NP-MRD: Showing NP-Card for (+)-Lupanine (NP0051278)

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Record Information

Version

2.0

Created at

2022-04-27 22:39:42 UTC

Updated at

2022-04-27 22:39:42 UTC

NP-MRD ID

NP0051278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Lupanine

Description

ZINC2556369 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. (+)-Lupanine is found in Ammodendron longiracemosum, Ammopiptanthus mongolicus, Argyrolobium frutescens, Argyrolobium lanceolatum, Argyrolobium lunare, Argyrolobium molle, Argyrolobium rupestre, Argyrolobium sankeyi, Argyrolobium speciosum, Argyrolobium tomentosum, Argyrolobium velutinum, Aspalathus capitata, Aspalathus chortophila, Aspalathus cordata, Aspalathus hirta, Aspalathus juniperina, Aspalathus longifolia, Aspalathus nivea, Aspalathus perfoliata, Baptisia alba, Baptisia simplicifolia, Bolusanthus speciosus, Camaecytisus absinthioides, Caulophyllum robustum, Caulophyllum thalictroides L. Michx. , Clathrotropis brachypetala , Cytisophyllum sessilifolium, Cytisus albus, Cytisus baeticus, Cytisus commutatus, Cytisus eriocarpus, Cytisus hirsutus, Cytisus jankae, Cytisus lasiosemius, Cytisus multiflorus , Cytisus reverchonii, Cytisus scoparius , Dermatophyllum secundiflorum, Dichilus gracilis, Dichilus lebeckioides, Dichilus pilosus, Dichilus reflexus, Dichilus strictus, Diplotropis martiusii, Echinosophora koreensis, Echinospartum horridum, Echinospartum lusitanicum, Euphorbia larica, Genista albida, Genista anatolica, Genista aucheri, Genista burdurensis, Genista cinerea, Genista corsica, Genista ephedroides, Genista germanica, Genista hispanica, Genista involucrata, Genista libanotica, Genista lydia, Genista osmariensis, Genista radiata, Genista sylvestris, Genista tejedensis, Genista triacanthos, Genista valentina, Gonocytisus angulatus, Haplormosia monophylla, Laburnum alpinum, Laburnum x watereri, Lebeckia bowieana, Lebeckia leipoldtiana, Lebeckia lotononoides, Lebeckia macrantha, Lebeckia melilotoides, Lebeckia plukenetiana, Lebeckia pungens, Lebeckia sericea, Lebeckia sessilifolia, Lebeckia simsiana, Lebeckia spinescens, Leontice ewersmannii, Leontice leontopetalum, Leontice robustum, Liparia parva, Liparia splendens, Lotononis adpressa, Lotononis bainesii, Lotononis calycina, Lotononis carinata, Lotononis curvicarpa, Lotononis eriantha, Lotononis lanceolata, Lotononis listii, Lotononis mucronata, Lotononis platycarpa, Lotononis wilmsii, Lotus aegeus, Lupinus albus , Lupinus graecus, Lupinus angustifolius , Lupinus arboreus, Lupinus argenteus, Lupinus argenteus var.stenophyllus., Lupinus hirsutus , Lupinus latifolius, Lupinus laxus, Lupinus luteus , Lupinus mutabilis, Lupinus paniculatus, Lupinus polyphyllus Lindl., Lupinus pubescens, Lupinus sericeus, Lupinus spp., Lupinus texensis, Maackia amurensis , Melolobium aethiopicum, Melolobium burchellii, Melolobium candicans, Melolobium exudans, Melolobium stipulatum, Melolobium wilmsii, Ormosia coarctata, Ormosia coccinea, Ormosia krugii, Pearsonia aristata, Pearsonia cajanifolia, Pearsonia obovata, Pearsonia sessilifolia, Petteria ramentacea, Piptanthus nepalensis, Podalyria buxifolia, Podalyria sericea, Polhillia brevicalyx, Polhillia canescens, Polhillia waltersii, Rafnia angulata, Rafnia elliptica, Rafnia opposita, Rafnia perfoliata, Rafnia racemosa, Retama sphaerocarpa , Rothia hirsuta, Sophora chrysophylla, Sophora davidii, Sophora flavescens , Sophora mollis , Sophora secundiflora , Sophora viciifolia, Spartidium saharae, Spartium junceum , Templetonia egena, Templetonia retusa, Thermopsis chinensis, Thermopsis lanceolata, Thermopsis lupinoides, Ulex airensis, Ulex australis, Ulex densus, Ulex europaeus , Ulex minor, Ulex jussiaei, Virgilia oroboides, Vitis vinifera, Wiborgia fusca, Wiborgia obcordata and Wiborgia sericea. Based on a literature review very few articles have been published on ZINC2556369.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
    3.0341    2.0506    1.7001 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    1.0897    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2715    0.6521    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2405   -0.7898   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9781   -1.0866   -0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7361   -0.8561   -0.0636 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5448   -0.8896   -1.0002 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3439    0.5041   -1.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3454    1.2792   -0.3911 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4983    1.1085    0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485    0.4497    0.5630 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6946    0.6519   -0.2867 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6396    1.4063    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0314    0.9550    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0962   -0.5339    0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0015   -1.2703   -0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6735   -0.7052    0.0933 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6455   -1.5289   -0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4844    1.2463   -0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1166    0.8082    0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2741   -1.4904    0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885   -0.9873   -0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9621   -2.1467   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9533   -0.4654   -1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6851   -1.6541    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328   -1.5096   -1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3151    0.4830   -2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3026    0.9921   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182    2.3402   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6919    2.1331    1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600    0.5818    1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1513    0.7151   -1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4786    1.0790    1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    2.4981    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233    1.4576    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1557    1.1111   -0.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0563   -0.9054    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0381   -0.6782    1.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724   -1.3196   -1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0150   -2.3225    0.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970   -2.3037   -1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2668   -2.1493    0.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11  2  1  0
 17 12  1  0
 11  6  1  0
 18  7  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  7 26  1  6
  8 27  1  0
  8 28  1  0
  9 29  1  6
 10 30  1  0
 10 31  1  0
 12 32  1  6
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
M  END


  Mrv1652304282200392D          

 18 21  0  0  1  0            999 V2000
    6.3404    2.0344    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
    5.6259    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -0.0281    0.0000 O   0  0  0  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
    4.9114    2.0344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6259    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281    2.6178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1646    1.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.6260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3281    0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9197    1.2094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9197    2.0344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    2.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908    2.0344    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
    2.2053    0.7969    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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051278

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCC[C@@H]2[C@@H]3C[C@H](CN12)[C@@H]1CCCCN1C3

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13+,14-/m1/s1

> <INCHI_KEY>
JYIJIIVLEOETIQ-YIYPIFLZSA-N

> <FORMULA>
C15H24N2O

> <MOLECULAR_WEIGHT>
248.37

> <EXACT_MASS>
248.188863401

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.773788780867505

> <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}]heptadecan-6-one

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
1.0759273119999997

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.75154362875031

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
71.44850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,9R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.835   3.798   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.835   2.258   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.502   1.488   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.502  -0.052   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.168   2.258   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.168   3.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.502   4.568   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.079   4.886   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.774   2.835   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.539   1.169   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.079   1.169   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.450   2.258   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.450   3.798   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.539   4.886   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.116   4.568   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.783   3.798   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.783   2.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.116   1.488   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    8                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄N₂O

Average Mass

248.3700 Da

Monoisotopic Mass

248.18886 Da

IUPAC Name

(1R,2R,9R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

Traditional Name

(1R,2R,9R,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one

CAS Registry Number

Not Available

SMILES

O=C1CCC[C@@H]2[C@@H]3C[C@H](CN12)[C@@H]1CCCCN1C3

InChI Identifier

InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13+,14-/m1/s1

InChI Key

JYIJIIVLEOETIQ-YIYPIFLZSA-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
Ammodendron longiracemosum	Plant	KNApSAcK
Ammopiptanthus mongolicus	LOTUS Database	35616633
Argyrolobium frutescens	Plant	KNApSAcK
Argyrolobium lanceolatum	Plant	KNApSAcK
Argyrolobium lunare	Plant	KNApSAcK
Argyrolobium molle	Plant	KNApSAcK
Argyrolobium rupestre	Plant	KNApSAcK
Argyrolobium sankeyi	Plant	KNApSAcK
Argyrolobium speciosum	Plant	KNApSAcK
Argyrolobium tomentosum	Plant	KNApSAcK
Argyrolobium velutinum	Plant	KNApSAcK
Aspalathus capitata	Plant	KNApSAcK
Aspalathus chortophila	Plant	KNApSAcK
Aspalathus cordata	Plant	KNApSAcK
Aspalathus hirta	Plant	KNApSAcK
Aspalathus juniperina	Plant	KNApSAcK
Aspalathus longifolia	Plant	KNApSAcK
Aspalathus nivea	Plant	KNApSAcK
Aspalathus perfoliata	Plant	KNApSAcK
Baptisia alba	Plant	KNApSAcK
Baptisia simplicifolia	Plant	KNApSAcK
Bolusanthus speciosus	LOTUS Database	35616633
Camaecytisus absinthioides	-	KNApSAcK
Caulophyllum robustum	LOTUS Database	35616633
Caulophyllum thalictroides L. Michx.	Plant	KNApSAcK
Clathrotropis brachypetala	Plant	KNApSAcK
Cytisophyllum sessilifolium	Plant	KNApSAcK
Cytisus albus	Plant	KNApSAcK
Cytisus baeticus	Plant	KNApSAcK
Cytisus commutatus	Plant	KNApSAcK
Cytisus eriocarpus	Plant	KNApSAcK
Cytisus hirsutus	Plant	KNApSAcK
Cytisus jankae	Plant	KNApSAcK
Cytisus lasiosemius	Plant	KNApSAcK
Cytisus multiflorus	Plant	KNApSAcK
Cytisus reverchonii	Plant	KNApSAcK
Cytisus scoparius	Plant	KNApSAcK
Dermatophyllum secundiflorum	LOTUS Database	35616633
Dichilus gracilis	Plant	KNApSAcK
Dichilus lebeckioides	Plant	KNApSAcK
Dichilus pilosus	Plant	KNApSAcK
Dichilus reflexus	Plant	KNApSAcK
Dichilus strictus	Plant	KNApSAcK
Diplotropis martiusii	Plant	KNApSAcK
Echinosophora koreensis	LOTUS Database	35616633
Echinospartum horridum	Plant	KNApSAcK
Echinospartum lusitanicum	Plant	KNApSAcK
Euphorbia larica	Plant	KNApSAcK
Genista albida	Plant	KNApSAcK
Genista anatolica	Plant	KNApSAcK
Genista aucheri	Plant	KNApSAcK
Genista burdurensis	Plant	KNApSAcK
Genista cinerea	Plant	KNApSAcK
Genista corsica	Plant	KNApSAcK
Genista ephedroides	Plant	KNApSAcK
Genista germanica	Plant	KNApSAcK
Genista hispanica	Plant	KNApSAcK
Genista involucrata	Plant	KNApSAcK
Genista libanotica	Plant	KNApSAcK
Genista lydia	LOTUS Database	35616633
Genista osmariensis	Plant	KNApSAcK
Genista radiata	Plant	KNApSAcK
Genista sylvestris	Plant	KNApSAcK
Genista tejedensis	Plant	KNApSAcK
Genista triacanthos	Plant	KNApSAcK
Genista valentina	Plant	KNApSAcK
Gonocytisus angulatus	Plant	KNApSAcK
Haplormosia monophylla	Plant	KNApSAcK
Laburnum alpinum	Plant	KNApSAcK
Laburnum watereri	Plant	KNApSAcK
Lebeckia bowieana	Plant	KNApSAcK
Lebeckia leipoldtiana	Plant	KNApSAcK
Lebeckia lotononoides	Plant	KNApSAcK
Lebeckia macrantha	Plant	KNApSAcK
Lebeckia melilotoides	Plant	KNApSAcK
Lebeckia plukenetiana	Plant	KNApSAcK
Lebeckia pungens	Plant	KNApSAcK
Lebeckia sericea	Plant	KNApSAcK
Lebeckia sessilifolia	Plant	KNApSAcK
Lebeckia simsiana	Plant	KNApSAcK
Lebeckia spinescens	Plant	KNApSAcK
Leontice ewersmannii	Plant	KNApSAcK
Leontice leontopetalum	LOTUS Database	35616633
Leontice robustum	Plant	KNApSAcK
Liparia parva	Plant	KNApSAcK
Liparia splendens	Plant	KNApSAcK
Lotononis adpressa	Plant	KNApSAcK
Lotononis bainesii	Plant	KNApSAcK
Lotononis calycina	Plant	KNApSAcK
Lotononis carinata	Plant	KNApSAcK
Lotononis curvicarpa	Plant	KNApSAcK
Lotononis eriantha	Plant	KNApSAcK
Lotononis lanceolata	Plant	KNApSAcK
Lotononis listii	Plant	KNApSAcK
Lotononis mucronata	Plant	KNApSAcK
Lotononis platycarpa	Plant	KNApSAcK
Lotononis wilmsii	Plant	KNApSAcK
Lotus aegeus	Plant	KNApSAcK
Lupinus albus	Plant	KNApSAcK
Lupinus albus var. graecus	Plant	KNApSAcK
Lupinus angustifolius	Plant	KNApSAcK
Lupinus arboreus	Plant	KNApSAcK
Lupinus argenteus	LOTUS Database	35616633
Lupinus argenteus var.stenophyllus.	Plant	KNApSAcK
Lupinus hirsutus	Plant	KNApSAcK
Lupinus latifolius	Plant	KNApSAcK
Lupinus laxus	Plant	KNApSAcK
Lupinus luteus	Plant	KNApSAcK
Lupinus mutabilis	Plant	KNApSAcK
Lupinus paniculatus	Plant	KNApSAcK
Lupinus polyphyllus	Plant	KNApSAcK
Lupinus pubescens	Plant	KNApSAcK
Lupinus sericeus	Plant	KNApSAcK
Lupinus spp.	Plant	KNApSAcK
Lupinus texensis	Plant	KNApSAcK
Maackia amurensis	Plant	KNApSAcK
Melolobium aethiopicum	Plant	KNApSAcK
Melolobium burchellii	Plant	KNApSAcK
Melolobium candicans	Plant	KNApSAcK
Melolobium exudans	Plant	KNApSAcK
Melolobium stipulatum	Plant	KNApSAcK
Melolobium wilmsii	Plant	KNApSAcK
Ormosia coarctata	LOTUS Database	35616633
Ormosia coccinea	Plant	KNApSAcK
Ormosia krugii	Plant	KNApSAcK
Pearsonia aristata	Plant	KNApSAcK
Pearsonia cajanifolia	Plant	KNApSAcK
Pearsonia obovata	Plant	KNApSAcK
Pearsonia sessilifolia	Plant	KNApSAcK
Petteria ramentacea	Plant	KNApSAcK
Piptanthus nepalensis	Plant	KNApSAcK
Podalyria buxifolia	Plant	KNApSAcK
Podalyria sericea	Plant	KNApSAcK
Polhillia brevicalyx	Plant	KNApSAcK
Polhillia canescens	Plant	KNApSAcK
Polhillia waltersii	Plant	KNApSAcK
Rafnia angulata	Plant	KNApSAcK
Rafnia elliptica	Plant	KNApSAcK
Rafnia opposita	Plant	KNApSAcK
Rafnia perfoliata	Plant	KNApSAcK
Rafnia racemosa	Plant	KNApSAcK
Retama sphaerocarpa	Plant	KNApSAcK
Rothia hirsuta	Plant	KNApSAcK
Sophora chrysophylla	Plant	KNApSAcK
Sophora davidii	LOTUS Database	35616633
Sophora flavescens	Plant	KNApSAcK
Sophora mollis	Plant	KNApSAcK
Sophora secundiflora	Plant	KNApSAcK
Sophora viciifolia	Plant	KNApSAcK
Spartidium saharae	Plant	KNApSAcK
Spartium junceum	Plant	KNApSAcK
Templetonia egena	Plant	KNApSAcK
Templetonia retusa	LOTUS Database	35616633
Thermopsis chinensis	Plant	KNApSAcK
Thermopsis lanceolata	Plant	KNApSAcK
Thermopsis lupinoides	Plant	KNApSAcK
Ulex airensis	Plant	KNApSAcK
Ulex australis	Plant	KNApSAcK
Ulex densus	Plant	KNApSAcK
Ulex europaeus	Plant	KNApSAcK
Ulex minor	Plant	KNApSAcK
Ulex parviflorus subsp. jussiaei	Plant	KNApSAcK
Virgilia oroboides	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Wiborgia fusca	Plant	KNApSAcK
Wiborgia obcordata	Plant	KNApSAcK
Wiborgia sericea	Plant	KNApSAcK

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
Quinolizidinone
Quinolizidine
Delta-lactam
Piperidinone
Piperidine
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Amine
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
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	2.34	ALOGPS
logP	1.08	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	9.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.45 m³·mol⁻¹	ChemAxon
Polarizability	28.77 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

Not Available

Chemspider ID

5029695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6575009

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Lupanine (NP0051278)

MOL for NP0051278 ((+)-Lupanine)

3D MOL for NP0051278 ((+)-Lupanine)

3D SDF for NP0051278 ((+)-Lupanine)

3D-SDF for NP0051278 ((+)-Lupanine)

PDB for NP0051278 ((+)-Lupanine)

3D PDB for NP0051278 ((+)-Lupanine)

SMILES for NP0051278 ((+)-Lupanine)

INCHI for NP0051278 ((+)-Lupanine)

Structure for NP0051278 ((+)-Lupanine)

3D Structure for NP0051278 ((+)-Lupanine)