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Showing NP-Card for Pseudotropine (NP0051330)

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Record Information
Version2.0
Created at2022-04-27 22:42:59 UTC
Updated at2022-04-27 22:42:59 UTC
NP-MRD IDNP0051330
Secondary Accession NumbersNone
Natural Product Identification
Common NamePseudotropine
Description Pseudotropine is found in Agrobacterium rhizogenes, Argyreia mollis, Atropa baetica, Atropa belladonna , Brugmansia arborea , Brugmansia suaveolens, Brugmansia candida, Cyphomandra betaceae, Datura ceratocaula , Datura innoxia , Datura metel , Datura stramonium x D.discolor , Duboisia myoporoides, Forsythia koreana, Hyoscyamus albus, Hyoscyamus niger , Hyoscyamus pusillus, Mandrogora offinarum, Mus musculus, Physalis minima, Physochlaina orientalis, Salpichora origanifolia, Schizanthus grahamii, Schizanthus pinnatus, Scopolia carniolica , Solandra grandiflora, Solanum tubersoum and Withania somnifera . Pseudotropine was first documented in 2009 (PMID: 19924779).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051330 (Pseudotropine)


  Mrv1652309272007472D          

 10 11  0  0  0  0            999 V2000
 9996.468210000.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.305110000.4002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.236210000.2062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.7316 9999.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.040710001.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9067 9999.5413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.554210000.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.382710000.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.292010001.3544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.042110000.0349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9  2  1  1  0  0  0
  6  2  1  1  0  0  0
  3 10  1  6  0  0  0
M  END
Download

3D MOL for NP0051330 (Pseudotropine)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -2.0337   -0.0791    1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6788   -0.0109    0.9261 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3441   -1.0333   -0.0641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6279   -0.4599   -1.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130    0.9636   -1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3562    1.2105    0.2126 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1077    1.1729   -0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8116   -0.0310    0.4822 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1215   -0.0346    0.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356   -1.3234    0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0671   -0.8090    2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7363   -0.4435    0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3298    0.9141    1.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9236   -1.9612    0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5029   -0.9599   -1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352   -0.4492   -2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1787    0.9595   -0.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184    1.6783   -1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849    2.1184    0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993    1.1074   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213    2.0787    0.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8770    0.1803    1.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340   -0.9383   -0.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644   -1.9460    1.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5877   -1.9043   -0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  6  2  1  0
 10  3  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  1
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  1
  7 20  1  0
  7 21  1  0
  8 22  1  1
  9 23  1  0
 10 24  1  0
 10 25  1  0
M  END
Download

3D SDF for NP0051330 (Pseudotropine)


  Mrv1652309272007472D          

 10 11  0  0  0  0            999 V2000
 9996.468210000.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.305110000.4002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.236210000.2062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.7316 9999.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.040710001.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9067 9999.5413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.554210000.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.382710000.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.292010001.3544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.042110000.0349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9  2  1  1  0  0  0
  6  2  1  1  0  0  0
  3 10  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@H]2CC[C@@H]1C[C@H](O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+

> <INCHI_KEY>
CYHOMWAPJJPNMW-JIGDXULJSA-N

> <FORMULA>
C8H15NO

> <MOLECULAR_WEIGHT>
141.2108

> <EXACT_MASS>
141.115364107

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.032836983327023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
0.03356066499999985

> <ALOGPS_LOGS>
0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.160811554696018

> <JCHEM_PKA_STRONGEST_BASIC>
9.695886905323272

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
40.5938

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.45e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pseudotropine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0051330 (Pseudotropine)

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PDB for NP0051330 (Pseudotropine)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8660.0748668.018   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8663.5038667.414   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8665.2418667.052   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.2998665.833   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8664.8768668.548   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.7598665.810   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.1018668.506   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8661.7818667.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.4788669.195   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8666.7458666.732   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    9    6                                                  
CONECT    3    4    5   10                                                  
CONECT    4    3    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4    8    2                                                  
CONECT    7    8    9                                                       
CONECT    8    6    7                                                       
CONECT    9    5    7    2                                                  
CONECT   10    3                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

Download
3D PDB for NP0051330 (Pseudotropine)
Download
SMILES for NP0051330 (Pseudotropine)
CN1[C@H]2CC[C@@H]1C[C@H](O)C2
Download
INCHI for NP0051330 (Pseudotropine)
InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+
Download
View in JSmol
Synonyms
ValueSource
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]octan-3-olChEBI
1AlphaH,5alphah-tropan-3alpha-olChEBI
3alpha-TropanolChEBI
8-Methyl-8-azabicyclo[3.2.1]octan-3-olChEBI
endo-8-Methyl-8-azabicyclo[3.2.1]octan-3-olChEBI
TropanolChEBI
1AlphaH,5alphah-tropan-3a-olGenerator
1AlphaH,5alphah-tropan-3α-olGenerator
3a-TropanolGenerator
3Α-tropanolGenerator
1αH,5αH-Tropan-3α-olPhytoBank
2,3-Dihydro-3alpha-hydroxy-8-methylnortropidinePhytoBank
2,3-Dihydro-3α-hydroxy-8-methylnortropidinePhytoBank
2,3-Dihydro-3alpha-hydroxytropidinePhytoBank
2,3-Dihydro-3α-hydroxytropidinePhytoBank
alpha-TropinePhytoBank
α-TropinePhytoBank
Chemical FormulaC8H15NO
Average Mass141.2108 Da
Monoisotopic Mass141.11536 Da
IUPAC Name(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol
Traditional Namepseudotropine
CAS Registry NumberNot Available
SMILES
CN1[C@H]2CC[C@@H]1C[C@H](O)C2
InChI Identifier
InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+
InChI KeyCYHOMWAPJJPNMW-JIGDXULJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agrobacterium rhizogenesLOTUS Database
Argyreia mollisPlant
Atropa baeticaPlant
Atropa belladonnaPlant
Brugmansia arboreaPlant
Brugmansia suaveolensLOTUS Database
Brugmansia x candidaLOTUS Database
Cyphomandra betaceaePlant
Datura ceratocaulaPlant
Datura inoxiaPlant
Datura metelPlant
Datura stramonium x D.discolorPlant
Duboisia myoporoidesLOTUS Database
Forsythia koreanaLOTUS Database
Hyoscyamus albusLOTUS Database
Hyoscyamus nigerPlant
Hyoscyamus pusillusLOTUS Database
Mandrogora offinarum-
Mus musculusLOTUS Database
Physalis minimaLOTUS Database
Physochlaina orientalisLOTUS Database
Salpichora origanifolia-
Schizanthus grahamiiLOTUS Database
Schizanthus pinnatusLOTUS Database
Scopolia carniolicaPlant
Solandra grandifloraLOTUS Database
Solanum tubersoumPlant
Withania somniferaPlant
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
    • 

  • N-alkylpyrrolidine
    • 

  • Cyclic alcohol
    • 

  • Pyrrolidine
    • 

  • Secondary alcohol
    • 

  • Tertiary amine
    • 

  • Tertiary aliphatic amine
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.86ALOGPS
logP0.034ChemAxon
logS0.66ALOGPS
pKa (Strongest Acidic)15.16ChemAxon
pKa (Strongest Basic)9.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.59 m³·mol⁻¹ChemAxon
Polarizability16.03 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002306  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTropine  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15884  
Good Scents IDNot Available
References
General References
  1. Molinie R, Kwiecien RA, Silvestre V, Robins RJ: Determination of nitrogen-15 isotope fractionation in tropine: evaluation of extraction protocols for isotope ratio measurement by isotope ratio mass spectrometry. Rapid Commun Mass Spectrom. 2009 Dec;23(24):4031-7. doi: 10.1002/rcm.4344. [PubMed:19924779  ] 
  2. Kwiecien RA, Molinie R, Paneth P, Silvestre V, Lebreton J, Robins RJ: Elucidation of the mechanism of N-demethylation catalyzed by cytochrome P450 monooxygenase is facilitated by exploiting nitrogen-15 heavy isotope effects. Arch Biochem Biophys. 2011 Jun 1;510(1):35-41. doi: 10.1016/j.abb.2011.03.007. Epub 2011 Mar 21. [PubMed:21420927  ] 
  3. Chiou WH, Chen GT, Kao CL, Gao YK: Syntheses of (-)-pelletierine and (-)-homopipecolic acid. Org Biomol Chem. 2012 Apr 7;10(13):2518-20. doi: 10.1039/c2ob06984a. Epub 2012 Feb 20. [PubMed:22349358  ]