NP-MRD: Showing NP-Card for (13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene (NP0296756)

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Record Information

Version

2.0

Created at

2022-09-10 06:31:46 UTC

Updated at

2022-09-10 06:31:46 UTC

NP-MRD ID

NP0296756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Gomezine, also known as apparicine or pericalline, 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. Based on a literature review very few articles have been published on Gomezine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
   -0.4937   -2.4931    1.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4562   -1.5263    0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7950   -0.7953    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9669   -1.3640    0.6701 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9845   -0.4977    0.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490   -0.6419    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1436    0.4611    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6198    1.6598    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2712    1.7733   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335    0.6905    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0826    0.5422    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2670    1.7131   -0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    1.1922   -1.0310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826    0.2074   -2.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4739   -1.0937   -1.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509   -1.4302   -0.3736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5448   -0.2578    0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6761   -0.4494    0.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5089    0.6807    1.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0581    1.0935   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599   -2.6945    1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3594   -3.1245    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1005   -2.3521    0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7702   -1.5832    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2304    0.4318    0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2771    2.5181    0.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8121    2.7038   -0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023    2.2871    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8142    2.3280   -1.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3175   -0.0109   -2.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0882    0.6342   -3.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594   -1.0813   -2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8946   -1.9541   -2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028   -2.3642   -0.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0224   -1.4738    0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497    1.2891    2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8415    1.3405    0.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4056    0.3124    1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8478    1.8031   -0.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366    1.5262    0.8412 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  6
  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


  Mrv1652309102208312D          

 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
   -0.2921   -0.2295    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>
NP0296756

> <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-MIJQFGFMSA-N

> <FORMULA>
C18H20N2

> <MOLECULAR_WEIGHT>
264.372

> <EXACT_MASS>
264.162648652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.510555879495048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(13R,14Z)-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>
85.06500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(13R,14Z)-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                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-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      -0.545  -0.428   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

Value	Source
Apparicine	MeSH
Pericalline	MeSH

Chemical Formula

C₁₈H₂₀N₂

Average Mass

264.3720 Da

Monoisotopic Mass

264.16265 Da

IUPAC Name

Not Available

Traditional Name

Not Available

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-MIJQFGFMSA-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

Not Available

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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Apparicine

METLIN ID

Not Available

PubChem Compound

6602271

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene (NP0296756)

MOL for NP0296756 ((13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

3D MOL for NP0296756 ((13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

3D SDF for NP0296756 ((13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

3D-SDF for NP0296756 ((13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

PDB for NP0296756 ((13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

3D PDB for NP0296756 ((13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

SMILES for NP0296756 ((13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

INCHI for NP0296756 ((13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

Structure for NP0296756 ((13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)

3D Structure for NP0296756 ((13r,14z)-14-ethylidene-12-methylidene-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene)