NP-MRD: Showing NP-Card for (-)-Dehydrosparteine (NP0068401)

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Record Information

Version

2.0

Created at

2022-04-28 13:34:11 UTC

Updated at

2022-04-28 13:34:11 UTC

NP-MRD ID

NP0068401

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Dehydrosparteine

Description

Sparteine, also known as lupinidine or pachycarpine, 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. Sparteine is a lupin alkaloid containing a tetracyclic bis-quinolizidine ring system derived from three C5 chains of lysine, or more specifically, L-lysine. Sparteine is a very strong basic compound (based on its pKa). Sparteine is a class 1a antiarrhythmic agent; a sodium channel blocker. It is the predominant alkaloid in Lupinus mutabilis, and is thought to chelate the bivalent cations calcium and magnesium. The deaminated cadaverine is not released from the enzyme, thus is can be assumed that the enzyme catalyzes the formation of the quinolizidine skeleton in a channeled fashion (Figure 2). (-)-Dehydrosparteine is found in Adenocarpus hispanicus, Ammopiptanthus mongolicus, Anabasis aphylla, Anagyris foetida, Anarthrophyllum desideratum, Baptisia australis, Bolusanthus speciosus, Cadia purpurea, Calobota saharae, Cytisophyllum sessilifolium, Cytisus scoparius, Dermatophyllum secundiflorum, Dicraeopetalum stipulare, Genista acanthoclada, Genista lobelii, Genista lydia, Genista majorica, Hesperolaburnum platycarpum, Laburnum anagyroides, Lamprolobium fruticosum, Leontice leontopetalum, Liparia splendens, Lupinus albus, Lupinus angustifolius, Lupinus arboreus, Lupinus argenteus, Lupinus cosentinii, Lupinus hintonii, Lupinus luteus, Lupinus mexicanus, Lupinus mutabilis, Lupinus pilosus, Lupinus polyphyllus, Lupinus pubescens, Lupinus pusillus, Lupinus sericeus, Lupinus texensis, Ormosia coarctata, Ormosia macrocalyx, Oxytropis ochrocephala, Pearsonia obovata, Plagiocarpus axillaris, Podalyria sericea, Polhillia brevicalyx, Prunus mahaleb, Retama sphaerocarpa, Retama spp., Rothia hirsuta, Sophora secundiflora, Spartium junceum, Thermopsis chinensis, Virgilia divaricata and Wiborgia fusca. The imine is then hydrolyzed to the corresponding aldehyde/amine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -3.8549    0.4164    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7948   -1.0686    0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6939   -1.6938   -0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942   -0.9279   -0.7546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2993   -1.4325   -0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -0.9864    0.7402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5025    0.1388    1.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7475    1.0910    0.1737 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5050    1.5804   -0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6586    0.8072   -0.3382 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8687    1.5805   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.8041   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0651   -0.6122    0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360   -1.2758   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6872   -0.3124    0.5109 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6846    0.4677   -0.8576 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0696    1.0263   -0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5282    0.8872    1.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9203    0.7771    0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7333   -1.3653    1.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7890   -1.4671    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1426   -2.1397   -1.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521   -2.6021    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038   -2.5585   -0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3654   -1.1118   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -1.7961    1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0947    0.6933    2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -0.2237    1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331    1.9500    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2962    1.7778   -1.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211    2.6130   -0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8541    2.4131   -0.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    2.0601    0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5185    0.8328   -1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203    1.3177    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2804   -0.6580    1.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9031   -1.1747   -0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5720   -1.3436   -1.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277   -2.2434    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0593    0.0060    1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    0.7742   -1.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715    0.8602   -1.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842    2.1188   -0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  1 17  1  0
 17 16  1  0
 16  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  7  1  0
 15  6  1  0
  7  6  1  0
 16  4  1  0
 15 10  1  0
  6 26  1  1
  5 24  1  0
  5 25  1  0
  3 22  1  0
  3 23  1  0
  2 20  1  0
  2 21  1  0
  1 18  1  0
  1 19  1  0
 17 42  1  0
 17 43  1  0
 16 41  1  6
  8 29  1  1
  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  1
  7 27  1  0
  7 28  1  0
M  END


  Mrv1652304022019532D          

 21 24  0  0  1  0            999 V2000
    6.3404   -0.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908   -1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404   -1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908   -0.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -1.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -1.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281   -1.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281    0.1990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5031   -1.7928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9114   -0.3844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9197   -1.2094    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9114   -1.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197   -0.3844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438    0.9612    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -2.5550    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -0.7969    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6819   -0.8937    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  5  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17  8  1  0  0  0  0
 17 10  1  0  0  0  0
 17 15  1  0  0  0  0
 12 18  1  6  0  0  0
 13 19  1  6  0  0  0
 14 20  1  1  0  0  0
 15 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0068401

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CN3CCCC[C@@]3([H])[C@]([H])(CN3CCCC[C@]13[H])C2

> <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+/m0/s1

> <INCHI_KEY>
SLRCCWJSBJZJBV-ZQDZILKHSA-N

> <FORMULA>
C15H26N2

> <MOLECULAR_WEIGHT>
234.387

> <EXACT_MASS>
234.209598845

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
28.77818105315011

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.027827476999999

> <ALOGPS_LOGS>
-2.40

> <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>
71.823

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.31e-01 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      11.835  -0.718   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.783  -2.258   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.835  -2.258   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.783  -0.718   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.502   0.052   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.117  -3.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.502  -3.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.117   0.052   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.774  -1.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.539   0.371   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.079  -3.347   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.079   0.371   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.539  -3.347   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.168  -0.718   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.450  -2.258   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       9.168  -2.258   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       5.450  -0.718   0.000  0.00  0.00           N+0
HETATM   18  H   UNK     0       8.668   1.794   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       5.950  -4.769   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0      10.502  -1.488   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       6.873  -1.668   0.000  0.00  0.00           H+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1   14                                                       
CONECT    6    2   15                                                       
CONECT    7    3   16                                                       
CONECT    8    4   17                                                       
CONECT    9   12   13                                                       
CONECT   10   12   17                                                       
CONECT   11   13   16                                                       
CONECT   12    9   10   14   18                                             
CONECT   13    9   11   15   19                                             
CONECT   14    5   12   16   20                                             
CONECT   15    6   13   17   21                                             
CONECT   16    7   11   14                                                  
CONECT   17    8   10   15                                                  
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
(-)-Sparteine	ChEBI
(7S,7AS,14S,14ar)-dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine	ChEBI
6beta,7alpha,9alpha,11alpha-Pachycarpine	ChEBI
[7S-(7alpha,7Aalpha,14alpha,14abeta)]-dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine	ChEBI
L-Sparteine	ChEBI
Lupinidine	ChEBI
6b,7a,9a,11a-Pachycarpine	Generator
6Β,7α,9α,11α-pachycarpine	Generator
[7S-(7a,7Aalpha,14a,14abeta)]-dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine	Generator
[7S-(7Α,7aalpha,14α,14abeta)]-dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine	Generator
Sparteine, (7R-(7alpha,7abeta,14alpha,14abeta))-isomer	MeSH
Sparteine, (-)-isomer	MeSH
Sparteine, (+)-isomer	MeSH
Pachycarpine	MeSH
Sparteine, (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer	MeSH
Sparteine monohydrochloride, (7R-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine hydrochloride, (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine, (7R-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine sulfate (1:1), (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sulfate anhydrous, sparteine	MeSH
Depasan retard	MeSH
Sparteine hydrochloride, (7R-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
alpha-Isosparteine	MeSH
beta-Isosparteine	MeSH
Sparteine sulfate (1:1), (7S-(7alpha,7aalpha,14alpha,14aalpha))-isomer	MeSH
Sparteine sulfate anhydrous	MeSH
Genisteine alkaloid	MeSH
Sparteine, (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
beta Isosparteine	MeSH
Sparteine sulfate	MeSH
Pachycarpine sulfate (1:1), pentahydrate, (7S-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
D-Sparteine	MeSH
Sparteine hydroiodide, (7R-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH
Sparteine, (7S-(7alpha,7abeta,14alpha,14abeta))-isomer	MeSH
Anhydrous, sparteine sulfate	MeSH
alpha Isosparteine	MeSH
Sparteine monohydroiodide, (7R-(7alpha,7aalpha,14alpha,14abeta))-isomer	MeSH

Chemical Formula

C₁₅H₂₆N₂

Average Mass

234.3870 Da

Monoisotopic Mass

234.20960 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@]12CN3CCCC[C@@]3([H])[C@]([H])(CN3CCCC[C@]13[H])C2

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+/m0/s1

InChI Key

SLRCCWJSBJZJBV-ZQDZILKHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Baptisia australis	LOTUS Database	35616633
Bolusanthus speciosus	LOTUS Database	35616633
Cadia purpurea	LOTUS Database	35616633
Calobota saharae	LOTUS Database	35616633
Cytisophyllum sessilifolium	LOTUS Database	35616633
Cytisus scoparius	LOTUS Database	35616633
Dermatophyllum secundiflorum	LOTUS Database	35616633
Dicraeopetalum stipulare	LOTUS Database	35616633
Genista acanthoclada	LOTUS Database	35616633
Genista lobelii	LOTUS Database	35616633
Genista lydia	LOTUS Database	35616633
Genista majorica	LOTUS Database	35616633
Hesperolaburnum platycarpum	LOTUS Database	35616633
Laburnum anagyroides	LOTUS Database	35616633
Lamprolobium fruticosum	LOTUS Database	35616633
Leontice leontopetalum	LOTUS Database	35616633
Liparia splendens	LOTUS Database	35616633
Lupinus albus	LOTUS Database	35616633
Lupinus angustifolius	LOTUS Database	35616633
Lupinus arboreus	LOTUS Database	35616633
Lupinus argenteus	LOTUS Database	35616633
Lupinus cosentinii	LOTUS Database	35616633
Lupinus hintonii	LOTUS Database	35616633
Lupinus luteus	LOTUS Database	35616633
Lupinus mexicanus	LOTUS Database	35616633
Lupinus mutabilis	LOTUS Database	35616633
Lupinus pilosus	LOTUS Database	35616633
Lupinus polyphyllus	LOTUS Database	35616633
Lupinus pubescens	LOTUS Database	35616633
Lupinus pusillus	LOTUS Database	35616633
Lupinus sericeus	LOTUS Database	35616633
Lupinus texensis	LOTUS Database	35616633
Ormosia coarctata	LOTUS Database	35616633
Ormosia macrocalyx	LOTUS Database	35616633
Oxytropis ochrocephala	LOTUS Database	35616633
Pearsonia obovata	LOTUS Database	35616633
Plagiocarpus axillaris	Plant	KNApSAcK
Podalyria sericea	LOTUS Database	35616633
Polhillia brevicalyx	LOTUS Database	35616633
Prunus mahaleb	LOTUS Database	35616633
Retama sphaerocarpa	LOTUS Database	35616633
Retama spp.	Plant	KNApSAcK
Rothia hirsuta	LOTUS Database	35616633
Sophora secundiflora	LOTUS Database	35616633
Spartium junceum	LOTUS Database	35616633
Thermopsis chinensis	LOTUS Database	35616633
Virgilia divaricata	LOTUS Database	35616633
Wiborgia fusca	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 alkaloid (CHEBI:28827 )
quinolizidine alkaloid fundamental parent (CHEBI:28827 )

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	2.98	ALOGPS
logP	2.03	ChemAxon
logS	-2.4	ALOGPS
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	28.78 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

Not Available

KEGG Compound ID

C10783

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sparteine

METLIN ID

Not Available

PubChem Compound

644020

PDB ID

Not Available

ChEBI ID

28827

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Dehydrosparteine (NP0068401)

MOL for NP0068401 ((-)-Dehydrosparteine)

3D MOL for NP0068401 ((-)-Dehydrosparteine)

3D SDF for NP0068401 ((-)-Dehydrosparteine)

3D-SDF for NP0068401 ((-)-Dehydrosparteine)

PDB for NP0068401 ((-)-Dehydrosparteine)

3D PDB for NP0068401 ((-)-Dehydrosparteine)

SMILES for NP0068401 ((-)-Dehydrosparteine)

INCHI for NP0068401 ((-)-Dehydrosparteine)

Structure for NP0068401 ((-)-Dehydrosparteine)

3D Structure for NP0068401 ((-)-Dehydrosparteine)