Hmdb loader

Showing metabocard for Flucytosine (HMDB0015231)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2023-02-21 17:18:27 UTC
HMDB IDHMDB0015231
Secondary Accession Numbers
  • HMDB15231
Metabolite Identification
Common NameFlucytosine
DescriptionFlucytosine is only found in individuals that have used or taken this drug. It is a fluorinated cytosine analog that is used as an antifungal agent. [PubChem]Although the exact mode of action is unknown, it has been proposed that flucytosine acts directly on fungal organisms by competitive inhibition of purine and pyrimidine uptake and indirectly by intracellular metabolism to 5-fluorouracil. Flucytosine enters the fungal cell via cytosine permease; thus, flucytosine is metabolized to 5-fluorouracil within fungal organisms. The 5-fluorouracil is extensively incorporated into fungal RNA and inhibits synthesis of both DNA and RNA. The result is unbalanced growth and death of the fungal organism. It also appears to be an inhibitor of fungal thymidylate synthase.
Structure
Data?1676999907
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015231 (Flucytosine)

1099
  Mrv0541 02231215142D          

  9  9  0  0  0  0            999 V2000
    2.0930    1.0808    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.6683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  8  2  0  0  0  0
  3  6  1  0  0  0  0
  3  8  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
Download

3D MOL for HMDB0015231 (Flucytosine)

HMDB0015231
     RDKit          3D
Flucytosine
 13 13  0  0  0  0  0  0  0  0999 V2000
    2.0470   -0.1754    0.1243 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355   -0.0214    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0447    1.1675   -0.0455 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919    1.3104   -0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259    2.4577   -0.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0555    0.2184   -0.1198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4942   -1.0204   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231   -1.1617    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794   -2.4110    0.1304 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6105    0.1014    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5413   -0.5861   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489    2.0408   -0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1165   -1.9202   -0.0291 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
  8  2  2  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  7 13  1  0
M  END
Download

3D SDF for HMDB0015231 (Flucytosine)

1099
  Mrv0541 02231215142D          

  9  9  0  0  0  0            999 V2000
    2.0930    1.0808    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.6683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  8  2  0  0  0  0
  3  6  1  0  0  0  0
  3  8  1  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015231

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=C(F)C=NC(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)

> <INCHI_KEY>
XRECTZIEBJDKEO-UHFFFAOYSA-N

> <FORMULA>
C4H4FN3O

> <MOLECULAR_WEIGHT>
129.0925

> <EXACT_MASS>
129.03383997

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
9.973904378734243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-amino-5-fluoro-1,2-dihydropyrimidin-2-one

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-0.9481628816666665

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.163186658693784

> <JCHEM_PKA_STRONGEST_BASIC>
1.0557196693239448

> <JCHEM_POLAR_SURFACE_AREA>
67.48

> <JCHEM_REFRACTIVITY>
38.2177

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flucytosine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0015231 (Flucytosine)

HMDB0015231
     RDKit          3D
Flucytosine
 13 13  0  0  0  0  0  0  0  0999 V2000
    2.0470   -0.1754    0.1243 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355   -0.0214    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0447    1.1675   -0.0455 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919    1.3104   -0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259    2.4577   -0.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0555    0.2184   -0.1198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4942   -1.0204   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231   -1.1617    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794   -2.4110    0.1304 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6105    0.1014    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5413   -0.5861   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489    2.0408   -0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1165   -1.9202   -0.0291 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
  8  2  2  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  7 13  1  0
M  END
Download

PDB for HMDB0015231 (Flucytosine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1099                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       3.907   2.017   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0       9.242  -1.063   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       6.574  -1.063   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       3.907  -1.063   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.908   1.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.241  -0.293   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.241   1.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.908  -0.293   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.574   2.017   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    6    8                                                       
CONECT    4    6                                                            
CONECT    5    8    9                                                       
CONECT    6    3    4    7                                                  
CONECT    7    1    6    9                                                  
CONECT    8    2    3    5                                                  
CONECT    9    5    7                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
Download

3D PDB for HMDB0015231 (Flucytosine)

COMPND    HMDB0015231
HETATM    1  N1  UNL     1       2.047  -0.175   0.124  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.636  -0.021   0.039  1.00  0.00           C  
HETATM    3  N2  UNL     1       0.045   1.167  -0.045  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.292   1.310  -0.126  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.826   2.458  -0.206  1.00  0.00           O  
HETATM    6  N3  UNL     1      -2.056   0.218  -0.120  1.00  0.00           N  
HETATM    7  C3  UNL     1      -1.494  -1.020  -0.034  1.00  0.00           C  
HETATM    8  C4  UNL     1      -0.123  -1.162   0.048  1.00  0.00           C  
HETATM    9  F1  UNL     1       0.379  -2.411   0.130  1.00  0.00           F  
HETATM   10  H1  UNL     1       2.610   0.101   0.960  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.541  -0.586  -0.691  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.649   2.041  -0.050  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.116  -1.920  -0.029  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3    8    8
CONECT    3    4   12
CONECT    4    5    5    6
CONECT    6    7    7
CONECT    7    8   13
CONECT    8    9
END
Download

SMILES for HMDB0015231 (Flucytosine)

NC1=C(F)C=NC(=O)N1
Download

INCHI for HMDB0015231 (Flucytosine)

InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
5-FCChEBI
5-FluorocystosineChEBI
5-FluorocytosineChEBI
AncobonChEBI
AncotilChEBI
FlucytosinaChEBI
FlucytosinumChEBI
5-FluorocytosinHMDB
5-FlurocytosineHMDB
FlucytosinHMDB
FluocytosineHMDB
FluorcytosineHMDB
Dermatech brand OF flucytosineHMDB
Roche brand OF flucytosineHMDB
AlcobonHMDB
CSP Brand OF flucytosineHMDB
ICN pharmaceuticals brand OF flucytosineHMDB
Allphar brand OF flucytosineHMDB
Chemical FormulaC4H4FN3O
Average Molecular Weight129.0925
Monoisotopic Molecular Weight129.03383997
IUPAC Name6-amino-5-fluoro-1,2-dihydropyrimidin-2-one
Traditional Nameflucytosine
CAS Registry Number2022-85-7
SMILES
NC1=C(F)C=NC(=O)N1
InChI Identifier
InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
InChI KeyXRECTZIEBJDKEO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentHalopyrimidines
Alternative Parents
Substituents
  • Aminopyrimidine
  • Halopyrimidine
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point296 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.92 g/LNot Available
LogP-1.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.92 g/LALOGPS
logP-0.24ALOGPS
logP-0.95ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)8.16ChemAxon
pKa (Strongest Basic)1.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.48 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.22 m³·mol⁻¹ChemAxon
Polarizability9.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+126.36330932474
DeepCCS[M-H]-123.65230932474
DeepCCS[M-2H]-160.38830932474
DeepCCS[M+Na]+135.10130932474
AllCCS[M+H]+128.032859911
AllCCS[M+H-H2O]+123.332859911
AllCCS[M+NH4]+132.532859911
AllCCS[M+Na]+133.832859911
AllCCS[M-H]-120.932859911
AllCCS[M+Na-2H]-123.032859911
AllCCS[M+HCOO]-125.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.1.34 minutes32390414
Predicted by Siyang on May 30, 20229.1912 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.22 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid89.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid561.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid346.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid75.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid237.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid65.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid291.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid275.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)401.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid608.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid117.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid759.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid220.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid240.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate610.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA259.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water206.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FlucytosineNC1=C(F)C=NC(=O)N12350.8Standard polar33892256
FlucytosineNC1=C(F)C=NC(=O)N11314.5Standard non polar33892256
FlucytosineNC1=C(F)C=NC(=O)N11449.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Flucytosine,1TMS,isomer #1C[Si](C)(C)NC1=C(F)C=NC(=O)[NH]11432.3Semi standard non polar33892256
Flucytosine,1TMS,isomer #1C[Si](C)(C)NC1=C(F)C=NC(=O)[NH]11345.3Standard non polar33892256
Flucytosine,1TMS,isomer #1C[Si](C)(C)NC1=C(F)C=NC(=O)[NH]12001.2Standard polar33892256
Flucytosine,1TMS,isomer #2C[Si](C)(C)N1C(N)=C(F)C=NC1=O1429.9Semi standard non polar33892256
Flucytosine,1TMS,isomer #2C[Si](C)(C)N1C(N)=C(F)C=NC1=O1368.2Standard non polar33892256
Flucytosine,1TMS,isomer #2C[Si](C)(C)N1C(N)=C(F)C=NC1=O2093.8Standard polar33892256
Flucytosine,2TMS,isomer #1C[Si](C)(C)N(C1=C(F)C=NC(=O)[NH]1)[Si](C)(C)C1443.7Semi standard non polar33892256
Flucytosine,2TMS,isomer #1C[Si](C)(C)N(C1=C(F)C=NC(=O)[NH]1)[Si](C)(C)C1419.2Standard non polar33892256
Flucytosine,2TMS,isomer #1C[Si](C)(C)N(C1=C(F)C=NC(=O)[NH]1)[Si](C)(C)C1825.2Standard polar33892256
Flucytosine,2TMS,isomer #2C[Si](C)(C)NC1=C(F)C=NC(=O)N1[Si](C)(C)C1595.3Semi standard non polar33892256
Flucytosine,2TMS,isomer #2C[Si](C)(C)NC1=C(F)C=NC(=O)N1[Si](C)(C)C1427.1Standard non polar33892256
Flucytosine,2TMS,isomer #2C[Si](C)(C)NC1=C(F)C=NC(=O)N1[Si](C)(C)C1823.4Standard polar33892256
Flucytosine,3TMS,isomer #1C[Si](C)(C)N(C1=C(F)C=NC(=O)N1[Si](C)(C)C)[Si](C)(C)C1682.5Semi standard non polar33892256
Flucytosine,3TMS,isomer #1C[Si](C)(C)N(C1=C(F)C=NC(=O)N1[Si](C)(C)C)[Si](C)(C)C1586.6Standard non polar33892256
Flucytosine,3TMS,isomer #1C[Si](C)(C)N(C1=C(F)C=NC(=O)N1[Si](C)(C)C)[Si](C)(C)C1660.6Standard polar33892256
Flucytosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=C(F)C=NC(=O)[NH]11694.4Semi standard non polar33892256
Flucytosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=C(F)C=NC(=O)[NH]11520.9Standard non polar33892256
Flucytosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=C(F)C=NC(=O)[NH]12114.0Standard polar33892256
Flucytosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(N)=C(F)C=NC1=O1670.2Semi standard non polar33892256
Flucytosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(N)=C(F)C=NC1=O1538.2Standard non polar33892256
Flucytosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(N)=C(F)C=NC1=O2172.4Standard polar33892256
Flucytosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=C(F)C=NC(=O)[NH]1)[Si](C)(C)C(C)(C)C1897.7Semi standard non polar33892256
Flucytosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=C(F)C=NC(=O)[NH]1)[Si](C)(C)C(C)(C)C1835.5Standard non polar33892256
Flucytosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=C(F)C=NC(=O)[NH]1)[Si](C)(C)C(C)(C)C1999.3Standard polar33892256
Flucytosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=C(F)C=NC(=O)N1[Si](C)(C)C(C)(C)C1978.9Semi standard non polar33892256
Flucytosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=C(F)C=NC(=O)N1[Si](C)(C)C(C)(C)C1759.1Standard non polar33892256
Flucytosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=C(F)C=NC(=O)N1[Si](C)(C)C(C)(C)C2023.4Standard polar33892256
Flucytosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=C(F)C=NC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2243.8Semi standard non polar33892256
Flucytosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=C(F)C=NC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2192.0Standard non polar33892256
Flucytosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=C(F)C=NC(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2026.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Flucytosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-5900000000-62cd06162d248f459f772017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flucytosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flucytosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , negative-QTOFsplash10-002r-9400000000-acd1b588a4052f6fc2dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , negative-QTOFsplash10-002r-9400000000-a4e7dd3c4c886861c0ea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , negative-QTOFsplash10-000i-9200000000-b3fb9cad9c2b375b08c62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , negative-QTOFsplash10-000i-9100000000-11fb61e55faa71878d872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , negative-QTOFsplash10-000i-9000000000-13935b6ab4a3d8adaa082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , negative-QTOFsplash10-000i-9000000000-cd981efe159dd44555f42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-a228aa7f5ecaf516455f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QTOF , positive-QTOFsplash10-001i-0900000000-ec5b7f7d9f3c75649dc22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QTOF , positive-QTOFsplash10-03e9-0900000000-15df2a7b685c4dd4ca172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , positive-QTOFsplash10-001i-0900000000-7110f8accb80c700a2a52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , positive-QTOFsplash10-001i-0900000000-89290e0501d587938afb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , positive-QTOFsplash10-001i-0900000000-7248b6df062077397b612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , positive-QTOFsplash10-001i-1900000000-df83e87e1bcbc8311be62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , positive-QTOFsplash10-01q9-3900000000-42649a5ceee8a4619fc32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine LC-ESI-QFT , positive-QTOFsplash10-08gr-9800000000-8cb7a586d34dd79135612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine 0V, Positive-QTOFsplash10-001i-0900000000-973610269bb11b2539b92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine 10V, Positive-QTOFsplash10-001i-0900000000-f98fd5ea350e99bcbb132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine 0V, Positive-QTOFsplash10-001i-0900000000-f0b5eaeae6c5f2a922c32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flucytosine 30V, Positive-QTOFsplash10-0bti-9300000000-c7808ed54724dbe0b4db2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flucytosine 10V, Positive-QTOFsplash10-001i-0900000000-3daf46ab201d0847e7162016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flucytosine 20V, Positive-QTOFsplash10-001i-4900000000-08676c044da012e585092016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flucytosine 40V, Positive-QTOFsplash10-0007-9000000000-fc78e7fb18ada3e97d982016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flucytosine 10V, Negative-QTOFsplash10-004i-2900000000-d0b2503a7f5865ac1efd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flucytosine 20V, Negative-QTOFsplash10-00nu-9100000000-ee11917ba44963a8210b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flucytosine 40V, Negative-QTOFsplash10-0006-9000000000-e5c5889e9b5cd0c8cae92016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01099 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01099 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01099
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3249
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFlucytosine
METLIN IDNot Available
PubChem Compound3366
PDB IDNot Available
ChEBI ID5100
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bertout S, Dunyach C, Drakulovski P, Reynes J, Mallie M: Comparison of the Sensititre YeastOne(R) dilution method with the Clinical Laboratory Standards Institute (CLSI) M27-A3 microbroth dilution reference method for determining MIC of eight antifungal agents on 102 yeast strains. Pathol Biol (Paris). 2011 Feb;59(1):48-51. doi: 10.1016/j.patbio.2010.07.020. Epub 2010 Sep 16. [PubMed:20843616 ]
  2. Kaouech E, Kallel K, Belhadj S, Anane S, Ben Chaabane T, Ben Fadhl K, Khedher A, Meddeb B, Ben Lakhal S, Chaker E: [Twenty-two cases of neuromeningeal cryptococcosis in Tunisia]. Med Mal Infect. 2009 Dec;39(12):914-9. doi: 10.1016/j.medmal.2009.02.004. Epub 2009 Apr 8. [PubMed:19359114 ]
  3. Park BJ, Park JC, Taguchi H, Fukushima K, Hyon SH, Takatori K: Antifungal susceptibility of epigallocatechin 3-O-gallate (EGCg) on clinical isolates of pathogenic yeasts. Biochem Biophys Res Commun. 2006 Aug 25;347(2):401-5. Epub 2006 Jun 15. [PubMed:16831406 ]

Enzymes

Enzyme Details
1. DNA (cytosine-5)-methyltransferase 1
General function:
Involved in DNA binding
Specific function:
Methylates CpG residues. Preferentially methylates hemimethylated DNA. Associates with DNA replication sites in S phase maintaining the methylation pattern in the newly synthesized strand, that is essential for epigenetic inheritance. Associates with chromatin during G2 and M phases to maintain DNA methylation independently of replication. It is responsible for maintaining methylation patterns established in development. DNA methylation is coordinated with methylation of histones. Mediates transcriptional repression by direct binding to HDAC2. In association with DNMT3B and via the recruitment of CTCFL/BORIS, involved in activation of BAG1 gene expression by modulating dimethylation of promoter histone H3 at H3K4 and H3K9.
Gene Name:
DNMT1
Uniprot ID:
P26358
Molecular weight:
184817.425
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Shieh FK, Reich NO: AdoMet-dependent methyl-transfer: Glu119 is essential for DNA C5-cytosine methyltransferase M.HhaI. J Mol Biol. 2007 Nov 9;373(5):1157-68. Epub 2007 Aug 19. [PubMed:17897676 ]
  4. Wyszynski MW, Gabbara S, Kubareva EA, Romanova EA, Oretskaya TS, Gromova ES, Shabarova ZA, Bhagwat AS: The cysteine conserved among DNA cytosine methylases is required for methyl transfer, but not for specific DNA binding. Nucleic Acids Res. 1993 Jan 25;21(2):295-301. [PubMed:8441637 ]