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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014467

Secondary Accession Numbers

HMDB14467

Metabolite Identification

Common Name

Floxuridine

Description

Floxuridine, also known as FUDR or 5FDU, 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. Floxuridine is a drug which is used for palliative management of gastrointestinal adenocarcinoma metastatic to the liver, when given by continuous regional intra-arterial infusion in carefully selected patients who are considered incurable by surgery or other means. also for the palliative management of liver cancer (usually administered by hepatic intra-arterial infusion). A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract. Floxuridine is an extremely weak basic (essentially neutral) compound (based on its pKa). Floxuridine exists in all living organisms, ranging from bacteria to humans.

Structure

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

322
  Mrv0541 02231214362D          

 17 18  0  0  1  0            999 V2000
    4.5079    1.9573    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7464   -1.0026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1816   -2.4547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7969   -2.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.3073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.5448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -1.7873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0790   -0.5177    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4115   -1.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4915   -1.7873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9764   -2.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2 10  1  0  0  0  0
  2 12  1  0  0  0  0
  9  3  1  1  0  0  0
  4 13  1  0  0  0  0
  5 14  2  0  0  0  0
  6 17  2  0  0  0  0
 10  7  1  6  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 14  1  0  0  0  0
  8 17  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014467

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

> <INCHI_KEY>
ODKNJVUHOIMIIZ-RRKCRQDMSA-N

> <FORMULA>
C9H11FN2O5

> <MOLECULAR_WEIGHT>
246.1924

> <EXACT_MASS>
246.065199677

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
20.77757990995401

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

> <ALOGPS_LOGP>
-1.15

> <JCHEM_LOGP>
-1.3151611686666662

> <ALOGPS_LOGS>
-0.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.907877307910667

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.678643455901932

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9780835982375358

> <JCHEM_POLAR_SURFACE_AREA>
99.09999999999998

> <JCHEM_REFRACTIVITY>
51.2578

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.08e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
floxuridine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 322                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       8.415   3.654   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0       6.993  -1.872   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.072  -4.582   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.954  -4.421   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.080   0.574   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.747   5.194   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       5.747   0.574   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.414   2.884   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.977  -3.336   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -0.966   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.501  -1.872   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.517  -3.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.423  -4.582   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   1.344   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   1.344   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   2.884   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747   3.654   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   10   12                                                       
CONECT    3    9                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6   17                                                            
CONECT    7   10   14   15                                                  
CONECT    8   14   17                                                       
CONECT    9    3   11   12                                                  
CONECT   10    2    7   11                                                  
CONECT   11    9   10                                                       
CONECT   12    2    9   13                                                  
CONECT   13    4   12                                                       
CONECT   14    5    7    8                                                  
CONECT   15    7   16                                                       
CONECT   16    1   15   17                                                  
CONECT   17    6    8   16                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0014467
HETATM    1  O1  UNL     1       5.239  -0.775  -0.701  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.031  -0.526  -0.419  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.211  -1.446   0.113  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.911  -1.179   0.417  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.161  -2.063   0.916  1.00  0.00           O  
HETATM    6  N2  UNL     1       1.386   0.039   0.193  1.00  0.00           N  
HETATM    7  C3  UNL     1       0.034   0.392   0.485  1.00  0.00           C  
HETATM    8  C4  UNL     1      -0.726   0.826  -0.776  1.00  0.00           C  
HETATM    9  C5  UNL     1      -2.133   0.865  -0.191  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.306   2.155   0.317  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.039  -0.161   0.905  1.00  0.00           C  
HETATM   12  C7  UNL     1      -3.066  -1.231   0.626  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.874  -1.841  -0.603  1.00  0.00           O  
HETATM   14  O5  UNL     1      -0.747  -0.650   0.915  1.00  0.00           O  
HETATM   15  C8  UNL     1       2.191   0.973  -0.339  1.00  0.00           C  
HETATM   16  C9  UNL     1       3.517   0.728  -0.658  1.00  0.00           C  
HETATM   17  F1  UNL     1       4.311   1.708  -1.201  1.00  0.00           F  
HETATM   18  H1  UNL     1       3.591  -2.403   0.299  1.00  0.00           H  
HETATM   19  H2  UNL     1      -0.061   1.224   1.205  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.610   0.005  -1.505  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.396   1.804  -1.138  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.899   0.613  -0.951  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.609   2.785  -0.001  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.269   0.257   1.902  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.168  -1.953   1.455  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.059  -0.695   0.576  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.456  -1.427  -1.296  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.833   1.976  -0.546  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4   18
CONECT    4    5    5    6
CONECT    6    7   15
CONECT    7    8   14   19
CONECT    8    9   20   21
CONECT    9   10   11   22
CONECT   10   23
CONECT   11   12   14   24
CONECT   12   13   25   26
CONECT   13   27
CONECT   15   16   16   28
CONECT   16   17
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil	ChEBI
1-beta-D-2'-Deoxyribofuranosyl-5-flurouracil	ChEBI
1beta-D-2'-Deoxyribofuranosyl-5-flurouracil	ChEBI
2'-Deoxy-5-fluorouridine	ChEBI
5-Fluoro-2'-deoxyuridine	ChEBI
5-Fluoro-2-desoxyuridine	ChEBI
5-Fluorodeoxyuridine	ChEBI
5-Fluorouracil 2'-deoxyriboside	ChEBI
5-Fluorouracil deoxyriboside	ChEBI
5FDU	ChEBI
beta-5-Fluoro-2'-deoxyuridine	ChEBI
Deoxyfluorouridine	ChEBI
FdU	ChEBI
Floxiridina	ChEBI
Floxuridin	ChEBI
Floxuridinum	ChEBI
Fluorodeoxyuridine	ChEBI
Fluoruridine deoxyribose	ChEBI
FUDR	Kegg
1-(2-Deoxy-b-D-ribofuranosyl)-5-fluorouracil	Generator
1-(2-Deoxy-β-D-ribofuranosyl)-5-fluorouracil	Generator
1-b-D-2'-Deoxyribofuranosyl-5-flurouracil	Generator
1-Β-D-2'-deoxyribofuranosyl-5-flurouracil	Generator
1b-D-2'-Deoxyribofuranosyl-5-flurouracil	Generator
1Β-D-2'-deoxyribofuranosyl-5-flurouracil	Generator
b-5-Fluoro-2'-deoxyuridine	Generator
Β-5-fluoro-2'-deoxyuridine	Generator
5 Fluorodeoxyuridine	HMDB
FDUR	HMDB
FDURD	HMDB
5-FUdR	HMDB

Chemical Formula

C₉H₁₁FN₂O₅

Average Molecular Weight

246.1924

Monoisotopic Molecular Weight

246.065199677

IUPAC Name

5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

floxuridine

CAS Registry Number

50-91-9

SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O

InChI Identifier

InChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

InChI Key

ODKNJVUHOIMIIZ-RRKCRQDMSA-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
Halopyrimidine
Hydroxypyrimidine
Pyrimidone
Aryl fluoride
Aryl halide
Hydropyrimidine
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Azacycle
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:60761 )
nucleoside analogue (CHEBI:60761 )
pyrimidine 2'-deoxyribonucleoside (CHEBI:60761 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0014467)
Kidney (HMDB: HMDB0014467)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014467)

Source

Exogenous

Exogenous (HMDB: HMDB0014467)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	150.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	40.8 g/L	Not Available
LogP	-1.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	40.8 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.3	ChemAxon
logS	-0.78	ALOGPS
pKa (Strongest Acidic)	7.68	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.1 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	51.26 m³·mol⁻¹	ChemAxon
Polarizability	20.78 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]+	161.275	30932474
DeepCCS	[M-H]-	158.88	30932474
DeepCCS	[M-2H]-	191.864	30932474
DeepCCS	[M+Na]+	167.188	30932474
AllCCS	[M+H]+	153.7	32859911
AllCCS	[M+H-H2O]+	149.9	32859911
AllCCS	[M+NH4]+	157.3	32859911
AllCCS	[M+Na]+	158.3	32859911
AllCCS	[M-H]-	151.5	32859911
AllCCS	[M+Na-2H]-	151.4	32859911
AllCCS	[M+HCOO]-	151.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Floxuridine	OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O	3149.7	Standard polar	33892256
Floxuridine	OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O	1955.1	Standard non polar	33892256
Floxuridine	OC[C@H]1O[C@H](C[C@@H]1O)N1C=C(F)C(=O)NC1=O	2301.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Floxuridine,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)C[C@@H]1O	2132.9	Semi standard non polar	33892256
Floxuridine,1TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=C(F)C(=O)[NH]C2=O)O[C@@H]1CO	2157.4	Semi standard non polar	33892256
Floxuridine,1TMS,isomer #3	C[Si](C)(C)N1C(=O)C(F)=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C1=O	2172.4	Semi standard non polar	33892256
Floxuridine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)C[C@@H]1O[Si](C)(C)C	2181.0	Semi standard non polar	33892256
Floxuridine,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O	2241.9	Semi standard non polar	33892256
Floxuridine,2TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)O[C@@H]1CO	2251.2	Semi standard non polar	33892256
Floxuridine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C	2262.9	Semi standard non polar	33892256
Floxuridine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C	2202.2	Standard non polar	33892256
Floxuridine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C	2499.3	Standard polar	33892256
Floxuridine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)C[C@@H]1O	2409.0	Semi standard non polar	33892256
Floxuridine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=C(F)C(=O)[NH]C2=O)O[C@@H]1CO	2415.6	Semi standard non polar	33892256
Floxuridine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C(F)=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C1=O	2424.3	Semi standard non polar	33892256
Floxuridine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)[NH]C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	2680.8	Semi standard non polar	33892256
Floxuridine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O	2697.2	Semi standard non polar	33892256
Floxuridine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)O[C@@H]1CO	2715.0	Semi standard non polar	33892256
Floxuridine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	2944.7	Semi standard non polar	33892256
Floxuridine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	2879.5	Standard non polar	33892256
Floxuridine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C2=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	2807.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Floxuridine EI-B (Non-derivatized)	splash10-00lr-9600000000-155a97133c7827d2a1ce	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Floxuridine CI-B (Non-derivatized)	splash10-001i-3900000000-44f00976f508bab47f36	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Floxuridine CI-B (Non-derivatized)	splash10-00kb-2910000000-2efae68e874a5fdba01c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Floxuridine EI-B (Non-derivatized)	splash10-00lr-9600000000-155a97133c7827d2a1ce	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Floxuridine CI-B (Non-derivatized)	splash10-001i-3900000000-44f00976f508bab47f36	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Floxuridine CI-B (Non-derivatized)	splash10-00kb-2910000000-2efae68e874a5fdba01c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Floxuridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0036-9340000000-625fd93cccce9bbf8234	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Floxuridine GC-MS (2 TMS) - 70eV, Positive	splash10-0gk9-8926000000-e5bea4ee2a8fa95520d5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Floxuridine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Floxuridine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 10V, Negative-QTOF	splash10-0ikd-5890000000-537ea470ce67d29de875	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 20V, Negative-QTOF	splash10-056r-2930000000-9edc79b79e109479fd9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 40V, Negative-QTOF	splash10-0006-9200000000-8d9d5de0ec79de7d99fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 10V, Negative-QTOF	splash10-002b-0290000000-39ab94dde23863db307a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 20V, Negative-QTOF	splash10-054o-5920000000-270199a759ef06b114d5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 40V, Negative-QTOF	splash10-0006-9300000000-4e1f643aecd55a3c5e1a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 10V, Positive-QTOF	splash10-001i-0900000000-e75f17c5e6c58cb63cc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 20V, Positive-QTOF	splash10-001i-1900000000-ab9d2ecf3f514e6cd7fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 40V, Positive-QTOF	splash10-01q9-7900000000-5b44e036090ffa5616c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 10V, Positive-QTOF	splash10-000t-0590000000-8342a1e97df40065538f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 20V, Positive-QTOF	splash10-001i-6910000000-971c4cc98bc9ce3fbe7b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxuridine 40V, Positive-QTOF	splash10-053r-3900000000-9ea95daa1bfdf562eb70	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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 DB00322	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00322	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00322

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5586

KEGG Compound ID

C11736

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Floxuridine

METLIN ID

Not Available

PubChem Compound

5790

PDB ID

Not Available

ChEBI ID

60761

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 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Konishi H, Morita K, Minouchi T, Nakajima M, Matsuda M, Yamaji A: Probable metabolic interaction of doxifluridine with phenytoin. Ann Pharmacother. 2002 May;36(5):831-4. [PubMed:11978162 ]
Konishi H, Yoshimoto T, Morita K, Minouchi T, Sato T, Yamaji A: Depression of phenytoin metabolic capacity by 5-fluorouracil and doxifluridine in rats. J Pharm Pharmacol. 2003 Jan;55(1):143-9. [PubMed:12625878 ]

Enzyme Details

2. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Ozawa S, Hamada M, Murayama N, Nakajima Y, Kaniwa N, Matsumoto Y, Fukuoka M, Sawada J, Ohno Y: Cytosolic and microsomal activation of doxifluridine and tegafur to produce 5-fluorouracil in human liver. Cancer Chemother Pharmacol. 2002 Dec;50(6):454-8. Epub 2002 Oct 26. [PubMed:12451471 ]

Enzyme Details

3. Thymidine kinase, cytosolic

General function:: Nucleotide transport and metabolism
Specific function:: Not Available
Gene Name:: TK1
Uniprot ID:: P04183
Molecular weight:: 25468.455

Reactions

Floxuridine + Adenosine triphosphate → 5-Fluorodeoxyuridine monophosphate + ADP	details

Enzyme Details

4. Thymidine kinase 2, mitochondrial

General function:: Involved in ATP binding
Specific function:: Deoxyribonucleoside kinase that phosphorylates thymidine, deoxycytidine, and deoxyuridine. Also phosphorylates anti-viral and anti-cancer nucleoside analogs.
Gene Name:: TK2
Uniprot ID:: O00142
Molecular weight:: 27561.495

Reactions

Floxuridine + Adenosine triphosphate → 5-Fluorodeoxyuridine monophosphate + ADP	details

Enzyme Details

5. Thymidine phosphorylase

General function:: Involved in transferase activity, transferring glycosyl groups
Specific function:: May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro. Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:: TYMP
Uniprot ID:: P19971
Molecular weight:: 49954.965

Reactions

Fluorouracil + Deoxyribose 1-phosphate → Floxuridine + Phosphate	details

References

Hara Y: [5'-Deoxy-5-fluorouridine enzymatic activation from the masked compound to 5-fluorouracil in human malignant tissues]. Gan To Kagaku Ryoho. 1984 Oct;11(10):2133-43. [PubMed:6237613 ]
Ozawa S, Hamada M, Murayama N, Nakajima Y, Kaniwa N, Matsumoto Y, Fukuoka M, Sawada J, Ohno Y: Cytosolic and microsomal activation of doxifluridine and tegafur to produce 5-fluorouracil in human liver. Cancer Chemother Pharmacol. 2002 Dec;50(6):454-8. Epub 2002 Oct 26. [PubMed:12451471 ]
Sadahiro S, Otani Y, Oya K, Ike H, Shimada H, Yamaguchi S, Hiki Y, Fujita H, Mitomi T: Thymidine phosphorylase expression and effect of doxifluridine: a phase II study. Oncol Rep. 2001 Jul-Aug;8(4):753-8. [PubMed:11410777 ]

Enzyme Details

6. Thymidylate synthase

General function:: Involved in thymidylate synthase activity
Specific function:: Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:: TYMS
Uniprot ID:: P04818
Molecular weight:: 35715.65

References

Ferguson PJ, Collins O, Dean NM, DeMoor J, Li CS, Vincent MD, Koropatnick J: Antisense down-regulation of thymidylate synthase to suppress growth and enhance cytotoxicity of 5-FUdR, 5-FU and Tomudex in HeLa cells. Br J Pharmacol. 1999 Aug;127(8):1777-86. [PubMed:10482907 ]
Kubota T: [Theoretical basis for low-dose CDDP/5-FU therapy]. Gan To Kagaku Ryoho. 1999 Oct;26(11):1536-41. [PubMed:10553409 ]
Kuwa K, Sakamoto S, Sassa S, Yoshimura S, Maemura M, Nakayama T: Effects of long-term administration of UFT plus leucovorin on colorectal tumors induced with 1,2-dimethylhydrazine in rats. Anticancer Res. 1999 Nov-Dec;19(6B):5139-42. [PubMed:10697523 ]
Kuwa K, Sakamoto S, Mitamura T, Kudo H, Suzuki S, Fukushima M: Effects of a low dose leucovorin with 5-fluorouracil derivative on colorectal tumors induced with 1,2-dimethylhydrazine in rats. Anticancer Res. 1999 Nov-Dec;19(6B):5143-8. [PubMed:10697524 ]
Murakami Y, Kazuno H, Emura T, Tsujimoto H, Suzuki N, Fukushima M: Different mechanisms of acquired resistance to fluorinated pyrimidines in human colorectal cancer cells. Int J Oncol. 2000 Aug;17(2):277-83. [PubMed:10891536 ]
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 Floxuridine (HMDB0014467)

MOL for HMDB0014467 (Floxuridine)

3D MOL for HMDB0014467 (Floxuridine)

3D SDF for HMDB0014467 (Floxuridine)

3D-SDF for HMDB0014467 (Floxuridine)

PDB for HMDB0014467 (Floxuridine)

3D PDB for HMDB0014467 (Floxuridine)

SMILES for HMDB0014467 (Floxuridine)

INCHI for HMDB0014467 (Floxuridine)

Structure for HMDB0014467 (Floxuridine)

3D Structure for HMDB0014467 (Floxuridine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

Reactions

Reactions

Reactions

References

References