Rolipram (CHEM017879)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:42:44 UTC
Update Date2016-11-09 01:15:41 UTC
Accession NumberCHEM017879
Identification
Common NameRolipram
ClassSmall Molecule
DescriptionA member of the lclass of pyrrolidin-2-ones that is pyrrolidin-2-one bearing a 3-(cyclopentyloxy)-4-methoxyphenyl substituent at the 4-position. It is a type IV-specific phosphodiesterase (PDE4) inhibitor.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinoneChEBI
RolipramumChEBI
ZK 62711ChEBI
RolipramMeSH
Chemical FormulaC16H21NO3
Average Molecular Mass275.348 g/mol
Monoisotopic Mass275.152 g/mol
CAS Registry Number61413-54-5
IUPAC Name3-[3-(cyclopentyloxy)-4-methoxyphenyl]-3,4-dihydro-2H-pyrrol-5-ol
Traditional Namerolipramum
SMILESCOC1=C(OC2CCCC2)C=C(C=C1)C1CN=C(O)C1
InChI IdentifierInChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)
InChI KeyHJORMJIFDVBMOB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPhenylpyrrolidines
Direct ParentPhenylpyrrolidines
Alternative Parents
Substituents
  • 3-phenylpyrrolidine
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • 2-pyrrolidone
  • Pyrrolidone
  • Pyrrole
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen 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 Solubility0.024 g/LALOGPS
logP3.16ALOGPS
logP2.05ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.83ChemAxon
pKa (Strongest Basic)6.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.05 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.69 m³·mol⁻¹ChemAxon
Polarizability30.07 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-2390000000-82a63560b02f568a09b2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0f89-3910000000-38dfbb97597c517723c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0090000000-560244a4d0d6418f226cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0090000000-9507b0584062362f343bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a6u-0590000000-63d3f57e5eff4592ddd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-1690000000-748a69ba652840c85f95Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0590000000-1ce7657ef60958653797Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f89-3910000000-38dfbb97597c517723c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0bwc-0930000000-2e82d6327e2160443665Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-3090000000-19f67be09f1f3fafa536Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-5390000000-151e38f8b148dfd1f327Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9100000000-1ac3fa59c900d8edef9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1090000000-bba4d18bee682d468b31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g0-4290000000-51ede755aa6fb15c5252Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9300000000-91caa1154cffdaecaafeSpectrum
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 IDDB01954
HMDB IDHMDB0257294
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRolipram
Chemspider ID4913
ChEBI ID104872
PubChem Compound IDNot Available
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=11163637
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11239354
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4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11555183
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11737051
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=11739553
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=11959789
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=11978843
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=11992650
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=12003795
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=12065724
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=12191588
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=12447004
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=12508846
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=15114341
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=15277469
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=15374348
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=15646801
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=15744818
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=15790951
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=15839805
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=15986861
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=16010295
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=16022866
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=16077397
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=16129118
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=16190900
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=16242629
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=16250839
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=16253125
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=16254133
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=16442096
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=16455619
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=16962789
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=16968783
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=17081698
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=17097801
38. https://www.ncbi.nlm.nih.gov/pubmed/?term=17390056
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=17489366
40. https://www.ncbi.nlm.nih.gov/pubmed/?term=18311187
41. https://www.ncbi.nlm.nih.gov/pubmed/?term=18347080
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=18424161
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=18437099
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=18554698
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=19554392
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=19569465