Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 17:43:22 UTC

Update Date

2019-07-23 07:14:40 UTC

HMDB ID

HMDB0060597

Secondary Accession Numbers

HMDB60597

Metabolite Identification

Common Name

Desacetyl-nitazoxanide

Description

Desacetyl-nitazoxanide is a metabolite of lamivudine. Lamivudine (2',3'-dideoxy-3'-thiacytidine, commonly called 3TC) is a potent nucleoside analog reverse transcriptase inhibitor (nRTI). It is marketed by GlaxoSmithKline with the brand names Zeffix, Heptovir, Epivir, and Epivir-HBV. Lamivudine has been used for treatment of chronic hepatitis B at a lower dose than for treatment of HIV. It improves the seroconversion of e-antigen positive hepatitis B and also improves histology staging of the liver. (Wikipedia )

Structure

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

  Mrv0541 06151310432D          

 18 19  0  0  0  0            999 V2000
    4.1801    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    3.1152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    1.8053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7676    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127    1.8053    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2827    0.3532    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.6183   -0.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4622    0.4394    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.3235    4.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  4 18  1  0  0  0  0
M  CHG  2  15   1  17  -1
M  END
> <DATABASE_ID>
HMDB0060597

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H7N3O4S/c14-7-4-2-1-3-6(7)9(15)12-10-11-5-8(18-10)13(16)17/h1-5,14H,(H,11,12,15)

> <INCHI_KEY>
FDTZUTSGGSRHQF-UHFFFAOYSA-N

> <FORMULA>
C10H7N3O4S

> <MOLECULAR_WEIGHT>
265.245

> <EXACT_MASS>
265.015726417

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
24.098561816195094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-N-(5-nitro-1,3-thiazol-2-yl)benzamide

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
2.210588246333333

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.357779652665764

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8067272289152

> <JCHEM_PKA_STRONGEST_BASIC>
-4.192500050777957

> <JCHEM_POLAR_SURFACE_AREA>
108.04

> <JCHEM_REFRACTIVITY>
64.73870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tizoxanide

> <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       7.803  10.435   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.137  11.205   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.470  10.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.470   8.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.137   8.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.803   8.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.137   6.585   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.470   5.815   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       7.803   5.815   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.803   4.275   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.049   3.370   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       8.573   1.905   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.033   1.905   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0       6.557   3.370   0.000  0.00  0.00           S+0
HETATM   15  N   UNK     0       6.128   0.659   0.000  0.00  0.00           N+1
HETATM   16  O   UNK     0       6.754  -0.748   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.596   0.820   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0      11.804   8.125   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   10                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    4                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₇N₃O₄S

Average Molecular Weight

265.245

Monoisotopic Molecular Weight

265.015726417

IUPAC Name

2-hydroxy-N-(5-nitro-1,3-thiazol-2-yl)benzamide

Traditional Name

tizoxanide

CAS Registry Number

Not Available

SMILES

OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O

InChI Identifier

InChI=1S/C10H7N3O4S/c14-7-4-2-1-3-6(7)9(15)12-10-11-5-8(18-10)13(16)17/h1-5,14H,(H,11,12,15)

InChI Key

FDTZUTSGGSRHQF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylamides

Alternative Parents

Substituents

Salicylamide
Benzamide
Nitroaromatic compound
Benzoyl
Nitrothiazole
2,5-disubstituted 1,3-thiazole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Azole
Heteroaromatic compound
Thiazole
Vinylogous acid
Organic nitro compound
Secondary carboxylic acid amide
Carboxamide group
C-nitro compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxoazanium
Organic zwitterion
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060597)

Organ

Kidney (HMDB: HMDB0060597)
Liver (HMDB: HMDB0060597)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060597)

Cellular substructure

Cytoplasm (HMDB: HMDB0060597)
Membrane (HMDB: HMDB0060597)

Source

Endogenous

Endogenous (HMDB: HMDB0060597)

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	0.042 g/L	ALOGPS
logP	2	ALOGPS
logP	2.21	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.81	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.04 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.74 m³·mol⁻¹	ChemAxon
Polarizability	24.1 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]+	158.095	31661259
DarkChem	[M-H]-	153.803	31661259
DeepCCS	[M+H]+	149.316	30932474
DeepCCS	[M-H]-	146.056	30932474
DeepCCS	[M-2H]-	181.309	30932474
DeepCCS	[M+Na]+	157.573	30932474
AllCCS	[M+H]+	155.7	32859911
AllCCS	[M+H-H2O]+	151.9	32859911
AllCCS	[M+NH4]+	159.1	32859911
AllCCS	[M+Na]+	160.1	32859911
AllCCS	[M-H]-	153.9	32859911
AllCCS	[M+Na-2H]-	153.5	32859911
AllCCS	[M+HCOO]-	153.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desacetyl-nitazoxanide	OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O	3570.1	Standard polar	33892256
Desacetyl-nitazoxanide	OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O	2560.6	Standard non polar	33892256
Desacetyl-nitazoxanide	OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O	2564.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Desacetyl-nitazoxanide,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC=C1C(=O)NC1=NC=C([N+](=O)[O-])S1	2555.8	Semi standard non polar	33892256
Desacetyl-nitazoxanide,1TMS,isomer #2	C[Si](C)(C)N(C(=O)C1=CC=CC=C1O)C1=NC=C([N+](=O)[O-])S1	2370.8	Semi standard non polar	33892256
Desacetyl-nitazoxanide,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C	2416.1	Semi standard non polar	33892256
Desacetyl-nitazoxanide,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C	2408.9	Standard non polar	33892256
Desacetyl-nitazoxanide,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C	2996.2	Standard polar	33892256
Desacetyl-nitazoxanide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)NC1=NC=C([N+](=O)[O-])S1	2820.5	Semi standard non polar	33892256
Desacetyl-nitazoxanide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=CC=C1O)C1=NC=C([N+](=O)[O-])S1	2638.3	Semi standard non polar	33892256
Desacetyl-nitazoxanide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C(C)(C)C	2890.7	Semi standard non polar	33892256
Desacetyl-nitazoxanide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C(C)(C)C	2824.9	Standard non polar	33892256
Desacetyl-nitazoxanide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C(C)(C)C	3137.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Desacetyl-nitazoxanide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9510000000-cfabe33d6048d7a80d4a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desacetyl-nitazoxanide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9810000000-66e8fba28bfba446bc01	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desacetyl-nitazoxanide 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 - Desacetyl-nitazoxanide 10V, Positive-QTOF	splash10-014i-0390000000-8ab032978b864510363b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyl-nitazoxanide 20V, Positive-QTOF	splash10-00xs-0930000000-33dfa1221d0eb554b8a4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyl-nitazoxanide 40V, Positive-QTOF	splash10-006x-9300000000-b0631aa65eb8f3014dd8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyl-nitazoxanide 10V, Negative-QTOF	splash10-03di-0090000000-b5ea2a0a2fe54b693ad8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyl-nitazoxanide 20V, Negative-QTOF	splash10-03di-2190000000-9f819010e0cd7df98c88	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyl-nitazoxanide 40V, Negative-QTOF	splash10-014l-9310000000-9d440f27de7c7690b1d5	2017-10-06	Wishart 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

Tizoxanide

METLIN ID

Not Available

PubChem Compound

394397

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 Desacetyl-nitazoxanide (HMDB0060597)

MOL for HMDB0060597 (Desacetyl-nitazoxanide)

3D MOL for HMDB0060597 (Desacetyl-nitazoxanide)

3D SDF for HMDB0060597 (Desacetyl-nitazoxanide)

3D-SDF for HMDB0060597 (Desacetyl-nitazoxanide)

PDB for HMDB0060597 (Desacetyl-nitazoxanide)

3D PDB for HMDB0060597 (Desacetyl-nitazoxanide)

SMILES for HMDB0060597 (Desacetyl-nitazoxanide)

INCHI for HMDB0060597 (Desacetyl-nitazoxanide)

Structure for HMDB0060597 (Desacetyl-nitazoxanide)

3D Structure for HMDB0060597 (Desacetyl-nitazoxanide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra