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Showing NP-Card for (1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol (NP0328849)

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Record Information
Version2.0
Created at2022-09-12 12:41:13 UTC
Updated at2022-09-12 12:41:13 UTC
NP-MRD IDNP0328849
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol
DescriptionTropine, also known as pseudotropine, 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. (1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol is found in Datura stramonium. (1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol was first documented in 2020 (PMID: 32823100). Based on a literature review a small amount of articles have been published on Tropine (PMID: 35050207) (PMID: 34967033) (PMID: 32852865) (PMID: 31705812).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0328849 ((1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol)


  Mrv1652309122214412D          

 10 11  0  0  1  0            999 V2000
    2.1787    0.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941   -0.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.9268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5174    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -0.9270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9667   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1497   -0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  2  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
M  END
Download

3D MOL for NP0328849 ((1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -2.4286   -0.2334   -0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235   -0.2488   -0.6382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3694    1.0047   -0.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1837    1.1891    1.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905   -0.1911    1.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284   -1.0811    0.3686 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9358   -1.4539   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7450   -0.3370   -0.6499 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7648   -0.0550    0.2812 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0024    0.8768   -1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8183    0.7657   -0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9044   -0.6344    0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7635   -0.9212   -1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8805    1.8743   -0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8147    1.5512    1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102    1.9299    1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4008   -0.2094    2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3694   -0.4974    2.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079   -1.9713    0.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7980   -2.2743   -0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4560   -1.9700    0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2993   -0.7217   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281    0.8968    0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8290    0.8790   -2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5672    1.8324   -0.8853 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  6
  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  6
  9 23  1  0
 10 24  1  0
 10 25  1  0
M  END
Download

3D SDF for NP0328849 ((1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol)


  Mrv1652309122214412D          

 10 11  0  0  1  0            999 V2000
    2.1787    0.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941   -0.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.9268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5174    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -0.9270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9667   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1497   -0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  2  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1[C@H]2CC[C@@H]1CC(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-DHBOJHSNSA-N

> <FORMULA>
C8H15NO

> <MOLECULAR_WEIGHT>
141.214

> <EXACT_MASS>
141.115364107

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.03625786399992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
0.03356066499999985

> <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>
40.593799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0328849 ((1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol)

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PDB for NP0328849 ((1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.067   0.476   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.602  -0.000   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.170   1.730   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.966   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.966  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.170  -1.730   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.671  -1.388   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.339  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.879  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.671   1.387   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0328849 ((1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol)
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SMILES for NP0328849 ((1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol)
CN1[C@H]2CC[C@@H]1CC(O)C2
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INCHI for NP0328849 ((1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol)
InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8?
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View in JSmol
Synonyms
ValueSource
Tropine hydrobromide, (endo)-isomerMeSH
Tropine hydrochloride, (exo)-isomerMeSH
PseudotropineMeSH
Tropine hydrochloride, (endo)-isomerMeSH
Tropine, (exo)-isomerMeSH
Chemical FormulaC8H15NO
Average Mass141.2140 Da
Monoisotopic Mass141.11536 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CN1[C@H]2CC[C@@H]1CC(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-DHBOJHSNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Datura stramoniumLOTUS Database
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 DescriptorsNot Available
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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002275  
Chemspider ID395864  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTropine  
METLIN IDNot Available
PubChem Compound449293  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yusoff YM, Abbott G, Young L, Edrada-Ebel R: Metabolomic Profiling of Malaysian and New Zealand Honey Using Concatenated NMR and HRMS Datasets. Metabolites. 2022 Jan 17;12(1):85. doi: 10.3390/metabo12010085. [PubMed:35050207  ] 
  2. Wang B, Chen T, Wang A, Fang J, Wang J, Yao W, Wu Y: Anisodamine affects the pigmentation, mineral density, craniofacial area, and eye development in zebrafish embryos. J Appl Toxicol. 2022 Jun;42(6):1067-1077. doi: 10.1002/jat.4278. Epub 2021 Dec  29. [PubMed:34967033  ] 
  3. Subhahar MB, Karakka Kal AK, Philip M, K Karatt T, N I, Vazhat RA, M P MA: Detection and identification of ACP-105 and its metabolites in equine urine using LC/MS/MS after oral administration. Drug Test Anal. 2021 Feb;13(2):299-317. doi: 10.1002/dta.2918. Epub 2020 Sep 6. [PubMed:32852865  ] 
  4. Yohannes A, Feng X, Yao S: Dispersive solid-phase extraction of racemic drugs using chiral ionic liquid-metal-organic framework composite sorbent. J Chromatogr A. 2020 Sep 13;1627:461395. doi: 10.1016/j.chroma.2020.461395. Epub  2020 Jul 6. [PubMed:32823100  ] 
  5. Qiu F, Zeng J, Wang J, Huang JP, Zhou W, Yang C, Lan X, Chen M, Huang SX, Kai G, Liao Z: Functional genomics analysis reveals two novel genes required for littorine biosynthesis. New Phytol. 2020 Mar;225(5):1906-1914. doi: 10.1111/nph.16317. Epub 2019 Nov 28. [PubMed:31705812  ] 
  6. LOTUS database [Link]