Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:45:56 UTC

Update Date

2021-09-26 23:02:16 UTC

HMDB ID

HMDB0250670

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cyclopentobarbital

Description

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

HMDB0250670
     RDKit          3D
Cyclopentobarbital
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.2223   -2.6619    0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0790   -2.1451    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0956   -1.1248   -0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5076    0.1921   -0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087    0.2265    0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036   -0.4849    1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974   -0.7477    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658   -0.2077   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -0.2589   -0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6177    1.0596   -1.5282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964    0.4743   -2.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385    2.4219   -1.4943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4658    2.9685   -0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7592    4.2016   -0.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683    2.1566    0.8530 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    0.7726    0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7763    0.0566    1.7362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1854   -2.3304    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2548   -3.4055    1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705   -2.5325    0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6608   -1.5447   -1.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816   -0.9746   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671    1.3168    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346   -0.8089    2.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2366   -1.2733    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478   -0.8479   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.8506    0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9744    0.3676   -1.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -1.3404   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799    3.0057   -2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0601    2.6181    1.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  4  1  0
  9  5  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 15 31  1  0
M  END


  Mrv1652309112109462D          

 17 18  0  0  0  0            999 V2000
    1.8883    0.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758    0.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5455   -0.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2669   -0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -0.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3616   -0.9738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6097    0.4334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3275    1.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8578    1.8407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5151    1.3519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0152    0.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277    0.8632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2669   -0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9344   -1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6794   -2.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1456   -2.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4005   -1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 13 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250670

> <DATABASE_NAME>
hmdb

> <SMILES>
C=CCC1(C2CCC=C2)C(=O)NC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O3/c1-2-7-12(8-5-3-4-6-8)9(15)13-11(17)14-10(12)16/h2-3,5,8H,1,4,6-7H2,(H2,13,14,15,16,17)

> <INCHI_KEY>
XOVJAYNMQDTIJD-UHFFFAOYSA-N

> <FORMULA>
C12H14N2O3

> <MOLECULAR_WEIGHT>
234.255

> <EXACT_MASS>
234.100442319

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.68614636460815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(cyclopent-2-en-1-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.2081843659999998

> <ALOGPS_LOGS>
-1.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.144758838360822

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.4754873811424085

> <JCHEM_POLAR_SURFACE_AREA>
75.27000000000001

> <JCHEM_REFRACTIVITY>
61.96240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclopentabarbital

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250670
     RDKit          3D
Cyclopentobarbital
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.2223   -2.6619    0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0790   -2.1451    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0956   -1.1248   -0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5076    0.1921   -0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087    0.2265    0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036   -0.4849    1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974   -0.7477    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658   -0.2077   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -0.2589   -0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6177    1.0596   -1.5282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964    0.4743   -2.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385    2.4219   -1.4943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4658    2.9685   -0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7592    4.2016   -0.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683    2.1566    0.8530 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    0.7726    0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7763    0.0566    1.7362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1854   -2.3304    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2548   -3.4055    1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705   -2.5325    0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6608   -1.5447   -1.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816   -0.9746   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671    1.3168    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346   -0.8089    2.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2366   -1.2733    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478   -0.8479   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.8506    0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9744    0.3676   -1.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -1.3404   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799    3.0057   -2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0601    2.6181    1.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  4  1  0
  9  5  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 15 31  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       3.525   0.542   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.008   0.809   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.018  -0.371   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.498  -0.103   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.015  -0.371   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.542  -1.818   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      -3.005   0.809   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -2.478   2.256   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.468   3.436   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -0.961   2.524   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.028   1.344   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.545   1.611   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.498  -1.643   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.744  -2.548   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.268  -4.013   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.272  -4.013   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.748  -2.548   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11   13                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13    4   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0250670
HETATM    1  C1  UNL     1      -2.222  -2.662   0.894  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.079  -2.145   0.411  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.096  -1.125  -0.660  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.508   0.192  -0.309  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.909   0.227   0.101  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.304  -0.485   1.296  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.597  -0.748   1.227  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.166  -0.208  -0.067  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.886  -0.259  -0.925  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.618   1.060  -1.528  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.396   0.474  -2.640  1.00  0.00           O  
HETATM   12  N1  UNL     1      -0.939   2.422  -1.494  1.00  0.00           N  
HETATM   13  C11 UNL     1      -1.466   2.969  -0.297  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.759   4.202  -0.257  1.00  0.00           O  
HETATM   15  N2  UNL     1      -1.668   2.157   0.853  1.00  0.00           N  
HETATM   16  C12 UNL     1      -1.336   0.773   0.799  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.776   0.057   1.736  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.185  -2.330   0.495  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.255  -3.406   1.672  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.170  -2.532   0.855  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.661  -1.545  -1.597  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.182  -0.975  -0.940  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.167   1.317   0.266  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.735  -0.809   2.187  1.00  0.00           H  
HETATM   25  H8  UNL     1       3.237  -1.273   1.956  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.948  -0.848  -0.471  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.483   0.851   0.060  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.974   0.368  -1.808  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.751  -1.340  -1.159  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.780   3.006  -2.360  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.060   2.618   1.706  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   20
CONECT    3    4   21   22
CONECT    4    5   10   16
CONECT    5    6    9   23
CONECT    6    7    7   24
CONECT    7    8   25
CONECT    8    9   26   27
CONECT    9   28   29
CONECT   10   11   11   12
CONECT   12   13   30
CONECT   13   14   14   15
CONECT   15   16   31
CONECT   16   17   17
END

HMDB0250670
     RDKit          3D
Cyclopentobarbital
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.2223   -2.6619    0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0790   -2.1451    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0956   -1.1248   -0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5076    0.1921   -0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087    0.2265    0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036   -0.4849    1.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974   -0.7477    1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658   -0.2077   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -0.2589   -0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6177    1.0596   -1.5282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964    0.4743   -2.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385    2.4219   -1.4943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4658    2.9685   -0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7592    4.2016   -0.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683    2.1566    0.8530 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    0.7726    0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7763    0.0566    1.7362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1854   -2.3304    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2548   -3.4055    1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705   -2.5325    0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6608   -1.5447   -1.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816   -0.9746   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671    1.3168    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346   -0.8089    2.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2366   -1.2733    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478   -0.8479   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.8506    0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9744    0.3676   -1.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -1.3404   -1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799    3.0057   -2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0601    2.6181    1.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  4  1  0
  9  5  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₂H₁₄N₂O₃

Average Molecular Weight

234.255

Monoisotopic Molecular Weight

234.100442319

IUPAC Name

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

Traditional Name

cyclopentabarbital

CAS Registry Number

Not Available

SMILES

C=CCC1(C2CCC=C2)C(=O)NC(=O)NC1=O

InChI Identifier

InChI=1S/C12H14N2O3/c1-2-7-12(8-5-3-4-6-8)9(15)13-11(17)14-10(12)16/h2-3,5,8H,1,4,6-7H2,(H2,13,14,15,16,17)

InChI Key

XOVJAYNMQDTIJD-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)

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	1.63	ALOGPS
logP	1.21	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	7.48	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	61.96 m³·mol⁻¹	ChemAxon
Polarizability	22.69 Å³	ChemAxon
Number of Rings	2	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]+	150.611	30932474
DeepCCS	[M-H]-	148.216	30932474
DeepCCS	[M-2H]-	181.395	30932474
DeepCCS	[M+Na]+	156.637	30932474
AllCCS	[M+H]+	153.0	32859911
AllCCS	[M+H-H2O]+	149.1	32859911
AllCCS	[M+NH4]+	156.6	32859911
AllCCS	[M+Na]+	157.7	32859911
AllCCS	[M-H]-	153.7	32859911
AllCCS	[M+Na-2H]-	153.7	32859911
AllCCS	[M+HCOO]-	153.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclopentobarbital	C=CCC1(C2CCC=C2)C(=O)NC(=O)NC1=O	3248.1	Standard polar	33892256
Cyclopentobarbital	C=CCC1(C2CCC=C2)C(=O)NC(=O)NC1=O	1824.0	Standard non polar	33892256
Cyclopentobarbital	C=CCC1(C2CCC=C2)C(=O)NC(=O)NC1=O	1899.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclopentobarbital,1TMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2003.1	Semi standard non polar	33892256
Cyclopentobarbital,1TMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1981.4	Standard non polar	33892256
Cyclopentobarbital,1TMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2865.3	Standard polar	33892256
Cyclopentobarbital,2TMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1892.8	Semi standard non polar	33892256
Cyclopentobarbital,2TMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2056.0	Standard non polar	33892256
Cyclopentobarbital,2TMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2535.5	Standard polar	33892256
Cyclopentobarbital,1TBDMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2221.7	Semi standard non polar	33892256
Cyclopentobarbital,1TBDMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2196.5	Standard non polar	33892256
Cyclopentobarbital,1TBDMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2968.0	Standard polar	33892256
Cyclopentobarbital,2TBDMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2363.6	Semi standard non polar	33892256
Cyclopentobarbital,2TBDMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2478.0	Standard non polar	33892256
Cyclopentobarbital,2TBDMS,isomer #1	C=CCC1(C2C=CCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2687.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclopentobarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-8940000000-1f32da2b4bee987870f3	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclopentobarbital 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 - Cyclopentobarbital 10V, Positive-QTOF	splash10-00kr-0790000000-38706230ee7783505599	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclopentobarbital 20V, Positive-QTOF	splash10-01bc-9700000000-ddc0a1bc2da1ed82957a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclopentobarbital 40V, Positive-QTOF	splash10-00ou-9100000000-362c5c3b3956616e11ea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclopentobarbital 10V, Negative-QTOF	splash10-001l-4490000000-e19436c017c8eee2990b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclopentobarbital 20V, Negative-QTOF	splash10-0006-9000000000-64e429c9344b2b2862bd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclopentobarbital 40V, Negative-QTOF	splash10-0006-9100000000-2b73e074bcac7d4f547c	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6212

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyclopentobarbital

METLIN ID

Not Available

PubChem Compound

6454

PDB ID

Not Available

ChEBI ID

Not Available

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 Cyclopentobarbital (HMDB0250670)

MOL for HMDB0250670 (Cyclopentobarbital)

3D MOL for HMDB0250670 (Cyclopentobarbital)

3D SDF for HMDB0250670 (Cyclopentobarbital)

3D-SDF for HMDB0250670 (Cyclopentobarbital)

PDB for HMDB0250670 (Cyclopentobarbital)

3D PDB for HMDB0250670 (Cyclopentobarbital)

SMILES for HMDB0250670 (Cyclopentobarbital)

INCHI for HMDB0250670 (Cyclopentobarbital)

Structure for HMDB0250670 (Cyclopentobarbital)

3D Structure for HMDB0250670 (Cyclopentobarbital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra