ContaminantDB: Aprobarbital

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:27:05 UTC

Update Date

2016-11-09 01:17:27 UTC

Accession Number

CHEM022293

Identification

Common Name

Aprobarbital

Class

Small Molecule

Description

Aprobarbital is a barbiturate derivative synthesized in the 1920s by Ernst Preiswerk. It was determined that the substance was capable of demonstrating sedative, hypnotic, and anticonvulsant effects. A primary treatment indicated for the use of aprobarbital was subsequently insomnia. Aprobarbital was never as widely used as more common barbiturate derivatives such as phenobarbital and is now rarely prescribed.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-(1-Methylethyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Allyl-5-isopropylbarbituric acid	ChEBI
5-Allyl-5-isopropylpyrimidine-2,4,6(1H,3H,5H)-trione	ChEBI
5-Isopropyl-5-allylbarbituric acid	ChEBI
Allypropymal	ChEBI
Alurate	ChEBI
5-Allyl-5-isopropylbarbitate	Generator
5-Allyl-5-isopropylbarbitic acid	Generator
5-Isopropyl-5-allylbarbitate	Generator
5-Isopropyl-5-allylbarbitic acid	Generator
Aluric acid	Generator
Alate	HMDB
Alic acid	HMDB
Allylpropymal	HMDB
Aprobarbitone	HMDB
Allylpropymal, monosodium salt	HMDB

Chemical Formula

C₁₀H₁₄N₂O₃

Average Molecular Mass

210.230 g/mol

Monoisotopic Mass

210.100 g/mol

CAS Registry Number

77-02-1

IUPAC Name

5-(prop-2-en-1-yl)-5-(propan-2-yl)-1,3-diazinane-2,4,6-trione

Traditional Name

aprobarbital

SMILES

CC(C)C1(CC=C)C(=O)NC(=O)NC1=O

InChI Identifier

InChI=1S/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15)

InChI Key

UORJNBVJVRLXMQ-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:2791 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.17 g/L	ALOGPS
logP	1.24	ALOGPS
logP	1.14	ChemAxon
logS	-1.6	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	3	ChemAxon
Refractivity	53.45 m³·mol⁻¹	ChemAxon
Polarizability	20.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9600000000-9ab2ab6ff36ccb20312f	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-03di-0090000000-b13a014a6928d0747567	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9600000000-9ab2ab6ff36ccb20312f	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-03di-0090000000-b13a014a6928d0747567	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-6900000000-8e2fadd8c703abf57cab	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-052g-9340000000-7606e92a526391d4fe69	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0390000000-181ed7f48a6f8b2be459	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0005-4900000000-c3ed55bedff14b2893f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000x-9000000000-7921b62ac5b52f86c373	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05mo-8950000000-b232a6440f5538b1f92e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9500000000-7ed9cf57a53d84095449	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-9200000000-55c099997913083a521f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0790000000-0080941b73c060d0c3ea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052b-9210000000-bb699f2867a4017b84e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9100000000-37fda3df56bd06c65a0a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2390000000-5fc08243ebac6ecef3e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9100000000-6264c5b2cdaf4d9ea453	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-6f85e6486e25545f181a	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01352

HMDB ID

HMDB0015441

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=5034548

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=8313534

Aprobarbital (CHEM022293)

Structure for CHEM022293: Aprobarbital