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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:27 UTC

HMDB ID

HMDB0015253

Secondary Accession Numbers

HMDB15253

Metabolite Identification

Common Name

Phenacemide

Description

Phenacemide is only found in individuals that have used or taken this drug. It is used to control certain seizures in the treatment of epilepsy. This medicine acts on the central nervous system (CNS) to reduce the number and severity of seizures. Phenacemide binds to and blocks neuronal sodium channels or voltage sensitive calcium channels. This blocks or suppresses neuronal depolarization and hypersynchronization. Hypersynchronization is what often causes seizures.

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1121                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       7.081  -0.239   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   2.071   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.747   2.071   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.081   4.381   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.414  -0.239   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -1.779   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747  -2.549   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -2.549   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747   0.531   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -4.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -4.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -4.859   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081   2.841   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   13                                                            
CONECT    3    9   13                                                       
CONECT    4   13                                                            
CONECT    5    6    9                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6   10                                                       
CONECT    8    6   11                                                       
CONECT    9    1    3    5                                                  
CONECT   10    7   12                                                       
CONECT   11    8   12                                                       
CONECT   12   10   11                                                       
CONECT   13    2    3    4                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Phenurone	Kegg
Carbamide phenylacetate	HMDB
Phenacetylcarbamide	HMDB
Phenacetylurea	HMDB
Phenylacetylurea	HMDB
Phenylacetyluree	HMDB
Phenuron	HMDB
(Phenylacetyl)urea	HMDB

Chemical Formula

C₉H₁₀N₂O₂

Average Molecular Weight

178.1879

Monoisotopic Molecular Weight

178.074227574

IUPAC Name

(2-phenylacetyl)urea

Traditional Name

phenacemide

CAS Registry Number

63-98-9

SMILES

NC(=O)NC(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C9H10N2O2/c10-9(13)11-8(12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,10,11,12,13)

InChI Key

XPFRXWCVYUEORT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetamides

Direct Parent

Phenylacetamides

Alternative Parents

Substituents

Phenylacetamide
N-acyl urea
Ureide
Dicarboximide
Carbonic acid derivative
Urea
Carboxylic acid derivative
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

acetamides (CHEBI:8049 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	215 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.06 g/L	Not Available
LogP	0.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	128.347	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000759

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.06 g/L	ALOGPS
logP	0.81	ALOGPS
logP	0.46	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.19 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.43 m³·mol⁻¹	ChemAxon
Polarizability	17.49 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
DarkChem	[M+H]+	140.759	31661259
DarkChem	[M-H]-	136.315	31661259
DeepCCS	[M+H]+	136.027	30932474
DeepCCS	[M-H]-	133.443	30932474
DeepCCS	[M-2H]-	169.205	30932474
DeepCCS	[M+Na]+	144.048	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	134.2	32859911
AllCCS	[M+NH4]+	142.4	32859911
AllCCS	[M+Na]+	143.5	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	138.4	32859911
AllCCS	[M+HCOO]-	139.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenacemide	NC(=O)NC(=O)CC1=CC=CC=C1	3009.5	Standard polar	33892256
Phenacemide	NC(=O)NC(=O)CC1=CC=CC=C1	1406.5	Standard non polar	33892256
Phenacemide	NC(=O)NC(=O)CC1=CC=CC=C1	1788.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenacemide,1TMS,isomer #1	C[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C1	1882.7	Semi standard non polar	33892256
Phenacemide,1TMS,isomer #1	C[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C1	1707.1	Standard non polar	33892256
Phenacemide,1TMS,isomer #1	C[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C1	2616.5	Standard polar	33892256
Phenacemide,1TMS,isomer #2	C[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C1	1752.5	Semi standard non polar	33892256
Phenacemide,1TMS,isomer #2	C[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C1	1775.2	Standard non polar	33892256
Phenacemide,1TMS,isomer #2	C[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C1	2606.9	Standard polar	33892256
Phenacemide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C	1924.7	Semi standard non polar	33892256
Phenacemide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C	1886.9	Standard non polar	33892256
Phenacemide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C	2482.2	Standard polar	33892256
Phenacemide,2TMS,isomer #2	C[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	1842.0	Semi standard non polar	33892256
Phenacemide,2TMS,isomer #2	C[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	1849.4	Standard non polar	33892256
Phenacemide,2TMS,isomer #2	C[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2320.9	Standard polar	33892256
Phenacemide,3TMS,isomer #1	C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C)[Si](C)(C)C	1867.4	Semi standard non polar	33892256
Phenacemide,3TMS,isomer #1	C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2015.9	Standard non polar	33892256
Phenacemide,3TMS,isomer #1	C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2142.9	Standard polar	33892256
Phenacemide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C1	2114.8	Semi standard non polar	33892256
Phenacemide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C1	1952.9	Standard non polar	33892256
Phenacemide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)NC(=O)CC1=CC=CC=C1	2632.5	Standard polar	33892256
Phenacemide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C1	1986.4	Semi standard non polar	33892256
Phenacemide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C1	1993.9	Standard non polar	33892256
Phenacemide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=O)C(=O)CC1=CC=CC=C1	2687.1	Standard polar	33892256
Phenacemide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2353.0	Semi standard non polar	33892256
Phenacemide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2293.2	Standard non polar	33892256
Phenacemide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)NC(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2555.1	Standard polar	33892256
Phenacemide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2278.5	Semi standard non polar	33892256
Phenacemide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2259.1	Standard non polar	33892256
Phenacemide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2495.1	Standard polar	33892256
Phenacemide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2531.7	Semi standard non polar	33892256
Phenacemide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2561.4	Standard non polar	33892256
Phenacemide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2472.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenacemide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-1bdb50bda427a0a6b759	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenacemide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kf-9200000000-38554ddfe2ad3808dc2a	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 10V, Positive-QTOF	splash10-004i-2900000000-bbe6000c85c6e7cad8d7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 20V, Positive-QTOF	splash10-014u-4900000000-65aecc6405e7dc3960db	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 40V, Positive-QTOF	splash10-0006-9100000000-470744c360a51861385e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 10V, Negative-QTOF	splash10-000x-7900000000-33581cec0b1c89a374a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 20V, Negative-QTOF	splash10-000x-7900000000-c6b59b20b89c19c87759	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 40V, Negative-QTOF	splash10-0006-9100000000-812937333ee84aac004a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 10V, Positive-QTOF	splash10-00kf-9600000000-eb2dcdcc261eec29fa08	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 20V, Positive-QTOF	splash10-0006-9100000000-6f93f0492b5f06695057	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 40V, Positive-QTOF	splash10-0006-9000000000-d3ddfb9a0b95dad2b026	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 10V, Negative-QTOF	splash10-0006-9000000000-2cca984c3d943209d9fe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 20V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenacemide 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01121	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01121	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01121

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007356

KNApSAcK ID

Not Available

Chemspider ID

4589

KEGG Compound ID

C07428

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenacemide

METLIN ID

Not Available

PubChem Compound

4753

PDB ID

Not Available

ChEBI ID

183000

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

Coker SB: The use of phenacemide for intractable partial complex epilepsy in children. Pediatr Neurol. 1986 Jul-Aug;2(4):230-2. [PubMed:3508693 ]
Coker SB, Holmes EW, Egel RT: Phenacemide therapy of complex partial epilepsy in children: determination of plasma drug concentrations. Neurology. 1987 Dec;37(12):1861-6. [PubMed:3683877 ]

Enzymes

Enzyme Details

1. Sodium channel protein type 1 subunit alpha

General function:: Involved in ion channel activity
Specific function:: Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient
Gene Name:: SCN1A
Uniprot ID:: P35498
Molecular weight:: 228969.5

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Wong MG, Defina JA, Andrews PR: Conformational analysis of clinically active anticonvulsant drugs. J Med Chem. 1986 Apr;29(4):562-72. [PubMed:3959032 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Phenacemide (HMDB0015253)

MOL for HMDB0015253 (Phenacemide)

3D MOL for HMDB0015253 (Phenacemide)

3D SDF for HMDB0015253 (Phenacemide)

3D-SDF for HMDB0015253 (Phenacemide)

PDB for HMDB0015253 (Phenacemide)

3D PDB for HMDB0015253 (Phenacemide)

SMILES for HMDB0015253 (Phenacemide)

INCHI for HMDB0015253 (Phenacemide)

Structure for HMDB0015253 (Phenacemide)

3D Structure for HMDB0015253 (Phenacemide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References