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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (2) Show 5 proteins XML

enzymes (3)transporters (2) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014343

Secondary Accession Numbers

HMDB14343

Metabolite Identification

Common Name

Oseltamivir

Description

Oseltamivir 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014343
     RDKit          3D
Oseltamivir
 50 50  0  0  0  0  0  0  0  0999 V2000
    4.5006    3.7687   -2.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7217    2.7383   -3.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8051    2.0373   -2.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1742    1.2894   -1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3719    1.1975   -0.9023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633    0.6076   -0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8690    0.6606   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053   -0.0938    0.1709 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3374    0.0635    0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0874    0.5851    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131   -0.3497    1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1347   -0.6436    0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516    1.9124    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167    2.5851    1.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966   -1.5247    0.1507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3124   -2.4055    0.9588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206   -3.4709    0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8684   -4.4108    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528   -3.6732   -0.8649 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9549   -1.5759    0.5470 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7362   -2.2543   -0.4618 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5738   -0.2156    0.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036    3.3471   -2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9359    4.0046   -1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5927    4.6835   -2.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125    3.2762   -3.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4263    2.0549   -3.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5914    1.2467   -1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    0.2771    1.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780    0.8664    1.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7579   -1.3028    1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7898    0.0199    2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500   -0.0339    0.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4734   -1.7153    0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7205   -0.3924   -0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    1.7490   -0.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638    2.5538    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9988    2.8260    2.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3787    1.8917    1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9668    3.5060    1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.8584   -0.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596   -2.2306    1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909   -3.9963    2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466   -5.4027    1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8120   -4.6600    0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -2.1042    1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -2.1564   -1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9730   -3.2269   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2459    0.2745    1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -0.3246    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 20 21  1  0
 20 22  1  0
 22  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  7 28  1  0
  8 29  1  1
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  6
 16 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  1
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
M  END

65028
  Mrv0541 02231214302D          

 22 22  0  0  1  0            999 V2000
    3.7935    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9370    0.6188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9370   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
  1 13  1  0  0  0  0
  2 16  1  0  0  0  0
  2 21  1  0  0  0  0
  3 16  2  0  0  0  0
  4 17  2  0  0  0  0
  7  5  1  6  0  0  0
  5 17  1  0  0  0  0
  8  6  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  2  0  0  0  0
 12 16  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 17 20  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014343

> <DATABASE_NAME>
hmdb

> <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_KEY>
VSZGPKBBMSAYNT-RRFJBIMHSA-N

> <FORMULA>
C16H28N2O4

> <MOLECULAR_WEIGHT>
312.4045

> <EXACT_MASS>
312.204907394

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.64840068047427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

> <ALOGPS_LOGP>
1.30

> <JCHEM_LOGP>
1.1625985496666666

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.033633753738549

> <JCHEM_PKA_STRONGEST_BASIC>
9.308437965946721

> <JCHEM_POLAR_SURFACE_AREA>
90.64999999999999

> <JCHEM_REFRACTIVITY>
84.20340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oseltamivir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014343
     RDKit          3D
Oseltamivir
 50 50  0  0  0  0  0  0  0  0999 V2000
    4.5006    3.7687   -2.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7217    2.7383   -3.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8051    2.0373   -2.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1742    1.2894   -1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3719    1.1975   -0.9023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633    0.6076   -0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8690    0.6606   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053   -0.0938    0.1709 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3374    0.0635    0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0874    0.5851    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131   -0.3497    1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1347   -0.6436    0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516    1.9124    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167    2.5851    1.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966   -1.5247    0.1507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3124   -2.4055    0.9588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206   -3.4709    0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8684   -4.4108    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528   -3.6732   -0.8649 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9549   -1.5759    0.5470 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7362   -2.2543   -0.4618 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5738   -0.2156    0.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036    3.3471   -2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9359    4.0046   -1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5927    4.6835   -2.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125    3.2762   -3.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4263    2.0549   -3.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5914    1.2467   -1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    0.2771    1.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780    0.8664    1.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7579   -1.3028    1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7898    0.0199    2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500   -0.0339    0.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4734   -1.7153    0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7205   -0.3924   -0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    1.7490   -0.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638    2.5538    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9988    2.8260    2.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3787    1.8917    1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9668    3.5060    1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.8584   -0.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596   -2.2306    1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909   -3.9963    2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466   -5.4027    1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8120   -4.6600    0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -2.1042    1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -2.1564   -1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9730   -3.2269   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2459    0.2745    1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -0.3246    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 20 21  1  0
 20 22  1  0
 22  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  7 28  1  0
  8 29  1  1
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  6
 16 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  1
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 65028                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.081   1.925   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415  -3.465   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.082  -3.465   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.081   3.465   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.748   3.465   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      12.416   1.925   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.748   1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.082  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748  -1.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747  -0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748  -2.695   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080   1.155   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -1.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   5.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415  -5.005   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.081  -5.775   0.000  0.00  0.00           C+0
CONECT    1    9   13                                                       
CONECT    2   16   21                                                       
CONECT    3   16                                                            
CONECT    4   17                                                            
CONECT    5    7   17                                                       
CONECT    6    8                                                            
CONECT    7    5    8    9                                                  
CONECT    8    6    7   10                                                  
CONECT    9    1    7   11                                                  
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11   16                                                  
CONECT   13    1   14   15                                                  
CONECT   14   13   18                                                       
CONECT   15   13   19                                                       
CONECT   16    2    3   12                                                  
CONECT   17    4    5   20                                                  
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   17                                                            
CONECT   21    2   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0014343
HETATM    1  C1  UNL     1       4.501   3.769  -2.347  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.722   2.738  -3.133  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.805   2.037  -2.314  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.174   1.289  -1.223  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.372   1.197  -0.902  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.163   0.608  -0.446  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.869   0.661  -0.728  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.005  -0.094   0.171  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.337   0.064   0.008  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.087   0.585   0.986  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.213  -0.350   1.361  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.135  -0.644   0.208  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.652   1.912   0.451  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.517   2.585   1.482  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.497  -1.525   0.151  1.00  0.00           C  
HETATM   16  N1  UNL     1      -0.312  -2.405   0.959  1.00  0.00           N  
HETATM   17  C13 UNL     1      -1.021  -3.471   0.395  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.868  -4.411   1.168  1.00  0.00           C  
HETATM   19  O4  UNL     1      -0.953  -3.673  -0.865  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.955  -1.576   0.547  1.00  0.00           C  
HETATM   21  N2  UNL     1       2.736  -2.254  -0.462  1.00  0.00           N  
HETATM   22  C16 UNL     1       2.574  -0.216   0.756  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.504   3.347  -2.092  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.936   4.005  -1.420  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.593   4.683  -2.938  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.113   3.276  -3.892  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.426   2.055  -3.632  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.591   1.247  -1.582  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.231   0.277   1.216  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.578   0.866   1.921  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.758  -1.303   1.689  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.790   0.020   2.234  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.050  -0.034   0.354  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.473  -1.715   0.257  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.721  -0.392  -0.774  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.152   1.749  -0.501  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.764   2.554   0.272  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.999   2.826   2.406  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.379   1.892   1.684  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.967   3.506   1.088  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.429  -1.858  -0.910  1.00  0.00           H  
HETATM   42  H20 UNL     1      -0.360  -2.231   1.982  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.191  -3.996   2.141  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.347  -5.403   1.302  1.00  0.00           H  
HETATM   45  H23 UNL     1      -2.812  -4.660   0.615  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.039  -2.104   1.536  1.00  0.00           H  
HETATM   47  H25 UNL     1       2.331  -2.156  -1.419  1.00  0.00           H  
HETATM   48  H26 UNL     1       2.973  -3.227  -0.211  1.00  0.00           H  
HETATM   49  H27 UNL     1       2.246   0.274   1.691  1.00  0.00           H  
HETATM   50  H28 UNL     1       3.661  -0.325   0.760  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   22
CONECT    7    8   28
CONECT    8    9   15   29
CONECT    9   10
CONECT   10   11   13   30
CONECT   11   12   31   32
CONECT   12   33   34   35
CONECT   13   14   36   37
CONECT   14   38   39   40
CONECT   15   16   20   41
CONECT   16   17   42
CONECT   17   18   19   19
CONECT   18   43   44   45
CONECT   20   21   22   46
CONECT   21   47   48
CONECT   22   49   50
END

HMDB0014343
     RDKit          3D
Oseltamivir
 50 50  0  0  0  0  0  0  0  0999 V2000
    4.5006    3.7687   -2.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7217    2.7383   -3.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8051    2.0373   -2.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1742    1.2894   -1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3719    1.1975   -0.9023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633    0.6076   -0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8690    0.6606   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053   -0.0938    0.1709 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3374    0.0635    0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0874    0.5851    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131   -0.3497    1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1347   -0.6436    0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516    1.9124    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5167    2.5851    1.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966   -1.5247    0.1507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3124   -2.4055    0.9588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206   -3.4709    0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8684   -4.4108    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528   -3.6732   -0.8649 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9549   -1.5759    0.5470 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7362   -2.2543   -0.4618 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5738   -0.2156    0.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036    3.3471   -2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9359    4.0046   -1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5927    4.6835   -2.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125    3.2762   -3.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4263    2.0549   -3.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5914    1.2467   -1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    0.2771    1.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780    0.8664    1.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7579   -1.3028    1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7898    0.0199    2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500   -0.0339    0.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4734   -1.7153    0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7205   -0.3924   -0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    1.7490   -0.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638    2.5538    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9988    2.8260    2.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3787    1.8917    1.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9668    3.5060    1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.8584   -0.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596   -2.2306    1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909   -3.9963    2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3466   -5.4027    1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8120   -4.6600    0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387   -2.1042    1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -2.1564   -1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9730   -3.2269   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2459    0.2745    1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -0.3246    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 20 21  1  0
 20 22  1  0
 22  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  7 28  1  0
  8 29  1  1
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  6
 16 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  1
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Oseltamivir	ChEBI
Agucort	ChEBI
Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate	ChEBI
GS-4104	ChEBI
HSDB 7433	ChEBI
Oseltamivirum	ChEBI
Tamiflu	ChEBI
Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid	Generator
Oseltamivir phosphate	HMDB

Chemical Formula

C₁₆H₂₈N₂O₄

Average Molecular Weight

312.4045

Monoisotopic Molecular Weight

312.204907394

IUPAC Name

ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Traditional Name

oseltamivir

CAS Registry Number

204255-11-8

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 Key

VSZGPKBBMSAYNT-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma 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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

diester (CHEBI:7798 )
primary amino compound (CHEBI:7798 )
acetamides (CHEBI:7798 )
amino acid ester (CHEBI:7798 )
cyclohexenecarboxylate ester (CHEBI:7798 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.69 g/L	Not Available
LogP	1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	180.66	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001297

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.69 g/L	ALOGPS
logP	1.3	ALOGPS
logP	1.16	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.03	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.65 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	84.2 m³·mol⁻¹	ChemAxon
Polarizability	34.65 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.448	31661259
DarkChem	[M-H]-	172.311	31661259
DeepCCS	[M+H]+	180.423	30932474
DeepCCS	[M-H]-	178.065	30932474
DeepCCS	[M-2H]-	212.479	30932474
DeepCCS	[M+Na]+	187.595	30932474
AllCCS	[M+H]+	179.7	32859911
AllCCS	[M+H-H2O]+	176.9	32859911
AllCCS	[M+NH4]+	182.3	32859911
AllCCS	[M+Na]+	183.1	32859911
AllCCS	[M-H]-	175.8	32859911
AllCCS	[M+Na-2H]-	176.6	32859911
AllCCS	[M+HCOO]-	177.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oseltamivir	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1	3444.4	Standard polar	33892256
Oseltamivir	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1	2261.5	Standard non polar	33892256
Oseltamivir	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1	2276.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oseltamivir,1TMS,isomer #1	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C)C1	2381.0	Semi standard non polar	33892256
Oseltamivir,1TMS,isomer #1	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C)C1	2282.1	Standard non polar	33892256
Oseltamivir,1TMS,isomer #1	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C)C1	3352.8	Standard polar	33892256
Oseltamivir,1TMS,isomer #2	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N)C1	2307.4	Semi standard non polar	33892256
Oseltamivir,1TMS,isomer #2	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N)C1	2211.1	Standard non polar	33892256
Oseltamivir,1TMS,isomer #2	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C)[C@@H](N)C1	3295.4	Standard polar	33892256
Oseltamivir,2TMS,isomer #1	CCOC(=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)C1	2334.0	Semi standard non polar	33892256
Oseltamivir,2TMS,isomer #1	CCOC(=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)C1	2390.2	Standard non polar	33892256
Oseltamivir,2TMS,isomer #1	CCOC(=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)C1	2873.6	Standard polar	33892256
Oseltamivir,2TMS,isomer #2	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N([Si](C)(C)C)[Si](C)(C)C)C1	2449.0	Semi standard non polar	33892256
Oseltamivir,2TMS,isomer #2	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N([Si](C)(C)C)[Si](C)(C)C)C1	2401.7	Standard non polar	33892256
Oseltamivir,2TMS,isomer #2	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N([Si](C)(C)C)[Si](C)(C)C)C1	3166.8	Standard polar	33892256
Oseltamivir,3TMS,isomer #1	CCOC(=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)C1	2404.4	Semi standard non polar	33892256
Oseltamivir,3TMS,isomer #1	CCOC(=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)C1	2511.4	Standard non polar	33892256
Oseltamivir,3TMS,isomer #1	CCOC(=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)C1	2739.1	Standard polar	33892256
Oseltamivir,1TBDMS,isomer #1	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C(C)(C)C)C1	2559.1	Semi standard non polar	33892256
Oseltamivir,1TBDMS,isomer #1	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C(C)(C)C)C1	2464.0	Standard non polar	33892256
Oseltamivir,1TBDMS,isomer #1	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N[Si](C)(C)C(C)(C)C)C1	3340.9	Standard polar	33892256
Oseltamivir,1TBDMS,isomer #2	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N)C1	2507.7	Semi standard non polar	33892256
Oseltamivir,1TBDMS,isomer #2	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N)C1	2396.9	Standard non polar	33892256
Oseltamivir,1TBDMS,isomer #2	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](N(C(C)=O)[Si](C)(C)C(C)(C)C)[C@@H](N)C1	3315.8	Standard polar	33892256
Oseltamivir,2TBDMS,isomer #1	CCOC(=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)C1	2709.4	Semi standard non polar	33892256
Oseltamivir,2TBDMS,isomer #1	CCOC(=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)C1	2745.4	Standard non polar	33892256
Oseltamivir,2TBDMS,isomer #1	CCOC(=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)C1	3049.9	Standard polar	33892256
Oseltamivir,2TBDMS,isomer #2	CCOC(=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)C1	2854.9	Semi standard non polar	33892256
Oseltamivir,2TBDMS,isomer #2	CCOC(=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)C1	2755.5	Standard non polar	33892256
Oseltamivir,2TBDMS,isomer #2	CCOC(=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)C1	3217.3	Standard polar	33892256
Oseltamivir,3TBDMS,isomer #1	CCOC(=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)C1	3043.8	Semi standard non polar	33892256
Oseltamivir,3TBDMS,isomer #1	CCOC(=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)C1	3021.8	Standard non polar	33892256
Oseltamivir,3TBDMS,isomer #1	CCOC(=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)C1	3011.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oseltamivir GC-MS (Non-derivatized) - 70eV, Positive	splash10-05bo-9280000000-03554fbfb24a606e4a9a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oseltamivir GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-QTOF , positive-QTOF	splash10-01t9-0193000000-f5d60d35ef59bb0d3d88	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-QTOF , positive-QTOF	splash10-014i-0930000000-4bafe71e1cfce532c69e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-QTOF , positive-QTOF	splash10-014i-0900000000-b47b81a2da926f1b38a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-QTOF , positive-QTOF	splash10-01bi-0900000000-e54a66b05b36ac125c76	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-QTOF , positive-QTOF	splash10-00dr-0900000000-a088a5ae7a49e423f645	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-004i-0090000000-a4689c9d2708c9864683	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-07fr-0393000000-c4ca6313b8a95857501f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-014i-0920000000-274bd00e87c126ea0431	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-014i-1900000000-ab2b530339386266bb5e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-00y3-3900000000-503de5f1484e1733b933	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-006x-6900000000-c732121f239f135b134c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-006x-9600000000-414288f436e77a96401f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-07fr-0393000000-782bc585f56c5193cc4e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-014i-0920000000-2a6c0c1f08190d6bbc0f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-014i-1900000000-3ea178c0a288c37e3e79	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-00y3-3900000000-0c790adae380f41f557a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-006x-6900000000-793d9a5e1ce9de381e4f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-006x-9600000000-ebf8dd7bcfb3a4844078	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oseltamivir LC-ESI-ITFT , positive-QTOF	splash10-004i-0090000000-f5e9b54d2909b3aff88d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oseltamivir 10V, Positive-QTOF	splash10-044j-1092000000-a5c51c03276e29381b54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oseltamivir 20V, Positive-QTOF	splash10-0gi0-1290000000-855d80ff3dbaf863b55b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oseltamivir 40V, Positive-QTOF	splash10-00di-9720000000-3020e017c27cf5688ae5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oseltamivir 10V, Negative-QTOF	splash10-03di-2089000000-aca6af58f0479c615bbc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oseltamivir 20V, Negative-QTOF	splash10-02t9-2091000000-dafdec8458549b80e2b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oseltamivir 40V, Negative-QTOF	splash10-0ap1-9830000000-e6541c125795bb30888f	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00198	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00198	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00198

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58540

KEGG Compound ID

C08092

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oseltamivir

METLIN ID

Not Available

PubChem Compound

65028

PDB ID

Not Available

ChEBI ID

7798

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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

Enzyme Details

1. Sialidase-2

General function:: Involved in exo-alpha-sialidase activity
Specific function:: Hydrolyzes sialylated compounds.
Gene Name:: NEU2
Uniprot ID:: Q9Y3R4
Molecular weight:: Not Available

References

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 ]

Enzyme Details

2. Sialidase-1

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

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 ]

Enzyme Details

3. Liver carboxylesterase 1

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

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 ]
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 ]
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

Enzyme Details

1. Solute carrier family 15 member 1

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

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 ]

Enzyme Details

2. Multidrug resistance-associated protein 4

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

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 ]

Showing metabocard for Oseltamivir (HMDB0014343)

MOL for HMDB0014343 (Oseltamivir)

3D MOL for HMDB0014343 (Oseltamivir)

3D SDF for HMDB0014343 (Oseltamivir)

3D-SDF for HMDB0014343 (Oseltamivir)

PDB for HMDB0014343 (Oseltamivir)

3D PDB for HMDB0014343 (Oseltamivir)

SMILES for HMDB0014343 (Oseltamivir)

INCHI for HMDB0014343 (Oseltamivir)

Structure for HMDB0014343 (Oseltamivir)

3D Structure for HMDB0014343 (Oseltamivir)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

Transporters

References

References