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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:25 UTC

HMDB ID

HMDB0015165

Secondary Accession Numbers

HMDB15165

Metabolite Identification

Common Name

Ethinamate

Description

Ethinamate, also known as valmid or etinamato, 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). Ethinamate is a drug which is used for the short-term treatment of insomnia, however, it generally has been replaced by other sedative-hypnotic agents. Ethinamate is an extremely weak acidic (essentially neutral) compound (based on its pKa). Ethinamate is a potentially toxic compound. A carbamate ester that is the 1-vinylcyclohexyl ester of carbamic acid.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1031                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.867   1.127   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.177  -0.207   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       8.177   2.460   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.097  -0.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.764  -0.977   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.431  -0.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.764  -2.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.431  -2.517   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.097  -3.287   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.327   1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.407   1.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.557   2.460   0.000  0.00  0.00           C+0
CONECT    1    4   11                                                       
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    1    5    6   10                                             
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6    9                                                       
CONECT    9    7    8                                                       
CONECT   10    4   12                                                       
CONECT   11    1    2    3                                                  
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Ethynylcyclohexanol carbamate	ChEBI
Aethinyl-cyclohexyl-carbamat	ChEBI
Ethinamatum	ChEBI
Etinamato	ChEBI
Valmid	Kegg
1-Ethynylcyclohexanol carbamic acid	Generator
Ethinamic acid	Generator
Ethinamat	HMDB
Ethinimate	HMDB
Etinamate	HMDB
USAF el-42	HMDB
Valamin	HMDB
Valmidate	HMDB
Valamid	HMDB
1-Ethynylcyclohexylcarbamate	HMDB

Chemical Formula

C₉H₁₃NO₂

Average Molecular Weight

167.205

Monoisotopic Molecular Weight

167.094628665

IUPAC Name

1-ethynylcyclohexyl carbamate

Traditional Name

ethinamate

CAS Registry Number

126-52-3

SMILES

NC(=O)OC1(CCCCC1)C#C

InChI Identifier

InChI=1S/C9H13NO2/c1-2-9(12-8(10)11)6-4-3-5-7-9/h1H,3-7H2,(H2,10,11)

InChI Key

GXRZIMHKGDIBEW-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
Carbamic acid ester
Carbonic acid derivative
Acetylide
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:4884 )
carbamate ester (CHEBI:4884 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015165)
Extracellular (HMDB: HMDB0015165)

Source

Exogenous

Exogenous (HMDB: HMDB0015165)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Sedative (HMDB: HMDB0015165)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	96 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.11 g/L	Not Available
LogP	1.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	1.09	ALOGPS
logP	1.54	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.57 m³·mol⁻¹	ChemAxon
Polarizability	17.73 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.827	31661259
DarkChem	[M-H]-	132.517	31661259
DeepCCS	[M+H]+	135.079	30932474
DeepCCS	[M-H]-	131.308	30932474
DeepCCS	[M-2H]-	168.575	30932474
DeepCCS	[M+Na]+	144.113	30932474
AllCCS	[M+H]+	137.5	32859911
AllCCS	[M+H-H2O]+	133.2	32859911
AllCCS	[M+NH4]+	141.5	32859911
AllCCS	[M+Na]+	142.7	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	138.1	32859911
AllCCS	[M+HCOO]-	139.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	3.87 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6841 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	60.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1534.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	310.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	123.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	193.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	234.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	400.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	470.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	332.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	962.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	269.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	978.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	272.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	482.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	281.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	167.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethinamate	NC(=O)OC1(CCCCC1)C#C	2050.4	Standard polar	33892256
Ethinamate	NC(=O)OC1(CCCCC1)C#C	1329.0	Standard non polar	33892256
Ethinamate	NC(=O)OC1(CCCCC1)C#C	1376.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethinamate,1TMS,isomer #1	C#CC1(OC(=O)N[Si](C)(C)C)CCCCC1	1503.6	Semi standard non polar	33892256
Ethinamate,1TMS,isomer #1	C#CC1(OC(=O)N[Si](C)(C)C)CCCCC1	1432.5	Standard non polar	33892256
Ethinamate,1TMS,isomer #1	C#CC1(OC(=O)N[Si](C)(C)C)CCCCC1	2074.9	Standard polar	33892256
Ethinamate,2TMS,isomer #1	C#CC1(OC(=O)N([Si](C)(C)C)[Si](C)(C)C)CCCCC1	1566.5	Semi standard non polar	33892256
Ethinamate,2TMS,isomer #1	C#CC1(OC(=O)N([Si](C)(C)C)[Si](C)(C)C)CCCCC1	1598.5	Standard non polar	33892256
Ethinamate,2TMS,isomer #1	C#CC1(OC(=O)N([Si](C)(C)C)[Si](C)(C)C)CCCCC1	2093.4	Standard polar	33892256
Ethinamate,1TBDMS,isomer #1	C#CC1(OC(=O)N[Si](C)(C)C(C)(C)C)CCCCC1	1707.9	Semi standard non polar	33892256
Ethinamate,1TBDMS,isomer #1	C#CC1(OC(=O)N[Si](C)(C)C(C)(C)C)CCCCC1	1639.2	Standard non polar	33892256
Ethinamate,1TBDMS,isomer #1	C#CC1(OC(=O)N[Si](C)(C)C(C)(C)C)CCCCC1	2247.0	Standard polar	33892256
Ethinamate,2TBDMS,isomer #1	C#CC1(OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC1	2002.8	Semi standard non polar	33892256
Ethinamate,2TBDMS,isomer #1	C#CC1(OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC1	1997.6	Standard non polar	33892256
Ethinamate,2TBDMS,isomer #1	C#CC1(OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC1	2298.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ethinamate EI-B (Non-derivatized)	splash10-054o-9000000000-115ca538c5db7623cd36	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethinamate CI-B (Non-derivatized)	splash10-004i-0900000000-3530aac44af3672b4ea8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethinamate EI-B (Non-derivatized)	splash10-054o-9000000000-115ca538c5db7623cd36	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethinamate CI-B (Non-derivatized)	splash10-004i-0900000000-3530aac44af3672b4ea8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethinamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9400000000-b2399bc8d370f3c24953	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethinamate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0arv-9100000000-713c62aa52e71fc3560a	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 10V, Positive-QTOF	splash10-016r-1900000000-eae16bf8bad39a8aa79b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 20V, Positive-QTOF	splash10-056r-4900000000-5017ae578b8cb02cd66d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 40V, Positive-QTOF	splash10-0ktf-9100000000-cd1eedbdd6d6fcbfa22e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 10V, Negative-QTOF	splash10-006x-9800000000-e408920834450f49d3fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 20V, Negative-QTOF	splash10-006x-9500000000-877c16eefea2f5a15d9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 40V, Negative-QTOF	splash10-0006-9300000000-b9a9228e0ee207499b99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 10V, Positive-QTOF	splash10-0a4i-2900000000-10552185ed182d4ba1e0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 20V, Positive-QTOF	splash10-0a4i-9700000000-cd8eef43ebf47b3d3b7b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 40V, Positive-QTOF	splash10-004i-9100000000-9313282cbda800790a68	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 10V, Negative-QTOF	splash10-0avl-2900000000-d0731a549bbc943d745e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 20V, Negative-QTOF	splash10-0006-9500000000-35acbd59dd232e271712	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethinamate 40V, Negative-QTOF	splash10-0006-9000000000-ff48c45d4a47d2073ba7	2021-10-11	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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 DB01031	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01031	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

DB01031

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3169

KEGG Compound ID

C07832

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethinamate

METLIN ID

Not Available

PubChem Compound

3284

PDB ID

Not Available

ChEBI ID

4884

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. Carbonic anhydrase 1

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:: CA1
Uniprot ID:: P00915
Molecular weight:: 28870.0

References

Parr JS, Khalifah RG: Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50. [PubMed:1460006 ]

Enzyme Details

2. Carbonic anhydrase 2

General function:: Involved in carbonate dehydratase activity
Specific function:: Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
Gene Name:: CA2
Uniprot ID:: P00918
Molecular weight:: 29245.895

References

Parr JS, Khalifah RG: Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50. [PubMed:1460006 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Ethinamate (HMDB0015165)

MOL for HMDB0015165 (Ethinamate)

3D MOL for HMDB0015165 (Ethinamate)

3D SDF for HMDB0015165 (Ethinamate)

3D-SDF for HMDB0015165 (Ethinamate)

PDB for HMDB0015165 (Ethinamate)

3D PDB for HMDB0015165 (Ethinamate)

SMILES for HMDB0015165 (Ethinamate)

INCHI for HMDB0015165 (Ethinamate)

Structure for HMDB0015165 (Ethinamate)

3D Structure for HMDB0015165 (Ethinamate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

References

References