NP-MRD: Showing NP-Card for Magellanine (NP0051053)

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Record Information

Version

2.0

Created at

2022-04-27 22:29:54 UTC

Updated at

2022-04-27 22:29:54 UTC

NP-MRD ID

NP0051053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Magellanine

Description

Magellanine belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Magellanine is found in Lycopodium magellanicum and Maytenus magellanica. Magellanine was first documented in 2002 (PMID: 12412091). Based on a literature review a significant number of articles have been published on Magellanine (PMID: 26207328) (PMID: 25299586) (PMID: 18044932) (PMID: 28869258) (PMID: 28079949) (PMID: 22201223).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 48  0  0  0  0  0  0  0  0999 V2000
    4.6704    2.1933    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3768    1.4952    0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3236    2.1223    0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1044    1.3552    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4038    1.5402    2.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192    0.3788    0.0413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3364    1.0509   -0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5901    0.2903   -0.5639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3847    0.7373    0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7140    0.1183    0.4883 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4780    0.9659   -0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5147   -1.2108   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1916   -1.8207    0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0843   -1.1047   -0.2686 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1371   -0.8813    0.5532 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1027   -2.0105    0.2293 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3739   -3.1939    0.0473 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7290   -1.5393   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -0.0420   -0.7676 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1769    0.0640    0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    2.8506   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0363    2.7006    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4288    1.3890   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4140    3.1667    1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007    2.1316   -0.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    0.9143   -1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2444    0.2859   -1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    0.2968    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392    1.8155    0.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8973    1.7944    0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679    0.4632   -0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8761    1.4727   -1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3031   -1.8900    0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406   -1.2859   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0996   -1.7848    1.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1977   -2.8734    0.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -1.5736   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -0.9020    1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394   -2.1382    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560   -3.3067   -0.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235   -2.0162   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356   -1.7243   -1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0257    0.5255   -1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9634   -0.4451    1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0483   -0.3752   -0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14  8  1  0
  8  7  1  0
  6  7  1  6
  6 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 19 20  1  0
 20  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  8  9  1  0
  9 10  1  0
 15 14  1  0
 15  6  1  0
  6  4  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
  8 27  1  6
  7 25  1  0
  7 26  1  0
 19 43  1  6
 18 41  1  0
 18 42  1  0
 16 39  1  1
 17 40  1  0
 15 38  1  1
 20 44  1  0
 20 45  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  9 28  1  0
  9 29  1  0
M  END


  Mrv1652304282200292D          

 20 23  0  0  1  0            999 V2000
   -0.5429   -1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860   -1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005   -1.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860   -0.3945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1715    0.0180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5429   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3431    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1635    0.9112    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4991    0.1576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0420   -1.0619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2216   -1.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6551   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398   -1.3590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6113   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9982    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0528   -1.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760    1.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2574   -1.6320    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  1  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
  5 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  1  0  0  0
 15 18  1  0  0  0  0
  9 19  1  6  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC[C@H]2[C@H](C[C@]34[C@H](C[C@H](O)[C@H]23)CC(C)=CC4=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H25NO2/c1-10-5-12-7-14(19)16-13-3-4-18(2)9-11(13)8-17(12,16)15(20)6-10/h6,11-14,16,19H,3-5,7-9H2,1-2H3/t11-,12+,13+,14+,16+,17-/m1/s1

> <INCHI_KEY>
ADRPSBGLUHNVOU-INSRFAMQSA-N

> <FORMULA>
C17H25NO2

> <MOLECULAR_WEIGHT>
275.392

> <EXACT_MASS>
275.188529049

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.410598003734925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,8S,9R,10S,12S)-10-hydroxy-5,14-dimethyl-5-azatetracyclo[7.7.0.0^{1,12}.0^{3,8}]hexadec-14-en-16-one

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
1.5058654840000005

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.07136109962921

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.895288167596828

> <JCHEM_PKA_STRONGEST_BASIC>
8.545474905966717

> <JCHEM_POLAR_SURFACE_AREA>
40.540000000000006

> <JCHEM_REFRACTIVITY>
79.9296

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,8S,9R,10S,12S)-10-hydroxy-5,14-dimethyl-5-azatetracyclo[7.7.0.0^{1,12}.0^{3,8}]hexadec-14-en-16-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.013  -2.276   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.320  -3.046   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.654  -2.276   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.988  -3.046   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.654  -0.736   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.320   0.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.013  -0.736   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.640   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.172   1.701   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.798   0.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.812  -1.982   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.280  -2.143   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.956  -3.013   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       6.421  -2.537   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.741  -1.030   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.597   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.565  -3.567   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.942   3.035   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.347  -3.046   0.000  0.00  0.00           C+0
CONECT    1    2    7   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10   13                                             
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    5                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
CONECT   18   15                                                            
CONECT   19    9                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₅NO₂

Average Mass

275.3920 Da

Monoisotopic Mass

275.18853 Da

IUPAC Name

(1S,3S,8S,9R,10S,12S)-10-hydroxy-5,14-dimethyl-5-azatetracyclo[7.7.0.0^{1,12}.0^{3,8}]hexadec-14-en-16-one

Traditional Name

(1S,3S,8S,9R,10S,12S)-10-hydroxy-5,14-dimethyl-5-azatetracyclo[7.7.0.0^{1,12}.0^{3,8}]hexadec-14-en-16-one

CAS Registry Number

Not Available

SMILES

CN1CC[C@H]2[C@H](C[C@]34[C@H](C[C@H](O)[C@H]23)CC(C)=CC4=O)C1

InChI Identifier

InChI=1S/C17H25NO2/c1-10-5-12-7-14(19)16-13-3-4-18(2)9-11(13)8-17(12,16)15(20)6-10/h6,11-14,16,19H,3-5,7-9H2,1-2H3/t11-,12+,13+,14+,16+,17-/m1/s1

InChI Key

ADRPSBGLUHNVOU-INSRFAMQSA-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
Lycopodium magellanicum	Plant	KNApSAcK
Maytenus magellanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Piperidine
Cyclic alcohol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Amine
Alcohol
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

piperidines (CHEBI:6634 )

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	1.33	ALOGPS
logP	1.51	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.9	ChemAxon
pKa (Strongest Basic)	8.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.93 m³·mol⁻¹	ChemAxon
Polarizability	31.41 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00001949

Chemspider ID

390919

KEGG Compound ID

C09886

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Magellanine

METLIN ID

Not Available

PubChem Compound

442489

PDB ID

Not Available

ChEBI ID

6634

Good Scents ID

Not Available

References

General References

Lin KW, Ananthan B, Tseng SF, Yan TH: Exceedingly Concise and Elegant Synthesis of (+)-Paniculatine, (-)-Magellanine, and (+)-Magellaninone. Org Lett. 2015 Aug 7;17(15):3938-40. doi: 10.1021/acs.orglett.5b01975. Epub 2015 Jul 24. [PubMed:26207328 ]
Jiang SZ, Lei T, Wei K, Yang YR: Collective total synthesis of tetracyclic diquinane Lycopodium alkaloids (+)-paniculatine, (-)-magellanine, (+)-magellaninone and analogues thereof. Org Lett. 2014 Nov 7;16(21):5612-5. doi: 10.1021/ol502679v. Epub 2014 Oct 9. [PubMed:25299586 ]
Kozaka T, Miyakoshi N, Mukai C: Stereoselective total syntheses of three Lycopodium alkaloids, (-)-magellanine, (+)-magellaninone, and (+)-paniculatine, based on two Pauson-Khand reactions. J Org Chem. 2007 Dec 21;72(26):10147-54. doi: 10.1021/jo702136b. Epub 2007 Nov 29. [PubMed:18044932 ]
Lindsay VNG, Murphy RA, Sarpong R: Effect of protic additives in Cu-catalysed asymmetric Diels-Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids. Chem Commun (Camb). 2017 Sep 14;53(74):10291-10294. doi: 10.1039/c7cc06367a. [PubMed:28869258 ]
McGee P, Betournay G, Barabe F, Barriault L: A 11-Steps Total Synthesis of Magellanine through a Gold(I)-Catalyzed Dehydro Diels-Alder Reaction. Angew Chem Int Ed Engl. 2017 May 22;56(22):6280-6283. doi: 10.1002/anie.201611606. Epub 2017 Jan 12. [PubMed:28079949 ]
Murphy RA, Sarpong R: Direct methoxypyridine functionalization approach to magellanine-type Lycopodium alkaloids. Org Lett. 2012 Jan 20;14(2):632-5. doi: 10.1021/ol203269f. Epub 2011 Dec 27. [PubMed:22201223 ]
Hong BC, Wu MF, Tseng HC, Liao JH: Enantioselective organocatalytic formal [3 + 3]-cycloaddition of alpha,beta-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol. Org Lett. 2006 May 25;8(11):2217-20. doi: 10.1021/ol060486+. [PubMed:16706490 ]
Yen CF, Liao CC: Concise and efficient total synthesis of Lycopodium alkaloid magellanine. Angew Chem Int Ed Engl. 2002 Nov 4;41(21):4090-3. doi: 10.1002/1521-3773(20021104)41:21<4090::AID-ANIE4090>3.0.CO;2-#. [PubMed:12412091 ]

Showing NP-Card for Magellanine (NP0051053)

MOL for NP0051053 (Magellanine)

3D MOL for NP0051053 (Magellanine)

3D SDF for NP0051053 (Magellanine)

3D-SDF for NP0051053 (Magellanine)

PDB for NP0051053 (Magellanine)

3D PDB for NP0051053 (Magellanine)

SMILES for NP0051053 (Magellanine)

INCHI for NP0051053 (Magellanine)

Structure for NP0051053 (Magellanine)

3D Structure for NP0051053 (Magellanine)