4-Hydroxytrimethoprim (CHEM045778)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:40:51 UTC
Update Date2016-11-09 01:23:24 UTC
Accession NumberCHEM045778
Identification
Common Name4-Hydroxytrimethoprim
ClassSmall Molecule
DescriptionAn aminopyrimidine, the structure of which is that of trimethoprim (pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge) carrying a 6-hydroxy substituent.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)-6-hydroxypyrimidineChEBI
2,4-Diamino-6-hydroxy-5-(3,4,5-trimethoxybenzyl)pyrimidineChEBI
6-Hydroxy TMPChEBI
6-Hydroxy trimethoprimChEBI
Chemical FormulaC14H18N4O4
Average Molecular Mass306.322 g/mol
Monoisotopic Mass306.133 g/mol
CAS Registry Number112678-48-5
IUPAC Name6-amino-2-imino-5-[(3,4,5-trimethoxyphenyl)methyl]-1,2-dihydropyrimidin-4-ol
Traditional Name6-amino-2-imino-5-[(3,4,5-trimethoxyphenyl)methyl]-1H-pyrimidin-4-ol
SMILESCOC1=CC(CC2=C(N)NC(=N)N=C2O)=CC(OC)=C1OC
InChI IdentifierInChI=1S/C14H18N4O4/c1-20-9-5-7(6-10(21-2)11(9)22-3)4-8-12(15)17-14(16)18-13(8)19/h5-6H,4H2,1-3H3,(H5,15,16,17,18,19)
InChI KeyFYJKTYLNKCUCLP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Aminopyrimidine
  • Pyrimidone
  • Monocyclic benzene moiety
  • Hydropyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Amine
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP0.7ALOGPS
logP0.7ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.03ChemAxon
pKa (Strongest Basic)3.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area122.18 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity100.34 m³·mol⁻¹ChemAxon
Polarizability30.39 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0119000000-a26a1d76d19e119b3871Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0696000000-7b5a4d0272d38c0205fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-4920000000-57013a42ec80f876b50dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2109000000-595f854b5ecbc961f047Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-6394000000-467664c523c88c378caeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016u-3490000000-c9663683e7add0a40dffSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID58969
PubChem Compound ID12577407
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=3377143