NP-MRD: Showing NP-Card for (1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene (NP0286762)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 15:29:32 UTC

Updated at

2022-09-09 15:29:32 UTC

NP-MRD ID

NP0286762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene

Description

Dehydrosparteine belongs to the class of organic compounds known as quinolizidines. Quinolizidines are compounds containing a quinolizidine moiety, which is a octahydro-2H-quinolizine derivative. (1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene is found in Adenocarpus hispanicus, Genista acanthoclada, Genista cinerascens, Plagiocarpus axillaris and Retama raetam. (1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene was first documented in 1986 (PMID: 3768256). Based on a literature review a significant number of articles have been published on Dehydrosparteine (PMID: 11549206) (PMID: 9264814) (PMID: 8646830) (PMID: 8528270) (PMID: 7741777) (PMID: 24248948).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
   -4.0776   -1.0946    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8612   -1.5865    0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084   -0.7926    0.5261 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3684   -1.3121    0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -1.2309   -0.6946 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5002   -0.3924   -1.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954    0.8875   -0.9014 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3910    1.5709   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4235    0.7187    0.1785 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192    1.5354    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8382    0.8459   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343   -0.5026    0.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7280   -1.2966    0.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663   -0.4574   -0.5750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8477    0.6163    0.1512 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2365    0.8587   -0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2828    0.3435    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9428   -1.7228    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7673   -2.6541    0.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4477   -2.3664    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1865   -0.7321    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5330   -2.2510   -1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412   -0.2387   -2.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209   -0.9563   -1.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2700    1.5777   -1.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070    2.2938   -1.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0371    2.1895    0.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    2.5020   -0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894    1.8083    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605    0.7380   -1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7206    1.4508   -0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8944   -1.0056    0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8253   -0.2643    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3045   -1.8345    0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618   -2.0439   -0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921   -0.2393   -1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362    1.2681    1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3319    0.3139   -1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462    1.9495   -0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2204    0.9461    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2853    0.5600    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  1 17  1  0
 17 16  1  0
 16 15  1  0
  5 14  1  0
 14 13  1  0
 13 12  1  0
 14  9  1  0
 15  7  1  0
 15  3  1  0
 12 32  1  0
 12 33  1  0
 11 30  1  0
 11 31  1  0
 10 28  1  0
 10 29  1  0
  8 26  1  0
  8 27  1  0
  7 25  1  6
  6 23  1  0
  6 24  1  0
  5 22  1  6
  4 20  1  0
  4 21  1  0
  2 19  1  0
  1 18  1  0
 17 40  1  0
 17 41  1  0
 16 38  1  0
 16 39  1  0
 15 37  1  1
 14 36  1  6
 13 34  1  0
 13 35  1  0
M  END


  Mrv1652309092217292D          

 17 20  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084   -0.5834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7469    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    1.4084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4084    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14  9  1  1  0  0  0
  7 15  1  0  0  0  0
 15  3  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1CCN2C[C@H]3C[C@H](CN4C=CCC[C@H]34)[C@@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h3,7,12-15H,1-2,4-6,8-11H2/t12-,13-,14-,15+/m1/s1

> <INCHI_KEY>
BWKNRAAXVUYXAH-TUVASFSCSA-N

> <FORMULA>
C15H24N2

> <MOLECULAR_WEIGHT>
232.371

> <EXACT_MASS>
232.193948781

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.973047763484974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,9R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadec-5-ene

> <JCHEM_LOGP>
2.0398065219999992

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.011578279086999

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
71.91610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,9R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadec-5-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.089  -1.089   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.629  -1.089   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.394   0.578   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.089   2.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.629   2.629   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.718   1.540   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.052   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.385   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.385  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.052  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.718   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    5    9                                                  
CONECT   15    7    3   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    1                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄N₂

Average Mass

232.3710 Da

Monoisotopic Mass

232.19395 Da

IUPAC Name

(1R,2R,9R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadec-5-ene

Traditional Name

(1R,2R,9R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadec-5-ene

CAS Registry Number

Not Available

SMILES

C1CCN2C[C@H]3C[C@H](CN4C=CCC[C@H]34)[C@@H]2C1

InChI Identifier

InChI=1S/C15H24N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h3,7,12-15H,1-2,4-6,8-11H2/t12-,13-,14-,15+/m1/s1

InChI Key

BWKNRAAXVUYXAH-TUVASFSCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Adenocarpus hispanicus	LOTUS Database	35616633
Genista acanthoclada	LOTUS Database	35616633
Genista cinerascens	LOTUS Database	35616633
Plagiocarpus axillaris	LOTUS Database	35616633
Retama raetam	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolizidines. Quinolizidines are compounds containing a quinolizidine moiety, which is a octahydro-2H-quinolizine derivative.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolizidines

Sub Class

Not Available

Direct Parent

Quinolizidines

Alternative Parents

Substituents

Quinolizidine
Tetrahydropyridine
Piperidine
Tertiary aliphatic amine
Tertiary amine
Allylamine
Azacycle
Enamine
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.04	ChemAxon
pKa (Strongest Basic)	9.01	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.92 m³·mol⁻¹	ChemAxon
Polarizability	27.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007688

Chemspider ID

4932634

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6427218

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lohmann PL, Rao ML, Ludwig M, Griese EU, Zanger UM, Morike K, Maier W, Bagli M: Influence of CYP2D6 genotype and medication on the sparteine metabolic ratio of psychiatric patients. Eur J Clin Pharmacol. 2001 Jul;57(4):289-95. doi: 10.1007/s002280100299. [PubMed:11549206 ]
Holoman J, Glasa J, Veningerova M, Prachar V, Lukacsova M: [Genetic polymorphism in sparteine oxidation--occurrence in healthy volunteers in Slovakia]. Bratisl Lek Listy. 1997 Feb;98(2):86-90. [PubMed:9264814 ]
Kevorkian JP, Michel C, Hofmann U, Jacqz-Aigrain E, Kroemer HK, Peraldi MN, Eichelbaum M, Jaillon P, Funck-Brentano C: Assessment of individual CYP2D6 activity in extensive metabolizers with renal failure: comparison of sparteine and dextromethorphan. Clin Pharmacol Ther. 1996 May;59(5):583-92. doi: 10.1016/S0009-9236(96)90187-3. [PubMed:8646830 ]
Crespi CL, Steimel DT, Penman BW, Korzekwa KR, Fernandez-Salguero P, Buters JT, Gelboin HV, Gonzalez FJ, Idle JR, Daly AK: Comparison of substrate metabolism by wild type CYP2D6 protein and a variant containing methionine, not valine, at position 374. Pharmacogenetics. 1995 Aug;5(4):234-43. doi: 10.1097/00008571-199508000-00007. [PubMed:8528270 ]
Volz M, Mitrovic V, Thiemer J, Schlepper M: Steady-state plasma kinetics of slow-release propafenone, its two isomers and its main metabolites. Arzneimittelforschung. 1995 Mar;45(3):246-9. [PubMed:7741777 ]
Wink M, Witte L: Quinolizidine alkaloids inGenista acanthoclada and its holoparasite,Cuscuta palaestina. J Chem Ecol. 1993 Mar;19(3):441-8. doi: 10.1007/BF00994317. [PubMed:24248948 ]
Yoshino H, Hattori Y, Imai H, Narabayashi H, Chiba K: [Sparteine oxidation by hepatic cytochrome P-450 in patients with Parkinson's disease]. Rinsho Shinkeigaku. 1993 Mar;33(3):261-5. [PubMed:8334787 ]
Ho JW, Moody DE: Gas chromatography/mass spectrometry assays for the determination of debrisoquine and sparteine metabolites in microsomal fractions of rat liver. Anal Biochem. 1992 Jun;203(2):348-51. doi: 10.1016/0003-2697(92)90323-y. [PubMed:1416032 ]
Lennard MS, Iyun AO, Jackson PR, Tucker GT, Woods HF: Evidence for a dissociation in the control of sparteine, debrisoquine and metoprolol metabolism in Nigerians. Pharmacogenetics. 1992 Apr;2(2):89-92. doi: 10.1097/00008571-199204000-00006. [PubMed:1302046 ]
Sindrup SH, Brosen K, Gram LF, Hallas J, Skjelbo E, Allen A, Allen GD, Cooper SM, Mellows G, Tasker TC, et al.: The relationship between paroxetine and the sparteine oxidation polymorphism. Clin Pharmacol Ther. 1992 Mar;51(3):278-87. doi: 10.1038/clpt.1992.23. [PubMed:1531950 ]
Schellens JH, Ghabrial H, van der Wart HH, Bakker EN, Wilkinson GR, Breimer DD: Differential effects of quinidine on the disposition of nifedipine, sparteine, and mephenytoin in humans. Clin Pharmacol Ther. 1991 Nov;50(5 Pt 1):520-8. doi: 10.1038/clpt.1991.177. [PubMed:1934865 ]
Chaudhuri A, Keller WJ: New mammalian metabolites of sparteine. Life Sci. 1990;47(4):319-25. doi: 10.1016/0024-3205(90)90590-n. [PubMed:2388532 ]
Schellens JH, van der Wart JH, Brugman M, Breimer DD: Influence of enzyme induction and inhibition on the oxidation of nifedipine, sparteine, mephenytoin and antipyrine in humans as assessed by a "cocktail" study design. J Pharmacol Exp Ther. 1989 May;249(2):638-45. [PubMed:2724144 ]
Tyndale RF, Inaba T, Kalow W: Evidence in humans for variant allozymes of the nondeficient sparteine/debrisoquine monooxygenase (P45OIID 1) in vitro. Drug Metab Dispos. 1989 May-Jun;17(3):334-40. [PubMed:2568917 ]
Schellens JH, van der Wart HH, Hoevers JW, Breimer DD: Gas chromatographic determination of sparteine and 2- and 5-dehydrosparteine in plasma and urine. J Chromatogr. 1988 Sep 23;431(1):203-9. doi: 10.1016/s0378-4347(00)83086-8. [PubMed:3235532 ]
Osikowska-Evers B, Dayer P, Meyer UA, Robertz GM, Eichelbaum M: Evidence for altered catalytic properties of the cytochrome P-450 involved in sparteine oxidation in poor metabolizers. Clin Pharmacol Ther. 1987 Mar;41(3):320-5. doi: 10.1038/clpt.1987.34. [PubMed:3816020 ]
Brosen K: Sparteine oxidation polymorphism in Greenlanders living in Denmark. Br J Clin Pharmacol. 1986 Oct;22(4):415-9. doi: 10.1111/j.1365-2125.1986.tb02911.x. [PubMed:3768256 ]
Brinn R, Brosen K, Gram LF, Haghfelt T, Otton SV: Sparteine oxidation is practically abolished in quinidine-treated patients. Br J Clin Pharmacol. 1986 Aug;22(2):194-7. doi: 10.1111/j.1365-2125.1986.tb05250.x. [PubMed:3756067 ]
Osikowska-Evers BA, Eichelbaum M: A sensitive capillary GC assay for the determination of sparteine oxidation products in microsomal fractions of human liver. Life Sci. 1986 May 12;38(19):1775-82. doi: 10.1016/0024-3205(86)90128-1. [PubMed:3702606 ]
Eichelbaum M, Reetz KP, Schmidt EK, Zekorn C: The genetic polymorphism of sparteine metabolism. Xenobiotica. 1986 May;16(5):465-81. doi: 10.3109/00498258609050252. [PubMed:3739368 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene (NP0286762)

MOL for NP0286762 ((1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene)

3D MOL for NP0286762 ((1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene)

3D SDF for NP0286762 ((1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene)

3D-SDF for NP0286762 ((1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene)

PDB for NP0286762 ((1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene)

3D PDB for NP0286762 ((1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene)

SMILES for NP0286762 ((1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene)

INCHI for NP0286762 ((1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene)

Structure for NP0286762 ((1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene)

3D Structure for NP0286762 ((1r,2r,9r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-5-ene)