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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:14:41 UTC
Update Date2021-09-14 15:45:34 UTC
HMDB IDHMDB0061044
Secondary Accession Numbers
  • HMDB61044
Metabolite Identification
Common NameHydroxy Ritonavir
DescriptionHydroxy Ritonavir 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
Data?1563866139
Synonyms
ValueSource
(2S)-N-[(2S,4S,5S)-4-Hydroxy-5-({hydroxy[(1,3-thiazol-5-yl)methoxy]methylidene}amino)-1,6-diphenylhexan-2-yl]-2-(N-{[2-(2-hydroxypropan-2-yl)-1,3-thiazol-4-yl]methyl}-N-methyl-(C-hydroxycarbonimidoyl)amino)-3-methylbutanimidateGenerator
Chemical FormulaC37H48N6O6S2
Average Molecular Weight736.944
Monoisotopic Molecular Weight736.307674678
IUPAC Name1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-3-hydroxy-5-[(2S)-2-[({[2-(2-hydroxypropan-2-yl)-1,3-thiazol-4-yl]methyl}(methyl)carbamoyl)amino]-3-methylbutanamido]-1,6-diphenylhexan-2-yl]carbamate
Traditional Name1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-3-hydroxy-5-[(2S)-2-[({[2-(2-hydroxypropan-2-yl)-1,3-thiazol-4-yl]methyl}(methyl)carbamoyl)amino]-3-methylbutanamido]-1,6-diphenylhexan-2-yl]carbamate
CAS Registry NumberNot Available
SMILES
CC(C)[C@H](NC(=O)N(C)CC1=CSC(=N1)C(C)(C)O)C(=O)N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)OCC1=CN=CS1)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C37H48N6O6S2/c1-24(2)32(42-35(46)43(5)20-28-22-50-34(40-28)37(3,4)48)33(45)39-27(16-25-12-8-6-9-13-25)18-31(44)30(17-26-14-10-7-11-15-26)41-36(47)49-21-29-19-38-23-51-29/h6-15,19,22-24,27,30-32,44,48H,16-18,20-21H2,1-5H3,(H,39,45)(H,41,47)(H,42,46)/t27-,30-,31-,32-/m0/s1
InChI KeyCLEDZMPJHBBTNZ-QJANCWQKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Fatty alcohol
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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 Solubility0.0018 g/LALOGPS
logP3.63ALOGPS
logP4.16ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)13.18ChemAxon
pKa (Strongest Basic)2.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area166.01 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity196.3 m³·mol⁻¹ChemAxon
Polarizability77.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+253.37930932474
DeepCCS[M-H]-251.55430932474
DeepCCS[M-2H]-285.54930932474
DeepCCS[M+Na]+259.32330932474
AllCCS[M+H]+267.932859911
AllCCS[M+H-H2O]+267.432859911
AllCCS[M+NH4]+268.432859911
AllCCS[M+Na]+268.532859911
AllCCS[M-H]-248.232859911
AllCCS[M+Na-2H]-252.832859911
AllCCS[M+HCOO]-257.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Hydroxy RitonavirCC(C)[C@H](NC(=O)N(C)CC1=CSC(=N1)C(C)(C)O)C(=O)N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)OCC1=CN=CS1)CC1=CC=CC=C16146.7Standard polar33892256
Hydroxy RitonavirCC(C)[C@H](NC(=O)N(C)CC1=CSC(=N1)C(C)(C)O)C(=O)N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)OCC1=CN=CS1)CC1=CC=CC=C13954.7Standard non polar33892256
Hydroxy RitonavirCC(C)[C@H](NC(=O)N(C)CC1=CSC(=N1)C(C)(C)O)C(=O)N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)OCC1=CN=CS1)CC1=CC=CC=C15418.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-9651428300-a8373b3458cb5b82b0812017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxy Ritonavir GC-MS (TBDMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 10V, Positive-QTOFsplash10-014r-0520401900-b8e73447a36dcdfd17352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 20V, Positive-QTOFsplash10-00li-0930300000-8202830e8fd481bc17722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 40V, Positive-QTOFsplash10-00li-1940000000-ecda95eeb4642fbd20772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 10V, Negative-QTOFsplash10-01bi-2910008300-ea5c6c41a18b696cdc5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 20V, Negative-QTOFsplash10-05fu-5612129400-93bff8f52cd8f1b7a2e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 40V, Negative-QTOFsplash10-0udr-8900000000-fa30d6ce6066995f38ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 10V, Negative-QTOFsplash10-03dr-2418005900-6c7c43ba0da145cdc4ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 20V, Negative-QTOFsplash10-000l-9305204100-70ee8d7273353de26e272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 40V, Negative-QTOFsplash10-0a4i-7901102000-565febdb3f0d04c57e592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 10V, Positive-QTOFsplash10-0019-0590100300-c2d53bf6cb76563b1f482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 20V, Positive-QTOFsplash10-000i-1920000000-3a5483420a8ac9cc0dd52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxy Ritonavir 40V, Positive-QTOFsplash10-000g-2900000000-8264e6ab30d1bf3019ca2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 Compound71749331
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