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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:19:42 UTC

Update Date

2021-09-26 22:58:17 UTC

HMDB ID

HMDB0248157

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Allobarbital

Description

Allobarbital 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 very few articles have been published on Allobarbital. This compound has been identified in human blood as reported by (PMID: 31557052 ). Allobarbital is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Allobarbital 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

  Mrv1652306031607012D          

 15 15  0  0  0  0            999 V2000
    0.1501    2.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586    2.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248157

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NC(=O)N=C(O)C1(CC=C)CC=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O3/c1-3-5-10(6-4-2)7(13)11-9(15)12-8(10)14/h3-4H,1-2,5-6H2,(H2,11,12,13,14,15)

> <INCHI_KEY>
FDQGNLOWMMVRQL-UHFFFAOYSA-N

> <FORMULA>
C10H12N2O3

> <MOLECULAR_WEIGHT>
208.217

> <EXACT_MASS>
208.084792254

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.741884313772932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-dihydroxy-5,5-bis(prop-2-en-1-yl)-2,5-dihydropyrimidin-2-one

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
1.7332577863333332

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.096643409163561

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3619548657374905

> <JCHEM_PKA_STRONGEST_BASIC>
-4.200070127522765

> <JCHEM_POLAR_SURFACE_AREA>
82.25

> <JCHEM_REFRACTIVITY>
54.1859

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
curral

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       0.280   5.204   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.163   4.402   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.797   4.937   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.173   3.222   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.667  -0.000   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7   10   11   13                                                  
CONECT    8   10   12   14                                                  
CONECT    9   11   12   15                                                  
CONECT   10    5    6    7    8                                             
CONECT   11    7    9                                                       
CONECT   12    8    9                                                       
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0248157
HETATM    1  C1  UNL     1       1.714   2.345  -0.718  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.988   1.288  -1.139  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.206  -0.050  -0.609  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.056  -0.702  -0.029  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.647   0.087   1.113  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.076   1.446   0.833  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.675   2.518   1.499  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.482  -1.982   0.550  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.441  -1.869   1.600  1.00  0.00           O  
HETATM   10  N1  UNL     1       0.114  -3.112   0.142  1.00  0.00           N  
HETATM   11  C9  UNL     1      -0.830  -3.337  -0.890  1.00  0.00           C  
HETATM   12  O2  UNL     1      -1.173  -4.482  -1.273  1.00  0.00           O  
HETATM   13  N2  UNL     1      -1.353  -2.143  -1.452  1.00  0.00           N  
HETATM   14  C10 UNL     1      -1.021  -0.979  -1.081  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.615   0.154  -1.716  1.00  0.00           O  
HETATM   16  H1  UNL     1       2.462   2.135   0.032  1.00  0.00           H  
HETATM   17  H2  UNL     1       1.569   3.332  -1.096  1.00  0.00           H  
HETATM   18  H3  UNL     1       0.224   1.443  -1.904  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.624  -0.726  -1.412  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.000  -0.023   0.172  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.495  -0.547   1.496  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.161   0.119   1.903  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.796   1.655   0.011  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.031   3.487   1.239  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.017   2.400   2.309  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.397  -2.610   2.289  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.630   0.152  -1.869  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   18
CONECT    3    4   19   20
CONECT    4    5    8   14
CONECT    5    6   21   22
CONECT    6    7    7   23
CONECT    7   24   25
CONECT    8    9   10   10
CONECT    9   26
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14
CONECT   14   15
CONECT   15   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Diallylbarbituric acid	ChEMBL, MeSH
Diallymal	ChEMBL
Diallylbarbitate	Generator
Diallylbarbitic acid	Generator
5,5-Diallylbarbituric acid	MeSH
Diallylmal	MeSH
Allobarbitone	MeSH
Diallyl barbituric acid	MeSH
Diallylbarbital	MeSH

Chemical Formula

C₁₀H₁₂N₂O₃

Average Molecular Weight

208.217

Monoisotopic Molecular Weight

208.084792254

IUPAC Name

4,6-dihydroxy-5,5-bis(prop-2-en-1-yl)-2,5-dihydropyrimidin-2-one

Traditional Name

curral

CAS Registry Number

Not Available

SMILES

OC1=NC(=O)N=C(O)C1(CC=C)CC=C

InChI Identifier

InChI=1S/C10H12N2O3/c1-3-5-10(6-4-2)7(13)11-9(15)12-8(10)14/h3-4H,1-2,5-6H2,(H2,11,12,13,14,15)

InChI Key

FDQGNLOWMMVRQL-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0248157)

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	0.74	ALOGPS
logP	1.73	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	1.36	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.25 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.19 m³·mol⁻¹	ChemAxon
Polarizability	19.74 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]+	148.349	30932474
DeepCCS	[M-H]-	145.954	30932474
DeepCCS	[M-2H]-	180.0	30932474
DeepCCS	[M+Na]+	154.733	30932474
AllCCS	[M+H]+	146.6	32859911
AllCCS	[M+H-H2O]+	142.5	32859911
AllCCS	[M+NH4]+	150.4	32859911
AllCCS	[M+Na]+	151.4	32859911
AllCCS	[M-H]-	144.7	32859911
AllCCS	[M+Na-2H]-	145.2	32859911
AllCCS	[M+HCOO]-	145.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Allobarbital	OC1=NC(=O)N=C(O)C1(CC=C)CC=C	3068.1	Standard polar	33892256
Allobarbital	OC1=NC(=O)N=C(O)C1(CC=C)CC=C	1694.8	Standard non polar	33892256
Allobarbital	OC1=NC(=O)N=C(O)C1(CC=C)CC=C	1742.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Allobarbital EI-B (Non-derivatized)	splash10-014l-9500000000-830bf2be43ff02dbb120	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allobarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-7910000000-b59872f99d947336b9ab	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allobarbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allobarbital GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allobarbital GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allobarbital GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allobarbital GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - Allobarbital 10V, Positive-QTOF	splash10-0a4i-0390000000-b2123105016ef72ec6f0	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 20V, Positive-QTOF	splash10-000i-4910000000-9855e9883b2e56a0aa7b	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 40V, Positive-QTOF	splash10-0f6x-9000000000-423710ea3224c150386f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 10V, Negative-QTOF	splash10-06r6-8950000000-f0586054ceb0d0d449a5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 20V, Negative-QTOF	splash10-0006-9500000000-ce29a95be81a38389061	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 40V, Negative-QTOF	splash10-0006-9200000000-6a2bef6e9f7c35c4f49d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 10V, Positive-QTOF	splash10-0a4i-0390000000-0515b18dd1e9703e4fb5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 20V, Positive-QTOF	splash10-00kf-9500000000-7f0bf5061ad2381b8241	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 40V, Positive-QTOF	splash10-014i-9000000000-350c1a09996d49356483	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 10V, Negative-QTOF	splash10-0a4i-0090000000-b77155856da9672967df	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 20V, Negative-QTOF	splash10-0006-9010000000-a3200b8349abde4d1ba0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allobarbital 40V, Negative-QTOF	splash10-0006-9000000000-c1e6706e9a12ea675399	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13577

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5635

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Allobarbital

METLIN ID

Not Available

PubChem Compound

5842

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1094161

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 Allobarbital (HMDB0248157)

MOL for HMDB0248157 (Allobarbital)

3D MOL for HMDB0248157 (Allobarbital)

3D SDF for HMDB0248157 (Allobarbital)

3D-SDF for HMDB0248157 (Allobarbital)

PDB for HMDB0248157 (Allobarbital)

3D PDB for HMDB0248157 (Allobarbital)

SMILES for HMDB0248157 (Allobarbital)

INCHI for HMDB0248157 (Allobarbital)

Structure for HMDB0248157 (Allobarbital)

3D Structure for HMDB0248157 (Allobarbital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra