Identification

Name
Thymine
Accession Number
DB03462  (EXPT03032)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-14705 / NSC-168663
Categories
UNII
QR26YLT7LT
CAS number
65-71-4
Weight
Average: 126.1133
Monoisotopic: 126.042927446
Chemical Formula
C5H6N2O2
InChI Key
RWQNBRDOKXIBIV-UHFFFAOYSA-N
InChI
InChI=1S/C5H6N2O2/c1-3-2-6-5(9)7-4(3)8/h2H,1H3,(H2,6,7,8,9)
IUPAC Name
5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
CC1=CNC(=O)NC1=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDeoxyribodipyrimidine photo-lyaseNot AvailableThermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
UThymidine phosphorylaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Pyrimidine MetabolismMetabolic
Dihydropyrimidinase DeficiencyDisease
beta-Ureidopropionase DeficiencyDisease
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
Pyrimidine Deoxyribonucleosides DegradationMetabolic
Pyrimidine MetabolismMetabolic
UMP Synthase Deficiency (Orotic Aciduria)Disease
Salvage Pathways of Pyrimidine DeoxyribonucleotidesMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Charles W. Murtiashaw, "Process for the production of O.sup. 2,2'-anhydro-1-(.beta.-D-arabinofuranosyl)thymine." U.S. Patent US5008384, issued February, 1988.

US5008384
General References
Not Available
External Links
Human Metabolome Database
HMDB0000262
KEGG Compound
C00178
PubChem Compound
1135
PubChem Substance
46507372
ChemSpider
1103
BindingDB
50134397
ChEBI
17821
ChEMBL
CHEMBL993
HET
TDR
Wikipedia
Thymine
PDB Entries
1iqu / 1tpt / 2hn9 / 2hrd / 2j0f / 2o5c / 2o5e / 3fs8 / 3ro7 / 4hn1
show 6 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)316 °CPhysProp
water solubility3820 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.62HANSCH,C ET AL. (1995)
logS-1.52ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility10.8 mg/mLALOGPS
logP-0.99ALOGPS
logP-0.46ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)10.02ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.33 m3·mol-1ChemAxon
Polarizability11.42 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9742
Blood Brain Barrier+0.979
Caco-2 permeable-0.7937
P-glycoprotein substrateNon-substrate0.7184
P-glycoprotein inhibitor INon-inhibitor0.9303
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9152
CYP450 2C9 substrateNon-substrate0.664
CYP450 2D6 substrateNon-substrate0.8776
CYP450 3A4 substrateNon-substrate0.7647
CYP450 1A2 substrateNon-inhibitor0.6534
CYP450 2C9 inhibitorNon-inhibitor0.9773
CYP450 2D6 inhibitorNon-inhibitor0.9786
CYP450 2C19 inhibitorNon-inhibitor0.9824
CYP450 3A4 inhibitorNon-inhibitor0.9653
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9922
Ames testNon AMES toxic0.923
CarcinogenicityNon-carcinogens0.9439
BiodegradationReady biodegradable0.6592
Rat acute toxicity1.5310 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9562
hERG inhibition (predictor II)Non-inhibitor0.9478
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0bt9-0960000000-50722d1f64f22b69e207
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0bta-0940000000-ff59d40c1a93e04954ab
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-05fr-7940000000-a0ebb190eba32aceac56
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0ab9-1980000000-5b95ad97f31d8176a0c6
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-004i-9500000000-74b6d7909610070d30d0
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0bt9-0960000000-50722d1f64f22b69e207
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0bta-0940000000-ff59d40c1a93e04954ab
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-05fr-7940000000-a0ebb190eba32aceac56
GC-MS Spectrum - GC-MSGC-MSsplash10-0ab9-1980000000-5b95ad97f31d8176a0c6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0bta-0930000000-a2d3bc738d3f9e60aeb7
Mass Spectrum (Electron Ionization)MSsplash10-056r-9400000000-5dd0bc0194a302d8ee95
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-004i-0900000000-a3779faac812139c6333
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-004i-0900000000-a3779faac812139c6333
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0udi-9200000000-0e7d9466530de47896d9
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-004i-9400000000-7ff00d5a94e12e6e1701
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-9100000000-1e96fdb2525aace8b29d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0a6r-9000000000-34edf89b8a99493ed897
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0a4i-9000000000-7d381bc0d559ed8150e9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4i-9000000000-90f8edce6ae2b6f83347
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0a4l-9000000000-445d07aed275008cfe2d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-056r-8900000000-96370e30b48d3270abaa
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0bwc-9600000000-b988fb9252c409b19c33
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-01q9-9100000000-8c82d68e9ec8594b1fff
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-001i-9000000000-f69c5d963b845f8b3cfb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0a4i-0900000000-3a9af2cf67d3f113fa7f
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-004i-0900000000-97549ff58b84351d860c
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-01q9-7900000000-5804e303580e1273f1a2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-004i-0900000000-deb5e6830bc01a0c870e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-1900000000-7f378c898bdb1944116e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-057i-9400000000-df8e4d4b901c8d1334fc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-9000000000-629132689aa512d344b2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-2900000000-878180774da717dee4ae
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-005c-9400000000-2bf425b661913858b12a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-87ca2758dbf67661c671
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9100000000-1e96fdb2525aace8b29d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a6r-9000000000-34edf89b8a99493ed897
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-fbf8dadffeee1dead341
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-0ee2bab9c37212ccf44e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4l-9000000000-599b8dcd618a9b96df4b
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-004i-0900000000-deb5e6830bc01a0c870e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-056r-8900000000-5284437492240f2b8a17
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0bwc-9600000000-b988fb9252c409b19c33
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01q9-9100000000-8c82d68e9ec8594b1fff
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-f69c5d963b845f8b3cfb
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0900000000-3a9af2cf67d3f113fa7f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0900000000-97549ff58b84351d860c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01q9-7900000000-5804e303580e1273f1a2
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Hydroxypyrimidines
Alternative Parents
Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Hydroxypyrimidine / Heteroaromatic compound / Azacycle / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Organooxygen compound / Organonitrogen compound / Aromatic heteromonocyclic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidone, pyrimidine nucleobase (CHEBI:17821) / pyrimidines (C00178) / a pyrimidine-related compound, a pyrimidine base (THYMINE)

Targets

Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Involved in repair of UV radiation-induced DNA damage. Catalyzes the light-dependent monomerization (300-600 nm) of cyclobutyl pyrimidine dimers (in cis-syn configuration), which are formed between...
Gene Name
phr
Uniprot ID
P61497
Uniprot Name
Deoxyribodipyrimidine photo-lyase
Molecular Weight
47900.455 Da
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]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Thymidine phosphorylase activity
Specific Function
The enzymes which catalyze the reversible phosphorolysis of pyrimidine nucleosides are involved in the degradation of these compounds and in their utilization as carbon and energy sources, or in th...
Gene Name
deoA
Uniprot ID
P07650
Uniprot Name
Thymidine phosphorylase
Molecular Weight
47206.655 Da
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]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:35