NP-MRD: Showing NP-Card for 1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one (NP0199483)

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Record Information

Version

2.0

Created at

2022-09-04 18:08:10 UTC

Updated at

2022-09-04 18:08:10 UTC

NP-MRD ID

NP0199483

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one

Description

Homoanatoxin, also known as homoantx, belongs to the class of organic compounds known as anatoxins. These are organic compounds containing or derived from anatoxin, homoanatoxin or other analogues. Anatoxins constitute a class of potent neurotoxic alkaloids. 1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one was first documented in 2021 (PMID: 32881159). Based on a literature review a small amount of articles have been published on Homoanatoxin (PMID: 35121419) (PMID: 32828056).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    4.0418   -0.3602    0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9673   -0.1682   -0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    0.5764   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    1.8066    0.2298 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5184    0.0445    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2485   -1.1925   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896   -1.9003   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124   -0.9818   -0.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462    0.0378    0.5352 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6739    1.4194   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1884    1.6794   -0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4563    1.0090    0.7248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4756    0.3109    1.4671 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867    0.5939    0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7810   -1.1996    1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -0.6404   -0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7182   -1.0946   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4693    0.4743   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0836   -1.7945   -0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928   -2.3328    0.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0341   -2.6771   -0.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0589   -0.5356   -1.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1312   -1.6304   -0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -0.1433    1.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2919    1.4024   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0327    2.1232    0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9808    2.7673   -0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0031    1.1988   -1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0513    1.7415    1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -0.5341    1.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12  5  1  0
 13  9  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  1
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  1
 13 30  1  0
M  END

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       3.983  -4.044   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.393  -2.621   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.331  -1.399   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.858  -1.600   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.742   0.024   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.831   1.113   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.831   2.653   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.742   3.742   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.202   3.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.113   2.653   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.113   1.113   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.202   0.024   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.666   1.883   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
2-(Propan-1-oxo-1-yl)-9-azabicyclo(4.2.1)non-2-ene	MeSH
HomoAnTx	MeSH

Chemical Formula

C₁₁H₁₇NO

Average Mass

179.2630 Da

Monoisotopic Mass

179.13101 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC(=O)C1=CCC[C@@H]2CC[C@H]1N2

InChI Identifier

InChI=1S/C11H17NO/c1-2-11(13)9-5-3-4-8-6-7-10(9)12-8/h5,8,10,12H,2-4,6-7H2,1H3/t8-,10-/m1/s1

InChI Key

VVMQRZZXKNDPOT-PSASIEDQSA-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 anatoxins. These are organic compounds containing or derived from anatoxin, homoanatoxin or other analogues. Anatoxins constitute a class of potent neurotoxic alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Anatoxins

Sub Class

Not Available

Direct Parent

Anatoxins

Alternative Parents

Substituents

Anatoxin skeleton
Azepine
Beta-aminoketone
Pyrrolidine
Ketone
Secondary aliphatic amine
Secondary amine
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

C00051747

Chemspider ID

61597976

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

126727

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

You L, Tong X, Te SH, Tran NH, Bte Sukarji NH, He Y, Gin KY: Multi-class secondary metabolites in cyanobacterial blooms from a tropical water body: Distribution patterns and real-time prediction. Water Res. 2022 Apr 1;212:118129. doi: 10.1016/j.watres.2022.118129. Epub 2022 Jan 29. [PubMed:35121419 ]
Beach DG, Rafuse C, Melanson JE, McCarron P: Rapid quantitative screening of cyanobacteria for production of anatoxins using direct analysis in real time high-resolution mass spectrometry. Rapid Commun Mass Spectrom. 2021 Jan 15;35(1):e8940. doi: 10.1002/rcm.8940. [PubMed:32881159 ]
Puddick J, van Ginkel R, Page CD, Murray JS, Greenhough HE, Bowater J, Selwood AI, Wood SA, Prinsep MR, Truman P, Munday R, Finch SC: Acute toxicity of dihydroanatoxin-a from Microcoleus autumnalis in comparison to anatoxin-a. Chemosphere. 2021 Jan;263:127937. doi: 10.1016/j.chemosphere.2020.127937. Epub 2020 Aug 13. [PubMed:32828056 ]
LOTUS database [Link]

Showing NP-Card for 1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one (NP0199483)

MOL for NP0199483 (1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one)

3D MOL for NP0199483 (1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one)

3D SDF for NP0199483 (1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one)

3D-SDF for NP0199483 (1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one)

PDB for NP0199483 (1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one)

3D PDB for NP0199483 (1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one)

SMILES for NP0199483 (1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one)

INCHI for NP0199483 (1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one)

Structure for NP0199483 (1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one)

3D Structure for NP0199483 (1-[(1r,6r)-9-azabicyclo[4.2.1]non-2-en-2-yl]propan-1-one)