Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:47:48 UTC
HMDB IDHMDB0014343
Secondary Accession Numbers
  • HMDB14343
Metabolite Identification
Common NameOseltamivir
DescriptionOseltamivir is only found in individuals that have used or taken this drug. It is an acetamido cyclohexene that is a structural homolog of sialic acid and inhibits neuraminidase. [PubChem]Oseltamivir is an ethyl ester prodrug requiring ester hydrolysis for conversion to the active form, oseltamivir carboxylate. The proposed mechanism of action of oseltamivir is inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release.
Structure
Data?1582753167
Synonyms
ValueSource
(-)-OseltamivirChEBI
AgucortChEBI
Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylateChEBI
GS-4104ChEBI
HSDB 7433ChEBI
OseltamivirumChEBI
TamifluChEBI
Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acidGenerator
Oseltamivir phosphateHMDB
Chemical FormulaC16H28N2O4
Average Molecular Weight312.4045
Monoisotopic Molecular Weight312.204907394
IUPAC Nameethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
Traditional Nameoseltamivir
CAS Registry Number204255-11-8
SMILES
CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1
InChI Identifier
InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1
InChI KeyVSZGPKBBMSAYNT-RRFJBIMHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Enoate ester
  • Acetamide
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxamide group
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Primary aliphatic amine
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.69 g/LNot Available
LogP1Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available180.66http://allccs.zhulab.cn/database/detail?ID=AllCCS00001297
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.69 g/LALOGPS
logP10(1.3) g/LALOGPS
logP10(1.16) g/LChemAxon
logS10(-2.7) g/LALOGPS
pKa (Strongest Acidic)14.03ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.65 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity84.2 m³·mol⁻¹ChemAxon
Polarizability34.65 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.44831661259
DarkChem[M-H]-172.31131661259
DeepCCS[M+H]+180.42330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OseltamivirCCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C13444.4Standard polar33892256
OseltamivirCCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C12261.5Standard non polar33892256
OseltamivirCCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C12276.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oseltamivir,1TMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C)C12381.0Semi standard non polar33892256
Oseltamivir,1TMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C)C12282.1Standard non polar33892256
Oseltamivir,1TMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C)C13352.8Standard polar33892256
Oseltamivir,1TMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N)C12307.4Semi standard non polar33892256
Oseltamivir,1TMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N)C12211.1Standard non polar33892256
Oseltamivir,1TMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N)C13295.4Standard polar33892256
Oseltamivir,2TMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N[Si](C)(C)C)C12334.0Semi standard non polar33892256
Oseltamivir,2TMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N[Si](C)(C)C)C12390.2Standard non polar33892256
Oseltamivir,2TMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N[Si](C)(C)C)C12873.6Standard polar33892256
Oseltamivir,2TMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N([Si](C)(C)C)[Si](C)(C)C)C12449.0Semi standard non polar33892256
Oseltamivir,2TMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N([Si](C)(C)C)[Si](C)(C)C)C12401.7Standard non polar33892256
Oseltamivir,2TMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N([Si](C)(C)C)[Si](C)(C)C)C13166.8Standard polar33892256
Oseltamivir,3TMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N([Si](C)(C)C)[Si](C)(C)C)C12404.4Semi standard non polar33892256
Oseltamivir,3TMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N([Si](C)(C)C)[Si](C)(C)C)C12511.4Standard non polar33892256
Oseltamivir,3TMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N([Si](C)(C)C)[Si](C)(C)C)C12739.1Standard polar33892256
Oseltamivir,1TBDMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C(C)(C)C)C12559.1Semi standard non polar33892256
Oseltamivir,1TBDMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C(C)(C)C)C12464.0Standard non polar33892256
Oseltamivir,1TBDMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C(C)(C)C)C13340.9Standard polar33892256
Oseltamivir,1TBDMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N)C12507.7Semi standard non polar33892256
Oseltamivir,1TBDMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N)C12396.9Standard non polar33892256
Oseltamivir,1TBDMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N)C13315.8Standard polar33892256
Oseltamivir,2TBDMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N[Si](C)(C)C(C)(C)C)C12709.4Semi standard non polar33892256
Oseltamivir,2TBDMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N[Si](C)(C)C(C)(C)C)C12745.4Standard non polar33892256
Oseltamivir,2TBDMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N[Si](C)(C)C(C)(C)C)C13049.9Standard polar33892256
Oseltamivir,2TBDMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C12854.9Semi standard non polar33892256
Oseltamivir,2TBDMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C12755.5Standard non polar33892256
Oseltamivir,2TBDMS,isomer #2CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C13217.3Standard polar33892256
Oseltamivir,3TBDMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C13043.8Semi standard non polar33892256
Oseltamivir,3TBDMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C13021.8Standard non polar33892256
Oseltamivir,3TBDMS,isomer #1CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C13011.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oseltamivir GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bo-9280000000-03554fbfb24a606e4a9a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oseltamivir GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-QTOF , positive-QTOFsplash10-01t9-0193000000-f5d60d35ef59bb0d3d882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-QTOF , positive-QTOFsplash10-014i-0930000000-4bafe71e1cfce532c69e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-QTOF , positive-QTOFsplash10-014i-0900000000-b47b81a2da926f1b38a02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-QTOF , positive-QTOFsplash10-01bi-0900000000-e54a66b05b36ac125c762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-QTOF , positive-QTOFsplash10-00dr-0900000000-a088a5ae7a49e423f6452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-a4689c9d2708c98646832017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-07fr-0393000000-c4ca6313b8a95857501f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-014i-0920000000-274bd00e87c126ea04312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-014i-1900000000-ab2b530339386266bb5e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-00y3-3900000000-503de5f1484e1733b9332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-006x-6900000000-c732121f239f135b134c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-006x-9600000000-414288f436e77a96401f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-07fr-0393000000-782bc585f56c5193cc4e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-014i-0920000000-2a6c0c1f08190d6bbc0f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-014i-1900000000-3ea178c0a288c37e3e792017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-00y3-3900000000-0c790adae380f41f557a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-006x-6900000000-793d9a5e1ce9de381e4f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-006x-9600000000-ebf8dd7bcfb3a48440782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-f5e9b54d2909b3aff88d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oseltamivir 10V, Positive-QTOFsplash10-044j-1092000000-a5c51c03276e29381b542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oseltamivir 20V, Positive-QTOFsplash10-0gi0-1290000000-855d80ff3dbaf863b55b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oseltamivir 40V, Positive-QTOFsplash10-00di-9720000000-3020e017c27cf5688ae52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oseltamivir 10V, Negative-QTOFsplash10-03di-2089000000-aca6af58f0479c615bbc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oseltamivir 20V, Negative-QTOFsplash10-02t9-2091000000-dafdec8458549b80e2b62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oseltamivir 40V, Negative-QTOFsplash10-0ap1-9830000000-e6541c125795bb30888f2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00198 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00198 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00198
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID58540
KEGG Compound IDC08092
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOseltamivir
METLIN IDNot Available
PubChem Compound65028
PDB IDNot Available
ChEBI ID7798
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. Kiso M, Mitamura K, Sakai-Tagawa Y, Shiraishi K, Kawakami C, Kimura K, Hayden FG, Sugaya N, Kawaoka Y: Resistant influenza A viruses in children treated with oseltamivir: descriptive study. Lancet. 2004 Aug 28-Sep 3;364(9436):759-65. [PubMed:15337401 ]
  2. Chokephaibulkit K, Uiprasertkul M, Puthavathana P, Chearskul P, Auewarakul P, Dowell SF, Vanprapar N: A child with avian influenza A (H5N1) infection. Pediatr Infect Dis J. 2005 Feb;24(2):162-6. [PubMed:15702046 ]
  3. Ward P, Small I, Smith J, Suter P, Dutkowski R: Oseltamivir (Tamiflu) and its potential for use in the event of an influenza pandemic. J Antimicrob Chemother. 2005 Feb;55 Suppl 1:i5-i21. [PubMed:15709056 ]
  4. de Jong MD, Tran TT, Truong HK, Vo MH, Smith GJ, Nguyen VC, Bach VC, Phan TQ, Do QH, Guan Y, Peiris JS, Tran TH, Farrar J: Oseltamivir resistance during treatment of influenza A (H5N1) infection. N Engl J Med. 2005 Dec 22;353(25):2667-72. [PubMed:16371632 ]

Enzymes

General function:
Involved in exo-alpha-sialidase activity
Specific function:
Hydrolyzes sialylated compounds.
Gene Name:
NEU2
Uniprot ID:
Q9Y3R4
Molecular weight:
Not Available
References
  1. Chavas LM, Kato R, Suzuki N, von Itzstein M, Mann MC, Thomson RJ, Dyason JC, McKimm-Breschkin J, Fusi P, Tringali C, Venerando B, Tettamanti G, Monti E, Wakatsuki S: Complexity in influenza virus targeted drug design: interaction with human sialidases. J Med Chem. 2010 Apr 8;53(7):2998-3002. doi: 10.1021/jm100078r. [PubMed:20222714 ]
General function:
Involved in exo-alpha-sialidase activity
Specific function:
Catalyzes the removal of sialic acid (N-acetylneuramic acid) moities from glycoproteins and glycolipids. To be active, it is strictly dependent on its presence in the multienzyme complex. Appears to have a preference for alpha 2-3 and alpha 2-6 sialyl linkage.
Gene Name:
NEU1
Uniprot ID:
Q99519
Molecular weight:
Not Available
References
  1. Chavas LM, Kato R, Suzuki N, von Itzstein M, Mann MC, Thomson RJ, Dyason JC, McKimm-Breschkin J, Fusi P, Tringali C, Venerando B, Tettamanti G, Monti E, Wakatsuki S: Complexity in influenza virus targeted drug design: interaction with human sialidases. J Med Chem. 2010 Apr 8;53(7):2998-3002. doi: 10.1021/jm100078r. [PubMed:20222714 ]
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
References
  1. Shi D, Yang J, Yang D, LeCluyse EL, Black C, You L, Akhlaghi F, Yan B: Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther. 2006 Dec;319(3):1477-84. Epub 2006 Sep 11. [PubMed:16966469 ]
  2. Wattanagoon Y, Stepniewska K, Lindegardh N, Pukrittayakamee S, Silachamroon U, Piyaphanee W, Singtoroj T, Hanpithakpong W, Davies G, Tarning J, Pongtavornpinyo W, Fukuda C, Singhasivanon P, Day NP, White NJ: Pharmacokinetics of high-dose oseltamivir in healthy volunteers. Antimicrob Agents Chemother. 2009 Mar;53(3):945-52. doi: 10.1128/AAC.00588-08. Epub 2008 Dec 22. [PubMed:19104028 ]
  3. Zhu HJ, Markowitz JS: Activation of the antiviral prodrug oseltamivir is impaired by two newly identified carboxylesterase 1 variants. Drug Metab Dispos. 2009 Feb;37(2):264-7. doi: 10.1124/dmd.108.024943. Epub 2008 Nov 20. [PubMed:19022936 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Ogihara T, Kano T, Wagatsuma T, Wada S, Yabuuchi H, Enomoto S, Morimoto K, Shirasaka Y, Kobayashi S, Tamai I: Oseltamivir (tamiflu) is a substrate of peptide transporter 1. Drug Metab Dispos. 2009 Aug;37(8):1676-81. doi: 10.1124/dmd.109.026922. Epub 2009 May 13. [PubMed:19439487 ]
General function:
Involved in ATP binding
Specific function:
May be an organic anion pump relevant to cellular detoxification
Gene Name:
ABCC4
Uniprot ID:
O15439
Molecular weight:
149525.3
References
  1. Ose A, Ito M, Kusuhara H, Yamatsugu K, Kanai M, Shibasaki M, Hosokawa M, Schuetz JD, Sugiyama Y: Limited brain distribution of [3R,4R,5S]-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (Ro 64-0802), a pharmacologically active form of oseltamivir, by active efflux across the blood-brain barrier mediated by organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistance-associated protein 4 (Mrp4/Abcc4). Drug Metab Dispos. 2009 Feb;37(2):315-21. doi: 10.1124/dmd.108.024018. Epub 2008 Nov 24. [PubMed:19029202 ]