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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:09:41 UTC
Update Date2021-09-26 22:53:15 UTC
HMDB IDHMDB0245052
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Chloro-3'-deoxyadenosine
Description2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. Purine 3'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3. Based on a literature review very few articles have been published on 2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-chloro-3'-deoxyadenosine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Chloro-3'-deoxyadenosine 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
SynonymsNot Available
Chemical FormulaC10H12ClN5O3
Average Molecular Weight285.69
Monoisotopic Molecular Weight285.062867
IUPAC Name2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
Traditional Name2-(6-amino-2-chloropurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
CAS Registry NumberNot Available
SMILES
NC1=NC(Cl)=NC2=C1N=CN2C1OC(CO)CC1O
InChI Identifier
InChI=1S/C10H12ClN5O3/c11-10-14-7(12)6-8(15-10)16(3-13-6)9-5(18)1-4(2-17)19-9/h3-5,9,17-18H,1-2H2,(H2,12,14,15)
InChI KeyHNSLUZJFGNTTEV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. Purine 3'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassPurine 3'-deoxyribonucleosides
Direct ParentPurine 3'-deoxyribonucleosides
Alternative Parents
Substituents
  • Purine 3'-deoxyribonucleoside
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • 2-halopyrimidine
  • Halopyrimidine
  • Aryl chloride
  • Aryl halide
  • N-substituted imidazole
  • Imidolactam
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Oxolane
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP-0.05ALOGPS
logP-0.49ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)13.53ChemAxon
pKa (Strongest Basic)1.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.31 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.6 m³·mol⁻¹ChemAxon
Polarizability26.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+159.09930932474
DeepCCS[M-H]-156.74130932474
DeepCCS[M-2H]-189.62730932474
DeepCCS[M+Na]+165.19330932474
AllCCS[M+H]+162.732859911
AllCCS[M+H-H2O]+159.232859911
AllCCS[M+NH4]+166.032859911
AllCCS[M+Na]+166.932859911
AllCCS[M-H]-160.532859911
AllCCS[M+Na-2H]-160.232859911
AllCCS[M+HCOO]-159.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Chloro-3'-deoxyadenosineNC1=NC(Cl)=NC2=C1N=CN2C1OC(CO)CC1O3435.0Standard polar33892256
2-Chloro-3'-deoxyadenosineNC1=NC(Cl)=NC2=C1N=CN2C1OC(CO)CC1O2140.2Standard non polar33892256
2-Chloro-3'-deoxyadenosineNC1=NC(Cl)=NC2=C1N=CN2C1OC(CO)CC1O2720.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Chloro-3'-deoxyadenosine,3TMS,isomer #1C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2C1OC(CO[Si](C)(C)C)CC1O[Si](C)(C)C2656.2Semi standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TMS,isomer #1C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2C1OC(CO[Si](C)(C)C)CC1O[Si](C)(C)C2637.4Standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TMS,isomer #1C[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2C1OC(CO[Si](C)(C)C)CC1O[Si](C)(C)C3618.8Standard polar33892256
2-Chloro-3'-deoxyadenosine,3TMS,isomer #2C[Si](C)(C)OCC1CC(O)C(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O12664.0Semi standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TMS,isomer #2C[Si](C)(C)OCC1CC(O)C(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O12826.6Standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TMS,isomer #2C[Si](C)(C)OCC1CC(O)C(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O13550.4Standard polar33892256
2-Chloro-3'-deoxyadenosine,3TMS,isomer #3C[Si](C)(C)OC1CC(CO)OC1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C212660.9Semi standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TMS,isomer #3C[Si](C)(C)OC1CC(CO)OC1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C212758.3Standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TMS,isomer #3C[Si](C)(C)OC1CC(CO)OC1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C213517.1Standard polar33892256
2-Chloro-3'-deoxyadenosine,4TMS,isomer #1C[Si](C)(C)OCC1CC(O[Si](C)(C)C)C(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O12675.1Semi standard non polar33892256
2-Chloro-3'-deoxyadenosine,4TMS,isomer #1C[Si](C)(C)OCC1CC(O[Si](C)(C)C)C(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O12761.2Standard non polar33892256
2-Chloro-3'-deoxyadenosine,4TMS,isomer #1C[Si](C)(C)OCC1CC(O[Si](C)(C)C)C(N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(Cl)N=C32)O13161.5Standard polar33892256
2-Chloro-3'-deoxyadenosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2C1OC(CO[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C3252.7Semi standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2C1OC(CO[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C3280.1Standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(Cl)=NC2=C1N=CN2C1OC(CO[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C3711.4Standard polar33892256
2-Chloro-3'-deoxyadenosine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1CC(O)C(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)O13197.7Semi standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1CC(O)C(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)O13435.4Standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1CC(O)C(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)O13616.4Standard polar33892256
2-Chloro-3'-deoxyadenosine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1CC(CO)OC1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C213174.1Semi standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1CC(CO)OC1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C213363.1Standard non polar33892256
2-Chloro-3'-deoxyadenosine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1CC(CO)OC1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C213588.3Standard polar33892256
2-Chloro-3'-deoxyadenosine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1CC(O[Si](C)(C)C(C)(C)C)C(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)O13352.5Semi standard non polar33892256
2-Chloro-3'-deoxyadenosine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1CC(O[Si](C)(C)C(C)(C)C)C(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)O13528.3Standard non polar33892256
2-Chloro-3'-deoxyadenosine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1CC(O[Si](C)(C)C(C)(C)C)C(N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(Cl)N=C32)O13441.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9120000000-ed684aa58b10350db3102021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Chloro-3'-deoxyadenosine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-3'-deoxyadenosine 10V, Positive-QTOFsplash10-00rj-4960000000-01f039c27e4b7d5cffab2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-3'-deoxyadenosine 20V, Positive-QTOFsplash10-00di-0900000000-fa3ec9f7b8f59958cd432021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-3'-deoxyadenosine 40V, Positive-QTOFsplash10-0089-0900000000-0586805f496ef280098e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-3'-deoxyadenosine 10V, Negative-QTOFsplash10-001i-0390000000-95c4d37aa191fac081182021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-3'-deoxyadenosine 20V, Negative-QTOFsplash10-0159-0900000000-1d4e2e816d6ef6821b762021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Chloro-3'-deoxyadenosine 40V, Negative-QTOFsplash10-001i-1900000000-585f0f2d3388ac4de09e2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-12Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-12Wishart 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 ID11430963
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14485373
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 ]