NP-MRD: Showing NP-Card for (-)-Strempeliopine (NP0067327)

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Record Information

Version

2.0

Created at

2022-04-28 11:56:38 UTC

Updated at

2022-04-28 11:56:38 UTC

NP-MRD ID

NP0067327

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Strempeliopine

Description

(1R,11R,15R,16S)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]Henicosa-5,7,9-trien-3-one belongs to the class of organic compounds known as schizozygine alkaloids. These are alkaloids with a structure based o the hexacyclic schizozygine skeleton, consisting of quinolizidine, indole, and piperidine. (-)-Strempeliopine is found in Strempeliopsis strempelioides. Based on a literature review very few articles have been published on (1R,11R,15R,16S)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]Henicosa-5,7,9-trien-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 49  0  0  0  0  0  0  0  0999 V2000
   -1.1095   -2.4050    2.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4237   -1.8137    1.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0418   -1.9106    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232   -0.8295    0.7354 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9761   -0.3875    1.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    0.6570    0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544    1.7608    0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4077    1.4793   -0.0598 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6742    2.2930   -0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8164    2.0728   -0.7968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0858    0.6262   -1.1315 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4574    0.1993   -0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7013    0.6091   -1.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8684    0.0627   -0.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8178   -0.9054    0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6056   -1.3389    0.7176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4472   -0.7690    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1091   -1.0265    0.5268 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2326   -0.3072   -0.3790 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5076   -1.3127   -1.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9404   -1.2144   -0.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981    0.3771    0.5171 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3813   -2.8868    1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3982   -1.8753    2.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    0.0836    2.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481   -1.2369    1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839    1.0813    1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1228    0.1620   -0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8472    2.6057    0.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1872    2.2000   -0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    2.0807   -1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8999    3.3730   -0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3279    2.7407   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1116    2.3419    0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227    0.4936   -2.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7517    1.3639   -2.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8372    0.3754   -1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7433   -1.3420    0.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5613   -2.1103    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4228   -1.1579   -2.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1843   -2.3618   -0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892   -0.3454   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5024   -2.1423   -0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3550    0.6401    1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  4  3  1  1
  4 21  1  0
 21 20  1  0
 19 20  1  6
 19 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  8 22  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  2  1  0
  5  4  1  0
 17 12  1  0
 22  4  1  0
 22 19  1  0
 18 19  1  0
  3 23  1  0
  3 24  1  0
 21 42  1  0
 21 43  1  0
 20 40  1  0
 20 41  1  0
 11 35  1  6
 10 33  1  0
 10 34  1  0
  9 31  1  0
  9 32  1  0
  7 29  1  0
  7 30  1  0
  6 27  1  0
  6 28  1  0
  5 25  1  0
  5 26  1  0
 22 44  1  1
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
M  END


  Mrv1652304282213572D          

 22 27  0  0  1  0            999 V2000
    3.1717    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5919    0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999   -0.0881    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2526   -0.7779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0762   -0.7307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4472    0.0062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521   -1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248   -1.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -1.4204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1579   -2.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343   -2.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816   -1.5147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579   -1.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -0.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -0.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946    0.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656    1.4328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1709    0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  1  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 13 12  1  1  0  0  0
  5 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
  4 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067327

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C[C@]23CC[C@]45[C@H](CCN(CCC2)[C@H]34)C2=CC=CC=C2N15

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O/c22-16-12-18-7-3-10-20-11-6-14-13-4-1-2-5-15(13)21(16)19(14,9-8-18)17(18)20/h1-2,4-5,14,17H,3,6-12H2/t14-,17-,18-,19+/m1/s1

> <INCHI_KEY>
BBBSLAHJKPIMRU-AXUOBQJMSA-N

> <FORMULA>
C19H22N2O

> <MOLECULAR_WEIGHT>
294.398

> <EXACT_MASS>
294.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.987496857340346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,11R,15R,16S)-4,14-diazahexacyclo[12.4.3.0^{1,15}.0^{4,16}.0^{5,10}.0^{11,16}]henicosa-5,7,9-trien-3-one

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
1.9803462819999988

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.73718882795264

> <JCHEM_POLAR_SURFACE_AREA>
23.55

> <JCHEM_REFRACTIVITY>
84.8394

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,11R,15R,16S)-4,14-diazahexacyclo[12.4.3.0^{1,15}.0^{4,16}.0^{5,10}.0^{11,16}]henicosa-5,7,9-trien-3-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       5.920   0.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.838   0.958   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.360  -0.164   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.205  -1.452   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.742  -1.364   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.435   0.012   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.146  -0.707   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.515  -0.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.810  -0.834   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.737  -2.373   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.368  -3.078   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.073  -2.246   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.587  -2.651   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.895  -4.027   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.357  -4.115   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.512  -2.827   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       1.975  -2.916   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.130  -1.628   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.822  -0.253   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.590   1.299   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.282   2.675   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.052   1.211   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   19   22                                             
CONECT    4    3    5   16                                                  
CONECT    5    4    1    6   13                                             
CONECT    6    5    7   20                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    4   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    3                                                       
CONECT   20    6   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂N₂O

Average Mass

294.3980 Da

Monoisotopic Mass

294.17321 Da

IUPAC Name

(1R,11R,15R,16S)-4,14-diazahexacyclo[12.4.3.0^{1,15}.0^{4,16}.0^{5,10}.0^{11,16}]henicosa-5,7,9-trien-3-one

Traditional Name

(1R,11R,15R,16S)-4,14-diazahexacyclo[12.4.3.0^{1,15}.0^{4,16}.0^{5,10}.0^{11,16}]henicosa-5,7,9-trien-3-one

CAS Registry Number

Not Available

SMILES

O=C1C[C@]23CC[C@]45[C@H](CCN(CCC2)[C@H]34)C2=CC=CC=C2N15

InChI Identifier

InChI=1S/C19H22N2O/c22-16-12-18-7-3-10-20-11-6-14-13-4-1-2-5-15(13)21(16)19(14,9-8-18)17(18)20/h1-2,4-5,14,17H,3,6-12H2/t14-,17-,18-,19+/m1/s1

InChI Key

BBBSLAHJKPIMRU-AXUOBQJMSA-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
Strempeliopsis strempelioides	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as schizozygine alkaloids. These are alkaloids with a structure based o the hexacyclic schizozygine skeleton, consisting of quinolizidine, indole, and piperidine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Schizozygine alkaloids

Sub Class

Not Available

Direct Parent

Schizozygine alkaloids

Alternative Parents

Substituents

Schizozygine skeleton
Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Azaspirodecane
Naphthyridine
Quinolizidine
Indole or derivatives
Caprolactam
Azepane
Delta-lactam
Aralkylamine
Piperidinone
Benzenoid
Piperidine
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organooxygen compound
Amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organonitrogen 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	2.38	ALOGPS
logP	1.98	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	8.74	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.84 m³·mol⁻¹	ChemAxon
Polarizability	32.99 Å³	ChemAxon
Number of Rings	6	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

Not Available

Chemspider ID

28286920

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44470882

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Strempeliopine (NP0067327)

MOL for NP0067327 ((-)-Strempeliopine)

3D MOL for NP0067327 ((-)-Strempeliopine)

3D SDF for NP0067327 ((-)-Strempeliopine)

3D-SDF for NP0067327 ((-)-Strempeliopine)

PDB for NP0067327 ((-)-Strempeliopine)

3D PDB for NP0067327 ((-)-Strempeliopine)

SMILES for NP0067327 ((-)-Strempeliopine)

INCHI for NP0067327 ((-)-Strempeliopine)

Structure for NP0067327 ((-)-Strempeliopine)

3D Structure for NP0067327 ((-)-Strempeliopine)