NP-MRD: Showing NP-Card for (-)-Goniomitine (NP0066882)

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Record Information

Version

2.0

Created at

2022-04-28 11:06:51 UTC

Updated at

2022-04-28 11:06:51 UTC

NP-MRD ID

NP0066882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Goniomitine

Description

Goniomitine belongs to the class of organic compounds known as naphthyridines. Naphthyridines are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom. (-)-Goniomitine is found in Gonioma malagasy. (-)-Goniomitine was first documented in 2014 (PMID: 25270053). Based on a literature review a significant number of articles have been published on Goniomitine (PMID: 27666731) (PMID: 30500039) (PMID: 35426314) (PMID: 30520199) (PMID: 28706345) (PMID: 28128515).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.1740   -2.6775    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347   -1.4382    0.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1339   -0.1769    0.6787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1877    0.9403    0.7999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6610    2.2981    0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5096    2.2579   -0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570    1.1060   -1.3264 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4357   -0.1142   -0.6053 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0036   -0.2192   -0.5523 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7455   -0.1928    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0708   -0.3252    0.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2666   -0.3436    1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6857    1.0291    1.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8351    0.8696    2.3379 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1082   -0.4385   -1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1865   -0.5943   -2.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9560   -0.6834   -3.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6639   -0.6158   -3.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017   -0.4611   -2.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8321   -0.3714   -1.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1113   -0.0350    1.8552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3399   -0.3035    1.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8870   -3.1047    1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259   -3.4464   -0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226   -2.4767   -0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -1.4502    1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6933   -1.3367   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5038    0.9223    1.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1028    0.6870    0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4876    2.8742   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4077    2.9012    1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582    2.1853    0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5407    3.2075   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7809    1.0399   -1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7937   -0.9174   -1.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0252   -0.9265    2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1116   -0.8139    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9310    1.5681    2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9964    1.6427    0.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6548    1.1306    1.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1873   -0.6443   -1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7880   -0.8050   -4.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565   -0.6833   -4.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -0.4100   -3.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6638   -0.7437    2.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570    0.9691    2.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7791    0.4157    2.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4853   -1.2953    2.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 21  1  0
 21 22  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  8  3  1  0
 20  9  1  0
 22  3  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  6
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
M  END


  Mrv1652304282213062D          

 22 25  0  0  1  0            999 V2000
    3.9995   -0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5835    0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5742    1.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9902    0.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029   -0.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2555    1.0022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3854    1.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004    1.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757    2.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3996    2.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    3.4568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7448    2.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9743    2.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444    1.2272    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4850    0.7073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3551   -0.1074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -0.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0560    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0739    0.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2038    1.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5667    1.4522    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 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
 16  7  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
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 15 21  1  1  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@]12CCCN[C@H]1N1C(CC2)=C(CCO)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H26N2O/c1-2-19-10-5-12-20-18(19)21-16-7-4-3-6-14(16)15(9-13-22)17(21)8-11-19/h3-4,6-7,18,20,22H,2,5,8-13H2,1H3/t18-,19+/m0/s1

> <INCHI_KEY>
CGWKMDYVWRDDRF-RBUKOAKNSA-N

> <FORMULA>
C19H26N2O

> <MOLECULAR_WEIGHT>
298.43

> <EXACT_MASS>
298.204513465

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.283404809407315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S,7R)-7-ethyl-1,3-diazatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-10,12,14,16-tetraen-11-yl]ethan-1-ol

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
3.6301675909999993

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.820850379980634

> <JCHEM_PKA_STRONGEST_BASIC>
9.53083858985724

> <JCHEM_POLAR_SURFACE_AREA>
37.19

> <JCHEM_REFRACTIVITY>
89.9573

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2S,7R)-7-ethyl-1,3-diazatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-10,12,14,16-tetraen-11-yl]ethanol

> <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       7.466  -0.718   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.556   0.370   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.159   1.858   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.672   2.258   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.582   1.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.979  -0.318   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.210   1.871   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.453   3.392   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.974   3.631   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.675   5.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.213   5.081   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.913   6.453   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.257   4.362   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.819   3.812   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.576   2.291   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.772   1.320   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.529  -0.200   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       1.091  -0.751   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.105   0.220   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.138   1.740   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.380   3.261   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.058   2.711   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   16                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20   21                                             
CONECT   16   15    7   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   15   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆N₂O

Average Mass

298.4300 Da

Monoisotopic Mass

298.20451 Da

IUPAC Name

2-[(2S,7R)-7-ethyl-1,3-diazatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-10,12,14,16-tetraen-11-yl]ethan-1-ol

Traditional Name

2-[(2S,7R)-7-ethyl-1,3-diazatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-10,12,14,16-tetraen-11-yl]ethanol

CAS Registry Number

Not Available

SMILES

CC[C@]12CCCN[C@H]1N1C(CC2)=C(CCO)C2=CC=CC=C12

InChI Identifier

InChI=1S/C19H26N2O/c1-2-19-10-5-12-20-18(19)21-16-7-4-3-6-14(16)15(9-13-22)17(21)8-11-19/h3-4,6-7,18,20,22H,2,5,8-13H2,1H3/t18-,19+/m0/s1

InChI Key

CGWKMDYVWRDDRF-RBUKOAKNSA-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
Gonioma malagasy	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthyridines. Naphthyridines are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Naphthyridines

Direct Parent

Naphthyridines

Alternative Parents

Substituents

Naphthyridine
3-alkylindole
Indole
Indole or derivatives
Piperidine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Azacycle
Amine
Primary alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen 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	3.11	ALOGPS
logP	3.63	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.82	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	37.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.96 m³·mol⁻¹	ChemAxon
Polarizability	35.28 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

C00024535

Chemspider ID

28284854

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24767757

PDB ID

Not Available

ChEBI ID

141908

Good Scents ID

Not Available

References

General References

Pritchett BP, Kikuchi J, Numajiri Y, Stoltz BM: Enantioselective Pd-Catalyzed Allylic Alkylation Reactions of Dihydropyrido[1,2-a]indolone Substrates: Efficient Syntheses of (-)-Goniomitine, (+)-Aspidospermidine, and (-)-Quebrachamine. Angew Chem Int Ed Engl. 2016 Oct 17;55(43):13529-13532. doi: 10.1002/anie.201608138. Epub 2016 Sep 26. [PubMed:27666731 ]
Mijangos MV, Miranda LD: A unified synthesis of topologically diverse Aspidosperma alkaloids through divergent iminium-trapping. Org Biomol Chem. 2018 Dec 12;16(48):9409-9419. doi: 10.1039/c8ob02621a. [PubMed:30500039 ]
Bell GE, Fyfe JWB, Israel EM, Slawin AMZ, Campbell M, Watson AJB: Synthesis of 2-BMIDA Indoles via Heteroannulation: Applications in Drug Scaffold and Natural Product Synthesis. Org Lett. 2022 Apr 29;24(16):3024-3027. doi: 10.1021/acs.orglett.2c00959. Epub 2022 Apr 15. [PubMed:35426314 ]
Bin HY, Wang K, Yang D, Yang XH, Xie JH, Zhou QL: Scalable Enantioselective Total Synthesis of (-)-Goniomitine. Angew Chem Int Ed Engl. 2019 Jan 21;58(4):1174-1177. doi: 10.1002/anie.201812822. Epub 2018 Dec 20. [PubMed:30520199 ]
Pritchett BP, Kikuchi J, Numajiri Y, Stoltz BM: A FISCHER INDOLIZATION STRATEGY TOWARD THE TOTAL SYNTHESIS OF (-)-GONIOMITINE. Heterocycles. 2017;95(2):1245-1253. doi: 10.3987/COM-16-S(S)80. Epub 2017 Feb 15. [PubMed:28706345 ]
Li H, Cheng P, Jiang L, Yang JL, Zu L: Bio-Inspired Fragmentations: Rapid Assembly of Indolones, 2-Quinolinones, and (-)-Goniomitine. Angew Chem Int Ed Engl. 2017 Mar 1;56(10):2754-2757. doi: 10.1002/anie.201611830. Epub 2017 Jan 27. [PubMed:28128515 ]
Vellucci JK, Beaudry CM: Total Synthesis of (+/-)-Goniomitine via Radical Translocation. Org Lett. 2015 Sep 18;17(18):4558-60. doi: 10.1021/acs.orglett.5b02277. Epub 2015 Sep 8. [PubMed:26348647 ]
Wagnieres O, Xu Z, Wang Q, Zhu J: Unified strategy to monoterpene indole alkaloids: total syntheses of (+/-)-goniomitine, (+/-)-1,2-dehydroaspidospermidine, (+/-)-aspidospermidine, (+/-)-vincadifformine, and (+/-)-kopsihainanine A. J Am Chem Soc. 2014 Oct 22;136(42):15102-8. doi: 10.1021/ja509329x. Epub 2014 Oct 13. [PubMed:25270053 ]
Zhou B, Du J, Yang Y, Li Y: Rhodium(III)-catalyzed intramolecular redox-neutral annulation of tethered alkynes: formal total synthesis of (+/-)-goniomitine. Chemistry. 2014 Sep 26;20(40):12768-72. doi: 10.1002/chem.201403973. Epub 2014 Aug 21. [PubMed:25145612 ]
Zhou S, Jia Y: Total synthesis of (-)-goniomitine. Org Lett. 2014 Jun 20;16(12):3416-8. doi: 10.1021/ol501341b. Epub 2014 Jun 2. [PubMed:24885528 ]

Showing NP-Card for (-)-Goniomitine (NP0066882)

MOL for NP0066882 ((-)-Goniomitine)

3D MOL for NP0066882 ((-)-Goniomitine)

3D SDF for NP0066882 ((-)-Goniomitine)

3D-SDF for NP0066882 ((-)-Goniomitine)

PDB for NP0066882 ((-)-Goniomitine)

3D PDB for NP0066882 ((-)-Goniomitine)

SMILES for NP0066882 ((-)-Goniomitine)

INCHI for NP0066882 ((-)-Goniomitine)

Structure for NP0066882 ((-)-Goniomitine)

3D Structure for NP0066882 ((-)-Goniomitine)