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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:26:06 UTC

Update Date

2021-09-26 23:04:03 UTC

HMDB ID

HMDB0251810

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Eniluracil

Description

Eniluracil belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Normally, 5-FU is rapidly broken down in the body by an enzyme known as dihydropyrimidine dehydrogenase (DPD). Eniluracil is a drug which is used for the treatment of cancer in combination with 5-fluorouracil. Eniluracil irreversibly inhibits DPD, thereby substantially slowing the breakdown of 5-FU and prolonging exposure of the tumor cells to the drug. Eniluracil is an orally active dihydropyrimidine dehydrogenase (DPD) inhibitor, designed to enhance activity of chemotaxic agents. Eniluracil is an extremely weak basic (essentially neutral) compound (based on its pKa). Eniluracil has received Orphan Drug status from the FDA for the treatment of hepatocellular cancer in combination with fluoropyrimidines (including 5-FU). Eniluracil, which was previously under development by GlaxoSmithKline (GSK), is being developed by Adherex to enhance the therapeutic value and effectiveness of 5-fluorouracil (5-FU), one of the world’s most widely-used oncology agents. 5-FU is widely used in the U.S. and is often first or second line therapy for a variety of cancers including colorectal, breast, gastric, head and neck, ovarian and basal cell cancer of the skin. It is under investigation by Adherex, under license from GlaxoSmithKline, for the treatment of cancer in combination with 5-fluorouracil (5-FU). Eniluracil could improve 5-FU by increasing its effectiveness, reducing its side effects and/or making it orally available. This compound has been identified in human blood as reported by (PMID: 31557052 ). Eniluracil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Eniluracil 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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
776c85	ChEMBL
5-Ethynyluracil	MeSH
Compound 776C	MeSH

Chemical Formula

C₆H₄N₂O₂

Average Molecular Weight

136.1082

Monoisotopic Molecular Weight

136.027277382

IUPAC Name

5-ethynyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

5-ethynyluracil

CAS Registry Number

Not Available

SMILES

O=C1NC=C(C#C)C(=O)N1

InChI Identifier

InChI=1S/C6H4N2O2/c1-2-4-3-7-6(10)8-5(4)9/h1,3H,(H2,7,8,9,10)

InChI Key

JOZGNYDSEBIJDH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

Pyrimidone
Hydropyrimidine
Vinylogous amide
Heteroaromatic compound
Lactam
Urea
Acetylide
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
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	-0.91	ALOGPS
logP	-0.82	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.39 m³·mol⁻¹	ChemAxon
Polarizability	12.05 Å³	ChemAxon
Number of Rings	1	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]+	127.053	30932474
DeepCCS	[M-H]-	124.17	30932474
DeepCCS	[M-2H]-	161.08	30932474
DeepCCS	[M+Na]+	135.904	30932474
AllCCS	[M+H]+	127.2	32859911
AllCCS	[M+H-H2O]+	122.5	32859911
AllCCS	[M+NH4]+	131.6	32859911
AllCCS	[M+Na]+	132.9	32859911
AllCCS	[M-H]-	123.3	32859911
AllCCS	[M+Na-2H]-	124.9	32859911
AllCCS	[M+HCOO]-	126.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eniluracil	O=C1NC=C(C#C)C(=O)N1	2187.0	Standard polar	33892256
Eniluracil	O=C1NC=C(C#C)C(=O)N1	1434.3	Standard non polar	33892256
Eniluracil	O=C1NC=C(C#C)C(=O)N1	1825.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Eniluracil,1TMS,isomer #1	C#CC1=CN([Si](C)(C)C)C(=O)[NH]C1=O	1679.1	Semi standard non polar	33892256
Eniluracil,1TMS,isomer #1	C#CC1=CN([Si](C)(C)C)C(=O)[NH]C1=O	1567.7	Standard non polar	33892256
Eniluracil,1TMS,isomer #1	C#CC1=CN([Si](C)(C)C)C(=O)[NH]C1=O	2267.0	Standard polar	33892256
Eniluracil,1TMS,isomer #2	C#CC1=C[NH]C(=O)N([Si](C)(C)C)C1=O	1618.5	Semi standard non polar	33892256
Eniluracil,1TMS,isomer #2	C#CC1=C[NH]C(=O)N([Si](C)(C)C)C1=O	1569.2	Standard non polar	33892256
Eniluracil,1TMS,isomer #2	C#CC1=C[NH]C(=O)N([Si](C)(C)C)C1=O	2230.0	Standard polar	33892256
Eniluracil,2TMS,isomer #1	C#CC1=CN([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1814.1	Semi standard non polar	33892256
Eniluracil,2TMS,isomer #1	C#CC1=CN([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1722.5	Standard non polar	33892256
Eniluracil,2TMS,isomer #1	C#CC1=CN([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2059.9	Standard polar	33892256
Eniluracil,1TBDMS,isomer #1	C#CC1=CN([Si](C)(C)C(C)(C)C)C(=O)[NH]C1=O	1923.8	Semi standard non polar	33892256
Eniluracil,1TBDMS,isomer #1	C#CC1=CN([Si](C)(C)C(C)(C)C)C(=O)[NH]C1=O	1808.5	Standard non polar	33892256
Eniluracil,1TBDMS,isomer #1	C#CC1=CN([Si](C)(C)C(C)(C)C)C(=O)[NH]C1=O	2357.1	Standard polar	33892256
Eniluracil,1TBDMS,isomer #2	C#CC1=C[NH]C(=O)N([Si](C)(C)C(C)(C)C)C1=O	1825.8	Semi standard non polar	33892256
Eniluracil,1TBDMS,isomer #2	C#CC1=C[NH]C(=O)N([Si](C)(C)C(C)(C)C)C1=O	1808.0	Standard non polar	33892256
Eniluracil,1TBDMS,isomer #2	C#CC1=C[NH]C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2309.2	Standard polar	33892256
Eniluracil,2TBDMS,isomer #1	C#CC1=CN([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2129.0	Semi standard non polar	33892256
Eniluracil,2TBDMS,isomer #1	C#CC1=CN([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2154.3	Standard non polar	33892256
Eniluracil,2TBDMS,isomer #1	C#CC1=CN([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2224.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Eniluracil GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-8900000000-dd78f7511ef0363019ea	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eniluracil 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 - Eniluracil 10V, Positive-QTOF	splash10-000i-0900000000-91f69a9c7425d6654254	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 20V, Positive-QTOF	splash10-00ko-9400000000-eb40a8fc8f91fb98cccf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 40V, Positive-QTOF	splash10-00kf-9000000000-16a33dacd870a54266ce	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 10V, Negative-QTOF	splash10-000l-7900000000-59cd76042099a05be418	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 20V, Negative-QTOF	splash10-0006-9000000000-21295633deb9b38ed3e3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 40V, Negative-QTOF	splash10-0006-9000000000-46955e1a964154bcde69	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 10V, Positive-QTOF	splash10-000i-1900000000-8262de422e825bf6ae45	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 20V, Positive-QTOF	splash10-00kv-9200000000-0cc027a8755e27b7cac8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 40V, Positive-QTOF	splash10-0002-9000000000-8246c659a113d53d4d1d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 10V, Negative-QTOF	splash10-000i-5900000000-520ed84c90966de174a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 20V, Negative-QTOF	splash10-0006-9000000000-c0461c2f89ca9cb548ae	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eniluracil 40V, Negative-QTOF	splash10-0006-9000000000-fd5b628f5d050c101042	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

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

DB03516

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

43157

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 Eniluracil (HMDB0251810)

MOL for HMDB0251810 (Eniluracil)

3D MOL for HMDB0251810 (Eniluracil)

3D SDF for HMDB0251810 (Eniluracil)

3D-SDF for HMDB0251810 (Eniluracil)

PDB for HMDB0251810 (Eniluracil)

3D PDB for HMDB0251810 (Eniluracil)

SMILES for HMDB0251810 (Eniluracil)

INCHI for HMDB0251810 (Eniluracil)

Structure for HMDB0251810 (Eniluracil)

3D Structure for HMDB0251810 (Eniluracil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra