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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 10:21:44 UTC
Update Date2021-09-26 23:05:04 UTC
HMDB IDHMDB0252470
Secondary Accession NumbersNone
Metabolite Identification
Common NameFosteabine
Description{[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(octadecyloxy)phosphinic acid belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Based on a literature review very few articles have been published on {[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(octadecyloxy)phosphinic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Fosteabine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fosteabine 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
Thumb
Synonyms
ValueSource
{[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(octadecyloxy)phosphinateGenerator
Chemical FormulaC27H50N3O8P
Average Molecular Weight575.684
Monoisotopic Molecular Weight575.33355258
IUPAC Name{[5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(octadecyloxy)phosphinic acid
Traditional Name[5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(octadecyloxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCOP(O)(=O)OCC1OC(C(O)C1O)N1C=CC(N)=NC1=O
InChI Identifier
InChI=1S/C27H50N3O8P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-36-39(34,35)37-21-22-24(31)25(32)26(38-22)30-19-18-23(28)29-27(30)33/h18-19,22,24-26,31-32H,2-17,20-21H2,1H3,(H,34,35)(H2,28,29,33)
InChI KeyYJTVZHOYBAOUTO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct ParentPyrimidine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Pyrimidine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Aminopyrimidine
  • Pyrimidone
  • Dialkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Primary amine
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.2ALOGPS
logP5ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)1.92ChemAxon
pKa (Strongest Basic)-0.21ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area164.14 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity148.19 m³·mol⁻¹ChemAxon
Polarizability65.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+210.35130932474
DeepCCS[M-H]-206.97830932474
DeepCCS[M-2H]-242.79630932474
DeepCCS[M+Na]+218.74430932474
AllCCS[M+H]+242.132859911
AllCCS[M+H-H2O]+241.132859911
AllCCS[M+NH4]+243.032859911
AllCCS[M+Na]+243.332859911
AllCCS[M-H]-233.232859911
AllCCS[M+Na-2H]-236.532859911
AllCCS[M+HCOO]-240.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FosteabineCCCCCCCCCCCCCCCCCCOP(O)(=O)OCC1OC(C(O)C1O)N1C=CC(N)=NC1=O4919.1Standard polar33892256
FosteabineCCCCCCCCCCCCCCCCCCOP(O)(=O)OCC1OC(C(O)C1O)N1C=CC(N)=NC1=O3908.6Standard non polar33892256
FosteabineCCCCCCCCCCCCCCCCCCOP(O)(=O)OCC1OC(C(O)C1O)N1C=CC(N)=NC1=O4583.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fosteabine,3TMS,isomer #1CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C4425.5Semi standard non polar33892256
Fosteabine,3TMS,isomer #1CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C4134.9Standard non polar33892256
Fosteabine,3TMS,isomer #1CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C5858.4Standard polar33892256
Fosteabine,3TMS,isomer #2CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C4465.6Semi standard non polar33892256
Fosteabine,3TMS,isomer #2CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C4215.5Standard non polar33892256
Fosteabine,3TMS,isomer #2CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C5718.0Standard polar33892256
Fosteabine,3TMS,isomer #3CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C4503.0Semi standard non polar33892256
Fosteabine,3TMS,isomer #3CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C4299.9Standard non polar33892256
Fosteabine,3TMS,isomer #3CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C5474.4Standard polar33892256
Fosteabine,3TMS,isomer #4CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O4490.3Semi standard non polar33892256
Fosteabine,3TMS,isomer #4CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O4312.7Standard non polar33892256
Fosteabine,3TMS,isomer #4CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O5722.5Standard polar33892256
Fosteabine,3TMS,isomer #5CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C4517.5Semi standard non polar33892256
Fosteabine,3TMS,isomer #5CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C4272.8Standard non polar33892256
Fosteabine,3TMS,isomer #5CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C5458.8Standard polar33892256
Fosteabine,3TMS,isomer #6CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O)C1O[Si](C)(C)C4496.7Semi standard non polar33892256
Fosteabine,3TMS,isomer #6CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O)C1O[Si](C)(C)C4292.9Standard non polar33892256
Fosteabine,3TMS,isomer #6CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O)C1O[Si](C)(C)C5712.5Standard polar33892256
Fosteabine,3TMS,isomer #7CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O)C1O)O[Si](C)(C)C4504.0Semi standard non polar33892256
Fosteabine,3TMS,isomer #7CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O)C1O)O[Si](C)(C)C4375.9Standard non polar33892256
Fosteabine,3TMS,isomer #7CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O)C1O)O[Si](C)(C)C5411.5Standard polar33892256
Fosteabine,4TMS,isomer #1CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C4441.3Semi standard non polar33892256
Fosteabine,4TMS,isomer #1CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C4214.2Standard non polar33892256
Fosteabine,4TMS,isomer #1CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)O[Si](C)(C)C5045.3Standard polar33892256
Fosteabine,4TMS,isomer #2CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C4439.7Semi standard non polar33892256
Fosteabine,4TMS,isomer #2CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C4209.4Standard non polar33892256
Fosteabine,4TMS,isomer #2CCCCCCCCCCCCCCCCCCOP(=O)(O)OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O[Si](C)(C)C5224.7Standard polar33892256
Fosteabine,4TMS,isomer #3CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C4424.9Semi standard non polar33892256
Fosteabine,4TMS,isomer #3CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C4273.8Standard non polar33892256
Fosteabine,4TMS,isomer #3CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O[Si](C)(C)C)C1O)O[Si](C)(C)C5044.9Standard polar33892256
Fosteabine,4TMS,isomer #4CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C4439.4Semi standard non polar33892256
Fosteabine,4TMS,isomer #4CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C4234.9Standard non polar33892256
Fosteabine,4TMS,isomer #4CCCCCCCCCCCCCCCCCCOP(=O)(OCC1OC(N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)C(O)C1O[Si](C)(C)C)O[Si](C)(C)C5029.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_2_6) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fosteabine GC-MS (TBDMS_2_7) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosteabine 10V, Positive-QTOFsplash10-004i-0210390000-c9b90f579d4eda9ef0212021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosteabine 20V, Positive-QTOFsplash10-03fr-2932130000-9ab9b54691ff8f66950d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosteabine 40V, Positive-QTOFsplash10-0a4l-9600000000-15652970932925f20e972021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosteabine 10V, Negative-QTOFsplash10-00di-0000090000-7473f0f9ee05806200dc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosteabine 20V, Negative-QTOFsplash10-00fs-9102260000-f560003a9144324923502021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fosteabine 40V, Negative-QTOFsplash10-004i-9000000000-6a38f8bcb788807e2e532021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21234581
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13491648
PDB IDNot Available
ChEBI IDNot Available
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. 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 ]