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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:32:21 UTC

Update Date

2021-09-26 23:11:43 UTC

HMDB ID

HMDB0256214

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pemoline

Description

Pemoline, 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

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

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Amino-5-phenyl-4(5H)-oxazolone	ChEBI
2-Imino-4-keto-5-phenyltetrahydrooxazole	ChEBI
2-Imino-5-phenyl-4-oxazolidinone	ChEBI
5-Phenyl-2-imino-4-oxazolidinone	ChEBI
5-Phenyl-2-imino-4-oxooxazolidine	ChEBI
5-Phenylisohydantion	ChEBI
Azoxodon	ChEBI
Betanamin	ChEBI
Cylert	ChEBI
Dantromin	ChEBI
Deltamine	ChEBI
Hyton	ChEBI
Myamin	ChEBI
Nitan	ChEBI
Notair	ChEBI
Pemolina	ChEBI
Pemolinum	ChEBI
Pheniminooxazolidinone	ChEBI
Phenylisohydantoin	ChEBI
Phenylpseudohydantoin	ChEBI
Abbott brand OF pemoline	MeSH
Lilly brand OF pemoline	MeSH
Compounds, pemoline	MeSH
Pemoline compounds	MeSH
Tradon	MeSH
Magnesium, pemoline	MeSH
Mallinckrodt brand OF pemoline	MeSH
PemADD	MeSH
Pemoline magnesium	MeSH
Phenoxazole	MeSH

Chemical Formula

C₉H₈N₂O₂

Average Molecular Weight

176.172

Monoisotopic Molecular Weight

176.05857751

IUPAC Name

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

Traditional Name

pemoline

CAS Registry Number

Not 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 Key

NRNCYVBFPDDJNE-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-oxazoles (CHEBI:7953 )

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	0.52	ALOGPS
logP	0.8	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.95	ChemAxon
pKa (Strongest Basic)	0.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	45.7 m³·mol⁻¹	ChemAxon
Polarizability	17.04 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]+	138.474	30932474
DeepCCS	[M-H]-	136.078	30932474
DeepCCS	[M-2H]-	171.031	30932474
DeepCCS	[M+Na]+	145.49	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	133.8	32859911
AllCCS	[M+NH4]+	142.6	32859911
AllCCS	[M+Na]+	143.8	32859911
AllCCS	[M-H]-	136.8	32859911
AllCCS	[M+Na-2H]-	137.2	32859911
AllCCS	[M+HCOO]-	137.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pemoline	NC1=NC(=O)C(O1)C1=CC=CC=C1	3003.6	Standard polar	33892256
Pemoline	NC1=NC(=O)C(O1)C1=CC=CC=C1	2090.7	Standard non polar	33892256
Pemoline	NC1=NC(=O)C(O1)C1=CC=CC=C1	1858.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pemoline,1TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C(C2=CC=CC=C2)O1	1949.2	Semi standard non polar	33892256
Pemoline,1TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C(C2=CC=CC=C2)O1	1828.5	Standard non polar	33892256
Pemoline,1TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)C(C2=CC=CC=C2)O1	2850.3	Standard polar	33892256
Pemoline,2TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C(C2=CC=CC=C2)O1)[Si](C)(C)C	1912.6	Semi standard non polar	33892256
Pemoline,2TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C(C2=CC=CC=C2)O1)[Si](C)(C)C	1951.6	Standard non polar	33892256
Pemoline,2TMS,isomer #1	C[Si](C)(C)N(C1=NC(=O)C(C2=CC=CC=C2)O1)[Si](C)(C)C	2662.9	Standard polar	33892256
Pemoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C(C2=CC=CC=C2)O1	2161.3	Semi standard non polar	33892256
Pemoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C(C2=CC=CC=C2)O1	2040.6	Standard non polar	33892256
Pemoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)C(C2=CC=CC=C2)O1	2887.6	Standard polar	33892256
Pemoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C(C2=CC=CC=C2)O1)[Si](C)(C)C(C)(C)C	2281.5	Semi standard non polar	33892256
Pemoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C(C2=CC=CC=C2)O1)[Si](C)(C)C(C)(C)C	2335.7	Standard non polar	33892256
Pemoline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=O)C(C2=CC=CC=C2)O1)[Si](C)(C)C(C)(C)C	2709.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pemoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-7900000000-ff16f04882fa6bc388b4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pemoline 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pemoline LC-ESI-qTof , Positive-QTOF	splash10-0a4i-1900000000-6304707e673e5496a706	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pemoline , positive-QTOF	splash10-0a4i-1900000000-6304707e673e5496a706	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pemoline 35V, Negative-QTOF	splash10-0006-9000000000-6312df1dd9b3c1da44a0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pemoline 35V, Positive-QTOF	splash10-0a4i-3900000000-355d61158f2b03978708	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pemoline 10V, Positive-QTOF	splash10-004i-0900000000-5fdd1bf70ae74ce0100a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pemoline 20V, Positive-QTOF	splash10-05r3-1900000000-9afcde2920ef21e932f6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pemoline 40V, Positive-QTOF	splash10-0aou-9700000000-37842f170bf0d611bc61	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pemoline 10V, Negative-QTOF	splash10-004i-1900000000-a834fbdc5b9e8c4b0eb3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pemoline 20V, Negative-QTOF	splash10-004i-9700000000-770e8d3a8e42b5bad6c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pemoline 40V, Negative-QTOF	splash10-0006-9100000000-6ded2f5c4a0ee37a0e13	2016-08-03	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

DB01230

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4561

KEGG Compound ID

C07899

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pemoline

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

7953

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 Pemoline (HMDB0256214)

MOL for HMDB0256214 (Pemoline)

3D MOL for HMDB0256214 (Pemoline)

3D SDF for HMDB0256214 (Pemoline)

3D-SDF for HMDB0256214 (Pemoline)

PDB for HMDB0256214 (Pemoline)

3D PDB for HMDB0256214 (Pemoline)

SMILES for HMDB0256214 (Pemoline)

INCHI for HMDB0256214 (Pemoline)

Structure for HMDB0256214 (Pemoline)

3D Structure for HMDB0256214 (Pemoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra