NP-MRD: Showing NP-Card for (2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane (NP0291555)

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Record Information

Version

1.0

Created at

2022-09-09 22:41:51 UTC

Updated at

2022-09-09 22:41:51 UTC

NP-MRD ID

NP0291555

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane

Description

Sparteine, also known as sparteine sulfate or beta-isosparteine, belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. (2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane is found in Adenocarpus hispanicus, Ammopiptanthus mongolicus, Anabasis aphylla, Anagyris foetida, Anarthrophyllum desideratum, Aspalathus spinosa, Baptisia australis, Baptisia simplicifolia, Bolusanthus speciosus, Calobota saharae, Cuscuta palaestina, Cytisophyllum sessilifolium, Cytisus scoparius, Cytisus praecox, Dermatophyllum secundiflorum, Dicraeopetalum stipulare, Genista lobelii, Genista lydia, Genista majorica, Hesperolaburnum platycarpum, Lamprolobium fruticosum, Leontice leontopetalum, Liparia vestita, Lupinus angustifolius, Lupinus arboreus, Lupinus arcticus, Lupinus argenteus, Lupinus hintonii, Lupinus luteus, Lupinus mexicanus, Lupinus mutabilis, Lupinus palaestinus, Lupinus polyphyllus, Lupinus pusillus, Lupinus texensis, Ormosia macrocalyx, Oxytropis ochrocephala, Pearsonia aristata, Pearsonia sessilifolia, Plagiocarpus axillaris, Podalyria cuneifolia, Polhillia canescens, Prunus mahaleb, Retama sphaerocarpa, Robynsiophyton vanderystii, Sophora secundiflora, Spartium junceum, Thermopsis lanceolata, Thermopsis montana and Virgilia divaricata. It was first documented in 2022 (PMID: 36068017). Based on a literature review a significant number of articles have been published on Sparteine (PMID: 35420019) (PMID: 35766744) (PMID: 35699313) (PMID: 35566183).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -3.7558   -0.7486    0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967    0.6922    1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6881    1.4062    0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5393    0.7064   -0.1272 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2993    1.3738   -0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897    0.9330   -1.3377 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2478   -0.1939   -2.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693   -1.2634   -1.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6864   -1.7268   -0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3672   -0.5956    0.2363 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3244   -0.8691    1.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273   -0.4668    0.9239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8583    0.9347    0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6824    1.3891   -0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7778    0.2701   -0.8236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5259   -0.6948    0.0053 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9459   -1.2126   -0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8264   -0.9559    0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4476   -1.3849    1.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881    0.8493    2.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4887    1.2000    1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096    2.4328    0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3698    1.4964   -0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590    2.4651   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    1.1187    0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941    1.7854   -1.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2035    0.1710   -2.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4300   -0.6047   -2.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0012   -2.1419   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3807   -2.4267    0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3298   -2.2234   -1.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3272   -1.9608    1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0215   -0.3443    2.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954   -0.4981    1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2422   -1.2108    0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0062    1.6592    1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7774    0.9769   -0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0617    2.1133    0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0257    1.8999   -1.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825   -0.2857   -1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -1.0380    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928   -0.7280   -1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9481   -2.2990   -0.3006 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  1  0
 17  1  1  0
 16  4  1  0
 15  6  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  6
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  6
 16 41  1  1
 17 42  1  0
 17 43  1  0
M  END


  Mrv1652309102200412D          

 17 20  0  0  1  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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  0  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  0  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  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  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  2  1  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  0  0  0  0
  6  7  1  0  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
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 10  1  6  0  0  0
  8 16  1  0  0  0  0
 16  4  1  1  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291555

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1CCN2CC3CC(CN4CCCC[C@H]34)[C@@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12?,13?,14-,15+

> <INCHI_KEY>
SLRCCWJSBJZJBV-ZMYVRHLSSA-N

> <FORMULA>
C15H26N2

> <MOLECULAR_WEIGHT>
234.387

> <EXACT_MASS>
234.209598845

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
28.362054023374824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecane

> <JCHEM_LOGP>
2.027827476999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.16023077227616

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
71.82300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecane

> <JCHEM_VEBER_RULE>
1

$$$$

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

View in JSmol

Synonyms

Value	Source
Anhydrous, sparteine sulfate	MeSH
D-Sparteine	MeSH
Sparteine hydrochloride, (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine hydroiodide, (7R-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine monohydroiodide, (7R-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine sulfate (1:1), (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer	MeSH
Sparteine, (+)-isomer	MeSH
Sparteine, (-)-isomer	MeSH
Sparteine, (7R-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sulfate anhydrous, sparteine	MeSH
alpha-Isosparteine	MeSH
Sparteine hydrochloride, (7R-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine monohydrochloride, (7R-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine sulfate (1:1), (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine sulfate anhydrous	MeSH
Sparteine, (7R-(7alpha,7abeta,14alpha,14abeta))-isomer	MeSH
Genisteine alkaloid	MeSH
L-Sparteine	MeSH
Sparteine sulfate	MeSH
Sparteine, (7S-(7alpha,7abeta,14alpha,14abeta))-isomer	MeSH
beta-Isosparteine	MeSH
Depasan retard	MeSH
Pachycarpine	MeSH
Pachycarpine sulfate (1:1), pentahydrate, (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine, (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer	MeSH
Sparteine, (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
alpha Isosparteine	MeSH
beta Isosparteine	MeSH

Chemical Formula

C₁₅H₂₆N₂

Average Mass

234.3870 Da

Monoisotopic Mass

234.20960 Da

IUPAC Name

(2R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecane

Traditional Name

(2R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecane

CAS Registry Number

Not Available

SMILES

C1CCN2CC3CC(CN4CCCC[C@H]34)[C@@H]2C1

InChI Identifier

InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12?,13?,14-,15+

InChI Key

SLRCCWJSBJZJBV-ZMYVRHLSSA-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
Ammopiptanthus mongolicus	LOTUS Database	35616633
Anabasis aphylla	LOTUS Database	35616633
Anagyris foetida	LOTUS Database	35616633
Anarthrophyllum desideratum	LOTUS Database	35616633
Aspalathus spinosa	LOTUS Database	35616633
Baptisia australis	LOTUS Database	35616633
Baptisia simplicifolia	LOTUS Database	35616633
Bolusanthus speciosus	LOTUS Database	35616633
Calobota saharae	LOTUS Database	35616633
Cuscuta palaestina	LOTUS Database	35616633
Cytisophyllum sessilifolium	LOTUS Database	35616633
Cytisus scoparius	LOTUS Database	35616633
Cytisus x praecox	LOTUS Database	35616633
Dermatophyllum secundiflorum	LOTUS Database	35616633
Dicraeopetalum stipulare	LOTUS Database	35616633
Genista lobelii	LOTUS Database	35616633
Genista lydia	LOTUS Database	35616633
Genista majorica	LOTUS Database	35616633
Hesperolaburnum platycarpum	LOTUS Database	35616633
Lamprolobium fruticosum	LOTUS Database	35616633
Leontice leontopetalum	LOTUS Database	35616633
Liparia vestita	LOTUS Database	35616633
Lupinus angustifolius	LOTUS Database	35616633
Lupinus arboreus	LOTUS Database	35616633
Lupinus arcticus	LOTUS Database	35616633
Lupinus argenteus	LOTUS Database	35616633
Lupinus hintonii	LOTUS Database	35616633
Lupinus luteus	LOTUS Database	35616633
Lupinus mexicanus	LOTUS Database	35616633
Lupinus mutabilis	LOTUS Database	35616633
Lupinus palaestinus	LOTUS Database	35616633
Lupinus polyphyllus	LOTUS Database	35616633
Lupinus pusillus	LOTUS Database	35616633
Lupinus texensis	LOTUS Database	35616633
Ormosia macrocalyx	LOTUS Database	35616633
Oxytropis ochrocephala	LOTUS Database	35616633
Pearsonia aristata	LOTUS Database	35616633
Pearsonia sessilifolia	LOTUS Database	35616633
Plagiocarpus axillaris	LOTUS Database	35616633
Podalyria cuneifolia	LOTUS Database	35616633
Polhillia canescens	LOTUS Database	35616633
Prunus mahaleb	LOTUS Database	35616633
Retama sphaerocarpa	LOTUS Database	35616633
Robynsiophyton vanderystii	LOTUS Database	35616633
Sophora secundiflora	LOTUS Database	35616633
Spartium junceum	LOTUS Database	35616633
Thermopsis lanceolata	LOTUS Database	35616633
Thermopsis montana	LOTUS Database	35616633
Virgilia divaricata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Sparteine, lupanine, and related alkaloids

Direct Parent

Sparteine, lupanine, and related alkaloids

Alternative Parents

Substituents

Sparteine-lupanine skeleton
Quinolizidine
Piperidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Quinolizidine alkaloids (C10783 )

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	2.03	ChemAxon
pKa (Strongest Basic)	9.16	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	71.82 m³·mol⁻¹	ChemAxon
Polarizability	28.36 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

C00002236

Chemspider ID

12944643

KEGG Compound ID

C10783

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sparteine

METLIN ID

Not Available

PubChem Compound

16212687

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Esteves T, Ferreira FA, Mota AT, Sanchez-Gonzalez A, Gil A, Andrade KHS, Afonso CAM, Ferreira FC: Greener Strategy for Lupanine Purification from Lupin Bean Wastewaters Using a Molecularly Imprinted Polymer. ACS Appl Mater Interfaces. 2022 Apr 27;14(16):18910-18921. doi: 10.1021/acsami.2c02053. Epub 2022 Apr 14. [PubMed:35420019 ]
Hidalgo M, Asmat Marrufo P, Lezama Asencio P, Ramos C, Chimoy Tunoque CA, Zolla G: Evaluation of in vitro susceptibility to sparteine in four strains of Mycobacterium tuberculosis. Rev Peru Med Exp Salud Publica. 2022 Jan-Mar;39(1):77-82. doi: 10.17843/rpmesp.2022.391.10136. Epub 2022 Jun 24. [PubMed:35766744 ]
Engel AM, Klevenhusen F, Moenning JL, Numata J, Fischer-Tenhagen C, Sachse B, Schafer B, Fry H, Kappenstein O, Pieper R: Investigations on the Transfer of Quinolizidine Alkaloids from Lupinus angustifolius into the Milk of Dairy Cows. J Agric Food Chem. 2022 Sep 21;70(37):11749-11758. doi: 10.1021/acs.jafc.2c02517. Epub 2022 Sep 6. [PubMed:36068017 ]
Choi A, Meijer AJHM, Silvestri IP, Coldham I: Kinetic Resolution of 2-Aryl-4-methylenepiperidines toward Enantioenriched Functionalizable Piperidine Fragments. J Org Chem. 2022 Jul 1;87(13):8819-8823. doi: 10.1021/acs.joc.2c00862. Epub 2022 Jun 14. [PubMed:35699313 ]
Bernal FA, Coy-Barrera E: Composition and Antifungal Activity of the Alkaloidal Fraction of Lupinus mirabilis Leaves: A Biochemometrics-Based Exploration. Molecules. 2022 Apr 29;27(9):2832. doi: 10.3390/molecules27092832. [PubMed:35566183 ]
LOTUS database [Link]

Showing NP-Card for (2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane (NP0291555)

MOL for NP0291555 ((2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane)

3D MOL for NP0291555 ((2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane)

3D SDF for NP0291555 ((2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane)

3D-SDF for NP0291555 ((2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane)

PDB for NP0291555 ((2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane)

3D PDB for NP0291555 ((2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane)

SMILES for NP0291555 ((2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane)

INCHI for NP0291555 ((2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane)

Structure for NP0291555 ((2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane)

3D Structure for NP0291555 ((2r,10s)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane)