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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:17:32 UTC
Update Date2021-09-14 15:40:57 UTC
HMDB IDHMDB0061088
Secondary Accession Numbers
  • HMDB61088
Metabolite Identification
Common NameDihydroartemisinin (DHA)
DescriptionFluoxetine glucuronide belongs to the class of organic compounds known as n-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a N-glycosidic bond. Fluoxetine glucuronide is a metabolite of fluoxetine. Fluoxetine (also known by the tradenames Prozac, Sarafem, Fontex, among others) is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. Fluoxetine glucuronide is a very strong basic compound (based on its pKa). In humans, fluoxetine glucuronide is involved in fluoxetine metabolism pathway. Fluoxetine went off-patent in August 2001 (Wikipedia). It was presented to the U.S. Food and Drug Administration in February 1977, with Eli Lilly receiving final approval to market the drug in December 1987. Fluoxetine was first documented in 1974 by scientists from Eli Lilly and Company.
Structure
Data?1563866144
Synonyms
ValueSource
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-[methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amino]oxane-2-carboxylateHMDB
Chemical FormulaC15H24O5
Average Molecular Weight284.3481
Monoisotopic Molecular Weight284.162373878
IUPAC Name(4R,5S,9S,10R,12S,13S)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-ol
Traditional Name(4R,5S,9S,10R,12S,13S)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-ol
CAS Registry NumberNot Available
SMILES
C[C@H]1CCC2[C@H](C)[C@H](O)O[C@H]3OC4(C)CC[C@H]1[C@]23OO4
InChI Identifier
InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11?,12+,13-,14?,15-/m0/s1
InChI KeyBJDCWCLMFKKGEE-AGQWIWFJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a N-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-glucuronides
Alternative Parents
Substituents
  • N-glucuronide
  • 1-n-glucuronide
  • Glycosyl compound
  • N-glycosyl compound
  • Trifluoromethylbenzene
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Benzenoid
  • Monosaccharide
  • Pyran
  • Oxane
  • Hemiaminal
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Alkyl fluoride
  • Organohalogen compound
  • Organofluoride
  • Carbonyl group
  • Organic oxide
  • Alkyl halide
  • Alcohol
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.16 g/LALOGPS
logP2.25ALOGPS
logP2.84ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)12.11ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.91 m³·mol⁻¹ChemAxon
Polarizability30.08 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available163.67231661259
DarkChem[M-H]-PredictedNot Available158.06831661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Dihydroartemisinin (DHA),1TMS,#12088.438https://arxiv.org/abs/1905.12712
Dihydroartemisinin (DHA),1TBDMS,#12342.9285https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05r0-5090000000-2c3d5f82fba0d14e9a072017-09-20View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00bl-9032000000-cf8c1ef663c36070166c2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-957508038617389e634a2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-2f125a25192ab9dac3ff2017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9120000000-c175280a233f4849aab72017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-0090000000-73c4d85a7f84863d34b52017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0090000000-03701af12b5b9b5f19d12017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2930000000-61834bfa8e89873f88312017-10-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-1345a6d7d83d2353d1d32021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-4ecf30250c7b7c1b48242021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-1090000000-987e60b5c92178e5b8052021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-dac20fbea8167508deeb2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-844f91982253be80d1352021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-2090000000-acb28e00350215015bd32021-09-09View 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 Compound71316864
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.