NP-MRD: Showing NP-Card for [(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol (NP0202658)

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Record Information

Version

2.0

Created at

2022-09-04 21:55:01 UTC

Updated at

2022-09-04 21:55:02 UTC

NP-MRD ID

NP0202658

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol

Description

Minfiensine belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. [(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol was first documented in 2016 (PMID: 27214235). Based on a literature review a small amount of articles have been published on Minfiensine (PMID: 29781616) (PMID: 29600847) (PMID: 28989658) (PMID: 28618154).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
    4.7988   -0.3201    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185    0.0674    0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3732   -0.1398    0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1057   -0.7955   -0.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873   -1.5316   -0.9193 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2723   -1.4030   -2.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424   -0.2166   -2.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005    0.0868   -0.6905 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1723    1.3796   -0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    1.4935    0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6993    2.8205    1.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0237    3.7850    0.7546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651    0.3049    1.3227 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2741   -0.8640    1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1569   -1.0971   -0.0585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2358   -2.0815   -0.1377 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -1.3174    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6841   -1.7489    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7111   -0.8496    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4718    0.4682    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464    0.9021   -0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2099   -0.0005   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -0.4056   -1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5744    0.4893    0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2705   -1.2267    0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7892    0.5591    1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0433    0.0192   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9334   -1.5065   -1.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428   -1.2566   -3.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405   -2.3146   -2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2732    0.6625   -2.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6379   -0.4614   -2.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3505    2.2174   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3636    2.7897    2.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7812    3.1000    1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7238    4.1791    1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444    0.5497    2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494   -1.7648    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5948   -0.6504    1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1844   -3.0919   -0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8433   -2.8065    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6934   -1.1502    0.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2969    1.1894    0.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0629    1.9375   -0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 13  3  1  0
 22 17  1  0
 15  5  1  0
 15  8  1  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  1
 14 38  1  0
 14 39  1  0
 16 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END


  Mrv1652309042223552D          

 22 26  0  0  1  0            999 V2000
    0.3574   -3.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9706   -2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9618   -1.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1396   -1.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1232   -0.2628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    0.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4236    1.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2119    0.6768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8544    0.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -0.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8570   -0.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2593   -1.5316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838   -1.0174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2726   -0.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9008   -0.0439    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6937   -0.4430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5558   -0.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3716   -0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8860    0.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845    1.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7687    1.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544    0.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  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  1  0  0  0  0
 10 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 14  1  6  0  0  0
  5 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 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
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
  8 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202658

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1/CN2CC[C@]34C=C(CO)[C@H]1C[C@]23NC1=CC=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O/c1-2-13-11-21-8-7-18-9-14(12-22)15(13)10-19(18,21)20-17-6-4-3-5-16(17)18/h2-6,9,15,20,22H,7-8,10-12H2,1H3/b13-2+/t15-,18+,19-/m0/s1

> <INCHI_KEY>
HICMXDKNSCMBDU-YLTHFTGLSA-N

> <FORMULA>
C19H22N2O

> <MOLECULAR_WEIGHT>
294.398

> <EXACT_MASS>
294.173213336

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.23423268449169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,9S,11S,12Z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{9,14}]octadeca-2,4,6,17-tetraen-18-yl]methanol

> <JCHEM_LOGP>
1.861724863333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.137438440797492

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.508116840581215

> <JCHEM_PKA_STRONGEST_BASIC>
7.41673162018115

> <JCHEM_POLAR_SURFACE_AREA>
35.5

> <JCHEM_REFRACTIVITY>
91.5815

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,9S,11S,12Z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{9,14}]octadeca-2,4,6,17-tetraen-18-yl]methanol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.667  -5.622   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.812  -4.519   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.795  -2.880   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.261  -2.125   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.230  -0.491   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.405   1.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.791   2.048   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.262   1.263   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.462   1.521   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.979  -0.135   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.333  -1.348   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.084  -2.859   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.330  -1.899   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.376  -1.418   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.682  -0.082   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.162  -0.827   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       4.771  -0.454   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.294  -0.683   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.254   0.521   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.691   1.954   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.168   2.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.208   0.980   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   15   22                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    5    8   16                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17    8                                                  
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

[(1R,9S,11S,12Z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{9,14}]octadeca-2,4,6,17-tetraen-18-yl]methanol

Traditional Name

[(1R,9S,11S,12Z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{9,14}]octadeca-2,4,6,17-tetraen-18-yl]methanol

CAS Registry Number

Not Available

SMILES

C\C=C1/CN2CC[C@]34C=C(CO)[C@H]1C[C@]23NC1=CC=CC=C41

InChI Identifier

InChI=1S/C19H22N2O/c1-2-13-11-21-8-7-18-9-14(12-22)15(13)10-19(18,21)20-17-6-4-3-5-16(17)18/h2-6,9,15,20,22H,7-8,10-12H2,1H3/b13-2+/t15-,18+,19-/m0/s1

InChI Key

HICMXDKNSCMBDU-YLTHFTGLSA-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 carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Pyrroloindole
Indole
Dihydroindole
Indolizidine
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrole
Pyrrolidine
Azacycle
Primary alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
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	1.86	ChemAxon
pKa (Strongest Acidic)	14.51	ChemAxon
pKa (Strongest Basic)	7.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	35.5 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.58 m³·mol⁻¹	ChemAxon
Polarizability	33.23 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

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

14526586

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu X, Zhang W, Wang Y, Zhang ZX, Jiao L, Liu Q: Cobalt-Catalyzed Regioselective Olefin Isomerization Under Kinetic Control. J Am Chem Soc. 2018 Jun 6;140(22):6873-6882. doi: 10.1021/jacs.8b01815. Epub 2018 May 29. [PubMed:29781616 ]
Zhang C, Ji W, Liu YA, Song C, Liao X: Total Synthesis of (+/-)-Minfiensine via a Formal [3+2] Cycloaddition. J Nat Prod. 2018 Apr 27;81(4):1065-1069. doi: 10.1021/acs.jnatprod.7b00873. Epub 2018 Mar 30. [PubMed:29600847 ]
Du K, Yang H, Guo P, Feng L, Xu G, Zhou Q, Chung LW, Tang W: Efficient syntheses of (-)-crinine and (-)-aspidospermidine, and the formal synthesis of (-)-minfiensine by enantioselective intramolecular dearomative cyclization. Chem Sci. 2017 Sep 1;8(9):6247-6256. doi: 10.1039/c7sc01859b. Epub 2017 Jul 3. [PubMed:28989658 ]
Yu Y, Li J, Jiang L, Zhang JR, Zu L: Catalytic Enantioselective Aza-pinacol Rearrangement. Angew Chem Int Ed Engl. 2017 Jul 24;56(31):9217-9221. doi: 10.1002/anie.201705539. Epub 2017 Jun 29. [PubMed:28618154 ]
Leverett CA, Li G, France S, Padwa A: IMDAF Cascade Approach toward the Synthesis of the Alkaloid (+/-)-Minfiensine. J Org Chem. 2016 Nov 4;81(21):10193-10203. doi: 10.1021/acs.joc.6b00771. Epub 2016 Jun 1. [PubMed:27214235 ]
LOTUS database [Link]

Showing NP-Card for [(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol (NP0202658)

MOL for NP0202658 ([(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol)

3D MOL for NP0202658 ([(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol)

3D SDF for NP0202658 ([(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol)

3D-SDF for NP0202658 ([(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol)

PDB for NP0202658 ([(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol)

3D PDB for NP0202658 ([(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol)

SMILES for NP0202658 ([(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol)

INCHI for NP0202658 ([(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol)

Structure for NP0202658 ([(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol)

3D Structure for NP0202658 ([(1r,9s,11s,12z)-12-ethylidene-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0⁹,¹⁴]octadeca-2,4,6,17-tetraen-18-yl]methanol)