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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:43 UTC

Update Date

2023-02-21 17:30:17 UTC

HMDB ID

HMDB0060998

Secondary Accession Numbers

HMDB60998

Metabolite Identification

Common Name

6-hydroxychlorzoxazone

Description

6-hydroxychlorzoxazone is a metabolite of chlorzoxazone. Chlorzoxazone is a centrally acting muscle relaxant used to treat muscle spasm and the resulting pain or discomfort. It acts on the spinal cord by depressing reflexes. It is sold as Muscol or Parafon Forte, a combination of chlorzoxazone and acetaminophen (Paracetamol). Possible side effects include dizziness, lightheadedness, malaise, nausea, vomiting, and liver dysfunction. Used with acetaminophen it has added risk of hepatoxicity, which is why the combination is not recommended. (Wikipedia)

Structure

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

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       5.198   1.303   0.000  0.00  0.00          Cl+0
HETATM    9  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.713   2.843   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    5    8                                                  
CONECT    4    1    6    9                                                  
CONECT    5    2    3   10                                                  
CONECT    6    2    4   12                                                  
CONECT    7    9   11   12                                                  
CONECT    8    3                                                            
CONECT    9    4    7                                                       
CONECT   10    5                                                            
CONECT   11    7                                                            
CONECT   12    6    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₇H₄ClNO₃

Average Molecular Weight

185.565

Monoisotopic Molecular Weight

184.987970706

IUPAC Name

5-chloro-1,3-benzoxazole-2,6-diol

Traditional Name

5-chloro-1,3-benzoxazole-2,6-diol

CAS Registry Number

1750-45-4

SMILES

OC1=NC2=C(O1)C=C(O)C(Cl)=C2

InChI Identifier

InChI=1S/C7H4ClNO3/c8-3-1-4-6(2-5(3)10)12-7(11)9-4/h1-2,10H,(H,9,11)

InChI Key

AGLXDWOTVQZHIQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazoles

Sub Class

Benzoxazolones

Direct Parent

Benzoxazolones

Alternative Parents

Substituents

Benzoxazolone
1-hydroxy-2-unsubstituted benzenoid
Aryl chloride
Aryl halide
Benzenoid
Azole
Oxazole
Heteroaromatic compound
Oxacycle
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0060998)
Membrane (HMDB: HMDB0060998)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060998)

Organ

Kidney (HMDB: HMDB0060998)
Liver (HMDB: HMDB0060998)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060998)

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	7.78 g/L	ALOGPS
logP	1.94	ALOGPS
logP	2	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	6.71	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.96 m³·mol⁻¹	ChemAxon
Polarizability	16.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	136.719	30932474
DeepCCS	[M-H]-	133.994	30932474
DeepCCS	[M-2H]-	169.846	30932474
DeepCCS	[M+Na]+	145.326	30932474
AllCCS	[M+H]+	136.7	32859911
AllCCS	[M+H-H2O]+	132.3	32859911
AllCCS	[M+NH4]+	140.9	32859911
AllCCS	[M+Na]+	142.1	32859911
AllCCS	[M-H]-	130.1	32859911
AllCCS	[M+Na-2H]-	130.6	32859911
AllCCS	[M+HCOO]-	131.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-hydroxychlorzoxazone	OC1=NC2=C(O1)C=C(O)C(Cl)=C2	3205.1	Standard polar	33892256
6-hydroxychlorzoxazone	OC1=NC2=C(O1)C=C(O)C(Cl)=C2	2030.6	Standard non polar	33892256
6-hydroxychlorzoxazone	OC1=NC2=C(O1)C=C(O)C(Cl)=C2	1616.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-hydroxychlorzoxazone,1TMS,isomer #1	C[Si](C)(C)OC1=NC2=CC(Cl)=C(O)C=C2O1	1871.6	Semi standard non polar	33892256
6-hydroxychlorzoxazone,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1Cl)N=C(O)O2	1957.8	Semi standard non polar	33892256
6-hydroxychlorzoxazone,2TMS,isomer #1	C[Si](C)(C)OC1=NC2=CC(Cl)=C(O[Si](C)(C)C)C=C2O1	1926.6	Semi standard non polar	33892256
6-hydroxychlorzoxazone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=CC(Cl)=C(O)C=C2O1	2108.1	Semi standard non polar	33892256
6-hydroxychlorzoxazone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1Cl)N=C(O)O2	2226.6	Semi standard non polar	33892256
6-hydroxychlorzoxazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=CC(Cl)=C(O[Si](C)(C)C(C)(C)C)C=C2O1	2446.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-hydroxychlorzoxazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-1900000000-465fac95ef740a76ddde	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-hydroxychlorzoxazone GC-MS (2 TMS) - 70eV, Positive	splash10-03mi-3191000000-3dd678a2857a78e036e1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-hydroxychlorzoxazone 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 - 6-hydroxychlorzoxazone 10V, Positive-QTOF	splash10-000i-0900000000-95b1d7a5768ce194fbad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 20V, Positive-QTOF	splash10-000i-0900000000-b701122ce4ae054db41c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 40V, Positive-QTOF	splash10-0udi-0900000000-feb1eacd6dd2ee3b1b89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 10V, Negative-QTOF	splash10-001i-0900000000-d9d79e75d7c856052434	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 20V, Negative-QTOF	splash10-001i-0900000000-2c15beef939dde4ccc15	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 40V, Negative-QTOF	splash10-000b-1900000000-ed44aa140b99fad643a6	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 10V, Positive-QTOF	splash10-000i-0900000000-29084e4eae31e34c970b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 20V, Positive-QTOF	splash10-000i-0900000000-7099f3b75030ee1b0df9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 40V, Positive-QTOF	splash10-0a7j-6900000000-204e795947fbdd02da77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 10V, Negative-QTOF	splash10-001i-0900000000-0f12a5e6fdb105f3aafd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 20V, Negative-QTOF	splash10-001i-0900000000-4a4fc8fe5356301dc946	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-hydroxychlorzoxazone 40V, Negative-QTOF	splash10-001i-9500000000-c592d1f45e854c90d422	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

2734

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 6-hydroxychlorzoxazone (HMDB0060998)

MOL for HMDB0060998 (6-hydroxychlorzoxazone)

3D MOL for HMDB0060998 (6-hydroxychlorzoxazone)

3D SDF for HMDB0060998 (6-hydroxychlorzoxazone)

3D-SDF for HMDB0060998 (6-hydroxychlorzoxazone)

PDB for HMDB0060998 (6-hydroxychlorzoxazone)

3D PDB for HMDB0060998 (6-hydroxychlorzoxazone)

SMILES for HMDB0060998 (6-hydroxychlorzoxazone)

INCHI for HMDB0060998 (6-hydroxychlorzoxazone)

Structure for HMDB0060998 (6-hydroxychlorzoxazone)

3D Structure for HMDB0060998 (6-hydroxychlorzoxazone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra