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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:21:45 UTC
Update Date2022-03-07 03:17:45 UTC
HMDB IDHMDB0060451
Secondary Accession Numbers
  • HMDB60451
Metabolite Identification
Common NameChloral hydrate
DescriptionChloral hydrate is a sedative and hypnotic drug as well as a chemical reagent and precursor. The name chloral hydrate indicates that it is formed from chloral (trichloroacetaldehyde) by the addition of one molecule of water. Its chemical formula is C2H3Cl3O2. It was discovered through the chlorination of ethanol in 1832 by Justus von Liebig in Gießen. Its sedative properties were first published in 1869 and subsequently, because of its easy synthesis, its use was widespread. (Wikipedia )
Structure
Data?1563866062
Synonyms
ValueSource
1,1,1-Trichloro-2,2-dihydroxyethaneChEBI
1,1,1-Trichloro-2,2-ethanediolChEBI
2,2,2-Trichloro-1,1-ethanediolChEBI
Aquachloral supprettesChEBI
Chloral monohydrateChEBI
ChloralhydratChEBI
Knockout dropsChEBI
NoctecChEBI
SomnoteChEBI
Trichloracetaldehyd-hydratChEBI
Trichloroacetaldehyde hydrateChEBI
Chloral monohydric acidGenerator
Trichloroacetaldehyde hydric acidGenerator
Chloral hydric acidGenerator
Hydrate, chloralHMDB
Chemical FormulaC2H3Cl3O2
Average Molecular Weight165.403
Monoisotopic Molecular Weight163.919862461
IUPAC Name2,2,2-trichloroethane-1,1-diol
Traditional Namechloral hydrate
CAS Registry NumberNot Available
SMILES
OC(O)C(Cl)(Cl)Cl
InChI Identifier
InChI=1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H
InChI KeyRNFNDJAIBTYOQL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassHalohydrins
Sub ClassChlorohydrins
Direct ParentChlorohydrins
Alternative Parents
Substituents
  • Chlorohydrin
  • Carbonyl hydrate
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
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
Water Solubility43.4 g/LALOGPS
logP0.88ALOGPS
logP0.69ChemAxon
logS-0.58ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.25 m³·mol⁻¹ChemAxon
Polarizability11.88 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+126.84830932474
DeepCCS[M-H]-124.30930932474
DeepCCS[M-2H]-160.62330932474
DeepCCS[M+Na]+135.44730932474
AllCCS[M+H]+132.432859911
AllCCS[M+H-H2O]+128.532859911
AllCCS[M+NH4]+136.032859911
AllCCS[M+Na]+137.032859911
AllCCS[M-H]-134.932859911
AllCCS[M+Na-2H]-138.932859911
AllCCS[M+HCOO]-143.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Chloral hydrateOC(O)C(Cl)(Cl)Cl2057.0Standard polar33892256
Chloral hydrateOC(O)C(Cl)(Cl)Cl712.2Standard non polar33892256
Chloral hydrateOC(O)C(Cl)(Cl)Cl1039.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chloral hydrate,1TMS,isomer #1C[Si](C)(C)OC(O)C(Cl)(Cl)Cl1164.6Semi standard non polar33892256
Chloral hydrate,2TMS,isomer #1C[Si](C)(C)OC(O[Si](C)(C)C)C(Cl)(Cl)Cl1277.9Semi standard non polar33892256
Chloral hydrate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(O)C(Cl)(Cl)Cl1387.4Semi standard non polar33892256
Chloral hydrate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(O[Si](C)(C)C(C)(C)C)C(Cl)(Cl)Cl1724.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chloral hydrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-9800000000-173349d19f15699bc4e22017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chloral hydrate GC-MS (2 TMS) - 70eV, Positivesplash10-0076-9410000000-21820ed226e58fbc8ae12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chloral hydrate 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 - Chloral hydrate 10V, Positive-QTOFsplash10-01ot-0900000000-c672e7ca577dd4cff3a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 20V, Positive-QTOFsplash10-03di-0900000000-66ddb4524d26c214f30a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 40V, Positive-QTOFsplash10-0002-0900000000-1f3f289553fa24dda5882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 10V, Negative-QTOFsplash10-03di-0900000000-f03879ddb1ed96167f282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 20V, Negative-QTOFsplash10-03dl-0900000000-251ef92040263c3150d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 40V, Negative-QTOFsplash10-004i-1900000000-584b46b94889a43b683f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 10V, Positive-QTOFsplash10-03di-0900000000-86a486dece507559a95d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 20V, Positive-QTOFsplash10-03di-0900000000-86a486dece507559a95d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 40V, Positive-QTOFsplash10-0159-3900000000-d50cea434c3e3f18ce682021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 10V, Negative-QTOFsplash10-03di-0900000000-56dff238afdaa1d31c632021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 20V, Negative-QTOFsplash10-03di-1900000000-81be9106d7645ecb03c52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chloral hydrate 40V, Negative-QTOFsplash10-03di-5900000000-c87e1310d672bcc236e22021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01563
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06899
BioCyc IDCPD0-1476
BiGG IDNot Available
Wikipedia LinkChloral hydrate
METLIN IDNot Available
PubChem Compound2707
PDB IDNot Available
ChEBI ID28142
Food Biomarker OntologyNot Available
VMH IDM01440
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Enzymes

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. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular weight:
40221.335
Reactions
Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Reactions
Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245
Reactions
Chloral hydrate + NAD → Trichloroacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
Reactions
Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Waterdetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
Reactions
Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Waterdetails
General function:
Involved in zinc ion binding
Specific function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular weight:
41480.985
Reactions
Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Waterdetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37
Reactions
Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Waterdetails
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular weight:
39072.275
Reactions
Chloral hydrate + NADH + Hydrogen Ion → 2,2,2-Trichloroethanol + NAD + Waterdetails

Only showing the first 10 proteins. There are 11 proteins in total.