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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 17:50:31 UTC

Update Date

2019-07-23 07:14:41 UTC

HMDB ID

HMDB0060603

Secondary Accession Numbers

HMDB60603

Metabolite Identification

Common Name

N-acetyl zonisamide

Description

N-acetyl zonisamide belongs to the class of organic compounds known as benzisoxazoles. These are aromatic compounds containing a benzene ring fused to an isoxazole ring. Isoxazole is five-membered ring with three carbon atoms, and an oxygen atom next to a nitrogen atom. N-acetyl zonisamide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 06151310462D          

 17 18  0  0  0  0            999 V2000
   -3.0743    2.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7153    2.4949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0124    1.0972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3769    0.1187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339    1.7326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060603

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NS(=O)(=O)CC1=NOC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H10N2O4S/c1-7(13)12-17(14,15)6-9-8-4-2-3-5-10(8)16-11-9/h2-5H,6H2,1H3,(H,12,13)

> <INCHI_KEY>
HXFUTAFSEXINIW-UHFFFAOYSA-N

> <FORMULA>
C10H10N2O4S

> <MOLECULAR_WEIGHT>
254.262

> <EXACT_MASS>
254.036127508

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
23.62702397756565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(1,2-benzoxazol-3-ylmethanesulfonyl)acetamide

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
0.09929473033333316

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.035278874779467

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7618489033955846

> <JCHEM_POLAR_SURFACE_AREA>
89.27

> <JCHEM_REFRACTIVITY>
59.864300000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(1,2-benzoxazol-3-ylmethanesulfonyl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      -5.739   3.833   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.232   3.513   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.202   4.657   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -3.756   2.048   0.000  0.00  0.00           N+0
HETATM    5  S   UNK     0      -2.250   1.728   0.000  0.00  0.00           S+0
HETATM    6  O   UNK     0      -2.570   0.222   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.930   3.234   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.173  -1.303   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -0.268  -2.549   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    9   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0060603
HETATM    1  C1  UNL     1       4.647   0.863   0.205  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.708  -0.293   0.136  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.960  -1.313   0.810  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.549  -0.242  -0.677  1.00  0.00           N  
HETATM    5  S1  UNL     1       1.501  -1.574  -0.732  1.00  0.00           S  
HETATM    6  O2  UNL     1       2.167  -2.835  -0.266  1.00  0.00           O  
HETATM    7  O3  UNL     1       1.104  -1.797  -2.173  1.00  0.00           O  
HETATM    8  C3  UNL     1       0.003  -1.320   0.185  1.00  0.00           C  
HETATM    9  C4  UNL     1      -0.691  -0.147  -0.407  1.00  0.00           C  
HETATM   10  N2  UNL     1      -0.342   0.643  -1.438  1.00  0.00           N  
HETATM   11  O4  UNL     1      -1.245   1.565  -1.627  1.00  0.00           O  
HETATM   12  C5  UNL     1      -2.221   1.453  -0.764  1.00  0.00           C  
HETATM   13  C6  UNL     1      -3.400   2.138  -0.512  1.00  0.00           C  
HETATM   14  C7  UNL     1      -4.209   1.707   0.530  1.00  0.00           C  
HETATM   15  C8  UNL     1      -3.891   0.640   1.312  1.00  0.00           C  
HETATM   16  C9  UNL     1      -2.717  -0.050   1.068  1.00  0.00           C  
HETATM   17  C10 UNL     1      -1.901   0.364   0.038  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.622   0.567   0.636  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.850   1.262  -0.812  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.240   1.653   0.880  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.371   0.621  -1.225  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.619  -2.234   0.159  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.234  -1.152   1.275  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.652   2.978  -1.127  1.00  0.00           H  
HETATM   25  H8  UNL     1      -5.120   2.237   0.724  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.517   0.300   2.124  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.433  -0.911   1.679  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    4
CONECT    4    5   21
CONECT    5    6    6    7    7
CONECT    5    8
CONECT    8    9   22   23
CONECT    9   10   10   17
CONECT   10   11
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   24
CONECT   14   15   15   25
CONECT   15   16   26
CONECT   16   17   17   27
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₀N₂O₄S

Average Molecular Weight

254.262

Monoisotopic Molecular Weight

254.036127508

IUPAC Name

N-(1,2-benzoxazol-3-ylmethanesulfonyl)acetamide

Traditional Name

N-(1,2-benzoxazol-3-ylmethanesulfonyl)acetamide

CAS Registry Number

68936-43-6

SMILES

CC(=O)NS(=O)(=O)CC1=NOC2=C1C=CC=C2

InChI Identifier

InChI=1S/C10H10N2O4S/c1-7(13)12-17(14,15)6-9-8-4-2-3-5-10(8)16-11-9/h2-5H,6H2,1H3,(H,12,13)

InChI Key

HXFUTAFSEXINIW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzisoxazoles. These are aromatic compounds containing a benzene ring fused to an isoxazole ring. Isoxazole is five-membered ring with three carbon atoms, and an oxygen atom next to a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzisoxazoles

Sub Class

Not Available

Direct Parent

Benzisoxazoles

Alternative Parents

Substituents

Benzisoxazole
Benzenoid
Azole
Isoxazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Acetamide
Heteroaromatic compound
Carboxylic acid derivative
Azacycle
Oxacycle
Carbonyl group
Organic nitrogen compound
Organosulfur compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060603)
Liver (HMDB: HMDB0060603)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060603)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060603)

Cellular substructure

Cytoplasm (HMDB: HMDB0060603)

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
Water Solubility	0.34 g/L	ALOGPS
logP	0.68	ALOGPS
logP	0.099	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.27 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.86 m³·mol⁻¹	ChemAxon
Polarizability	23.63 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
DarkChem	[M+H]+	158.285	31661259
DarkChem	[M-H]-	156.029	31661259
DeepCCS	[M+H]+	148.471	30932474
DeepCCS	[M-H]-	146.076	30932474
DeepCCS	[M-2H]-	179.106	30932474
DeepCCS	[M+Na]+	154.527	30932474
AllCCS	[M+H]+	154.6	32859911
AllCCS	[M+H-H2O]+	150.9	32859911
AllCCS	[M+NH4]+	158.1	32859911
AllCCS	[M+Na]+	159.1	32859911
AllCCS	[M-H]-	152.9	32859911
AllCCS	[M+Na-2H]-	152.8	32859911
AllCCS	[M+HCOO]-	152.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-acetyl zonisamide	CC(=O)NS(=O)(=O)CC1=NOC2=C1C=CC=C2	3580.7	Standard polar	33892256
N-acetyl zonisamide	CC(=O)NS(=O)(=O)CC1=NOC2=C1C=CC=C2	1944.5	Standard non polar	33892256
N-acetyl zonisamide	CC(=O)NS(=O)(=O)CC1=NOC2=C1C=CC=C2	2118.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-acetyl zonisamide,1TMS,isomer #1	CC(=O)N([Si](C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	2241.5	Semi standard non polar	33892256
N-acetyl zonisamide,1TMS,isomer #1	CC(=O)N([Si](C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	2314.2	Standard non polar	33892256
N-acetyl zonisamide,1TMS,isomer #1	CC(=O)N([Si](C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	3313.0	Standard polar	33892256
N-acetyl zonisamide,1TBDMS,isomer #1	CC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	2534.7	Semi standard non polar	33892256
N-acetyl zonisamide,1TBDMS,isomer #1	CC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	2568.5	Standard non polar	33892256
N-acetyl zonisamide,1TBDMS,isomer #1	CC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)CC1=NOC2=CC=CC=C12	3301.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-acetyl zonisamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-3910000000-5a7d8e1c427a0684b7b8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-acetyl zonisamide 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 - N-acetyl zonisamide 10V, Positive-QTOF	splash10-0a4i-0190000000-51d40a0d88672ba57ee6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 20V, Positive-QTOF	splash10-000e-6890000000-c4383652f18b7b5930d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 40V, Positive-QTOF	splash10-0006-9330000000-8e259063340318b889ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 10V, Negative-QTOF	splash10-0udi-0090000000-52423f69a78cf20e2ed2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 20V, Negative-QTOF	splash10-0w29-3290000000-0ce93ec4b0d763a36a3d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 40V, Negative-QTOF	splash10-002f-9200000000-0ce57a264a8d0e33cc2a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 10V, Negative-QTOF	splash10-014i-0910000000-b00936a0cfeaee3142e5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 20V, Negative-QTOF	splash10-014i-1900000000-0c3861c975d77ca27421	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 40V, Negative-QTOF	splash10-0006-9300000000-52511db437debaf5486d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 10V, Positive-QTOF	splash10-03e9-0590000000-b4721c4db57567508371	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 20V, Positive-QTOF	splash10-001i-0900000000-ad26c4d7bdc9a532d683	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl zonisamide 40V, Positive-QTOF	splash10-004i-9700000000-32c2b247a83db4e7919d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10467478

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

Not Available

Showing metabocard for N-acetyl zonisamide (HMDB0060603)

MOL for HMDB0060603 (N-acetyl zonisamide)

3D MOL for HMDB0060603 (N-acetyl zonisamide)

3D SDF for HMDB0060603 (N-acetyl zonisamide)

3D-SDF for HMDB0060603 (N-acetyl zonisamide)

PDB for HMDB0060603 (N-acetyl zonisamide)

3D PDB for HMDB0060603 (N-acetyl zonisamide)

SMILES for HMDB0060603 (N-acetyl zonisamide)

INCHI for HMDB0060603 (N-acetyl zonisamide)

Structure for HMDB0060603 (N-acetyl zonisamide)

3D Structure for HMDB0060603 (N-acetyl zonisamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra