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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:44 UTC
Update Date2023-02-21 17:21:10 UTC
HMDB IDHMDB0031667
Secondary Accession Numbers
  • HMDB31667
Metabolite Identification
Common NameNor-psi-tropine
DescriptionNor-psi-tropine, also known as nortropin or tropigenin, belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Based on a literature review a small amount of articles have been published on Nor-psi-tropine.
Structure
Data?1677000069
Synonyms
ValueSource
1-alpha-H,5-alpha-H-Nortropan-3-beta-olHMDB
2,3-Dihydro-3-hydroxy-nortropidineHMDB
3-beta-NortropanolHMDB
3-Hydroxy-nortropaneHMDB
8-Azabicyclo(3.2.1)octan-3-ol, exo- (9ci)HMDB
8-Azabicyclo[3.2.1]octan-3-ol, 9ciHMDB
endo-8-Azabicyclo[3.2.1]octan-3-olHMDB
exo-8-Azabicyclo(3.2.1)octan-3-olHMDB
exo-FormHMDB
Nor-tropanolHMDB
Nor-y-tropineHMDB
NorpseudotropineHMDB
NortropinHMDB
NortropineHMDB
PseudonortropineHMDB
PseudotropigenineHMDB
TropigeninHMDB
TropigenineHMDB
Chemical FormulaC7H13NO
Average Molecular Weight127.1842
Monoisotopic Molecular Weight127.099714043
IUPAC Name8-azabicyclo[3.2.1]octan-3-ol
Traditional Name8-azabicyclo[3.2.1]octan-3-ol
CAS Registry Number501-33-7
SMILES
OC1CC2CCC(C1)N2
InChI Identifier
InChI=1S/C7H13NO/c9-7-3-5-1-2-6(4-7)8-5/h5-9H,1-4H2
InChI KeyYYMCYJLIYNNOMK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassTropane alkaloids
Sub ClassNot Available
Direct ParentTropane alkaloids
Alternative Parents
Substituents
  • Tropane alkaloid
  • Piperidine
  • Cyclic alcohol
  • Pyrrolidine
  • Secondary alcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point134.5 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility303 g/LALOGPS
logP-0.06ALOGPS
logP-0.35ChemAxon
logS0.38ALOGPS
pKa (Strongest Acidic)15.16ChemAxon
pKa (Strongest Basic)10.72ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability14.16 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.21231661259
DarkChem[M-H]-120.14531661259
DeepCCS[M+H]+131.81430932474
DeepCCS[M-H]-129.18930932474
DeepCCS[M-2H]-165.68630932474
DeepCCS[M+Na]+140.46630932474
AllCCS[M+H]+130.132859911
AllCCS[M+H-H2O]+125.432859911
AllCCS[M+NH4]+134.432859911
AllCCS[M+Na]+135.732859911
AllCCS[M-H]-124.332859911
AllCCS[M+Na-2H]-126.032859911
AllCCS[M+HCOO]-127.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Nor-psi-tropineOC1CC2CCC(C1)N21996.0Standard polar33892256
Nor-psi-tropineOC1CC2CCC(C1)N21210.2Standard non polar33892256
Nor-psi-tropineOC1CC2CCC(C1)N21325.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nor-psi-tropine,1TMS,isomer #1C[Si](C)(C)OC1CC2CCC(C1)N21246.7Semi standard non polar33892256
Nor-psi-tropine,1TMS,isomer #2C[Si](C)(C)N1C2CCC1CC(O)C21374.8Semi standard non polar33892256
Nor-psi-tropine,2TMS,isomer #1C[Si](C)(C)OC1CC2CCC(C1)N2[Si](C)(C)C1410.1Semi standard non polar33892256
Nor-psi-tropine,2TMS,isomer #1C[Si](C)(C)OC1CC2CCC(C1)N2[Si](C)(C)C1460.1Standard non polar33892256
Nor-psi-tropine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CC2CCC(C1)N21514.1Semi standard non polar33892256
Nor-psi-tropine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2CCC1CC(O)C21621.4Semi standard non polar33892256
Nor-psi-tropine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CC2CCC(C1)N2[Si](C)(C)C(C)(C)C1899.6Semi standard non polar33892256
Nor-psi-tropine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CC2CCC(C1)N2[Si](C)(C)C(C)(C)C1910.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Nor-psi-tropine GC-MS (1 TMS)splash10-001j-9400000000-2729f49fcd134c7aa5fd2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Nor-psi-tropine GC-MS (Non-derivatized)splash10-001j-9400000000-2729f49fcd134c7aa5fd2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nor-psi-tropine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-9100000000-cc3c39e7429b64a21add2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nor-psi-tropine GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9400000000-6e5301d34eae94b454f02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nor-psi-tropine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 10V, Positive-QTOFsplash10-03fr-0900000000-737db543cc351b4febe72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 20V, Positive-QTOFsplash10-03fr-1900000000-4e385b616d8cacec918b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 40V, Positive-QTOFsplash10-03yi-9300000000-08548012b5b1a4befbef2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 10V, Negative-QTOFsplash10-004i-0900000000-622b17d3601ede1c53d92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 20V, Negative-QTOFsplash10-004i-0900000000-4759f5d462554080f29f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 40V, Negative-QTOFsplash10-00mk-9300000000-34ce96bafe39648dab3d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 10V, Positive-QTOFsplash10-004i-0900000000-2d0b886d38b6a8e410132021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 20V, Positive-QTOFsplash10-03di-0900000000-4ece63ae52d4d6df914b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 40V, Positive-QTOFsplash10-01qc-9300000000-d094e3e46d7efd45590e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 10V, Negative-QTOFsplash10-004i-0900000000-5fce2f371fcc2700e0fc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 20V, Negative-QTOFsplash10-004i-0900000000-5fce2f371fcc2700e0fc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nor-psi-tropine 40V, Negative-QTOFsplash10-00di-0900000000-230fc672df5e0c0982a52021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008327
KNApSAcK IDC00057413
Chemspider ID61455
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68147
PDB IDNot Available
ChEBI ID165181
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. Hofner K, Oelke M, Machtens S, Grunewald V: Trospium chloride--an effective drug in the treatment of overactive bladder and detrusor hyperreflexia. World J Urol. 2001 Nov;19(5):336-43. [PubMed:11760782 ]
  2. Xia Y, Chackalamannil S, Greenlee WJ, Jayne C, Neustadt B, Stamford A, Vaccaro H, Xu XL, Baker H, O'Neill K, Woods M, Hawes B, Kowalski T: Discovery of a nortropanol derivative as a potent and orally active GPR119 agonist for type 2 diabetes. Bioorg Med Chem Lett. 2011 Jun 1;21(11):3290-6. doi: 10.1016/j.bmcl.2011.04.035. Epub 2011 Apr 14. [PubMed:21536438 ]
  3. Schmitz G, Braun V: Cell-bound and secreted proteases of Serratia marcescens. J Bacteriol. 1985 Mar;161(3):1002-9. [PubMed:2579058 ]
  4. Sargent MG, Lampen JO: A mechanism for penicillinasesecretion in Bacillus licheniformis. Proc Natl Acad Sci U S A. 1970 Apr;65(4):962-9. [PubMed:5266165 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .