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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:57:22 UTC
Update Date2021-09-26 23:03:40 UTC
HMDB IDHMDB0251589
Secondary Accession NumbersNone
Metabolite Identification
Common NameDoravirine
DescriptionDoravirine belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. A) or moderate (Child-Pugh Class. Doravirine is a moderately basic compound (based on its pKa). No dosage adjustment of doravirine is required in patients with mild, moderate, or severe renal impairment. C), or <18 years of age is unknown . Once administered and absorbed into the plasma circulation, unchanged doravirine is the major circulating component, followed by its M9 metabolite - a product of cytochrome P450 3A4/5 mediated oxidative metabolism, resulting in the addition of oxygen to doravirine's triazolone ring - as the most abundant doravirine metabolite present . Doravirine is subsequently available by itself or as a combination product of doravirine (100 mg), lamivudine (300 mg), and tenofovir disoproxil fumarate (300 mg) . The pharmacokinetics of doravirine in patients with end-stage renal disease or undergoing dialysis, severe hepatic impairment (Child-Pugh. This compound has been identified in human blood as reported by (PMID: 31557052 ). Doravirine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Doravirine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
MK-1439DORAVIRINEChEMBL
Chemical FormulaC17H11ClF3N5O3
Average Molecular Weight425.749
Monoisotopic Molecular Weight425.050251565
IUPAC Name3-chloro-5-({1-[(5-hydroxy-4-methyl-4H-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl}oxy)benzonitrile
Traditional Name3-chloro-5-({1-[(5-hydroxy-4-methyl-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)pyridin-3-yl}oxy)benzonitrile
CAS Registry NumberNot Available
SMILES
CN1C(O)=NN=C1CN1C=CC(=C(OC2=CC(=CC(Cl)=C2)C#N)C1=O)C(F)(F)F
InChI Identifier
InChI=1S/C17H11ClF3N5O3/c1-25-13(23-24-16(25)28)8-26-3-2-12(17(19,20)21)14(15(26)27)29-11-5-9(7-22)4-10(18)6-11/h2-6H,8H2,1H3,(H,24,28)
InChI KeyZIAOVIPSKUPPQW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentDiarylethers
Alternative Parents
Substituents
  • Diaryl ether
  • Benzonitrile
  • Phenoxy compound
  • Phenol ether
  • Chlorobenzene
  • Dihydropyridine
  • Halobenzene
  • Pyridinone
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Hydropyridine
  • Pyridine
  • Benzenoid
  • Azole
  • 1,2,4-triazole
  • Heteroaromatic compound
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Hydrocarbon derivative
  • Organic oxide
  • Cyanide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl fluoride
  • Organofluoride
  • Alkyl halide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP3.47ALOGPS
logP2.19ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.26ChemAxon
pKa (Strongest Basic)1.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area104.27 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.37 m³·mol⁻¹ChemAxon
Polarizability35.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+186.21730932474
DeepCCS[M-H]-183.69930932474
DeepCCS[M-2H]-218.26630932474
DeepCCS[M+Na]+193.47130932474
AllCCS[M+H]+188.932859911
AllCCS[M+H-H2O]+186.432859911
AllCCS[M+NH4]+191.232859911
AllCCS[M+Na]+191.932859911
AllCCS[M-H]-184.432859911
AllCCS[M+Na-2H]-183.632859911
AllCCS[M+HCOO]-182.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DoravirineCN1C(O)=NN=C1CN1C=CC(=C(OC2=CC(=CC(Cl)=C2)C#N)C1=O)C(F)(F)F3718.0Standard polar33892256
DoravirineCN1C(O)=NN=C1CN1C=CC(=C(OC2=CC(=CC(Cl)=C2)C#N)C1=O)C(F)(F)F2798.4Standard non polar33892256
DoravirineCN1C(O)=NN=C1CN1C=CC(=C(OC2=CC(=CC(Cl)=C2)C#N)C1=O)C(F)(F)F3115.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Doravirine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0wmi-1539200000-bc5dd78c5dc9b16615e92021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doravirine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doravirine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doravirine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 10V, Positive-QTOFsplash10-004i-1102900000-85159263a4e1f67db4fd2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 20V, Positive-QTOFsplash10-02ta-0219100000-d6ddc6a4128222a041d12017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 40V, Positive-QTOFsplash10-053i-8928000000-39d7c30b07d1de9e85d92017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 10V, Negative-QTOFsplash10-014i-2009000000-f1affba5de17dc10816d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 20V, Negative-QTOFsplash10-014i-1109100000-d953f236c324da9b53292017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 40V, Negative-QTOFsplash10-0zfu-4912000000-7eac1fbcbbae47e7fb502017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 10V, Positive-QTOFsplash10-004i-0000900000-c2c10af104f690d1e43c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 20V, Positive-QTOFsplash10-004r-0109400000-f42cb9021f31cd5b24ab2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 40V, Positive-QTOFsplash10-0f9i-3819000000-209cda74b17fdb5cce5f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 10V, Negative-QTOFsplash10-00di-0401900000-17fb69f803a4a3e2aa132021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 20V, Negative-QTOFsplash10-0udi-5809000000-c18aeb067425b79800672021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doravirine 40V, Negative-QTOFsplash10-001i-9001000000-7e76979acba163304f232021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12301
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 LinkDoravirine
METLIN IDNot Available
PubChem Compound58460047
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]