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Showing metabocard for Pemoline (HMDB0256214)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 16:32:21 UTC
Update Date2021-09-26 23:11:43 UTC
HMDB IDHMDB0256214
Secondary Accession NumbersNone
Metabolite Identification
Common NamePemoline
DescriptionPemoline, also known as cylert or azoxodon, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Pemoline is a drug which is used for treatment of attention deficit hyperactivity disorder (adhd). Based on a literature review a significant number of articles have been published on Pemoline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pemoline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pemoline 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0256214 (Pemoline)

1230
  Mrv0541 02231215202D          

 13 14  0  0  1  0            999 V2000
    2.3888    0.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    0.2653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    1.3049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587    1.9724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562   -0.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7236    0.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707   -1.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -1.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    1.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707   -2.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -2.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562   -2.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 10  1  0  0  0  0
  2  7  2  0  0  0  0
  3  7  1  0  0  0  0
  3 10  2  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
 11 13  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
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3D MOL for HMDB0256214 (Pemoline)

HMDB0256214
     RDKit          3D
Pemoline
 21 22  0  0  0  0  0  0  0  0999 V2000
    4.1138    0.5870   -0.2651 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8484   -0.0091    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7623   -1.1595    0.6487 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -1.4291    0.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259   -2.5774    0.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7468   -0.0837    0.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494    0.0134    0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5426   -1.0041    0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8948   -0.8555    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3321    0.3202   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471    1.3714   -0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340    1.1975   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6013    0.5449   -0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464    1.4144    0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6453    0.1510   -1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207    0.3943    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2390   -1.9485    1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5891   -1.6921    0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627    0.4642   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8362    2.2909   -0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4346    2.0095   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13  2  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
M  END
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3D SDF for HMDB0256214 (Pemoline)

1230
  Mrv0541 02231215202D          

 13 14  0  0  1  0            999 V2000
    2.3888    0.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    0.2653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    1.3049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587    1.9724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562    0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562   -0.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7236    0.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707   -1.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -1.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    1.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707   -2.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -2.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562   -2.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 10  1  0  0  0  0
  2  7  2  0  0  0  0
  3  7  1  0  0  0  0
  3 10  2  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
 11 13  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256214

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)C(O1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12)

> <INCHI_KEY>
NRNCYVBFPDDJNE-UHFFFAOYSA-N

> <FORMULA>
C9H8N2O2

> <MOLECULAR_WEIGHT>
176.172

> <EXACT_MASS>
176.05857751

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.040561196005214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-5-phenyl-4,5-dihydro-1,3-oxazol-4-one

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
0.800027732

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.953646792407326

> <JCHEM_PKA_STRONGEST_BASIC>
0.9878962542048974

> <JCHEM_POLAR_SURFACE_AREA>
64.67999999999999

> <JCHEM_REFRACTIVITY>
45.70230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pemoline

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0256214 (Pemoline)

HMDB0256214
     RDKit          3D
Pemoline
 21 22  0  0  0  0  0  0  0  0999 V2000
    4.1138    0.5870   -0.2651 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8484   -0.0091    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7623   -1.1595    0.6487 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -1.4291    0.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259   -2.5774    0.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7468   -0.0837    0.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6494    0.0134    0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5426   -1.0041    0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8948   -0.8555    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3321    0.3202   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471    1.3714   -0.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340    1.1975   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6013    0.5449   -0.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464    1.4144    0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6453    0.1510   -1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207    0.3943    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2390   -1.9485    1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5891   -1.6921    0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627    0.4642   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8362    2.2909   -0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4346    2.0095   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13  2  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 12 21  1  0
M  END
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PDB for HMDB0256214 (Pemoline)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1230                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.459   0.971   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   0.495   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       6.475   2.436   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.030   3.682   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.705   0.066   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.705  -1.474   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.951   0.971   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.039  -2.244   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.371  -2.244   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.935   2.436   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.039  -3.784   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.371  -3.784   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.705  -4.554   0.000  0.00  0.00           C+0
CONECT    1    5   10                                                       
CONECT    2    7                                                            
CONECT    3    7   10                                                       
CONECT    4   10                                                            
CONECT    5    1    6    7                                                  
CONECT    6    5    8    9                                                  
CONECT    7    2    3    5                                                  
CONECT    8    6   11                                                       
CONECT    9    6   12                                                       
CONECT   10    1    3    4                                                  
CONECT   11    8   13                                                       
CONECT   12    9   13                                                       
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0256214 (Pemoline)

COMPND    HMDB0256214
HETATM    1  N1  UNL     1       4.114   0.587  -0.265  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.848  -0.009   0.078  1.00  0.00           C  
HETATM    3  N2  UNL     1       2.762  -1.159   0.649  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.351  -1.429   0.837  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.926  -2.577   0.955  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.747  -0.084   0.834  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.649   0.013   0.483  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.543  -1.004   0.645  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.895  -0.856   0.278  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.332   0.320  -0.250  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.447   1.371  -0.426  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.134   1.197  -0.058  1.00  0.00           C  
HETATM   13  O2  UNL     1       1.601   0.545  -0.148  1.00  0.00           O  
HETATM   14  H1  UNL     1       4.446   1.414   0.266  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.645   0.151  -1.045  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.021   0.394   1.800  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.239  -1.949   1.064  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.589  -1.692   0.420  1.00  0.00           H  
HETATM   19  H6  UNL     1      -4.363   0.464  -0.541  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.836   2.291  -0.849  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.435   2.009  -0.190  1.00  0.00           H  
CONECT    1    2   14   15
CONECT    2    3    3   13
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   13   16
CONECT    7    8    8   12
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   11   19
CONECT   11   12   12   20
CONECT   12   21
END
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SMILES for HMDB0256214 (Pemoline)

NC1=NC(=O)C(O1)C1=CC=CC=C1
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INCHI for HMDB0256214 (Pemoline)

InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12)
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC9H8N2O2
Average Molecular Weight176.172
Monoisotopic Molecular Weight176.05857751
IUPAC Name2-amino-5-phenyl-4,5-dihydro-1,3-oxazol-4-one
Traditional Namepemoline
CAS Registry NumberNot Available
SMILES
NC1=NC(=O)C(O1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12)
InChI KeyNRNCYVBFPDDJNE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Oxazoline
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01230
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4561
KEGG Compound IDC07899
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPemoline
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID7953
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]