NP-MRD: Showing NP-Card for anatoxin-a (NP0262755)

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Record Information

Version

2.0

Created at

2022-09-08 05:43:06 UTC

Updated at

2022-09-08 05:43:06 UTC

NP-MRD ID

NP0262755

Secondary Accession Numbers

None

Natural Product Identification

Common Name

anatoxin-a

Description

Anatoxin a, also known as antx-a, 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. Anatoxin a is a very strong basic compound (based on its pKa). Anatoxin a is a potentially toxic compound. Anatoxin a binding is irreversible, and the Anatoxin a nAchR complex cannot be broken down by acetylcholinesterase. Thus, the nAchR is temporarily locked open and after a period of time becomes desensitized. In this desensitized state the nAchRs no longer let cations pass through, which ultimately leads to a blockage of neuromuscular transmission. Anatoxin a is an agonist of both neuronal α4β2 and α4 nicotinic acetylcholine receptors present in the CNS as well as the α12βγδ muscle-type nAchRs that are present at the neuromuscular junction. Anatoxin a also shows much less potency in the CNS than in neuromuscular junctions. In hippocampal and brain stem neurons, a 5 to 10 times greater concentration of Anatoxin a was necessary to activate nAchRs than what was required in the PNS. Anatoxin a has an affinity for these receptors that is about 20 times greater than that of acetylcholine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0       3.393   6.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.831   1.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.742   0.024   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.831   2.653   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.113   1.113   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.113   2.653   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.331   5.164   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.202   0.024   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.742   3.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.202   3.742   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.666   1.883   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       5.858   5.365   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    8                                                       
CONECT    4    2    9                                                       
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7    1    9   12                                                  
CONECT    8    3    5   11                                                  
CONECT    9    4    7   10                                                  
CONECT   10    6    9   11                                                  
CONECT   11    8   10                                                       
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol

Synonyms

Value	Source
ANTX-a	MeSH
Anatoxin I	MeSH
Anatoxin-a	MeSH
(+)-Anatoxin	ChEMBL

Chemical Formula

C₁₀H₁₅NO

Average Mass

165.2322 Da

Monoisotopic Mass

165.11536 Da

IUPAC Name

1-{9-azabicyclo[4.2.1]non-2-en-2-yl}ethan-1-one

Traditional Name

anatoxin-a

CAS Registry Number

Not Available

SMILES

CC(=O)C1=CCCC2CCC1N2

InChI Identifier

InChI=1S/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3

InChI Key

SGNXVBOIDPPRJJ-UHFFFAOYSA-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

tropane alkaloid (CHEBI:2706 )
Tropane alkaloids (C10841 )
Anatoxins (C10841 )

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	1.25	ALOGPS
logP	1.19	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	19.12	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.83 m³·mol⁻¹	ChemAxon
Polarizability	18.59 Å³	ChemAxon
Number of Rings	2	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

C00002273

Chemspider ID

Not Available

KEGG Compound ID

C10841

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

431734

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for anatoxin-a (NP0262755)

MOL for NP0262755 (anatoxin-a)

3D MOL for NP0262755 (anatoxin-a)

3D SDF for NP0262755 (anatoxin-a)

3D-SDF for NP0262755 (anatoxin-a)

PDB for NP0262755 (anatoxin-a)

3D PDB for NP0262755 (anatoxin-a)

SMILES for NP0262755 (anatoxin-a)

INCHI for NP0262755 (anatoxin-a)

Structure for NP0262755 (anatoxin-a)

3D Structure for NP0262755 (anatoxin-a)