NP-MRD: Showing NP-Card for (13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene (NP0259314)

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Record Information

Version

2.0

Created at

2022-09-08 01:08:43 UTC

Updated at

2022-09-08 01:08:43 UTC

NP-MRD ID

NP0259314

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene

Description

Apparicine belongs to the class of organic compounds known as vallesaman alkaloids. These are alkaloids with a structure that is based on the vallesaman skeleton, a tetracyclic compound that contains a piperidine ring fused to an indole. (13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene is found in Tabernaemontana divaricata, Ochrosia elliptica, Ochrosia moorei, Strempeliopsis strempelioides, Tabernaemontana corymbosa, Tabernaemontana elegans, Tabernaemontana pachysiphon, Tabernaemontana ventricosa and Trachelospermum jasminoides. (13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene was first documented in 2007 (PMID: 17488126). Based on a literature review a significant number of articles have been published on Apparicine (PMID: 18412397) (PMID: 32098650) (PMID: 31302343) (PMID: 30987224) (PMID: 30169038) (PMID: 24927230).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
   -0.7572    2.5231    0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6517    1.2373    0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904    0.6818    0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784    1.4219    0.3246 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9077    0.6992    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2319    1.0492    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2283    0.1385   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8388   -1.1413   -0.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5018   -1.4945   -0.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5343   -0.5647   -0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1588   -0.5779   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870   -1.8573   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -1.8516   -0.0666 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8846   -1.5735    1.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427   -0.4699    1.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9642    0.6102    0.7164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5268   -0.1346   -0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312    0.3148   -1.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291    1.5460   -0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8490   -1.3386   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0811    3.1198   -0.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7259    3.0007    0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770    2.4151    0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5273    2.0418    0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2801    0.3844   -0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6223   -1.8599   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2278   -2.4766   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4144   -1.9080   -1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201   -2.7357   -0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1685   -1.3668    1.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1736   -2.5150    1.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7646   -0.8126    2.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2840    0.0306    2.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6011    1.3972    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0517   -0.2392   -1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3348    1.6013   -1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5527    1.5144    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8022    2.4611   -0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -1.1264   -1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108   -2.1443   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  2  0
 17 20  1  0
 20 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
  2  1  2  3
  2  3  1  0
  3 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
 16 17  1  0
  4  3  1  0
 12 13  1  0
  5 10  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 18 35  1  0
 20 39  1  0
 20 40  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  1
  1 21  1  0
  1 22  1  0
 12 28  1  0
 12 29  1  0
  9 27  1  0
  8 26  1  0
  7 25  1  0
  6 24  1  0
  4 23  1  0
M  END


  Mrv1652309082203082D          

 20 23  0  0  1  0            999 V2000
    2.4234    1.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873    1.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9870    0.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6941    1.1442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168    0.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356    0.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6322    0.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3099   -0.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9945   -0.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1726   -0.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7355   -0.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9316   -0.9699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6205   -0.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4711    0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4834    0.9707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0463    0.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326    0.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564    1.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2320   -0.5328    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  2  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
 16 15  1  1  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259314

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\CN2CC[C@H]1C(=C)C1=C(C2)C2=CC=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C18H20N2/c1-3-13-10-20-9-8-14(13)12(2)18-16(11-20)15-6-4-5-7-17(15)19-18/h3-7,14,19H,2,8-11H2,1H3/b13-3-/t14-/m0/s1

> <INCHI_KEY>
LCVACABZTLIWCE-SUSILRQXSA-N

> <FORMULA>
C18H20N2

> <MOLECULAR_WEIGHT>
264.372

> <EXACT_MASS>
264.162648652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.52060877140487

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(13R,14E)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0^{3,11}.0^{4,9}]heptadeca-3(11),4,6,8-tetraene

> <JCHEM_LOGP>
3.2359401079999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.871441754137734

> <JCHEM_PKA_STRONGEST_BASIC>
7.644879920499149

> <JCHEM_POLAR_SURFACE_AREA>
19.03

> <JCHEM_REFRACTIVITY>
85.065

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(13R,14E)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0^{3,11}.0^{4,9}]heptadeca-3(11),4,6,8-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       4.524   3.677   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.270   2.159   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.576   1.343   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.896   2.136   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.058   1.126   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.586   1.313   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.513   0.084   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.912  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.383  -1.522   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.456  -0.292   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.922  -0.158   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.106  -1.464   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.606  -1.811   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.025  -0.673   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.746   0.535   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.769   1.812   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.953   0.506   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.434   0.760   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.105   2.202   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.300  -0.995   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀N₂

Average Mass

264.3720 Da

Monoisotopic Mass

264.16265 Da

IUPAC Name

(13R,14E)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0^{3,11}.0^{4,9}]heptadeca-3(11),4,6,8-tetraene

Traditional Name

(13R,14E)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0^{3,11}.0^{4,9}]heptadeca-3(11),4,6,8-tetraene

CAS Registry Number

Not Available

SMILES

C\C=C1\CN2CC[C@H]1C(=C)C1=C(C2)C2=CC=CC=C2N1

InChI Identifier

InChI=1S/C18H20N2/c1-3-13-10-20-9-8-14(13)12(2)18-16(11-20)15-6-4-5-7-17(15)19-18/h3-7,14,19H,2,8-11H2,1H3/b13-3-/t14-/m0/s1

InChI Key

LCVACABZTLIWCE-SUSILRQXSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ervatamia coronaria	LOTUS Database	35616633
Ochrosia elliptica	LOTUS Database	35616633
Ochrosia moorei	LOTUS Database	35616633
Strempeliopsis strempelioides	LOTUS Database	35616633
Tabernaemontana corymbosa	LOTUS Database	35616633
Tabernaemontana elegans	LOTUS Database	35616633
Tabernaemontana pachysiphon	LOTUS Database	35616633
Tabernaemontana ventricosa	LOTUS Database	35616633
Trachelospermum jasminoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vallesaman alkaloids. These are alkaloids with a structure that is based on the vallesaman skeleton, a tetracyclic compound that contains a piperidine ring fused to an indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Vallesaman alkaloids

Sub Class

Not Available

Direct Parent

Vallesaman alkaloids

Alternative Parents

Substituents

Vallesaman-skeleton
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
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	3.24	ChemAxon
pKa (Strongest Acidic)	14.87	ChemAxon
pKa (Strongest Basic)	7.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	19.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.06 m³·mol⁻¹	ChemAxon
Polarizability	30.52 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

C00001689

Chemspider ID

5288661

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Apparicine

METLIN ID

Not Available

PubChem Compound

6912322

PDB ID

Not Available

ChEBI ID

182901

Good Scents ID

Not Available

References

General References

Carroll AR, Addepalli R, Fechner G, Smith J, Guymer GP, Forster PI, Quinn RJ: Alkaloids from the Australian rainforest tree Ochrosia moorei. J Nat Prod. 2008 Jun;71(6):1063-5. doi: 10.1021/np070655e. Epub 2008 Apr 16. [PubMed:18412397 ]
Kalshetti MG, Argade NP: The indole-based subincanadine alkaloids and their biogenetic congeners. Alkaloids Chem Biol. 2020;83:187-223. doi: 10.1016/bs.alkal.2019.12.001. Epub 2020 Jan 27. [PubMed:32098650 ]
Shi BB, Chen J, Bao MF, Zeng Y, Cai XH: Alkaloids isolated from Tabernaemontana bufalina display xanthine oxidase inhibitory activity. Phytochemistry. 2019 Oct;166:112060. doi: 10.1016/j.phytochem.2019.112060. Epub 2019 Jul 11. [PubMed:31302343 ]
Zhou J, Du SY, Dong HJ, Fang L, Feng JH: Preparative Separation of Monoterpenoid Indole Alkaloid Epimers from Ervatamia yunnanensis Tsiang by pH-Zone-Refining Counter-Current Chromatography Combined with Preparative High-Performance Liquid Chromatography. Molecules. 2019 Apr 3;24(7). pii: molecules24071316. doi: 10.3390/molecules24071316. [PubMed:30987224 ]
Cai YS, Sarotti AM, Zhou TL, Huang R, Qiu G, Tian C, Miao ZH, Mandi A, Kurtan T, Cao S, Yang SP: Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata. J Nat Prod. 2018 Sep 28;81(9):1976-1983. doi: 10.1021/acs.jnatprod.8b00191. Epub 2018 Aug 31. [PubMed:30169038 ]
Chauhan PS, Weinreb SM: Convergent approach to the tetracyclic core of the apparicine class of indole alkaloids via a key intermolecular nitrosoalkene conjugate addition. J Org Chem. 2014 Jul 3;79(13):6389-93. doi: 10.1021/jo501067u. Epub 2014 Jun 20. [PubMed:24927230 ]
Gogoi RR, Gogoi D, Bezbaruah RL: Virtual Screening of compounds from Tabernaemontana divaricata for potential anti-bacterial activity. Bioinformation. 2014 Mar 19;10(3):152-6. doi: 10.6026/97320630010152. eCollection 2014. [PubMed:24748755 ]
Chierrito TP, Aguiar AC, de Andrade IM, Ceravolo IP, Goncalves RA, de Oliveira AJ, Krettli AU: Anti-malarial activity of indole alkaloids isolated from Aspidosperma olivaceum. Malar J. 2014 Apr 14;13:142. doi: 10.1186/1475-2875-13-142. [PubMed:24731256 ]
Hullatti K, Pathade N, Mandavkar Y, Godavarthi A, Biradi M: Bioactivity-guided isolation of cytotoxic constituents from three medicinal plants. Pharm Biol. 2013 May;51(5):601-6. doi: 10.3109/13880209.2012.753919. Epub 2013 Jan 31. [PubMed:23363069 ]
Bennasar ML, Zulaica E, Sole D, Roca T, Garcia-Diaz D, Alonso S: Total synthesis of the bridged indole alkaloid apparicine. J Org Chem. 2009 Nov 6;74(21):8359-68. doi: 10.1021/jo901986v. [PubMed:19824689 ]
Bennasar ML, Zulaica E, Sole D, Alonso S: The first total synthesis of (+/-)-apparicine. Chem Commun (Camb). 2009 Jun 21;(23):3372-4. doi: 10.1039/b903577j. Epub 2009 Apr 27. [PubMed:19503874 ]
Bennasar ML, Roca T, Garcia-Diaz D: Novel 7- and 8-endo 2-indolylacyl radical cyclizations: efficient construction of azepino- and azocinoindoles. J Org Chem. 2007 Jun 8;72(12):4562-5. doi: 10.1021/jo070322m. Epub 2007 May 9. [PubMed:17488126 ]
LOTUS database [Link]

Showing NP-Card for (13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene (NP0259314)

MOL for NP0259314 ((13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

3D MOL for NP0259314 ((13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

3D SDF for NP0259314 ((13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

3D-SDF for NP0259314 ((13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

PDB for NP0259314 ((13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

3D PDB for NP0259314 ((13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

SMILES for NP0259314 ((13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

INCHI for NP0259314 ((13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

Structure for NP0259314 ((13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

3D Structure for NP0259314 ((13r,14e)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)