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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:46:37 UTC
Update Date2021-09-14 15:48:17 UTC
HMDB IDHMDB0060599
Secondary Accession Numbers
  • HMDB60599
Metabolite Identification
Common NameLamivudine sulfoxide
DescriptionLamivudine sulfoxide belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others. Lamivudine sulfoxide is an extremely weak basic (essentially neutral) compound (based on its pKa). lamivudine sulfoxide can be biosynthesized from lamivudine through its interaction with the enzyme sulfotransferase 1A1. In humans, lamivudine sulfoxide is involved in lamivudine metabolism pathway. Nitazoxanide, also known by the brand names Alinia and Annita (and by Daxon, Dexidex, Kidonax, Mitafar, Pacovanton, and Paramix in Mexico, by Nitax, Zox, Nitazox, Niazid and Toza in Bangladesh) is a synthetic nitrothiazolyl-salicylamide derivative and an antiprotozoal agent. It is poorly soluble in ethanol and practically insoluble in water. Lamivudine sulfoxide is a metabolite of nitazoxanide. Nitazoxanide is a light yellow crystalline powder.
Structure
Data?1563866080
Synonyms
ValueSource
Lamivudine sulphoxideGenerator
Chemical FormulaC8H11N3O4S
Average Molecular Weight245.256
Monoisotopic Molecular Weight245.047026545
IUPAC Name4-amino-1-[(2S,5R)-2-(hydroxymethyl)-3-oxo-1,3λ⁴-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
Traditional Name4-amino-1-[(2S,5R)-2-(hydroxymethyl)-3-oxo-1,3λ⁴-oxathiolan-5-yl]pyrimidin-2-one
CAS Registry NumberNot Available
SMILES
NC1=NC(=O)N(C=C1)[C@H]1CS(=O)[C@@H](CO)O1
InChI Identifier
InChI=1S/C8H11N3O4S/c9-5-1-2-11(8(13)10-5)6-4-16(14)7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+,16?/m1/s1
InChI KeyLJMQAXFNQNADRZ-FYZWQCAOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassNucleoside and nucleotide analogues
Sub ClassNot Available
Direct ParentNucleoside and nucleotide analogues
Alternative Parents
Substituents
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Pyrimidine
  • Imidolactam
  • Monothioacetal
  • Oxathiolane
  • Heteroaromatic compound
  • Sulfoxide
  • Oxacycle
  • Azacycle
  • Sulfinyl compound
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility60.6 g/LALOGPS
logP-2.1ALOGPS
logP-2.5ChemAxon
logS-0.61ALOGPS
pKa (Strongest Acidic)14.01ChemAxon
pKa (Strongest Basic)-0.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.12 m³·mol⁻¹ChemAxon
Polarizability21.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.17331661259
DarkChem[M-H]-151.25431661259
DeepCCS[M+H]+150.11930932474
DeepCCS[M-H]-147.72330932474
DeepCCS[M-2H]-180.82930932474
DeepCCS[M+Na]+156.10730932474
AllCCS[M+H]+153.032859911
AllCCS[M+H-H2O]+149.332859911
AllCCS[M+NH4]+156.532859911
AllCCS[M+Na]+157.532859911
AllCCS[M-H]-149.832859911
AllCCS[M+Na-2H]-149.932859911
AllCCS[M+HCOO]-150.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lamivudine sulfoxideNC1=NC(=O)N(C=C1)[C@H]1CS(=O)[C@@H](CO)O13811.2Standard polar33892256
Lamivudine sulfoxideNC1=NC(=O)N(C=C1)[C@H]1CS(=O)[C@@H](CO)O12426.7Standard non polar33892256
Lamivudine sulfoxideNC1=NC(=O)N(C=C1)[C@H]1CS(=O)[C@@H](CO)O12736.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lamivudine sulfoxide,1TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)CS1=O2452.8Semi standard non polar33892256
Lamivudine sulfoxide,1TMS,isomer #2C[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C12513.9Semi standard non polar33892256
Lamivudine sulfoxide,2TMS,isomer #1C[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C)O2)C=C12522.5Semi standard non polar33892256
Lamivudine sulfoxide,2TMS,isomer #1C[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C)O2)C=C12706.4Standard non polar33892256
Lamivudine sulfoxide,2TMS,isomer #1C[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C)O2)C=C13461.2Standard polar33892256
Lamivudine sulfoxide,2TMS,isomer #2C[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C2466.0Semi standard non polar33892256
Lamivudine sulfoxide,2TMS,isomer #2C[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C2792.7Standard non polar33892256
Lamivudine sulfoxide,2TMS,isomer #2C[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C3377.5Standard polar33892256
Lamivudine sulfoxide,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CS1=O2487.1Semi standard non polar33892256
Lamivudine sulfoxide,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CS1=O2794.4Standard non polar33892256
Lamivudine sulfoxide,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)CS1=O3023.4Standard polar33892256
Lamivudine sulfoxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)CS1=O2725.9Semi standard non polar33892256
Lamivudine sulfoxide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C12779.7Semi standard non polar33892256
Lamivudine sulfoxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C=C12994.8Semi standard non polar33892256
Lamivudine sulfoxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C=C13185.1Standard non polar33892256
Lamivudine sulfoxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@H]2CS(=O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C=C13467.5Standard polar33892256
Lamivudine sulfoxide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C(C)(C)C2936.0Semi standard non polar33892256
Lamivudine sulfoxide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C(C)(C)C3282.1Standard non polar33892256
Lamivudine sulfoxide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@H]2CS(=O)[C@@H](CO)O2)C=C1)[Si](C)(C)C(C)(C)C3339.4Standard polar33892256
Lamivudine sulfoxide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CS1=O3151.9Semi standard non polar33892256
Lamivudine sulfoxide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CS1=O3454.8Standard non polar33892256
Lamivudine sulfoxide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)CS1=O3211.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lamivudine sulfoxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-8910000000-0a97c81e597d46d13cec2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lamivudine sulfoxide GC-MS (1 TMS) - 70eV, Positivesplash10-0jbi-6900000000-73ae3c3a3bc573a6595d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lamivudine sulfoxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 10V, Positive-QTOFsplash10-03di-0910000000-63f9bb8a8fb1f78ab9f32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 20V, Positive-QTOFsplash10-03di-3900000000-04a8a42440e4100195072017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 40V, Positive-QTOFsplash10-03di-9700000000-c7cc0fb6f0db073b654f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 10V, Negative-QTOFsplash10-0007-1970000000-742b32f84394a407678f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 20V, Negative-QTOFsplash10-0006-4900000000-01d178cf401a4d93caf62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 40V, Negative-QTOFsplash10-0007-9000000000-15e4d8cb62057a01e18e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 10V, Positive-QTOFsplash10-03di-0900000000-61fe3ac4032a2baf1b892021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 20V, Positive-QTOFsplash10-03di-2900000000-230b224d4d0dd71d0a492021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 40V, Positive-QTOFsplash10-02t9-9200000000-a6bfc3e9e9eb515dc6392021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 10V, Negative-QTOFsplash10-000l-0950000000-48771aeea64e340f29892021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 20V, Negative-QTOFsplash10-0gvx-4900000000-3064775e4cd9496d78362021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lamivudine sulfoxide 40V, Negative-QTOFsplash10-0006-9400000000-82532a473432d6e507e32021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound452020
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available