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Showing metabocard for Chloroacetaldehyde (HMDB0013860)

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enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:15 UTC
Update Date2023-02-21 17:18:06 UTC
HMDB IDHMDB0013860
Secondary Accession Numbers
  • HMDB13860
Metabolite Identification
Common NameChloroacetaldehyde
DescriptionBeing bifunctional, chloroacetaldehyde is a versatile precursor to many heterocyclic compounds. It condenses with thiourea derivatives to give aminothiazoles. This reaction was once important as a precursor to sulfathiazole, one of the first sulfa drugs. Chloroacetaldehyde is the organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hydrate (acetal), ClCH2CH(OH)2. Chloroacetaldehyde is a useful intermediate in the synthesis, e.g. of 2-aminothiazole or many pharmaceutical compounds. Another use is to facilitate bark removal from tree trunks.
Structure
Data?1676999886
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013860 (Chloroacetaldehyde)


  Mrv1652305271900052D          

  5  4  0  0  0  0            999 V2000
    8.7175   -3.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7175   -2.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0030   -3.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4319   -3.8778    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2885   -3.4652    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
M  END
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3D MOL for HMDB0013860 (Chloroacetaldehyde)

HMDB0013860
     RDKit          3D
Chloroacetaldehyde
  7  6  0  0  0  0  0  0  0  0999 V2000
    1.7651   -0.6793   -0.0726 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564    0.1453   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633   -0.2452   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5483    1.2259    0.0798 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1044    1.1972    0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8578   -0.8109   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7563   -0.8331    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  3  6  1  0
  3  7  1  0
M  END
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3D SDF for HMDB0013860 (Chloroacetaldehyde)


  Mrv1652305271900052D          

  5  4  0  0  0  0            999 V2000
    8.7175   -3.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7175   -2.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0030   -3.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4319   -3.8778    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2885   -3.4652    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013860

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(=O)CCl

> <INCHI_IDENTIFIER>
InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2

> <INCHI_KEY>
QSKPIOLLBIHNAC-UHFFFAOYSA-N

> <FORMULA>
C2H3ClO

> <MOLECULAR_WEIGHT>
78.498

> <EXACT_MASS>
77.987242425

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
6.468590813558276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-chloroacetaldehyde

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
0.15538184333333332

> <ALOGPS_LOGS>
0.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.06985889603622

> <JCHEM_PKA_STRONGEST_BASIC>
-7.285431629612898

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
16.4715

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chloroacetaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0013860 (Chloroacetaldehyde)

HMDB0013860
     RDKit          3D
Chloroacetaldehyde
  7  6  0  0  0  0  0  0  0  0999 V2000
    1.7651   -0.6793   -0.0726 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564    0.1453   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5633   -0.2452   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5483    1.2259    0.0798 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1044    1.1972    0.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8578   -0.8109   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7563   -0.8331    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  3  6  1  0
  3  7  1  0
M  END
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PDB for HMDB0013860 (Chloroacetaldehyde)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      16.273  -6.469   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.273  -4.929   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.939  -7.239   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      17.606  -7.239   0.000  0.00  0.00           H+0
HETATM    5 Cl   UNK     0      13.605  -6.468   0.000  0.00  0.00          Cl+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1    5                                                       
CONECT    4    1                                                            
CONECT    5    3                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0013860 (Chloroacetaldehyde)

COMPND    HMDB0013860
HETATM    1  O1  UNL     1       1.765  -0.679  -0.073  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.856   0.145  -0.015  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.563  -0.245  -0.013  1.00  0.00           C  
HETATM    4 CL1  UNL     1      -1.548   1.226   0.080  1.00  0.00          CL  
HETATM    5  H1  UNL     1       1.104   1.197   0.035  1.00  0.00           H  
HETATM    6  H2  UNL     1      -0.858  -0.811  -0.924  1.00  0.00           H  
HETATM    7  H3  UNL     1      -0.756  -0.833   0.909  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    5
CONECT    3    4    6    7
END
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SMILES for HMDB0013860 (Chloroacetaldehyde)

[H]C(=O)CCl
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INCHI for HMDB0013860 (Chloroacetaldehyde)

InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Chloro-1-ethanalChEBI
2-ChloroethanalChEBI
ChloroaldehydeChEBI
MonochloroacetaldehydeChEBI
2-Chloro-acetaldehydeHMDB
2-ChloroacetaldehydeHMDB
CH2ClCHOHMDB
ChloroacetalaldehydeHMDB
Chloroacetaldehyde monomerHMDB
ChloroethanalHMDB
Rcra waste number P023HMDB
Chloroacetaldehyde hydrateHMDB
Chemical FormulaC2H3ClO
Average Molecular Weight78.498
Monoisotopic Molecular Weight77.987242425
IUPAC Name2-chloroacetaldehyde
Traditional Namechloroacetaldehyde
CAS Registry Number107-20-0
SMILES
[H]C(=O)CCl
InChI Identifier
InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2
InChI KeyQSKPIOLLBIHNAC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organochlorides. Organochlorides are compounds containing a chemical bond between a carbon atom and a chlorine atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganochlorides
Sub ClassNot Available
Direct ParentOrganochlorides
Alternative Parents
Substituents
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-16.3 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility161 g/LALOGPS
logP0.18ALOGPS
logP0.16ChemAxon
logS0.31ALOGPS
pKa (Strongest Acidic)14.07ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.47 m³·mol⁻¹ChemAxon
Polarizability6.47 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]+119.92530932474
DeepCCS[M-H]-117.32130932474
DeepCCS[M-2H]-153.5730932474
DeepCCS[M+Na]+128.4130932474
AllCCS[M+H]+123.332859911
AllCCS[M+H-H2O]+118.932859911
AllCCS[M+NH4]+127.532859911
AllCCS[M+Na]+128.732859911
AllCCS[M-H]-149.032859911
AllCCS[M+Na-2H]-155.732859911
AllCCS[M+HCOO]-163.132859911

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. Predicted by Afia on May 17, 2022.2.37 minutes32390414
Predicted by Siyang on May 30, 202214.1024 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.96 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid240.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1581.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid603.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid241.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid467.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid283.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid505.9 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 Acid644.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)748.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1072.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid408.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1190.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid439.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid503.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate774.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA506.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water250.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Chloroacetaldehyde[H]C(=O)CCl888.8Standard polar33892256
Chloroacetaldehyde[H]C(=O)CCl497.3Standard non polar33892256
Chloroacetaldehyde[H]C(=O)CCl568.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chloroacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCl844.1Semi standard non polar33892256
Chloroacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCl739.7Standard non polar33892256
Chloroacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCl1006.4Standard polar33892256
Chloroacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCl1075.2Semi standard non polar33892256
Chloroacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCl986.1Standard non polar33892256
Chloroacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCl1205.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chloroacetaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-24afbbb98f664db692292017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chloroacetaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-9000000000-37aafbd8f12ae548e09b2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 10V, Positive-QTOFsplash10-004i-9000000000-54aa5db6a89c270c5cb82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 20V, Positive-QTOFsplash10-004i-9000000000-773bd9fcaa86caff6ffb2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 40V, Positive-QTOFsplash10-03dl-9000000000-e828fa0840b3f7c4a6952016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 10V, Negative-QTOFsplash10-004i-9000000000-ceaa73e80f8d51802baf2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 20V, Negative-QTOFsplash10-004l-9000000000-ffa9949420745b970ff22016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 40V, Negative-QTOFsplash10-0006-9000000000-1fa707d184f90bd8818b2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 10V, Negative-QTOFsplash10-001i-9000000000-f424357781d65db3ab6d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 20V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 40V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 10V, Positive-QTOFsplash10-0006-9000000000-bb8955b86fdaa5f7a9722021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 20V, Positive-QTOFsplash10-0006-9000000000-f6a8970f823dd410d9362021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloroacetaldehyde 40V, Positive-QTOFsplash10-0006-9000000000-87bbaed151efac0845912021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry 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 IDNot Available
KEGG Compound IDC06754
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChloroacetaldehyde
METLIN IDNot Available
PubChem Compound33
PDB IDNot Available
ChEBI ID27871
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
2. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails
Enzyme Details
3. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails