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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:04 UTC

HMDB ID

HMDB0015662

Secondary Accession Numbers

HMDB15662

Metabolite Identification

Common Name

Fosaprepitant

Description

Fosaprepitant is only found in individuals that have used or taken this drug. It is an intravenously administered antiemetic drug. It is a prodrug of Aprepitant. It aids in the prevention of acute and delayed nausea and vomiting associated with chemotherapy treatment.Aprepitant has been shown in animal models to inhibit emesis induced by cytotoxic chemotherapeutic agents, such as cisplatin, via central actions. Animal and human Positron Emission Tomography (PET) studies with Aprepitant have shown that it crosses the blood brain barrier and occupies brain NK1 receptors. Animal and human studies show that Aprepitant augments the antiemetic activity of the 5-HT₃-receptor antagonist ondansetron and the corticosteroid ethasone and inhibits both the acute and delayed phases of cisplatin induced emesis.In summary, the active form of fosaprepitant is as an NK1 antagonist which is because it blocks signals given off by NK1 receptors. This therefore decreases the likelihood of vomiting in patients experiencing.

Structure

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

219090
  Mrv0541 02241212492D          

 41 44  0  0  1  0            999 V2000
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    3.0790   -2.2299    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0702    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.7682    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    2.1972    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    4.7828    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    3.9578    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    3.9578    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4922   -2.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3484   -3.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4521   -3.0504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 38 40  1  0  0  0  0
M  END

HMDB0015662
     RDKit          3D
Fosaprepitant
 63 66  0  0  0  0  0  0  0  0999 V2000
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    3.6475   -1.0365    0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

219090
  Mrv0541 02241212492D          

 41 44  0  0  1  0            999 V2000
    8.5947   -3.9756    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.2299    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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 17 36  1  0  0  0  0
 18 36  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  1  0  0  0
 21 22  1  0  0  0  0
 23 26  1  0  0  0  0
 24 27  2  0  0  0  0
 24 28  1  0  0  0  0
 25 29  1  0  0  0  0
 25 30  1  0  0  0  0
 27 31  1  0  0  0  0
 28 32  2  0  0  0  0
 29 33  2  0  0  0  0
 29 34  1  0  0  0  0
 31 35  2  0  0  0  0
 32 35  1  0  0  0  0
 33 37  1  0  0  0  0
 34 38  2  0  0  0  0
 37 39  2  0  0  0  0
 37 41  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015662

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(N2)P(O)(O)=O)[C@H]1C1=CC=C(F)C=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C23H22F7N4O6P/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)40-20-19(13-2-4-17(24)5-3-13)33(6-7-39-20)11-18-31-21(35)34(32-18)41(36,37)38/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H,31,32,35)(H2,36,37,38)/t12-,19+,20-/m1/s1

> <INCHI_KEY>
BARDROPHSZEBKC-OITMNORJSA-N

> <FORMULA>
C23H22F7N4O6P

> <MOLECULAR_WEIGHT>
614.4066

> <EXACT_MASS>
614.116518403

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
49.92109284745744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-5-oxo-2,5-dihydro-1H-1,2,4-triazol-1-yl)phosphonic acid

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.4006789286538854

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.148697136990222

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0232240490887041

> <JCHEM_PKA_STRONGEST_BASIC>
5.689656532048464

> <JCHEM_POLAR_SURFACE_AREA>
123.92999999999999

> <JCHEM_REFRACTIVITY>
138.63040000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fosaprepitant

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015662
     RDKit          3D
Fosaprepitant
 63 66  0  0  0  0  0  0  0  0999 V2000
   -3.1856    1.8352   -2.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5417    0.7677   -1.1440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6618    1.3834   -0.2826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999    0.9000   -0.4898 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2168    1.9053   -1.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1365    1.1337   -2.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592    0.3515   -1.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8058    0.4034    0.2057 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2022   -0.7731    0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475   -1.0365    0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632   -0.1539    0.3170 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361   -0.8169    0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8576   -0.3798   -0.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5561   -2.0865    0.8031 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7677   -3.3189    1.0039 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.5354   -4.1034    2.2795 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2876   -2.5893    1.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8516   -4.3745   -0.3113 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680   -2.1750    1.0621 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5345    0.8607    0.6552 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6969    2.2367    1.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6451    3.0762    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7941    4.3492    1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873    4.7511    2.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1557    5.9892    2.7665 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490    3.8941    2.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1202    2.5975    2.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -0.1232   -0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0445   -0.0130    0.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0206   -0.8904    1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5936   -0.8425    2.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7377   -0.0460    2.5625 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0179   -2.1184    2.9432 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6697   -0.4611    3.4849 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5228   -1.8965    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0383   -2.0160   -0.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5186   -3.0381   -1.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4587   -3.8746   -2.1500 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8485   -2.4004   -3.0709 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5604   -3.7871   -1.3929 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0794   -1.1465   -1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922    1.5424   -3.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341    1.9825   -1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847    2.7796   -1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    0.0968   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487   -0.0059   -1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6605    1.8319   -2.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5367    0.4546   -2.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    0.6822   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0249   -0.7006   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6302   -1.6430    0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9686   -0.6729    2.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5614   -2.3225    0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3236   -4.0549   -1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -3.0267    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237    0.2208    1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714    2.7362   -0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5374    5.0089    0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499    4.2628    3.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8619    1.9205    2.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848    0.7595    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2836   -2.5940    0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6809   -1.2318   -2.3607 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 14 19  1  0
  8 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
  2 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 30 35  2  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  1  0
 37 40  1  0
 36 41  2  0
 20  4  1  0
 27 21  1  0
 41 28  1  0
 19 10  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  6
  4 46  1  6
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  9 51  1  0
  9 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  1
 22 57  1  0
 23 58  1  0
 26 59  1  0
 27 60  1  0
 29 61  1  0
 35 62  1  0
 41 63  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 219090                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  P   UNK     0      16.043  -7.421   0.000  0.00  0.00           P+0
HETATM    2  F   UNK     0       5.747  -4.162   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       3.080   1.998   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       5.184   1.434   0.000  0.00  0.00           F+0
HETATM    5  F   UNK     0       3.644   4.101   0.000  0.00  0.00           F+0
HETATM    6  F   UNK     0       7.081   8.928   0.000  0.00  0.00           F+0
HETATM    7  F   UNK     0       8.621   7.388   0.000  0.00  0.00           F+0
HETATM    8  F   UNK     0       5.541   7.388   0.000  0.00  0.00           F+0
HETATM    9  O   UNK     0      12.416   1.228   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       9.748   1.228   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      17.719  -4.520   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      16.670  -8.828   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      17.450  -6.795   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      14.637  -8.048   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      12.416  -1.852   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      13.911  -5.694   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      15.157  -3.536   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      15.417  -6.014   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      11.082  -1.082   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.082   0.458   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.750  -1.082   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.750   0.458   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.416  -3.392   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.748  -1.852   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.748   2.768   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.750  -4.162   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.415  -1.082   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.748  -3.392   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.415   3.538   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.082   3.538   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.081  -1.852   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.415  -4.162   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.415   5.078   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.081   2.768   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.081  -3.392   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.187  -4.680   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.081   5.848   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.747   3.538   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.747   5.078   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.414   2.768   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.081   7.388   0.000  0.00  0.00           C+0
CONECT    1   12   13   14   18                                             
CONECT    2   35                                                            
CONECT    3   40                                                            
CONECT    4   40                                                            
CONECT    5   40                                                            
CONECT    6   41                                                            
CONECT    7   41                                                            
CONECT    8   41                                                            
CONECT    9   20   22                                                       
CONECT   10   20   25                                                       
CONECT   11   36                                                            
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15   19   21   23                                                  
CONECT   16   18   26                                                       
CONECT   17   26   36                                                       
CONECT   18    1   16   36                                                  
CONECT   19   15   20   24                                                  
CONECT   20    9   10   19                                                  
CONECT   21   15   22                                                       
CONECT   22    9   21                                                       
CONECT   23   15   26                                                       
CONECT   24   19   27   28                                                  
CONECT   25   10   29   30                                                  
CONECT   26   16   17   23                                                  
CONECT   27   24   31                                                       
CONECT   28   24   32                                                       
CONECT   29   25   33   34                                                  
CONECT   30   25                                                            
CONECT   31   27   35                                                       
CONECT   32   28   35                                                       
CONECT   33   29   37                                                       
CONECT   34   29   38                                                       
CONECT   35    2   31   32                                                  
CONECT   36   11   17   18                                                  
CONECT   37   33   39   41                                                  
CONECT   38   34   39   40                                                  
CONECT   39   37   38                                                       
CONECT   40    3    4    5   38                                             
CONECT   41    6    7    8   37                                             
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

COMPND    HMDB0015662
HETATM    1  C1  UNL     1      -3.186   1.835  -2.023  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.542   0.768  -1.144  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.662   1.383  -0.283  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.400   0.900  -0.490  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.217   1.905  -1.348  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.136   1.134  -2.064  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.059   0.352  -1.177  1.00  0.00           C  
HETATM    8  N1  UNL     1       1.806   0.403   0.206  1.00  0.00           N  
HETATM    9  C6  UNL     1       2.202  -0.773   0.945  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.648  -1.036   0.781  1.00  0.00           C  
HETATM   11  N2  UNL     1       4.563  -0.154   0.317  1.00  0.00           N  
HETATM   12  C8  UNL     1       5.736  -0.817   0.337  1.00  0.00           C  
HETATM   13  O3  UNL     1       6.858  -0.380  -0.011  1.00  0.00           O  
HETATM   14  N3  UNL     1       5.556  -2.087   0.803  1.00  0.00           N  
HETATM   15  P1  UNL     1       6.768  -3.319   1.004  1.00  0.00           P  
HETATM   16  O4  UNL     1       6.535  -4.103   2.279  1.00  0.00           O  
HETATM   17  O5  UNL     1       8.288  -2.589   1.148  1.00  0.00           O  
HETATM   18  O6  UNL     1       6.852  -4.374  -0.311  1.00  0.00           O  
HETATM   19  N4  UNL     1       4.268  -2.175   1.062  1.00  0.00           N  
HETATM   20  C9  UNL     1       0.534   0.861   0.655  1.00  0.00           C  
HETATM   21  C10 UNL     1       0.697   2.237   1.281  1.00  0.00           C  
HETATM   22  C11 UNL     1       1.645   3.076   0.725  1.00  0.00           C  
HETATM   23  C12 UNL     1       1.794   4.349   1.238  1.00  0.00           C  
HETATM   24  C13 UNL     1       0.987   4.751   2.300  1.00  0.00           C  
HETATM   25  F1  UNL     1       1.156   5.989   2.767  1.00  0.00           F  
HETATM   26  C14 UNL     1       0.049   3.894   2.838  1.00  0.00           C  
HETATM   27  C15 UNL     1      -0.120   2.597   2.331  1.00  0.00           C  
HETATM   28  C16 UNL     1      -3.548  -0.123  -0.561  1.00  0.00           C  
HETATM   29  C17 UNL     1      -4.045  -0.013   0.721  1.00  0.00           C  
HETATM   30  C18 UNL     1      -5.021  -0.890   1.171  1.00  0.00           C  
HETATM   31  C19 UNL     1      -5.594  -0.842   2.551  1.00  0.00           C  
HETATM   32  F2  UNL     1      -6.738  -0.046   2.563  1.00  0.00           F  
HETATM   33  F3  UNL     1      -6.018  -2.118   2.943  1.00  0.00           F  
HETATM   34  F4  UNL     1      -4.670  -0.461   3.485  1.00  0.00           F  
HETATM   35  C20 UNL     1      -5.523  -1.897   0.349  1.00  0.00           C  
HETATM   36  C21 UNL     1      -5.038  -2.016  -0.922  1.00  0.00           C  
HETATM   37  C22 UNL     1      -5.519  -3.038  -1.881  1.00  0.00           C  
HETATM   38  F5  UNL     1      -4.459  -3.875  -2.150  1.00  0.00           F  
HETATM   39  F6  UNL     1      -5.848  -2.400  -3.071  1.00  0.00           F  
HETATM   40  F7  UNL     1      -6.560  -3.787  -1.393  1.00  0.00           F  
HETATM   41  C23 UNL     1      -4.079  -1.147  -1.344  1.00  0.00           C  
HETATM   42  H1  UNL     1      -3.192   1.542  -3.091  1.00  0.00           H  
HETATM   43  H2  UNL     1      -4.234   1.983  -1.737  1.00  0.00           H  
HETATM   44  H3  UNL     1      -2.585   2.780  -1.957  1.00  0.00           H  
HETATM   45  H4  UNL     1      -1.966   0.097  -1.876  1.00  0.00           H  
HETATM   46  H5  UNL     1      -0.349  -0.006  -1.121  1.00  0.00           H  
HETATM   47  H6  UNL     1       1.661   1.832  -2.741  1.00  0.00           H  
HETATM   48  H7  UNL     1       0.537   0.455  -2.706  1.00  0.00           H  
HETATM   49  H8  UNL     1       3.099   0.682  -1.464  1.00  0.00           H  
HETATM   50  H9  UNL     1       2.025  -0.701  -1.517  1.00  0.00           H  
HETATM   51  H10 UNL     1       1.630  -1.643   0.602  1.00  0.00           H  
HETATM   52  H11 UNL     1       1.969  -0.673   2.034  1.00  0.00           H  
HETATM   53  H12 UNL     1       8.561  -2.323   0.241  1.00  0.00           H  
HETATM   54  H13 UNL     1       6.324  -4.055  -1.073  1.00  0.00           H  
HETATM   55  H14 UNL     1       3.763  -3.027   1.441  1.00  0.00           H  
HETATM   56  H15 UNL     1       0.224   0.221   1.504  1.00  0.00           H  
HETATM   57  H16 UNL     1       2.271   2.736  -0.097  1.00  0.00           H  
HETATM   58  H17 UNL     1       2.537   5.009   0.810  1.00  0.00           H  
HETATM   59  H18 UNL     1      -0.550   4.263   3.647  1.00  0.00           H  
HETATM   60  H19 UNL     1      -0.862   1.921   2.762  1.00  0.00           H  
HETATM   61  H20 UNL     1      -3.685   0.759   1.379  1.00  0.00           H  
HETATM   62  H21 UNL     1      -6.284  -2.594   0.666  1.00  0.00           H  
HETATM   63  H22 UNL     1      -3.681  -1.232  -2.361  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3   28   45
CONECT    3    4
CONECT    4    5   20   46
CONECT    5    6
CONECT    6    7   47   48
CONECT    7    8   49   50
CONECT    8    9   20
CONECT    9   10   51   52
CONECT   10   11   11   19
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   19
CONECT   15   16   16   17   18
CONECT   17   53
CONECT   18   54
CONECT   19   55
CONECT   20   21   56
CONECT   21   22   22   27
CONECT   22   23   57
CONECT   23   24   24   58
CONECT   24   25   26
CONECT   26   27   27   59
CONECT   27   60
CONECT   28   29   29   41
CONECT   29   30   61
CONECT   30   31   35   35
CONECT   31   32   33   34
CONECT   35   36   62
CONECT   36   37   41   41
CONECT   37   38   39   40
CONECT   41   63
END

HMDB0015662
     RDKit          3D
Fosaprepitant
 63 66  0  0  0  0  0  0  0  0999 V2000
   -3.1856    1.8352   -2.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5417    0.7677   -1.1440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6618    1.3834   -0.2826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999    0.9000   -0.4898 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2168    1.9053   -1.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1365    1.1337   -2.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592    0.3515   -1.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8058    0.4034    0.2057 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2022   -0.7731    0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475   -1.0365    0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632   -0.1539    0.3170 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361   -0.8169    0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8576   -0.3798   -0.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5561   -2.0865    0.8031 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7677   -3.3189    1.0039 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.5354   -4.1034    2.2795 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2876   -2.5893    1.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8516   -4.3745   -0.3113 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680   -2.1750    1.0621 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5345    0.8607    0.6552 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6969    2.2367    1.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6451    3.0762    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7941    4.3492    1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873    4.7511    2.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1557    5.9892    2.7665 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490    3.8941    2.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1202    2.5975    2.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480   -0.1232   -0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0445   -0.0130    0.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0206   -0.8904    1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5936   -0.8425    2.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7377   -0.0460    2.5625 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0179   -2.1184    2.9432 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6697   -0.4611    3.4849 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5228   -1.8965    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0383   -2.0160   -0.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5186   -3.0381   -1.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4587   -3.8746   -2.1500 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8485   -2.4004   -3.0709 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5604   -3.7871   -1.3929 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0794   -1.1465   -1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922    1.5424   -3.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2341    1.9825   -1.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847    2.7796   -1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    0.0968   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487   -0.0059   -1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6605    1.8319   -2.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5367    0.4546   -2.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    0.6822   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0249   -0.7006   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6302   -1.6430    0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9686   -0.6729    2.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5614   -2.3225    0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3236   -4.0549   -1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -3.0267    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237    0.2208    1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714    2.7362   -0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5374    5.0089    0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499    4.2628    3.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8619    1.9205    2.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848    0.7595    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2836   -2.5940    0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6809   -1.2318   -2.3607 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 14 19  1  0
  8 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
  2 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 30 35  2  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  1  0
 37 40  1  0
 36 41  2  0
 20  4  1  0
 27 21  1  0
 41 28  1  0
 19 10  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  6
  4 46  1  6
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  9 51  1  0
  9 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  1
 22 57  1  0
 23 58  1  0
 26 59  1  0
 27 60  1  0
 29 61  1  0
 35 62  1  0
 41 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Fosaprepitantum	ChEBI
L-758,298	ChEBI
L-758298	ChEBI
Emend for injection	HMDB
Fosaprepitant dimeglumine	HMDB

Chemical Formula

C₂₃H₂₂F₇N₄O₆P

Average Molecular Weight

614.4066

Monoisotopic Molecular Weight

614.116518403

IUPAC Name

(3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-5-oxo-2,5-dihydro-1H-1,2,4-triazol-1-yl)phosphonic acid

Traditional Name

fosaprepitant

CAS Registry Number

172673-20-0

SMILES

C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(N2)P(O)(O)=O)[C@H]1C1=CC=C(F)C=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F

InChI Identifier

InChI=1S/C23H22F7N4O6P/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)40-20-19(13-2-4-17(24)5-3-13)33(6-7-39-20)11-18-31-21(35)34(32-18)41(36,37)38/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H,31,32,35)(H2,36,37,38)/t12-,19+,20-/m1/s1

InChI Key

BARDROPHSZEBKC-OITMNORJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazinanes

Sub Class

Morpholines

Direct Parent

Phenylmorpholines

Alternative Parents

Substituents

Phenylmorpholine
Trifluoromethylbenzene
Fluorobenzene
Halobenzene
Aralkylamine
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Azole
Heteroaromatic compound
1,2,4-triazole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Oxacycle
Acetal
Alkyl fluoride
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alkyl halide
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

morpholines (CHEBI:64321 )
triazoles (CHEBI:64321 )
phosphoramide (CHEBI:64321 )
(trifluoromethyl)benzenes (CHEBI:64321 )
cyclic acetal (CHEBI:64321 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015662)

Source

Exogenous

Exogenous (HMDB: HMDB0015662)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0063 g/L	ALOGPS
logP	2.89	ALOGPS
logP	2.4	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	1.02	ChemAxon
pKa (Strongest Basic)	5.69	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	123.93 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	138.63 m³·mol⁻¹	ChemAxon
Polarizability	49.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	214.533	30932474
DeepCCS	[M-H]-	212.593	30932474
DeepCCS	[M-2H]-	246.037	30932474
DeepCCS	[M+Na]+	220.274	30932474
AllCCS	[M+H]+	226.2	32859911
AllCCS	[M+H-H2O]+	224.9	32859911
AllCCS	[M+NH4]+	227.4	32859911
AllCCS	[M+Na]+	227.7	32859911
AllCCS	[M-H]-	215.2	32859911
AllCCS	[M+Na-2H]-	215.8	32859911
AllCCS	[M+HCOO]-	216.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.56 minutes	32390414
Predicted by Siyang on May 30, 2022	16.0376 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.41 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	43.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2629.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	251.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	201.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	208.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	749.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	836.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1339.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	601.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1520.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	448.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	457.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	125.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	22.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fosaprepitant	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(N2)P(O)(O)=O)[C@H]1C1=CC=C(F)C=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F	3604.4	Standard polar	33892256
Fosaprepitant	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(N2)P(O)(O)=O)[C@H]1C1=CC=C(F)C=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F	3221.7	Standard non polar	33892256
Fosaprepitant	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(N2)P(O)(O)=O)[C@H]1C1=CC=C(F)C=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F	3466.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fosaprepitant,1TMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3233.2	Semi standard non polar	33892256
Fosaprepitant,1TMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3133.5	Standard non polar	33892256
Fosaprepitant,1TMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3951.8	Standard polar	33892256
Fosaprepitant,1TMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O)N2[Si](C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3296.0	Semi standard non polar	33892256
Fosaprepitant,1TMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O)N2[Si](C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3190.1	Standard non polar	33892256
Fosaprepitant,1TMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O)N2[Si](C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	4099.2	Standard polar	33892256
Fosaprepitant,2TMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3286.7	Semi standard non polar	33892256
Fosaprepitant,2TMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3106.6	Standard non polar	33892256
Fosaprepitant,2TMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3678.1	Standard polar	33892256
Fosaprepitant,2TMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C)N2[Si](C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3346.7	Semi standard non polar	33892256
Fosaprepitant,2TMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C)N2[Si](C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3139.7	Standard non polar	33892256
Fosaprepitant,2TMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C)N2[Si](C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3810.8	Standard polar	33892256
Fosaprepitant,3TMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N2[Si](C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3426.0	Semi standard non polar	33892256
Fosaprepitant,3TMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N2[Si](C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3127.5	Standard non polar	33892256
Fosaprepitant,3TMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N2[Si](C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3626.4	Standard polar	33892256
Fosaprepitant,1TBDMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C(C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3421.9	Semi standard non polar	33892256
Fosaprepitant,1TBDMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C(C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3275.3	Standard non polar	33892256
Fosaprepitant,1TBDMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C(C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	4041.4	Standard polar	33892256
Fosaprepitant,1TBDMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O)N2[Si](C)(C)C(C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3488.2	Semi standard non polar	33892256
Fosaprepitant,1TBDMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O)N2[Si](C)(C)C(C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3340.3	Standard non polar	33892256
Fosaprepitant,1TBDMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O)N2[Si](C)(C)C(C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	4093.8	Standard polar	33892256
Fosaprepitant,2TBDMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3659.4	Semi standard non polar	33892256
Fosaprepitant,2TBDMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3397.3	Standard non polar	33892256
Fosaprepitant,2TBDMS,isomer #1	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[NH]2)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3865.5	Standard polar	33892256
Fosaprepitant,2TBDMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3709.3	Semi standard non polar	33892256
Fosaprepitant,2TBDMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3439.8	Standard non polar	33892256
Fosaprepitant,2TBDMS,isomer #2	C[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(P(=O)(O)O[Si](C)(C)C(C)(C)C)N2[Si](C)(C)C(C)(C)C)[C@H]1C1=CC=C(F)C=C1)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1	3936.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fosaprepitant GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-0469020000-a9d53cff50121f0ac397	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 10V, Positive-QTOF	splash10-014l-1291148000-89d7ce5293bc9b67d05c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 20V, Positive-QTOF	splash10-0a4l-0090120000-90a954db621c91e2b6b9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 40V, Positive-QTOF	splash10-01pk-9640000000-5e645105fbd967a5973f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 10V, Negative-QTOF	splash10-0006-9320110000-e5a11eb20cb539f51093	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 20V, Negative-QTOF	splash10-0a4l-2091220000-cdeb0047166d8b481ca8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 40V, Negative-QTOF	splash10-0006-9130000000-4475aa8dcea01509b8cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 10V, Positive-QTOF	splash10-05mo-0098017000-b3c70a835cf33fa90790	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 20V, Positive-QTOF	splash10-05mx-0092033000-6371fe9f0667b041c9a2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 40V, Positive-QTOF	splash10-0ffx-0791000000-0e95b35ac4fd4a5233e1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 10V, Negative-QTOF	splash10-03di-0001019000-0dac5bd74f2a8ef931e7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 20V, Negative-QTOF	splash10-0bvi-8696383000-679567e6c5615842e08c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosaprepitant 40V, Negative-QTOF	splash10-000t-6310910000-d9ef03984b10377db0eb	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB06717	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06717	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06717

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

189912

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fosaprepitant_dimeglumine

METLIN ID

Not Available

PubChem Compound

219090

PDB ID

Not Available

ChEBI ID

64321

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

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Navari RM: Fosaprepitant: a neurokinin-1 receptor antagonist for the prevention of chemotherapy-induced nausea and vomiting. Expert Rev Anticancer Ther. 2008 Nov;8(11):1733-42. doi: 10.1586/14737140.8.11.1733. [PubMed:18983233 ]
Sanchez RI, Wang RW, Newton DJ, Bakhtiar R, Lu P, Chiu SH, Evans DC, Huskey SE: Cytochrome P450 3A4 is the major enzyme involved in the metabolism of the substance P receptor antagonist aprepitant. Drug Metab Dispos. 2004 Nov;32(11):1287-92. Epub 2004 Aug 10. [PubMed:15304427 ]

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Navari RM: Fosaprepitant: a neurokinin-1 receptor antagonist for the prevention of chemotherapy-induced nausea and vomiting. Expert Rev Anticancer Ther. 2008 Nov;8(11):1733-42. doi: 10.1586/14737140.8.11.1733. [PubMed:18983233 ]

Enzyme Details

3. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Navari RM: Fosaprepitant: a neurokinin-1 receptor antagonist for the prevention of chemotherapy-induced nausea and vomiting. Expert Rev Anticancer Ther. 2008 Nov;8(11):1733-42. doi: 10.1586/14737140.8.11.1733. [PubMed:18983233 ]

Enzyme Details

4. Substance-P receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is a receptor for the tachykinin neuropeptide substance P. It is probably associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of affinity of this receptor to tachykinins is:substance P > substance K > neuromedin-K
Gene Name:: TACR1
Uniprot ID:: P25103
Molecular weight:: 46250.5

References

Poli-Bigelli S, Rodrigues-Pereira J, Carides AD, Julie Ma G, Eldridge K, Hipple A, Evans JK, Horgan KJ, Lawson F: Addition of the neurokinin 1 receptor antagonist aprepitant to standard antiemetic therapy improves control of chemotherapy-induced nausea and vomiting. Results from a randomized, double-blind, placebo-controlled trial in Latin America. Cancer. 2003 Jun 15;97(12):3090-8. [PubMed:12784346 ]
Zhao MM, McNamara JM, Ho GJ, Emerson KM, Song ZJ, Tschaen DM, Brands KM, Dolling UH, Grabowski EJ, Reider PJ, Cottrell IF, Ashwood MS, Bishop BC: Practical asymmetric synthesis of aprepitant, a potent human NK-1 receptor antagonist, via a stereoselective Lewis acid-catalyzed trans acetalization reaction. J Org Chem. 2002 Sep 20;67(19):6743-7. [PubMed:12227806 ]
Bergstrom M, Hargreaves RJ, Burns HD, Goldberg MR, Sciberras D, Reines SA, Petty KJ, Ogren M, Antoni G, Langstrom B, Eskola O, Scheinin M, Solin O, Majumdar AK, Constanzer ML, Battisti WP, Bradstreet TE, Gargano C, Hietala J: Human positron emission tomography studies of brain neurokinin 1 receptor occupancy by aprepitant. Biol Psychiatry. 2004 May 15;55(10):1007-12. [PubMed:15121485 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Fosaprepitant (HMDB0015662)

MOL for HMDB0015662 (Fosaprepitant)

3D MOL for HMDB0015662 (Fosaprepitant)

3D SDF for HMDB0015662 (Fosaprepitant)

3D-SDF for HMDB0015662 (Fosaprepitant)

PDB for HMDB0015662 (Fosaprepitant)

3D PDB for HMDB0015662 (Fosaprepitant)

SMILES for HMDB0015662 (Fosaprepitant)

INCHI for HMDB0015662 (Fosaprepitant)

Structure for HMDB0015662 (Fosaprepitant)

3D Structure for HMDB0015662 (Fosaprepitant)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References