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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:36:51 UTC

Update Date

2022-09-22 17:44:21 UTC

HMDB ID

HMDB0248870

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Barbital

Description

Barbital, also known as barbitone or DEBA, belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups. Based on a literature review a significant number of articles have been published on Barbital. This compound has been identified in human blood as reported by (PMID: 31557052 ). Barbital is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Barbital is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1483                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   0.976   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   0.976   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.748  -3.644   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.414  -1.334   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.081  -1.334   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.748   0.976   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.518   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   0.206   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.437   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   3.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -2.104   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   13                                                            
CONECT    4    9   13                                                       
CONECT    5   10   13                                                       
CONECT    6    7    8    9   10                                             
CONECT    7    6   11                                                       
CONECT    8    6   12                                                       
CONECT    9    1    4    6                                                  
CONECT   10    2    5    6                                                  
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    3    4    5                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4,6(1H,3H,5H)-Pyrimidinetrione	ChEBI
5,5-Diethyl-pyrimidine-2,4,6-trione	ChEBI
5,5-Diethylpyrimidine-2,4,6(1H,3H,5H)-trione	ChEBI
Barbitone	ChEBI
DEBA	ChEBI
Diethylmalonyl urea	ChEBI
Veronal	ChEBI
Diemal	HMDB
Medinal	HMDB
Ethylbarbital	HMDB
Diethylmalonylurea	HMDB
Dormileno	HMDB
Barbital faes brand	HMDB
Faes brand OF barbital	HMDB
5,5-Diethylbarbitate	HMDB
5,5-Diethylbarbitic acid	HMDB
Barbital	ChEBI

Chemical Formula

C₈H₁₂N₂O₃

Average Molecular Weight

184.1925

Monoisotopic Molecular Weight

184.08479226

IUPAC Name

5,5-diethyl-1,3-diazinane-2,4,6-trione

Traditional Name

barbital

CAS Registry Number

Not Available

SMILES

CCC1(CC)C(=O)NC(=O)NC1=O

InChI Identifier

InChI=1S/C8H12N2O3/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13)

InChI Key

FTOAOBMCPZCFFF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Barbituric acid derivatives

Alternative Parents

Substituents

Barbiturate
N-acyl urea
Ureide
1,3-diazinane
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

barbiturates (CHEBI:31252 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0248870)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.73	ALOGPS
logP	0.72	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.27 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.25 m³·mol⁻¹	ChemAxon
Polarizability	17.59 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
DeepCCS	[M+H]+	136.577	30932474
DeepCCS	[M-H]-	132.745	30932474
DeepCCS	[M-2H]-	170.36	30932474
DeepCCS	[M+Na]+	145.9	30932474
AllCCS	[M+H]+	140.3	32859911
AllCCS	[M+H-H2O]+	136.1	32859911
AllCCS	[M+NH4]+	144.2	32859911
AllCCS	[M+Na]+	145.4	32859911
AllCCS	[M-H]-	139.3	32859911
AllCCS	[M+Na-2H]-	140.3	32859911
AllCCS	[M+HCOO]-	141.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.9879 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1993.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	396.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	249.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	125.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	435.3 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	650.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	983.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	392.0 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	1375.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	305.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	326.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	430.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	294.3 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	66.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Barbital	CCC1(CC)C(=O)NC(=O)NC1=O	2979.5	Standard polar	33892256
Barbital	CCC1(CC)C(=O)NC(=O)NC1=O	1598.3	Standard non polar	33892256
Barbital	CCC1(CC)C(=O)NC(=O)NC1=O	1457.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Barbital,1TMS,isomer #1	CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1521.8	Semi standard non polar	33892256
Barbital,1TMS,isomer #1	CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1670.3	Standard non polar	33892256
Barbital,1TMS,isomer #1	CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2599.6	Standard polar	33892256
Barbital,2TMS,isomer #1	CCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1508.2	Semi standard non polar	33892256
Barbital,2TMS,isomer #1	CCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1725.2	Standard non polar	33892256
Barbital,2TMS,isomer #1	CCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2128.0	Standard polar	33892256
Barbital,1TBDMS,isomer #1	CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	1754.5	Semi standard non polar	33892256
Barbital,1TBDMS,isomer #1	CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	1909.5	Standard non polar	33892256
Barbital,1TBDMS,isomer #1	CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2661.2	Standard polar	33892256
Barbital,2TBDMS,isomer #1	CCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	1937.1	Semi standard non polar	33892256
Barbital,2TBDMS,isomer #1	CCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2185.4	Standard non polar	33892256
Barbital,2TBDMS,isomer #1	CCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2277.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Barbital CI-B (Non-derivatized)	splash10-000i-0900000000-90fb45d882d2c3ed038f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Barbital EI-B (Non-derivatized)	splash10-052f-9400000000-fa1289872f9f35015abc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Barbital EI-B (Non-derivatized)	splash10-052f-9500000000-856a7fe5dbfd28d00c38	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Barbital EI-B (Non-derivatized)	splash10-0a4l-2900000000-42c0874d0bac13cc2d94	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Barbital EI-B (Non-derivatized)	splash10-0a4u-5900000000-497f9ee367181a6df30a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Barbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-5900000000-3c6687662491f8ac6aee	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Barbital 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 - Barbital 10V, Positive-QTOF	splash10-000i-0900000000-c495e9edac16920b65b4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 20V, Positive-QTOF	splash10-03di-7900000000-627b3602d7bf9ff96913	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 40V, Positive-QTOF	splash10-01bc-9000000000-d5dcaa6c067db4967029	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 10V, Negative-QTOF	splash10-000x-5900000000-f428d3f140303ddec9f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 20V, Negative-QTOF	splash10-0006-9500000000-d71d709919480c7a3bc3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 40V, Negative-QTOF	splash10-000x-9200000000-52b1e79e0c2b3207d3bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 10V, Positive-QTOF	splash10-000i-0900000000-8f066f6c9186aa8a423c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 20V, Positive-QTOF	splash10-0a4i-2900000000-79cebb3b5178fd42c3ee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 40V, Positive-QTOF	splash10-00r2-9100000000-3dc4615a6b3e3654eeca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 10V, Negative-QTOF	splash10-001i-0900000000-3869e238b86b938f0f0e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 20V, Negative-QTOF	splash10-0006-9300000000-79aafc1759978cac7fa6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Barbital 40V, Negative-QTOF	splash10-0006-9000000000-8313d221f9f4df0b679a	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01483

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00031180

Chemspider ID

2206

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Barbital

METLIN ID

Not Available

PubChem Compound

2294

PDB ID

Not Available

ChEBI ID

31252

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Barbital (HMDB0248870)

MOL for HMDB0248870 (Barbital)

3D MOL for HMDB0248870 (Barbital)

3D SDF for HMDB0248870 (Barbital)

3D-SDF for HMDB0248870 (Barbital)

PDB for HMDB0248870 (Barbital)

3D PDB for HMDB0248870 (Barbital)

SMILES for HMDB0248870 (Barbital)

INCHI for HMDB0248870 (Barbital)

Structure for HMDB0248870 (Barbital)

3D Structure for HMDB0248870 (Barbital)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra