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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014882

Secondary Accession Numbers

HMDB14882

Metabolite Identification

Common Name

Zileuton

Description

Leukotrienes are substances that induce numerous biological effects including augmentation of neutrophil and eosinophil migration, neutrophil and monocyte aggregation, leukocyte adhesion, increased capillary permeability, and smooth muscle contraction. These effects contribute to inflammation, edema, mucus secretion, and bronchoconstriction in the airways of asthmatic patients. Zileuton relieves such symptoms through its selective inhibition of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid. Specifically, it inhibits leukotriene LTB4, LTC4, LTD4, and LTE4 formation. Both the R(+) and S(-) enantiomers are pharmacologically active as 5-lipoxygenase inhibitors in in vitro systems.

Structure

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

744
  Mrv0541 02231214582D          

 16 17  0  0  1  0            999 V2000
    3.8597    1.1874    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -0.9055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162    0.5235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -0.1910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162   -0.9055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662    0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -0.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  0  0  0  0
  2  4  1  0  0  0  0
  3 16  2  0  0  0  0
  4  6  1  0  0  0  0
  4 16  1  0  0  0  0
  5 16  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  2  0  0  0  0
 10 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014882

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O2S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)16-10/h2-7,15H,1H3,(H2,12,14)

> <INCHI_KEY>
MWLSOWXNZPKENC-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O2S

> <MOLECULAR_WEIGHT>
236.29

> <EXACT_MASS>
236.061948328

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.13772048218238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
2.006172834999999

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.837783092710643

> <JCHEM_PKA_STRONGEST_BASIC>
-5.494153581458328

> <JCHEM_POLAR_SURFACE_AREA>
66.56

> <JCHEM_REFRACTIVITY>
61.95950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zileuton

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 744                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       7.205   2.216   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.644  -1.690   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.724   0.977   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      10.414  -0.357   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      12.724  -1.690   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.644   0.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.104   0.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748   0.207   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.205  -0.262   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   1.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.414   2.311   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -0.563   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   2.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   0.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   1.747   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.954  -0.357   0.000  0.00  0.00           C+0
CONECT    1    7   10                                                       
CONECT    2    4                                                            
CONECT    3   16                                                            
CONECT    4    2    6   16                                                  
CONECT    5   16                                                            
CONECT    6    4    7   11                                                  
CONECT    7    1    6    9                                                  
CONECT    8    9   10   12                                                  
CONECT    9    7    8                                                       
CONECT   10    1    8   13                                                  
CONECT   11    6                                                            
CONECT   12    8   14                                                       
CONECT   13   10   15                                                       
CONECT   14   12   15                                                       
CONECT   15   13   14                                                       
CONECT   16    3    4    5                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0014882
HETATM    1  C1  UNL     1       1.908  -0.757  -2.086  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.539   0.474  -1.300  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.179   0.354  -0.714  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.824  -0.533  -0.922  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.971  -0.363  -0.212  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.141  -1.149  -0.256  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.205  -0.832   0.531  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.248   0.225   1.399  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.105   1.003   1.451  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.007   0.693   0.652  1.00  0.00           C  
HETATM   11  S1  UNL     1      -0.468   1.408   0.455  1.00  0.00           S  
HETATM   12  N1  UNL     1       2.450   0.729  -0.211  1.00  0.00           N  
HETATM   13  O1  UNL     1       3.154   1.909  -0.236  1.00  0.00           O  
HETATM   14  C11 UNL     1       2.663  -0.144   0.862  1.00  0.00           C  
HETATM   15  N2  UNL     1       3.574   0.177   1.891  1.00  0.00           N  
HETATM   16  O2  UNL     1       2.035  -1.227   0.909  1.00  0.00           O  
HETATM   17  H1  UNL     1       1.646  -1.698  -1.591  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.014  -0.717  -2.246  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.453  -0.651  -3.090  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.577   1.329  -1.997  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.661  -1.351  -1.660  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.216  -2.006  -0.905  1.00  0.00           H  
HETATM   23  H7  UNL     1      -5.121  -1.443   0.500  1.00  0.00           H  
HETATM   24  H8  UNL     1      -5.117   0.432   2.001  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.059   1.854   2.110  1.00  0.00           H  
HETATM   26  H10 UNL     1       4.068   1.672   0.051  1.00  0.00           H  
HETATM   27  H11 UNL     1       4.569   0.445   1.693  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.314   0.170   2.922  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   12   20
CONECT    3    4    4   11
CONECT    4    5   21
CONECT    5    6    6   10
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11
CONECT   12   13   14
CONECT   13   26
CONECT   14   15   16   16
CONECT   15   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea	ChEBI
Leutrol	ChEBI
N-(1-Benzo(b)thien-2-ylethyl)-N-hydroxyurea	ChEBI
N-[1-(Benzo[b]thiophen-2-yl)ethyl]-N-hydroxyurea	ChEBI
Zileutonum	ChEBI
Zyflo	ChEBI
Abbot 64077	HMDB

Chemical Formula

C₁₁H₁₂N₂O₂S

Average Molecular Weight

236.29

Monoisotopic Molecular Weight

236.061948328

IUPAC Name

1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea

Traditional Name

zileuton

CAS Registry Number

111406-87-2

SMILES

CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1

InChI Identifier

InChI=1S/C11H12N2O2S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)16-10/h2-7,15H,1H3,(H2,12,14)

InChI Key

MWLSOWXNZPKENC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiophenes

Sub Class

1-benzothiophenes

Direct Parent

1-benzothiophenes

Alternative Parents

Substituents

1-benzothiophene
2,3,5-trisubstituted thiophene
Benzenoid
Heteroaromatic compound
Thiophene
Carbonic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ureas (CHEBI:10112 )
1-benzothiophenes (CHEBI:10112 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014882)
Membrane (HMDB: HMDB0014882)

Source

Exogenous

Exogenous (HMDB: HMDB0014882)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	144.2 - 145.2 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.054 g/L	Not Available
LogP	0.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.054 g/L	ALOGPS
logP	2.01	ALOGPS
logP	2.01	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.96 m³·mol⁻¹	ChemAxon
Polarizability	24.14 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]+	152.239	31661259
DarkChem	[M-H]-	147.337	31661259
DeepCCS	[M+H]+	143.906	30932474
DeepCCS	[M-H]-	141.548	30932474
DeepCCS	[M-2H]-	175.721	30932474
DeepCCS	[M+Na]+	150.598	30932474
AllCCS	[M+H]+	151.3	32859911
AllCCS	[M+H-H2O]+	147.5	32859911
AllCCS	[M+NH4]+	154.9	32859911
AllCCS	[M+Na]+	156.0	32859911
AllCCS	[M-H]-	153.3	32859911
AllCCS	[M+Na-2H]-	153.5	32859911
AllCCS	[M+HCOO]-	153.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.97 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0849 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.74 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	197.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1093.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	357.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	141.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	196.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	74.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	336.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	348.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	255.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	832.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	301.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1229.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	264.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	286.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	396.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	309.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	133.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zileuton	CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1	3535.7	Standard polar	33892256
Zileuton	CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1	1933.2	Standard non polar	33892256
Zileuton	CC(N(O)C(N)=O)C1=CC2=CC=CC=C2S1	2252.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zileuton,1TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N[Si](C)(C)C	2191.4	Semi standard non polar	33892256
Zileuton,1TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N[Si](C)(C)C	2219.7	Standard non polar	33892256
Zileuton,1TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N[Si](C)(C)C	3186.9	Standard polar	33892256
Zileuton,2TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2246.4	Semi standard non polar	33892256
Zileuton,2TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2343.4	Standard non polar	33892256
Zileuton,2TMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2890.0	Standard polar	33892256
Zileuton,1TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N[Si](C)(C)C(C)(C)C	2443.6	Semi standard non polar	33892256
Zileuton,1TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N[Si](C)(C)C(C)(C)C	2405.0	Standard non polar	33892256
Zileuton,1TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N[Si](C)(C)C(C)(C)C	3224.1	Standard polar	33892256
Zileuton,2TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2698.2	Semi standard non polar	33892256
Zileuton,2TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2683.4	Standard non polar	33892256
Zileuton,2TBDMS,isomer #1	CC(C1=CC2=CC=CC=C2S1)N(O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2983.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zileuton GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-5900000000-908922c27d630436d92c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zileuton 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 - Zileuton 35V, Positive-QTOF	splash10-03di-0900000000-e9bb299df09f1a4bd261	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zileuton 35V, Negative-QTOF	splash10-0006-9420000000-25fe799bd1579e6c70e7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 10V, Positive-QTOF	splash10-000l-0890000000-11bd11a737d7518926f3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 20V, Positive-QTOF	splash10-01p6-3950000000-6c73d72fe4a0c46d1d46	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 40V, Positive-QTOF	splash10-03dr-3900000000-bbd6a4285b05c7584d16	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 10V, Negative-QTOF	splash10-0006-8950000000-009b3f6f4b890a437b14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 20V, Negative-QTOF	splash10-0006-7920000000-b16eff6e7f5c11222359	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 40V, Negative-QTOF	splash10-0006-9500000000-ddee52c368588e30fb4a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 10V, Positive-QTOF	splash10-03di-0900000000-9a8f24b5e7475646d26f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 20V, Positive-QTOF	splash10-03di-0900000000-1edc93b959a49e8d51e4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 40V, Positive-QTOF	splash10-06r6-2900000000-5118f97aeab8b353956f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 10V, Negative-QTOF	splash10-0006-9100000000-057eaef1fb4e4e66fe8b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 20V, Negative-QTOF	splash10-001l-3900000000-5ba80581ea5127376812	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zileuton 40V, Negative-QTOF	splash10-000x-9600000000-17761becea77a94b9db1	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB00744	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00744	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00744

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54531

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zileuton

METLIN ID

Not Available

PubChem Compound

60490

PDB ID

Not Available

ChEBI ID

10112

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

Berger W, De Chandt MT, Cairns CB: Zileuton: clinical implications of 5-Lipoxygenase inhibition in severe airway disease. Int J Clin Pract. 2007 Apr;61(4):663-76. [PubMed:17394438 ]
Wenzel SE, Kamada AK: Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma. Ann Pharmacother. 1996 Jul-Aug;30(7-8):858-64. [PubMed:8826571 ]
Malo PE, Bell RL, Shaughnessy TK, Summers JB, Brooks DW, Carter GW: The 5-lipoxygenase inhibitory activity of zileuton in in vitro and in vivo models of antigen-induced airway anaphylaxis. Pulm Pharmacol. 1994 Apr;7(2):73-9. [PubMed:8081074 ]

Showing metabocard for Zileuton (HMDB0014882)

MOL for HMDB0014882 (Zileuton)

3D MOL for HMDB0014882 (Zileuton)

3D SDF for HMDB0014882 (Zileuton)

3D-SDF for HMDB0014882 (Zileuton)

PDB for HMDB0014882 (Zileuton)

3D PDB for HMDB0014882 (Zileuton)

SMILES for HMDB0014882 (Zileuton)

INCHI for HMDB0014882 (Zileuton)

Structure for HMDB0014882 (Zileuton)

3D Structure for HMDB0014882 (Zileuton)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra