Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:05:55 UTC

Update Date

2021-09-26 23:04:42 UTC

HMDB ID

HMDB0252247

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Fiacitabine

Description

NSC 382097;FIAC;FOAC belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Based on a literature review very few articles have been published on NSC 382097;FIAC;FOAC. This compound has been identified in human blood as reported by (PMID: 31557052 ). Fiacitabine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fiacitabine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0252247
     RDKit          3D
Fiacitabine
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.9000   -0.3258    0.1424 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5273   -0.3775   -0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -1.5748   -0.3195 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -1.7033   -0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508   -2.8624   -0.7502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9086   -0.6028   -0.7649 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895   -0.8020   -1.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    0.4061   -1.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    0.7504   -0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8339    1.8220   -0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2424    2.9755   -0.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -0.5774    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0517   -0.6192    1.3831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -1.4859    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736   -2.7732   -0.2519 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161    0.6358   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7546    0.7573   -0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6853    2.6191   -0.0800 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.2484   -0.6020    1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -0.0067   -0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5192   -1.4941   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    0.9969    0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398    2.0505    0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6261    1.4795   -1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850    2.8060   -1.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1742   -0.8619   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469   -0.7795    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6534   -1.3686    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7993    1.5180   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 17  2  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  7 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
M  END


  Mrv1652309112112062D          

 18 19  0  0  0  0            999 V2000
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -0.5465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8538   -1.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -2.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486   -1.9986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2032   -0.2916    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    3.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    2.4134    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
  9 16  1  0  0  0  0
  3 17  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252247

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)N(C=C1I)C1OC(CO)C(O)C1F

> <INCHI_IDENTIFIER>
InChI=1S/C9H11FIN3O4/c10-5-6(16)4(2-15)18-8(5)14-1-3(11)7(12)13-9(14)17/h1,4-6,8,15-16H,2H2,(H2,12,13,17)

> <INCHI_KEY>
GIMSJJHKKXRFGV-UHFFFAOYSA-N

> <FORMULA>
C9H11FIN3O4

> <MOLECULAR_WEIGHT>
371.107

> <EXACT_MASS>
370.97783

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
27.30034530004857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-1-[3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2-dihydropyrimidin-2-one

> <ALOGPS_LOGP>
-0.17

> <JCHEM_LOGP>
-0.9207400583333332

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.690168004598533

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.719689100768814

> <JCHEM_PKA_STRONGEST_BASIC>
-2.464417799568461

> <JCHEM_POLAR_SURFACE_AREA>
108.38000000000001

> <JCHEM_REFRACTIVITY>
66.2017

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-amino-1-[3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252247
     RDKit          3D
Fiacitabine
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.9000   -0.3258    0.1424 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5273   -0.3775   -0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -1.5748   -0.3195 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -1.7033   -0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508   -2.8624   -0.7502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9086   -0.6028   -0.7649 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895   -0.8020   -1.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    0.4061   -1.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    0.7504   -0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8339    1.8220   -0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2424    2.9755   -0.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -0.5774    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0517   -0.6192    1.3831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -1.4859    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736   -2.7732   -0.2519 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161    0.6358   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7546    0.7573   -0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6853    2.6191   -0.0800 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.2484   -0.6020    1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -0.0067   -0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5192   -1.4941   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    0.9969    0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398    2.0505    0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6261    1.4795   -1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850    2.8060   -1.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1742   -0.8619   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469   -0.7795    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6534   -1.3686    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7993    1.5180   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 17  2  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  7 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.802   3.735   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.136   4.505   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.469   3.735   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.803   1.425   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       5.136   1.425   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.381  -1.020   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.906  -2.485   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.366  -2.485   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.890  -1.020   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.460  -3.731   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.087  -5.138   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.811  -3.731   0.000  0.00  0.00           O+0
HETATM   16  F   UNK     0       7.846  -0.544   0.000  0.00  0.00           F+0
HETATM   17  N   UNK     0       5.136   6.045   0.000  0.00  0.00           N+0
HETATM   18  I   UNK     0       2.468   4.505   0.000  0.00  0.00           I+0
CONECT    1    2    7                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1    8                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    8                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16    9                                                            
CONECT   17    3                                                            
CONECT   18    2                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0252247
HETATM    1  N1  UNL     1       4.900  -0.326   0.142  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.527  -0.378  -0.169  1.00  0.00           C  
HETATM    3  N2  UNL     1       2.955  -1.575  -0.319  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.669  -1.703  -0.613  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.151  -2.862  -0.750  1.00  0.00           O  
HETATM    6  N3  UNL     1       0.909  -0.603  -0.765  1.00  0.00           N  
HETATM    7  C3  UNL     1      -0.490  -0.802  -1.085  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.085   0.406  -1.319  1.00  0.00           O  
HETATM    9  C4  UNL     1      -1.821   0.750  -0.179  1.00  0.00           C  
HETATM   10  C5  UNL     1      -2.834   1.822  -0.471  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.242   2.976  -0.932  1.00  0.00           O  
HETATM   12  C6  UNL     1      -2.474  -0.577   0.143  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.052  -0.619   1.383  1.00  0.00           O  
HETATM   14  C7  UNL     1      -1.243  -1.486   0.037  1.00  0.00           C  
HETATM   15  F1  UNL     1      -1.574  -2.773  -0.252  1.00  0.00           F  
HETATM   16  C8  UNL     1       1.416   0.636  -0.628  1.00  0.00           C  
HETATM   17  C9  UNL     1       2.755   0.757  -0.323  1.00  0.00           C  
HETATM   18  I1  UNL     1       3.685   2.619  -0.080  1.00  0.00           I  
HETATM   19  H1  UNL     1       5.248  -0.602   1.076  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.578  -0.007  -0.571  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.519  -1.494  -1.951  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.133   0.997   0.624  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.340   2.050   0.503  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.626   1.480  -1.149  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.285   2.806  -1.149  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.174  -0.862  -0.684  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.047  -0.779   1.331  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.653  -1.369   0.960  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.799   1.518  -0.752  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3    3   17
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   16
CONECT    7    8   14   21
CONECT    8    9
CONECT    9   10   12   22
CONECT   10   11   23   24
CONECT   11   25
CONECT   12   13   14   26
CONECT   13   27
CONECT   14   15   28
CONECT   16   17   17   29
CONECT   17   18
END

HMDB0252247
     RDKit          3D
Fiacitabine
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.9000   -0.3258    0.1424 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5273   -0.3775   -0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -1.5748   -0.3195 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -1.7033   -0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508   -2.8624   -0.7502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9086   -0.6028   -0.7649 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895   -0.8020   -1.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    0.4061   -1.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    0.7504   -0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8339    1.8220   -0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2424    2.9755   -0.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -0.5774    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0517   -0.6192    1.3831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -1.4859    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736   -2.7732   -0.2519 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4161    0.6358   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7546    0.7573   -0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6853    2.6191   -0.0800 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.2484   -0.6020    1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776   -0.0067   -0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5192   -1.4941   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    0.9969    0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398    2.0505    0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6261    1.4795   -1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850    2.8060   -1.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1742   -0.8619   -0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469   -0.7795    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6534   -1.3686    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7993    1.5180   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 17  2  1  0
 14  7  1  0
  1 19  1  0
  1 20  1  0
  7 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₁₁FIN₃O₄

Average Molecular Weight

371.107

Monoisotopic Molecular Weight

370.97783

IUPAC Name

4-amino-1-[3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2-dihydropyrimidin-2-one

Traditional Name

4-amino-1-[3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one

CAS Registry Number

Not Available

SMILES

NC1=NC(=O)N(C=C1I)C1OC(CO)C(O)C1F

InChI Identifier

InChI=1S/C9H11FIN3O4/c10-5-6(16)4(2-15)18-8(5)14-1-3(11)7(12)13-9(14)17/h1,4-6,8,15-16H,2H2,(H2,12,13,17)

InChI Key

GIMSJJHKKXRFGV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Pyrimidine 2'-deoxyribonucleoside
Pyrimidone
Halopyrimidine
Aminopyrimidine
Imidolactam
Pyrimidine
Hydropyrimidine
Aryl iodide
Aryl halide
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Halohydrin
Fluorohydrin
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organoiodide
Organofluoride
Organohalogen compound
Amine
Alkyl halide
Alkyl fluoride
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	-0.17	ALOGPS
logP	-0.92	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.72	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.2 m³·mol⁻¹	ChemAxon
Polarizability	27.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	168.347	30932474
DeepCCS	[M-H]-	165.989	30932474
DeepCCS	[M-2H]-	199.089	30932474
DeepCCS	[M+Na]+	174.44	30932474
AllCCS	[M+H]+	174.8	32859911
AllCCS	[M+H-H2O]+	171.7	32859911
AllCCS	[M+NH4]+	177.6	32859911
AllCCS	[M+Na]+	178.4	32859911
AllCCS	[M-H]-	161.5	32859911
AllCCS	[M+Na-2H]-	162.1	32859911
AllCCS	[M+HCOO]-	162.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fiacitabine	NC1=NC(=O)N(C=C1I)C1OC(CO)C(O)C1F	3563.7	Standard polar	33892256
Fiacitabine	NC1=NC(=O)N(C=C1I)C1OC(CO)C(O)C1F	1992.9	Standard non polar	33892256
Fiacitabine	NC1=NC(=O)N(C=C1I)C1OC(CO)C(O)C1F	2655.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fiacitabine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N(C2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C2F)C=C1I	2569.2	Semi standard non polar	33892256
Fiacitabine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N(C2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C2F)C=C1I	2429.5	Standard non polar	33892256
Fiacitabine,3TMS,isomer #1	C[Si](C)(C)NC1=NC(=O)N(C2OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C2F)C=C1I	2791.7	Standard polar	33892256
Fiacitabine,3TMS,isomer #2	C[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(F)C1O	2562.9	Semi standard non polar	33892256
Fiacitabine,3TMS,isomer #2	C[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(F)C1O	2579.8	Standard non polar	33892256
Fiacitabine,3TMS,isomer #2	C[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(F)C1O	2847.5	Standard polar	33892256
Fiacitabine,3TMS,isomer #3	C[Si](C)(C)OC1C(CO)OC(N2C=C(I)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C1F	2573.3	Semi standard non polar	33892256
Fiacitabine,3TMS,isomer #3	C[Si](C)(C)OC1C(CO)OC(N2C=C(I)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C1F	2536.9	Standard non polar	33892256
Fiacitabine,3TMS,isomer #3	C[Si](C)(C)OC1C(CO)OC(N2C=C(I)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C1F	2772.3	Standard polar	33892256
Fiacitabine,4TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(F)C1O[Si](C)(C)C	2548.6	Semi standard non polar	33892256
Fiacitabine,4TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(F)C1O[Si](C)(C)C	2573.0	Standard non polar	33892256
Fiacitabine,4TMS,isomer #1	C[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(F)C1O[Si](C)(C)C	2513.9	Standard polar	33892256
Fiacitabine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2F)C=C1I	3290.2	Semi standard non polar	33892256
Fiacitabine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2F)C=C1I	3035.6	Standard non polar	33892256
Fiacitabine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=O)N(C2OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2F)C=C1I	3073.1	Standard polar	33892256
Fiacitabine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)C(F)C1O	3261.6	Semi standard non polar	33892256
Fiacitabine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)C(F)C1O	3178.5	Standard non polar	33892256
Fiacitabine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)C(F)C1O	3067.2	Standard polar	33892256
Fiacitabine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C(CO)OC(N2C=C(I)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)C1F	3252.6	Semi standard non polar	33892256
Fiacitabine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C(CO)OC(N2C=C(I)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)C1F	3117.2	Standard non polar	33892256
Fiacitabine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C(CO)OC(N2C=C(I)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)C1F	2999.9	Standard polar	33892256
Fiacitabine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)C(F)C1O[Si](C)(C)C(C)(C)C	3441.8	Semi standard non polar	33892256
Fiacitabine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)C(F)C1O[Si](C)(C)C(C)(C)C	3307.8	Standard non polar	33892256
Fiacitabine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(N2C=C(I)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)C(F)C1O[Si](C)(C)C(C)(C)C	2911.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-9012000000-de34233ed0639e543ce4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fiacitabine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-04	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 - Fiacitabine 10V, Positive-QTOF	splash10-000i-0090000000-00aee80a64821d245c2f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fiacitabine 20V, Positive-QTOF	splash10-000i-0090000000-e0e901b5b2565f6b9837	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fiacitabine 40V, Positive-QTOF	splash10-000i-5090000000-7f6a95f73d0b2a59956b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fiacitabine 10V, Negative-QTOF	splash10-014r-0089000000-9c1e1d953461692b164e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fiacitabine 20V, Negative-QTOF	splash10-002k-1090000000-84b6564f71ec7358f20c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fiacitabine 40V, Negative-QTOF	splash10-0006-9100000000-783dd69b7e6067d9d174	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

304152

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

343110

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Fiacitabine (HMDB0252247)

MOL for HMDB0252247 (Fiacitabine)

3D MOL for HMDB0252247 (Fiacitabine)

3D SDF for HMDB0252247 (Fiacitabine)

3D-SDF for HMDB0252247 (Fiacitabine)

PDB for HMDB0252247 (Fiacitabine)

3D PDB for HMDB0252247 (Fiacitabine)

SMILES for HMDB0252247 (Fiacitabine)

INCHI for HMDB0252247 (Fiacitabine)

Structure for HMDB0252247 (Fiacitabine)

3D Structure for HMDB0252247 (Fiacitabine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra