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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:35 UTC
HMDB IDHMDB0014335
Secondary Accession Numbers
  • HMDB14335
Metabolite Identification
Common NameEthchlorvynol
DescriptionEthchlorvynol is only found in individuals that have used or taken this drug. It is a sedative and hypnotic drug. It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists. [Wikipedia ]Although the exact mechanism of action is unknown, ethchlorvynol appears to depress the central nervous system in a manner similar to that of barbiturates. Barbiturates bind at a distinct binding sites associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Structure
Data?1582753166
Synonyms
ValueSource
1-Chloro-3-ethyl-1-penten-4-yn-3-olChEBI
1-Chloro-3-ethyl-pent-1-en-4-yn-3-olChEBI
3-(beta-Chlorovinyl)-1-pentyn-3-olChEBI
beta-Chlorovinyl ethyl ethynyl carbinolChEBI
EtclorvinolChEBI
EthchlorvynolumChEBI
Ethyl beta-chlorovinyl ethynyl carbinolChEBI
3-(b-Chlorovinyl)-1-pentyn-3-olGenerator
3-(Β-chlorovinyl)-1-pentyn-3-olGenerator
b-Chlorovinyl ethyl ethynyl carbinolGenerator
Β-chlorovinyl ethyl ethynyl carbinolGenerator
Ethyl b-chlorovinyl ethynyl carbinolGenerator
Ethyl β-chlorovinyl ethynyl carbinolGenerator
Aethyl-chlorvynolHMDB
EtchlorvinoloHMDB
EthchlorovynolHMDB
EthchlorvinolHMDB
EthchlorvinylHMDB
EthclorvynolHMDB
EthochlorvynolHMDB
EthychlorvynolHMDB
Chemical FormulaC7H9ClO
Average Molecular Weight144.599
Monoisotopic Molecular Weight144.034192617
IUPAC Name1-chloro-3-ethylpent-1-en-4-yn-3-ol
Traditional Nameetclorvinol
CAS Registry Number113-18-8
SMILES
[H]C(Cl)=CC(O)(CC)C#C
InChI Identifier
InChI=1S/C7H9ClO/c1-3-7(9,4-2)5-6-8/h1,5-6,9H,4H2,2H3
InChI KeyZEHYJZXQEQOSON-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ynones. These are organic compounds containing the ynone functional group, an alpha,beta unsaturated ketone group with the general structure RC#C-C(=O)R' (R' not H).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentYnones
Alternative Parents
Substituents
  • Ynone
  • Tertiary alcohol
  • Acetylide
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.14 g/LNot Available
LogP1.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.45ALOGPS
logP1.62ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.88ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.64 m³·mol⁻¹ChemAxon
Polarizability14.77 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]+127.6530932474
DeepCCS[M-H]-124.95530932474
DeepCCS[M-2H]-161.27230932474
DeepCCS[M+Na]+136.41330932474
AllCCS[M+H]+133.432859911
AllCCS[M+H-H2O]+129.232859911
AllCCS[M+NH4]+137.332859911
AllCCS[M+Na]+138.432859911
AllCCS[M-H]-130.932859911
AllCCS[M+Na-2H]-133.732859911
AllCCS[M+HCOO]-136.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethchlorvynol[H]C(Cl)=CC(O)(CC)C#C1523.2Standard polar33892256
Ethchlorvynol[H]C(Cl)=CC(O)(CC)C#C979.0Standard non polar33892256
Ethchlorvynol[H]C(Cl)=CC(O)(CC)C#C981.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethchlorvynol,1TMS,isomer #1C#CC(C=CCl)(CC)O[Si](C)(C)C1136.7Semi standard non polar33892256
Ethchlorvynol,1TBDMS,isomer #1C#CC(C=CCl)(CC)O[Si](C)(C)C(C)(C)C1361.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ethchlorvynol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9100000000-2996a215de7a6e7538152017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethchlorvynol GC-MS (1 TMS) - 70eV, Positivesplash10-009i-9600000000-5560a4de50772eb686d42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethchlorvynol 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 - Ethchlorvynol 10V, Positive-QTOFsplash10-0002-3900000000-198eb76a2aa919525f422017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 20V, Positive-QTOFsplash10-0002-3900000000-e1616a7a6e75f2940d8c2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 40V, Positive-QTOFsplash10-0159-9000000000-b25f488adecb3fd0ff422017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 10V, Negative-QTOFsplash10-0006-4900000000-2980fab2cceb6fc961072017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 20V, Negative-QTOFsplash10-0006-3900000000-a6b1e1a57494f22868dd2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 40V, Negative-QTOFsplash10-0a59-9400000000-b1fe9dd4623953d5d8ba2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 10V, Positive-QTOFsplash10-004i-6900000000-725ac670d608f579f9b12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 20V, Positive-QTOFsplash10-016u-9200000000-376cadd129a6109c15002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 40V, Positive-QTOFsplash10-002b-9100000000-33378000f2ae89d4dfd82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 10V, Negative-QTOFsplash10-0006-3900000000-ab92305130e98160aea22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 20V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethchlorvynol 40V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00189 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00189 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00189
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444534
KEGG Compound IDC07833
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthchlorvynol
METLIN IDNot Available
PubChem Compound5281077
PDB IDNot Available
ChEBI ID4882
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

General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Smeyatsky N, Baldwin D, Botros W, Gura R, Kurian T, Lambert MT, Patel AG, Steinert J, Priest RG: The treatment of sleep disorders. S Afr Med J. 1992 May 2;Suppl:1-8. [PubMed:1585214 ]
  4. Feller DJ, Crabbe JC: Effect of alcohols and other hypnotics in mice selected for differential sensitivity to hypothermic actions of ethanol. J Pharmacol Exp Ther. 1991 Mar;256(3):947-53. [PubMed:2005589 ]
  5. Authors unspecified: Hypnotic drugs. Med Lett Drugs Ther. 2000 Aug 7;42(1084):71-2. [PubMed:10932303 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA2
Uniprot ID:
P47869
Molecular weight:
51325.9
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA3
Uniprot ID:
P34903
Molecular weight:
55164.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA4
Uniprot ID:
P48169
Molecular weight:
61622.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA5
Uniprot ID:
P31644
Molecular weight:
52145.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA6
Uniprot ID:
Q16445
Molecular weight:
51023.7
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRB1
Uniprot ID:
P18505
Molecular weight:
54234.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRB2
Uniprot ID:
P47870
Molecular weight:
59149.9
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRB3
Uniprot ID:
P28472
Molecular weight:
54115.0
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]