NP-MRD: Showing NP-Card for (2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene (NP0236107)

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Record Information

Version

2.0

Created at

2022-09-06 18:55:38 UTC

Updated at

2022-09-06 18:55:38 UTC

NP-MRD ID

NP0236107

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene

Description

(2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene is found in Hapalosiphon delicatulus. (2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene was first documented in 2018 (PMID: 29656506). Based on a literature review a small amount of articles have been published on hapalindole U (PMID: 32302487) (PMID: 29531360) (PMID: 31284716) (PMID: 31354873).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
    2.0983    2.5964   -0.4113 C   0  0  0  0  0  3  0  0  0  0  0  0
    1.9994    1.4701   -0.1875 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.8646    0.1046    0.1013 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5329   -0.3739   -0.3426 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1991    0.2925   -1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9054    0.8259   -2.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045    1.3043   -3.6071 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516    1.0964   -3.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5183    1.3418   -3.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6136    0.9745   -2.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4531    0.3386   -1.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1843    0.0802   -1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1145    0.4697   -1.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884   -0.5884    0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9571   -0.2257    1.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184   -2.0813   -0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5655   -0.0336    0.6367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2535   -0.3830    2.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405    0.3322    2.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731   -0.1217    1.5609 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5655   -1.5592    1.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3414    0.7416    1.8832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5491    0.2136    1.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6401   -0.4215   -0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5207   -1.4850   -0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9730    0.8446   -2.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2613    1.7612   -4.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6324    1.8332   -4.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6189    1.1855   -3.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3062    0.0486   -1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683   -0.7268    2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0693    0.8576    1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9423   -0.6450    0.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7953   -2.5668   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3692   -2.2363   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1408   -2.5430    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6784    1.0880    0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0328    0.1235    2.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1980   -1.4527    2.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2870    0.1742    3.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8658    1.4018    2.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6872   -2.2328    1.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204   -1.5872    2.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1621   -1.9608    0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358    1.8024    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7047   -0.8581    1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4384    0.7800    2.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  3  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 20 22  1  1
 22 23  2  3
  3 20  1  0
 13  5  1  0
 14 17  1  0
 13  8  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 19 40  1  0
 19 41  1  0
 18 38  1  0
 18 39  1  0
 17 37  1  1
  4 25  1  6
  3 24  1  6
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
M  CHG  2   1  -1   2   1
M  END


  Mrv1652309062220552D          

 23 26  0  0  1  0            999 V2000
    4.3769   -1.3341    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.4208   -0.5102    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.4648    0.3136    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7732    0.7635    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0378    0.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8236   -0.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9997   -0.4495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348    0.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8065    1.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481    1.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902    1.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1257    2.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    2.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6889    2.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172    1.5874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5526    1.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441    1.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2002    0.6875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0220    0.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5995   -0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4243   -0.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  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
  5 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 22 23  2  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0236107

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(CC[C@H]2[C@H]([C@H]1[N+]#[C-])C1=CNC3=CC=CC(=C13)C2(C)C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2/c1-6-21(4)11-10-15-18(19(21)22-5)13-12-23-16-9-7-8-14(17(13)16)20(15,2)3/h6-9,12,15,18-19,23H,1,10-11H2,2-4H3/t15-,18+,19+,21-/m0/s1

> <INCHI_KEY>
SLUFHMQYBPOTFZ-ZRRCRCOKSA-N

> <FORMULA>
C21H24N2

> <MOLECULAR_WEIGHT>
304.437

> <EXACT_MASS>
304.193948781

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.64277757641079

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4R,7S)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraene

> <JCHEM_LOGP>
2.801166809790722

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.78209209889061

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.95733983323619

> <JCHEM_POLAR_SURFACE_AREA>
20.15

> <JCHEM_REFRACTIVITY>
103.90400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,7S)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       8.170  -2.490   0.000  0.00  0.00           C-1
HETATM    2  N   UNK     0       8.252  -0.952   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       8.334   0.585   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.043   1.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.671   0.727   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.271  -0.760   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.733  -0.839   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.182   0.599   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.745   1.152   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.505   2.674   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.703   3.642   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.462   3.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.380   1.567   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.835   3.803   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.909   5.034   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.886   4.928   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.125   2.963   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.498   3.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.789   2.821   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.707   1.283   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.241   1.148   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.452  -0.064   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.992  -0.093   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
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   14                                                  
CONECT   13   12    5    8                                                  
CONECT   14   12   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14    4   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    3   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄N₂

Average Mass

304.4370 Da

Monoisotopic Mass

304.19395 Da

IUPAC Name

(2S,3R,4R,7S)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraene

Traditional Name

(2S,3R,4R,7S)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraene

CAS Registry Number

Not Available

SMILES

C[C@@]1(CC[C@H]2[C@H]([C@H]1[N+]#[C-])C1=CNC3=CC=CC(=C13)C2(C)C)C=C

InChI Identifier

InChI=1S/C21H24N2/c1-6-21(4)11-10-15-18(19(21)22-5)13-12-23-16-9-7-8-14(17(13)16)20(15,2)3/h6-9,12,15,18-19,23H,1,10-11H2,2-4H3/t15-,18+,19+,21-/m0/s1

InChI Key

SLUFHMQYBPOTFZ-ZRRCRCOKSA-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
Hapalosiphon delicatulus	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	2.8	ChemAxon
pKa (Strongest Acidic)	15.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	103.9 m³·mol⁻¹	ChemAxon
Polarizability	35.64 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

C00027101

Chemspider ID

10375686

KEGG Compound ID

Not Available

BioCyc ID

CPD-20791

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16069589

PDB ID

Not Available

ChEBI ID

141613

Good Scents ID

Not Available

References

General References

Khatri Y, Hohlman RM, Mendoza J, Li S, Lowell AN, Asahara H, Sherman DH: Multicomponent Microscale Biosynthesis of Unnatural Cyanobacterial Indole Alkaloids. ACS Synth Biol. 2020 Jun 19;9(6):1349-1360. doi: 10.1021/acssynbio.0c00038. Epub 2020 May 7. [PubMed:32302487 ]
Dethe DH, Das S, Kumar VB, Mir NA: Enantiospecific Total Syntheses of (+)-Hapalindole H and (-)-12-epi-Hapalindole U. Chemistry. 2018 Jun 26;24(36):8980-8984. doi: 10.1002/chem.201800970. Epub 2018 May 28. [PubMed:29656506 ]
Newmister SA, Li S, Garcia-Borras M, Sanders JN, Yang S, Lowell AN, Yu F, Smith JL, Williams RM, Houk KN, Sherman DH: Structural basis of the Cope rearrangement and cyclization in hapalindole biogenesis. Nat Chem Biol. 2018 Apr;14(4):345-351. doi: 10.1038/s41589-018-0003-x. Epub 2018 Mar 12. [PubMed:29531360 ]
Knoot CJ, Khatri Y, Hohlman RM, Sherman DH, Pakrasi HB: Engineered Production of Hapalindole Alkaloids in the Cyanobacterium Synechococcus sp. UTEX 2973. ACS Synth Biol. 2019 Aug 16;8(8):1941-1951. doi: 10.1021/acssynbio.9b00229. Epub 2019 Jul 19. [PubMed:31284716 ]
Awakawa T, Abe I: Molecular basis for the plasticity of aromatic prenyltransferases in hapalindole biosynthesis. Beilstein J Org Chem. 2019 Jul 11;15:1545-1551. doi: 10.3762/bjoc.15.157. eCollection 2019. [PubMed:31354873 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene (NP0236107)

MOL for NP0236107 ((2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

3D MOL for NP0236107 ((2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

3D SDF for NP0236107 ((2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

3D-SDF for NP0236107 ((2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

PDB for NP0236107 ((2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

3D PDB for NP0236107 ((2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

SMILES for NP0236107 ((2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

INCHI for NP0236107 ((2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

Structure for NP0236107 ((2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)

3D Structure for NP0236107 ((2s,3r,4r,7s)-4-ethenyl-3-isocyano-4,8,8-trimethyl-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraene)