NP-MRD: Showing NP-Card for (+)-Pericyclivine (NP0068141)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 13:08:38 UTC

Updated at

2022-04-28 13:08:38 UTC

NP-MRD ID

NP0068141

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Pericyclivine

Description

Methyl (1S,12R,13R,14S,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]Octadeca-2(10),4,6,8-tetraene-13-carboxylate belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. (+)-Pericyclivine is found in Catharanthus roseus , Gabunia odoratissima, Tabernaemontana coffeoides Boj., Tabernaemontana johnstonii (Stapf) Pichon, Tabernaemontana pachysiphon and Tabernaemontana pachysiphon Stapf. . Based on a literature review very few articles have been published on methyl (1S,12R,13R,14S,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]Octadeca-2(10),4,6,8-tetraene-13-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 50  0  0  0  0  0  0  0  0999 V2000
   -4.1988    1.9652   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8118    2.4779   -1.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8615    1.7058   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318    2.0826   -1.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2068    1.1457   -0.3869 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867   -0.2687   -0.8510 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8286   -0.3320   -1.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0066    0.2835   -0.8921 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6118    0.3116    0.6167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1450   -0.8118    1.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -1.2794    2.3625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3477   -1.4511    0.9758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8464   -2.5303    1.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3257    0.9287    0.9378 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8179    0.1575    1.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9297   -0.2611    0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5646   -0.5215   -0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6699   -0.9028   -1.3591 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6806   -0.8864   -0.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0148   -1.1830   -0.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8909   -1.0832    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4503   -0.6843    1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1203   -0.3872    1.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801   -0.4911    0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3702    1.5609   -2.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4031    1.1973   -0.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8844    2.8291   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6239    3.5077   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365    2.0311   -2.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2522    3.0772   -0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349   -1.0126   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2634   -1.3423   -2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721    0.1830   -2.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9298   -0.1975   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736    1.1323    0.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5016   -3.1213    1.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0788   -3.2287    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353   -2.1247    2.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3954    1.9521    1.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428    0.8920    2.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285   -0.6602    2.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6246   -1.1488   -2.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3698   -1.4971   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9239   -1.3198    0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1668   -0.6193    2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7415   -0.0752    2.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 17  6  1  0
  6  7  1  0
  7  8  1  0
  8  3  1  0
  3  4  1  0
  4  5  1  0
  3  2  2  0
  2  1  1  0
  8  9  1  0
  5 14  1  0
 24 16  1  0
  5  6  1  0
 24 19  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
  9 35  1  1
 14 39  1  1
 15 40  1  0
 15 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
  6 31  1  1
  7 32  1  0
  7 33  1  0
  8 34  1  1
  4 29  1  0
  4 30  1  0
  2 28  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END


  Mrv1652304282215082D          

 24 28  0  0  1  0            999 V2000
   -0.7779   -0.9460    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2774   -1.6159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5479   -1.5269    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6659   -0.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -0.1239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531   -0.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938    0.2226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9861   -0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828   -0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -1.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3569   -1.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731   -1.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -1.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    0.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -0.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127    0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955    0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6068   -2.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4266   -2.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1165   -3.0358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460   -3.7922    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  1  6  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  2  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
  5 16  1  0  0  0  0
  1 16  1  6  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  2 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068141

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1[C@H]2CC3=C(NC4=CC=CC=C34)[C@@H]3C[C@@H]1\C(CN23)=C/C

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O2/c1-3-11-10-22-16-9-14-12-6-4-5-7-15(12)21-19(14)17(22)8-13(11)18(16)20(23)24-2/h3-7,13,16-18,21H,8-10H2,1-2H3/b11-3-/t13-,16-,17+,18-/m1/s1

> <INCHI_KEY>
VXRAIAAMNNTQES-WLDRUEIOSA-N

> <FORMULA>
C20H22N2O2

> <MOLECULAR_WEIGHT>
322.408

> <EXACT_MASS>
322.168127956

$$$$

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      -1.452  -1.766   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.518  -3.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.023  -2.850   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.243  -1.321   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.408  -0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.086  -0.555   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.282   0.416   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.574  -0.422   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.061  -0.023   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.151  -1.111   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.754  -2.599   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.266  -2.998   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.177  -1.910   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.639  -1.992   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.573  -3.212   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.357  -0.555   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.323   0.125   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.299  -0.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.450   0.787   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.912   0.301   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.133  -4.428   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.663  -4.602   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.217  -5.667   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.832  -7.079   0.000  0.00  0.00           C+0
CONECT    1    2   16   18                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    6   15                                                  
CONECT   15   14    3                                                       
CONECT   16    5    1                                                       
CONECT   17    4   18                                                       
CONECT   18   17    1   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    2   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,12R,13R,14S,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0,.0,.0,]octadeca-2(10),4,6,8-tetraene-13-carboxylic acid	Generator

Chemical Formula

C₂₀H₂₂N₂O₂

Average Mass

322.4080 Da

Monoisotopic Mass

322.16813 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1[C@H]2CC3=C(NC4=CC=CC=C34)[C@@H]3C[C@@H]1\C(CN23)=C/C

InChI Identifier

InChI=1S/C20H22N2O2/c1-3-11-10-22-16-9-14-12-6-4-5-7-15(12)21-19(14)17(22)8-13(11)18(16)20(23)24-2/h3-7,13,16-18,21H,8-10H2,1-2H3/b11-3-/t13-,16-,17+,18-/m1/s1

InChI Key

VXRAIAAMNNTQES-WLDRUEIOSA-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
Catharanthus roseus	Plant	KNApSAcK
Gabunia odoratissima	-	KNApSAcK
Tabernaemontana coffeoides Boj.	Plant	KNApSAcK
Tabernaemontana johnstonii (Stapf) Pichon	Plant	KNApSAcK
Tabernaemontana pachysiphon	LOTUS Database	35616633
Tabernaemontana pachysiphon Stapf.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Vobasan skeleton
Sarpagine-skeleton
Pyridoindole
Beta-carboline
3-alkylindole
Piperidinecarboxylic acid
Indole or derivatives
Indole
Quinuclidine
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Methyl ester
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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

Not Available

METLIN ID

Not Available

PubChem Compound

163189580

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Pericyclivine (NP0068141)

MOL for NP0068141 ((+)-Pericyclivine)

3D MOL for NP0068141 ((+)-Pericyclivine)

3D SDF for NP0068141 ((+)-Pericyclivine)

3D-SDF for NP0068141 ((+)-Pericyclivine)

PDB for NP0068141 ((+)-Pericyclivine)

3D PDB for NP0068141 ((+)-Pericyclivine)

SMILES for NP0068141 ((+)-Pericyclivine)

INCHI for NP0068141 ((+)-Pericyclivine)

Structure for NP0068141 ((+)-Pericyclivine)

3D Structure for NP0068141 ((+)-Pericyclivine)