NP-MRD: Showing NP-Card for Tacamonine (NP0067353)

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Record Information

Version

2.0

Created at

2022-04-28 12:06:40 UTC

Updated at

2022-04-28 12:06:41 UTC

NP-MRD ID

NP0067353

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tacamonine

Description

Tacamonine belongs to the class of organic compounds known as tacaman alkaloids. These are alkaloids containing the pentacyclic tacaman skeleton, which consists of a pyrido[1,2-a]indole fused to a quinolizine. Tacaman alkaloids are obtained from a precursor to a pseudoaspidospermidine (type II skeleton) derivative, by the formation of new bonds at C-20/C-3 and C-140/C-17. Tacamonine is found in Tabernaemontana eglandulosa. Tacamonine was first documented in 2005 (PMID: 15876084). Based on a literature review a small amount of articles have been published on Tacamonine (PMID: 16755041) (PMID: 18318547) (PMID: 31647242) (PMID: 16901143).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
   -5.2067    0.8195    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3204   -0.2903    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9530   -0.2493   -0.0376 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0869   -1.3819    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036   -1.4293   -0.5076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0436   -2.5853   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3874   -2.4589   -0.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1137   -3.4140   -0.7239 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9743   -1.1611   -0.2688 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802   -0.1239   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879    1.0401   -0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2017    0.6739    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745    1.4073    0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715    0.7409    0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5475   -0.6366    0.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3935   -1.3738    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2138   -0.7062   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1549    2.3030   -0.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2147    2.1624    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7941    0.8713    0.3416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2281    1.0313    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2581   -0.0931   -0.5967 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0558    1.0599   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2665    0.4676    0.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1189    1.7181    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7974   -1.2597    0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583   -0.2555    1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0670   -0.3749   -1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6236   -2.3364    0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332   -1.1695    1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948   -1.6377   -1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911   -2.8440    0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880   -3.5093   -0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    2.4889    0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4903    1.2976    0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4768   -1.1582    0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3903   -2.4492    0.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6947    3.1449    0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1251    2.5984   -1.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2048    2.5756    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708    2.9033   -0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    1.7979   -0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5760    1.4167    1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033    0.3794   -1.6154 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  2  0
  7  9  1  0
  9 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10 22  1  0
 22 20  1  0
 20 19  1  0
 19 18  1  0
 20 21  1  0
 21  3  1  0
 22  5  1  0
 10  9  1  0
 12 17  1  0
 18 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  6
  4 29  1  0
  4 30  1  0
  5 31  1  6
  6 32  1  0
  6 33  1  0
 16 37  1  0
 15 36  1  0
 14 35  1  0
 13 34  1  0
 22 44  1  6
 19 40  1  0
 19 41  1  0
 18 38  1  0
 18 39  1  0
 21 42  1  0
 21 43  1  0
M  END


  Mrv1652304282214062D          

 22 26  0  0  1  0            999 V2000
    6.5058    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4665   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7333   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0392    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0784    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1617    1.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7907    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2434   -0.1829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250   -1.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961   -0.2772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9671    0.4596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5144    1.1494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8854    1.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7091    1.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6908    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    0.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7724   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251   -0.4187    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14  8  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067353

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1C[C@@H]2CC(=O)N3C4=CC=CC=C4C4=C3[C@@H]2N(CC4)C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O/c1-2-12-9-13-10-17(22)21-16-6-4-3-5-14(16)15-7-8-20(11-12)18(13)19(15)21/h3-6,12-13,18H,2,7-11H2,1H3/t12-,13-,18-/m1/s1

> <INCHI_KEY>
YXXIRYIEQNZFNH-SNUQEOBHSA-N

> <FORMULA>
C19H22N2O

> <MOLECULAR_WEIGHT>
294.398

> <EXACT_MASS>
294.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.983207242700345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(13R,15R,19R)-13-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-17-one

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
2.725423449

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.745785111299064

> <JCHEM_PKA_STRONGEST_BASIC>
6.747851952599808

> <JCHEM_POLAR_SURFACE_AREA>
25.240000000000002

> <JCHEM_REFRACTIVITY>
87.12370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(13R,15R,19R)-13-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-17-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      12.144   1.476   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.071  -0.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.702  -0.768   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.407   0.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.480   1.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.849   2.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.769   2.322   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.076   0.946   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.921  -0.341   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.228  -1.717   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.073  -3.004   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.691  -1.805   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.846  -0.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.539   0.858   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.694   2.146   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.386   3.521   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.924   3.609   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.156   2.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.464   0.682   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.309  -0.606   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.926   0.594   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.234  -0.782   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   17                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    7                                                       
CONECT   18   15   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   13                                                       
CONECT   21   19   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂N₂O

Average Mass

294.3980 Da

Monoisotopic Mass

294.17321 Da

IUPAC Name

(13R,15R,19R)-13-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-17-one

Traditional Name

(13R,15R,19R)-13-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-17-one

CAS Registry Number

Not Available

SMILES

CC[C@@H]1C[C@@H]2CC(=O)N3C4=CC=CC=C4C4=C3[C@@H]2N(CC4)C1

InChI Identifier

InChI=1S/C19H22N2O/c1-2-12-9-13-10-17(22)21-16-6-4-3-5-14(16)15-7-8-20(11-12)18(13)19(15)21/h3-6,12-13,18H,2,7-11H2,1H3/t12-,13-,18-/m1/s1

InChI Key

YXXIRYIEQNZFNH-SNUQEOBHSA-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
Tabernaemontana eglandulosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tacaman alkaloids. These are alkaloids containing the pentacyclic tacaman skeleton, which consists of a pyrido[1,2-a]indole fused to a quinolizine. Tacaman alkaloids are obtained from a precursor to a pseudoaspidospermidine (type II skeleton) derivative, by the formation of new bonds at C-20/C-3 and C-140/C-17.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tacaman alkaloids

Sub Class

Not Available

Direct Parent

Tacaman alkaloids

Alternative Parents

Substituents

Tacaman alkaloid
Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Naphthyridine
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Benzenoid
Piperidine
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Lactam
Organoheterocyclic compound
Azacycle
Amine
Organonitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.5	ALOGPS
logP	2.73	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	19.75	ChemAxon
pKa (Strongest Basic)	6.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.24 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.12 m³·mol⁻¹	ChemAxon
Polarizability	33.98 Å³	ChemAxon
Number of Rings	5	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

C00025084

Chemspider ID

8147290

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9971698

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ihara M: Syntheses of biologically active natural products and leading compounds for new pharmaceuticals employing effective construction of a polycyclic skeleton. Chem Pharm Bull (Tokyo). 2006 Jun;54(6):765-74. doi: 10.1248/cpb.54.765. [PubMed:16755041 ]
England DB, Padwa A: General access to the vinca and tacaman alkaloids using a Rh(II)-catalyzed cyclization/cycloaddition cascade. J Org Chem. 2008 Apr 4;73(7):2792-802. doi: 10.1021/jo8001003. Epub 2008 Mar 5. [PubMed:18318547 ]
Smith MW, Ferreira J, Hunter R, Venter GA, Su H: Synthesis of (+)-Tacamonine via Stereoselective Radical Cyclization. Org Lett. 2019 Nov 1;21(21):8740-8745. doi: 10.1021/acs.orglett.9b03308. Epub 2019 Oct 24. [PubMed:31647242 ]
Deiters A, Pettersson M, Martin SF: General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloids. J Org Chem. 2006 Aug 18;71(17):6547-61. doi: 10.1021/jo061032t. [PubMed:16901143 ]
Takasu K, Nishida N, Tomimura A, Ihara M: Convenient synthesis of substituted piperidinones from alpha,beta-unsaturated amides: formal synthesis of deplancheine, tacamonine, and paroxetine. J Org Chem. 2005 May 13;70(10):3957-62. doi: 10.1021/jo050261x. [PubMed:15876084 ]

Showing NP-Card for Tacamonine (NP0067353)

MOL for NP0067353 (Tacamonine)

3D MOL for NP0067353 (Tacamonine)

3D SDF for NP0067353 (Tacamonine)

3D-SDF for NP0067353 (Tacamonine)

PDB for NP0067353 (Tacamonine)

3D PDB for NP0067353 (Tacamonine)

SMILES for NP0067353 (Tacamonine)

INCHI for NP0067353 (Tacamonine)

Structure for NP0067353 (Tacamonine)

3D Structure for NP0067353 (Tacamonine)