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Record Information
Version4.0
Creation Date2013-07-09 16:05:52 UTC
Update Date2017-09-27 08:43:56 UTC
HMDB IDHMDB0060896
Secondary Accession Numbers
  • HMDB60896
Metabolite Identification
Common NameN-Desmethylritonavir
DescriptionN-Desmethylritonavir is a metabolite of ritonavir. Ritonavir, with trade name Norvir, is an antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS. Ritonavir is frequently prescribed with HAART, not for its antiviral action, but as it inhibits the same host enzyme that metabolizes other protease inhibitors. This inhibition leads to higher plasma concentrations of these latter drugs, allowing the clinician to lower their dose and frequency and improving their clinical efficacy. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC36H46N6O5S2
Average Molecular Weight706.918
Monoisotopic Molecular Weight706.297109992
IUPAC Name(2S)-N-[(2S,4S,5S)-4-hydroxy-5-{[hydroxy(1,3-thiazol-5-ylmethoxy)methylidene]amino}-1,6-diphenylhexan-2-yl]-3-methyl-2-[({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl}-C-hydroxycarbonimidoyl)amino]butanimidic acid
Traditional Name(2S)-N-[(2S,4S,5S)-4-hydroxy-5-{[hydroxy(1,3-thiazol-5-ylmethoxy)methylidene]amino}-1,6-diphenylhexan-2-yl]-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl]-C-hydroxycarbonimidoyl}amino)-3-methylbutanimidic acid
CAS Registry NumberNot Available
SMILES
CC(C)[C@H](NC(O)=NCC1=CSC(=N1)C(C)C)C(O)=N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)N=C(O)OCC1=CN=CS1)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C36H46N6O5S2/c1-23(2)32(42-35(45)38-18-28-21-48-34(40-28)24(3)4)33(44)39-27(15-25-11-7-5-8-12-25)17-31(43)30(16-26-13-9-6-10-14-26)41-36(46)47-20-29-19-37-22-49-29/h5-14,19,21-24,27,30-32,43H,15-18,20H2,1-4H3,(H,39,44)(H,41,46)(H2,38,42,45)/t27-,30-,31-,32-/m0/s1
InChI KeySQANVQYLDPEULW-QJANCWQKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-carbamoyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an carbamoyl group at its terminal nitrogen atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentN-carbamoyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • Valine or derivatives
  • N-carbamoyl-alpha-amino acid or derivatives
  • Alpha-amino acid amide
  • Amphetamine or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Carbamic acid ester
  • Thiazole
  • Carboxamide group
  • Urea
  • Carbonic acid derivative
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Azacycle
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0031 g/LALOGPS
logP4.49ALOGPS
logP7.17ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)6.05ChemAxon
pKa (Strongest Basic)4.94ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area165.04 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity191.53 m³·mol⁻¹ChemAxon
Polarizability76.11 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1910222100-89732b17d8c790c3b99eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4m-3910210000-4cb94eb79b22ac28e6a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9710000000-aba73178dacb99ba8806View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0k96-2800190100-a4b6562fbed1b5262c9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-3601291000-3db5fee86254594e5287View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-ac1d10b21725cf71361fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00084
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB 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 CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available