NP-MRD: Showing NP-Card for Lycobergine (NP0051051)

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Record Information

Version

2.0

Created at

2022-04-27 22:29:48 UTC

Updated at

2022-04-27 22:29:48 UTC

NP-MRD ID

NP0051051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lycobergine

Description

Lycoflexine belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. Lycobergine is found in Austrolycopodium fastigiatum, Lycopodium serratum, Lycopodium inundatum, Lycopodium carolinianum, Lycopodium clavatum var. borbonicum , Lycopodium clavatum var. inflexum , Lycopodium deuterodensum, Lycopodium fastigiatum, Lycopodium japonicum, Lycopodium serratum var. serratum f. intermedium, Lycopodium serratum var. serratum f. serratum, Lycopodium phlegmaria and Phlegmariurus varius. Lycobergine was first documented in 2011 (PMID: 21473623). Based on a literature review a small amount of articles have been published on Lycoflexine (PMID: 23650145) (PMID: 26287979) (PMID: 24295384) (PMID: 22519642).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 48  0  0  0  0  0  0  0  0999 V2000
    4.4421    0.0019   -1.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0859    0.3950   -0.7203 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0568    0.5126   -1.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255   -0.0094   -1.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0318   -0.1075   -2.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1781   -0.4349   -0.1497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1503   -1.8791   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301   -2.3608   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6288   -1.4715   -0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9706   -0.5516    0.3800 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6652    0.6282   -0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997    1.8787    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4495    1.4822   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8241    0.4739    0.4245 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8996   -0.2206    1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346    1.3300    1.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    1.9333    2.3841 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3005    1.2180    1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3597   -0.2659    0.8282 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6540   -0.7034    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1488   -0.0306   -0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7711    0.8494   -1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3783   -0.9570   -1.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3123    1.3241   -0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9546    1.5756   -2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4840    0.0277   -2.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3727   -2.3238   -1.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3786   -2.4209    0.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8354   -2.7921    0.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053   -3.2924   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5407   -2.1392   -0.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.0623   -1.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0953    0.5936   -1.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5090    0.7769    0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2175    2.6588   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071    2.2459    1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6651    1.1873   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433    2.4335   -0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2881    0.4691    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4260   -1.0522    1.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9729    1.5213    1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    1.8551    0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -0.7868    1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012   -1.6296   -0.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3730   -0.8806    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 20  1  0
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 14 16  1  1
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10 15  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  4  1  6
  4  5  2  0
  4  3  1  0
  3  2  1  0
  6 19  1  0
 15 14  1  0
  6 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
 20 44  1  0
 20 45  1  0
 19 43  1  1
 18 41  1  0
 18 42  1  0
 13 37  1  0
 13 38  1  0
 12 35  1  0
 12 36  1  0
 11 33  1  0
 11 34  1  0
 15 39  1  0
 15 40  1  0
  9 31  1  0
  9 32  1  0
  8 29  1  0
  8 30  1  0
  7 27  1  0
  7 28  1  0
  3 25  1  0
  3 26  1  0
M  END


  Mrv1652304282200292D          

 20 23  0  0  1  0            999 V2000
    5.5884    0.8277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1252    1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    1.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8392    2.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9428    0.7081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4060    0.0254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2288    0.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998   -0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1238   -0.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4411   -0.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    0.4786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4321    0.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812    1.7673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    2.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2465    2.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696    1.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4786    1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6286    0.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208   -0.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4113    0.8875    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
  5  3  1  1  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
  9 10  2  0  0  0  0
 11  9  1  6  0  0  0
  5 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
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
  1 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051051

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H]2CC(=O)[C@]34CCCN(C3)CCC[C@]24C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H25NO2/c1-12-8-13-10-14(19)16-4-2-6-18(11-16)7-3-5-17(13,16)15(20)9-12/h12-13H,2-11H2,1H3/t12-,13+,16+,17-/m1/s1

> <INCHI_KEY>
SJIMDGIDDDGXLI-OSRSDYAFSA-N

> <FORMULA>
C17H25NO2

> <MOLECULAR_WEIGHT>
275.392

> <EXACT_MASS>
275.188529049

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.906479428251437

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,6R,9S)-6-methyl-13-azatetracyclo[11.3.1.0^{1,9}.0^{4,9}]heptadecane-2,8-dione

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.431905596666666

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.74075607896298

> <JCHEM_PKA_STRONGEST_BASIC>
8.595507603475335

> <JCHEM_POLAR_SURFACE_AREA>
37.38

> <JCHEM_REFRACTIVITY>
78.1761

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,6R,9S)-6-methyl-13-azatetracyclo[11.3.1.0^{1,9}.0^{4,9}]heptadecane-2,8-dione

> <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      10.432   1.545   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.567   2.819   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.031   2.708   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.167   3.982   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.360   1.322   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.224   0.047   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.760   0.159   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.280  -1.169   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.831  -0.646   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.557  -1.510   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.881   0.893   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.540   1.824   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.885   3.299   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.560   4.726   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.060   4.236   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.663   2.773   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.760   2.078   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.040   0.516   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.519  -0.009   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.968   1.657   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   11   16                                             
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12   19                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    5                                                       
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   11                                                       
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,4S,6R,9S)-6-methyl-13-azatetracyclo[11.3.1.0^{1,9}.0^{4,9}]heptadecane-2,8-dione

Traditional Name

(1S,4S,6R,9S)-6-methyl-13-azatetracyclo[11.3.1.0^{1,9}.0^{4,9}]heptadecane-2,8-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H]2CC(=O)[C@]34CCCN(C3)CCC[C@]24C(=O)C1

InChI Identifier

InChI=1S/C17H25NO2/c1-12-8-13-10-14(19)16-4-2-6-18(11-16)7-3-5-17(13,16)15(20)9-12/h12-13H,2-11H2,1H3/t12-,13+,16+,17-/m1/s1

InChI Key

SJIMDGIDDDGXLI-OSRSDYAFSA-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
Austrolycopodium fastigiatum	LOTUS Database	35616633
Huperzia serrata	Plant	KNApSAcK
Lycopodiella inundata	Plant	KNApSAcK
Lycopodium carolinianum	Plant	KNApSAcK
Lycopodium clavatum var. borbonicum	Plant	KNApSAcK
Lycopodium clavatum var. inflexum	Plant	KNApSAcK
Lycopodium deuterodensum	Plant	KNApSAcK
Lycopodium fastigiatum	Plant	KNApSAcK
Lycopodium japonicum	LOTUS Database	35616633
Lycopodium serratum var. serratum f. intermedium	Plant	KNApSAcK
Lycopodium serratum var. serratum f. serratum	Plant	KNApSAcK
Phlegmariurus phlegmaria	Plant	KNApSAcK
Phlegmariurus varius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Azepane
Piperidine
Ketone
Tertiary amine
Tertiary aliphatic amine
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

azaspiro compound (CHEBI:6593 )

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	2.2	ALOGPS
logP	2.43	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	18.74	ChemAxon
pKa (Strongest Basic)	8.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.38 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.18 m³·mol⁻¹	ChemAxon
Polarizability	30.91 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

C00001946

Chemspider ID

390917

KEGG Compound ID

C09879

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442486

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Itoh N, Iwata T, Sugihara H, Inagaki F, Mukai C: Total syntheses of (+/-)-fawcettimine, (+/-)-fawcettidine, (+/-)-lycoflexine, and (+/-)-lycoposerramine-Q. Chemistry. 2013 Jun 24;19(26):8665-72. doi: 10.1002/chem.201300364. Epub 2013 May 6. [PubMed:23650145 ]
Liu YC, Fan M, Jiang WW, Liu F, Wu XD, He J, Cheng X, Peng LY, Su J, Zhang ZJ, Zhao QS: Four new fawcettimine-related alkaloids from Phlegmariurus squarrosus. J Asian Nat Prod Res. 2015;17(10):967-75. doi: 10.1080/10286020.2015.1043281. Epub 2015 Aug 19. [PubMed:26287979 ]
Xu K, Cheng B, Li Y, Xu T, Yu C, Zhang J, Ma Z, Zhai H: Stereocontrolled total syntheses of (+/-)-fawcettimine, (+/-)-lycoflexine, and (+/-)-lycoflexine N-oxide. Org Lett. 2014 Jan 3;16(1):196-9. doi: 10.1021/ol403185g. Epub 2013 Dec 2. [PubMed:24295384 ]
Pan G, Williams RM: Unified total syntheses of fawcettimine class alkaloids: fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B. J Org Chem. 2012 May 18;77(10):4801-11. doi: 10.1021/jo3006045. Epub 2012 May 7. [PubMed:22519642 ]
Yang YR, Shen L, Huang JZ, Xu T, Wei K: Application of the Helquist annulation in Lycopodium alkaloid synthesis: unified total syntheses of (-)-8-deoxyserratinine, (+)-fawcettimine, and (+)-lycoflexine. J Org Chem. 2011 May 20;76(10):3684-90. doi: 10.1021/jo1023188. Epub 2011 Apr 7. [PubMed:21473623 ]

Showing NP-Card for Lycobergine (NP0051051)

MOL for NP0051051 (Lycobergine)

3D MOL for NP0051051 (Lycobergine)

3D SDF for NP0051051 (Lycobergine)

3D-SDF for NP0051051 (Lycobergine)

PDB for NP0051051 (Lycobergine)

3D PDB for NP0051051 (Lycobergine)

SMILES for NP0051051 (Lycobergine)

INCHI for NP0051051 (Lycobergine)

Structure for NP0051051 (Lycobergine)

3D Structure for NP0051051 (Lycobergine)