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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9) Show 9 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014335

Secondary Accession Numbers

HMDB14335

Metabolite Identification

Common Name

Ethchlorvynol

Description

Ethchlorvynol 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 It has been used to treat insomnia, but has been largely superseded and is only offered where an intolerance or allergy to other drugs exists.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 GABA_A 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Chloro-3-ethyl-1-penten-4-yn-3-ol	ChEBI
1-Chloro-3-ethyl-pent-1-en-4-yn-3-ol	ChEBI
3-(beta-Chlorovinyl)-1-pentyn-3-ol	ChEBI
beta-Chlorovinyl ethyl ethynyl carbinol	ChEBI
Etclorvinol	ChEBI
Ethchlorvynolum	ChEBI
Ethyl beta-chlorovinyl ethynyl carbinol	ChEBI
3-(b-Chlorovinyl)-1-pentyn-3-ol	Generator
3-(Β-chlorovinyl)-1-pentyn-3-ol	Generator
b-Chlorovinyl ethyl ethynyl carbinol	Generator
Β-chlorovinyl ethyl ethynyl carbinol	Generator
Ethyl b-chlorovinyl ethynyl carbinol	Generator
Ethyl β-chlorovinyl ethynyl carbinol	Generator
Aethyl-chlorvynol	HMDB
Etchlorvinolo	HMDB
Ethchlorovynol	HMDB
Ethchlorvinol	HMDB
Ethchlorvinyl	HMDB
Ethclorvynol	HMDB
Ethochlorvynol	HMDB
Ethychlorvynol	HMDB

Chemical Formula

C₇H₉ClO

Average Molecular Weight

144.599

Monoisotopic Molecular Weight

144.034192617

IUPAC Name

1-chloro-3-ethylpent-1-en-4-yn-3-ol

Traditional Name

etclorvinol

CAS Registry Number

113-18-8

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 Key

ZEHYJZXQEQOSON-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).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ynones

Alternative Parents

Substituents

Ynone
Tertiary alcohol
Acetylide
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Hydrocarbon derivative
Organochloride
Organohalogen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:4882 )
tertiary alcohol (CHEBI:4882 )
organochlorine compound (CHEBI:4882 )
enyne (CHEBI:4882 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

sedative (HMDB: HMDB0014335)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.14 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.62	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.88	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	38.64 m³·mol⁻¹	ChemAxon
Polarizability	14.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	127.65	30932474
DeepCCS	[M-H]-	124.955	30932474
DeepCCS	[M-2H]-	161.272	30932474
DeepCCS	[M+Na]+	136.413	30932474
AllCCS	[M+H]+	133.4	32859911
AllCCS	[M+H-H2O]+	129.2	32859911
AllCCS	[M+NH4]+	137.3	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	130.9	32859911
AllCCS	[M+Na-2H]-	133.7	32859911
AllCCS	[M+HCOO]-	136.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethchlorvynol	[H]C(Cl)=CC(O)(CC)C#C	1523.2	Standard polar	33892256
Ethchlorvynol	[H]C(Cl)=CC(O)(CC)C#C	979.0	Standard non polar	33892256
Ethchlorvynol	[H]C(Cl)=CC(O)(CC)C#C	981.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethchlorvynol,1TMS,isomer #1	C#CC(C=CCl)(CC)O[Si](C)(C)C	1136.7	Semi standard non polar	33892256
Ethchlorvynol,1TBDMS,isomer #1	C#CC(C=CCl)(CC)O[Si](C)(C)C(C)(C)C	1361.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethchlorvynol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9100000000-2996a215de7a6e753815	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethchlorvynol GC-MS (1 TMS) - 70eV, Positive	splash10-009i-9600000000-5560a4de50772eb686d4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethchlorvynol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 10V, Positive-QTOF	splash10-0002-3900000000-198eb76a2aa919525f42	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 20V, Positive-QTOF	splash10-0002-3900000000-e1616a7a6e75f2940d8c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 40V, Positive-QTOF	splash10-0159-9000000000-b25f488adecb3fd0ff42	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 10V, Negative-QTOF	splash10-0006-4900000000-2980fab2cceb6fc96107	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 20V, Negative-QTOF	splash10-0006-3900000000-a6b1e1a57494f22868dd	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 40V, Negative-QTOF	splash10-0a59-9400000000-b1fe9dd4623953d5d8ba	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 10V, Positive-QTOF	splash10-004i-6900000000-725ac670d608f579f9b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 20V, Positive-QTOF	splash10-016u-9200000000-376cadd129a6109c1500	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 40V, Positive-QTOF	splash10-002b-9100000000-33378000f2ae89d4dfd8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 10V, Negative-QTOF	splash10-0006-3900000000-ab92305130e98160aea2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 20V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethchlorvynol 40V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00189	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00189	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00189

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444534

KEGG Compound ID

C07833

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethchlorvynol

METLIN ID

Not Available

PubChem Compound

5281077

PDB ID

Not Available

ChEBI ID

4882

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Gamma-aminobutyric acid receptor subunit alpha-1

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

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 ]
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 ]
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 ]
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 ]
Authors unspecified: Hypnotic drugs. Med Lett Drugs Ther. 2000 Aug 7;42(1084):71-2. [PubMed:10932303 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Gamma-aminobutyric acid receptor subunit alpha-2

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

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 ]
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 ]

Enzyme Details

3. Gamma-aminobutyric acid receptor subunit alpha-3

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

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 ]
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 ]

Enzyme Details

4. Gamma-aminobutyric acid receptor subunit alpha-4

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

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 ]
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 ]

Enzyme Details

5. Gamma-aminobutyric acid receptor subunit alpha-5

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

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 ]
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 ]

Enzyme Details

6. Gamma-aminobutyric acid receptor subunit alpha-6

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

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 ]
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 ]

Enzyme Details

7. Gamma-aminobutyric acid receptor subunit beta-1

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

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 ]
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 ]

Enzyme Details

8. Gamma-aminobutyric acid receptor subunit beta-2

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

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 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

9. Gamma-aminobutyric acid receptor subunit beta-3

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

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 ]
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 ]

Showing metabocard for Ethchlorvynol (HMDB0014335)

MOL for HMDB0014335 (Ethchlorvynol)

3D MOL for HMDB0014335 (Ethchlorvynol)

3D SDF for HMDB0014335 (Ethchlorvynol)

3D-SDF for HMDB0014335 (Ethchlorvynol)

PDB for HMDB0014335 (Ethchlorvynol)

3D PDB for HMDB0014335 (Ethchlorvynol)

SMILES for HMDB0014335 (Ethchlorvynol)

INCHI for HMDB0014335 (Ethchlorvynol)

Structure for HMDB0014335 (Ethchlorvynol)

3D Structure for HMDB0014335 (Ethchlorvynol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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