETATM    5 CL1  UNL     1       0.978  -0.551   1.931  1.00  0.00          CL  
HETATM    6 CL2  UNL     1       2.488   1.200   0.126  1.00  0.00          CL  
HETATM    7 CL3  UNL     1       1.597  -1.413  -0.810  1.00  0.00          CL  
HETATM    8  H1  UNL     1      -1.077  -1.318  -0.269  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.792  -0.064   0.783  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.930   0.118  -1.049  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3    4
CONECT    4    5    6    7
END
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SMILES for HMDB0244030 (1,1,1-Trichloroacetone)

CC(=O)C(Cl)(Cl)Cl
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INCHI for HMDB0244030 (1,1,1-Trichloroacetone)

InChI=1S/C3H3Cl3O/c1-2(7)3(4,5)6/h1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,1,1-Trichloro-2-propanoneHMDB
1,1,1-TCPHMDB
1,1,1-TrichloroacetoneMeSH
Chemical FormulaC3H3Cl3O
Average Molecular Weight161.41
Monoisotopic Molecular Weight159.9249478
IUPAC Name1,1,1-trichloropropan-2-one
Traditional Name1,1,1-trichloroacetone
CAS Registry NumberNot Available
SMILES
CC(=O)C(Cl)(Cl)Cl
InChI Identifier
InChI=1S/C3H3Cl3O/c1-2(7)3(4,5)6/h1H3
InChI KeySMZHKGXSEAGRTI-UHFFFAOYSA-N
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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.36ALOGPS
logP1.86ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)16.22ChemAxon
pKa (Strongest Basic)-8.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.71 m³·mol⁻¹ChemAxon
Polarizability12.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+126.14530932474
DeepCCS[M-H]-123.45930932474
DeepCCS[M-2H]-159.84430932474
DeepCCS[M+Na]+134.87130932474
AllCCS[M+H]+130.032859911
AllCCS[M+H-H2O]+126.132859911
AllCCS[M+NH4]+133.732859911
AllCCS[M+Na]+134.732859911
AllCCS[M-H]-134.032859911
AllCCS[M+Na-2H]-138.032859911
AllCCS[M+HCOO]-142.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.4.58 minutes32390414
Predicted by Siyang on May 30, 202213.0366 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.67 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1560.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid536.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid211.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid395.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid224.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid476.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid543.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)420.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1004.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid357.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1113.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid391.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid379.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate638.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA447.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water175.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,1,1-TrichloroacetoneCC(=O)C(Cl)(Cl)Cl1301.6Standard polar33892256
1,1,1-TrichloroacetoneCC(=O)C(Cl)(Cl)Cl777.9Standard non polar33892256
1,1,1-TrichloroacetoneCC(=O)C(Cl)(Cl)Cl848.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,1,1-Trichloroacetone,1TMS,isomer #1C=C(O[Si](C)(C)C)C(Cl)(Cl)Cl1033.6Semi standard non polar33892256
1,1,1-Trichloroacetone,1TMS,isomer #1C=C(O[Si](C)(C)C)C(Cl)(Cl)Cl1066.7Standard non polar33892256
1,1,1-Trichloroacetone,1TMS,isomer #1C=C(O[Si](C)(C)C)C(Cl)(Cl)Cl1261.1Standard polar33892256
1,1,1-Trichloroacetone,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(Cl)(Cl)Cl1269.0Semi standard non polar33892256
1,1,1-Trichloroacetone,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(Cl)(Cl)Cl1255.1Standard non polar33892256
1,1,1-Trichloroacetone,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(Cl)(Cl)Cl1426.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1,1,1-Trichloroacetone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-7f40a916040726c2da9a2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,1,1-Trichloroacetone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 10V, Positive-QTOFsplash10-03di-0900000000-6861e43375b358857ad92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 20V, Positive-QTOFsplash10-03di-0900000000-f7323da13d3fc83f7e772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 40V, Positive-QTOFsplash10-0006-5900000000-d880873d7348f7d0f5ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 10V, Negative-QTOFsplash10-0a4i-0900000000-c85a2b75a7c3662684fc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 20V, Negative-QTOFsplash10-0a4i-1900000000-b49600a487732c38d6cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 40V, Negative-QTOFsplash10-0a4l-2900000000-13bc90f0ab7be4a50c1d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 10V, Positive-QTOFsplash10-03di-0900000000-8e068c30dc466d7ef3752021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 20V, Positive-QTOFsplash10-03di-0900000000-8e068c30dc466d7ef3752021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 40V, Positive-QTOFsplash10-00xr-1900000000-9f78049ec7d57a97008b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 10V, Negative-QTOFsplash10-0a4i-0900000000-ad69a92a50d73e5341a42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 20V, Negative-QTOFsplash10-0a4i-0900000000-ad69a92a50d73e5341a42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,1,1-Trichloroacetone 40V, Negative-QTOFsplash10-0a4i-3900000000-a58b4b7f20e81cf5367f2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID12926
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1,1,1-Trichloroacetone
METLIN IDNot Available
PubChem Compound13514
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]