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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 00:26:20 UTC
Update Date2022-09-22 17:45:01 UTC
HMDB IDHMDB0247432
Secondary Accession NumbersNone
Metabolite Identification
Common Name8-Cyclopentyl-1,3-dipropylxanthine
Description8-Cyclopentyl-1,3-dipropylxanthine, also known as 1,3-DPCPX or 1,3-dipropyl-8-cyclopentylxanthine, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Based on a literature review very few articles have been published on 8-Cyclopentyl-1,3-dipropylxanthine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-cyclopentyl-1,3-dipropylxanthine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Cyclopentyl-1,3-dipropylxanthine 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
1,3-Dipropyl-8-cyclopentylxanthineChEBI
1,3-DPCPXChEBI
CPXChEBI
DipropylcyclopentylxanthineChEBI
PD-116,948ChEBI
PD-116948ChEBI
8-Cyclopentyl-3,7-dihydro-1,3-dipropyl-1H-purin-2,6-dioneHMDB
8-Cyclopentyl-1,3-dipropylxanthineChEBI
Chemical FormulaC16H24N4O2
Average Molecular Weight304.394
Monoisotopic Molecular Weight304.189926029
IUPAC Name8-cyclopentyl-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione
Traditional Namedipropylcyclopentylxanthine
CAS Registry NumberNot Available
SMILES
CCCN1C2=C(N=C(N2)C2CCCC2)C(=O)N(CCC)C1=O
InChI Identifier
InChI=1S/C16H24N4O2/c1-3-9-19-14-12(15(21)20(10-4-2)16(19)22)17-13(18-14)11-7-5-6-8-11/h11H,3-10H2,1-2H3,(H,17,18)
InChI KeyFFBDFADSZUINTG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP3.39ALOGPS
logP2.74ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)11.57ChemAxon
pKa (Strongest Basic)2.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.21 m³·mol⁻¹ChemAxon
Polarizability34.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+175.61530932474
DeepCCS[M-H]-173.25730932474
DeepCCS[M-2H]-206.14330932474
DeepCCS[M+Na]+181.70830932474
AllCCS[M+H]+171.932859911
AllCCS[M+H-H2O]+168.932859911
AllCCS[M+NH4]+174.732859911
AllCCS[M+Na]+175.532859911
AllCCS[M-H]-173.032859911
AllCCS[M+Na-2H]-173.032859911
AllCCS[M+HCOO]-173.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-Cyclopentyl-1,3-dipropylxanthineCCCN1C2=C(N=C(N2)C2CCCC2)C(=O)N(CCC)C1=O3221.9Standard polar33892256
8-Cyclopentyl-1,3-dipropylxanthineCCCN1C2=C(N=C(N2)C2CCCC2)C(=O)N(CCC)C1=O2603.0Standard non polar33892256
8-Cyclopentyl-1,3-dipropylxanthineCCCN1C2=C(N=C(N2)C2CCCC2)C(=O)N(CCC)C1=O2539.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Cyclopentyl-1,3-dipropylxanthine,1TMS,isomer #1CCCN1C(=O)C2=C(N([Si](C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O2538.3Semi standard non polar33892256
8-Cyclopentyl-1,3-dipropylxanthine,1TMS,isomer #1CCCN1C(=O)C2=C(N([Si](C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O2607.6Standard non polar33892256
8-Cyclopentyl-1,3-dipropylxanthine,1TMS,isomer #1CCCN1C(=O)C2=C(N([Si](C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O3340.5Standard polar33892256
8-Cyclopentyl-1,3-dipropylxanthine,1TBDMS,isomer #1CCCN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O2683.8Semi standard non polar33892256
8-Cyclopentyl-1,3-dipropylxanthine,1TBDMS,isomer #1CCCN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O2830.1Standard non polar33892256
8-Cyclopentyl-1,3-dipropylxanthine,1TBDMS,isomer #1CCCN1C(=O)C2=C(N([Si](C)(C)C(C)(C)C)C(C3CCCC3)=N2)N(CCC)C1=O3386.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01t9-1190000000-d206dc4a175f584b34ab2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine , positive-QTOFsplash10-00fr-3891000000-282be93d6a4f82333c332017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 10V, Positive-QTOFsplash10-0a4i-0039000000-2b4e1e54df86f28f7e512017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 20V, Positive-QTOFsplash10-03di-2191000000-de6778fefa6b6103af7e2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 40V, Positive-QTOFsplash10-0006-9540000000-02bdb2babcc0d8e976b62017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 10V, Negative-QTOFsplash10-0udi-0059000000-7fb897a6ec851c8892f12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 20V, Negative-QTOFsplash10-0ik9-0294000000-602d9f5f88dad43a57f82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 40V, Negative-QTOFsplash10-014i-8790000000-8675dd5df97ca5fcadaf2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 10V, Positive-QTOFsplash10-0a4i-0009000000-8afd581d108fc4ab5bbf2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 20V, Positive-QTOFsplash10-0a4i-0019000000-40b8fad5b5cd148bf8902021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 40V, Positive-QTOFsplash10-0gir-0492000000-0dfafda85c08bc9e0b9d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 10V, Negative-QTOFsplash10-0udi-0009000000-b3ce92e14ecef0f640db2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 20V, Negative-QTOFsplash10-0udi-0139000000-0de5f9b3dbe2c1f94e722021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Cyclopentyl-1,3-dipropylxanthine 40V, Negative-QTOFsplash10-00r6-4590000000-813b85b7d0affa982ab12021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12946
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1289
KEGG Compound IDC13709
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDipropylcyclopentylxanthine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID73282
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 ]