NP-MRD: Showing NP-Card for (2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane (NP0321751)

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Record Information

Version

2.0

Created at

2022-09-12 00:07:41 UTC

Updated at

2022-09-12 00:07:41 UTC

NP-MRD ID

NP0321751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane

Description

Epibatidine belongs to the class of organic compounds known as epibatidine analogues. Epibatidine analogues are compounds containing an epibatidine moiety, with a structure characterized by a 2-chloropyridine moiety connected to an 7-azabicyclo[2.2.1]Heptane in exo position. (2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane is found in Epipedobates anthonyi. It was first documented in 2021 (PMID: 34407206). Based on a literature review a significant number of articles have been published on Epibatidine (PMID: 35049904) (PMID: 36062901) (PMID: 35234149) (PMID: 34358124).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202072D          

 14 16  0  0  1  0            999 V2000
   -2.6944    2.1918    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    2.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5510    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5510    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1635    0.5418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1635   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8780   -0.6957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5925   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8780    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717    0.1293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799    0.9543    0.0000 N   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  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  6  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ClC1=CC=C(C=N1)[C@H]1C[C@@H]2CCC1N2

> <INCHI_IDENTIFIER>
InChI=1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2/t8-,9+,10?/m0/s1

> <INCHI_KEY>
NLPRAJRHRHZCQQ-QIIDTADFSA-N

> <FORMULA>
C11H13ClN2

> <MOLECULAR_WEIGHT>
208.69

> <EXACT_MASS>
208.0767261

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.074557291361486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4S)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane

> <JCHEM_LOGP>
1.8435768270000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.53983127735407

> <JCHEM_POLAR_SURFACE_AREA>
24.92

> <JCHEM_REFRACTIVITY>
57.3916

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4S)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1 Cl   UNK     0      -5.029   4.091   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0      -3.696   3.321   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.362   4.091   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.028   3.321   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.028   1.781   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.305   1.011   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.305  -0.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.639  -1.299   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.973  -0.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.973   1.011   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.639   1.781   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.254   0.241   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.362   1.011   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -3.696   1.781   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11    8                                                       
CONECT   13    5   14                                                       
CONECT   14   13    2                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₃ClN₂

Average Mass

208.6900 Da

Monoisotopic Mass

208.07673 Da

IUPAC Name

(2R,4S)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane

Traditional Name

(2R,4S)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane

CAS Registry Number

Not Available

SMILES

ClC1=CC=C(C=N1)[C@H]1C[C@@H]2CCC1N2

InChI Identifier

InChI=1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2/t8-,9+,10?/m0/s1

InChI Key

NLPRAJRHRHZCQQ-QIIDTADFSA-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
Epipedobates anthonyi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epibatidine analogues. Epibatidine analogues are compounds containing an epibatidine moiety, with a structure characterized by a 2-chloropyridine moiety connected to an 7-azabicyclo[2.2.1]Heptane in exo position.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Epibatidine analogues

Sub Class

Not Available

Direct Parent

Epibatidine analogues

Alternative Parents

Substituents

Epibatidine-skeleton
Pyrrolidinylpyridine
2-halopyridine
Aralkylamine
Pyridine
Aryl halide
Aryl chloride
Heteroaromatic compound
Pyrrolidine
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen 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	1.84	ChemAxon
pKa (Strongest Basic)	10.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	24.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	57.39 m³·mol⁻¹	ChemAxon
Polarizability	22.07 Å³	ChemAxon
Number of Rings	3	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

C00028244

Chemspider ID

94811

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Epibatidine

METLIN ID

Not Available

PubChem Compound

105084

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kem WR, Andrud K, Bruno G, Xing H, Soti F, Talley TT, Taylor P: Interactions of Nereistoxin and Its Analogs with Vertebrate Nicotinic Acetylcholine Receptors and Molluscan ACh Binding Proteins. Mar Drugs. 2022 Jan 4;20(1). pii: md20010049. doi: 10.3390/md20010049. [PubMed:35049904 ]
Frara N, Barbe MF, Giaddui D, Braverman AS, Amin M, Yu D, Ruggieri MR Sr: Dog and human bladders have different neurogenic and nicotinic responses in inner versus outer detrusor muscle layers. Am J Physiol Regul Integr Comp Physiol. 2022 Oct 1;323(4):R589-R600. doi: 10.1152/ajpregu.00084.2022. Epub 2022 Sep 5. [PubMed:36062901 ]
Bueno RV, Davis S, Dawson A, Ondachi PW, Carroll FI, Hunter WN: Interactions between 2'-fluoro-(carbamoylpyridinyl)deschloroepibatidine analogues and acetylcholine-binding protein inform on potent antagonist activity against nicotinic receptors. Acta Crystallogr D Struct Biol. 2022 Mar 1;78(Pt 3):353-362. doi: 10.1107/S2059798322000754. Epub 2022 Feb 21. [PubMed:35234149 ]
Mulcahy MJ, Huard SM, Paulo JA, Wang JH, McKinney S, Marks MJ, Henderson BJ, Lester HA: Protein profiling in the habenula after chronic (-)-menthol exposure in mice. J Neurochem. 2021 Sep;158(6):1345-1358. doi: 10.1111/jnc.15495. Epub 2021 Sep 2. [PubMed:34407206 ]
Hansen TVA, Grencis RK, Issouf M, Neveu C, Charvet CL: Functional Characterization of the Oxantel-Sensitive Acetylcholine Receptor from Trichuris muris. Pharmaceuticals (Basel). 2021 Jul 20;14(7):698. doi: 10.3390/ph14070698. [PubMed:34358124 ]
LOTUS database [Link]

Showing NP-Card for (2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane (NP0321751)

MOL for NP0321751 ((2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

3D MOL for NP0321751 ((2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

3D SDF for NP0321751 ((2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

3D-SDF for NP0321751 ((2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

PDB for NP0321751 ((2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

3D PDB for NP0321751 ((2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

SMILES for NP0321751 ((2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

INCHI for NP0321751 ((2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

Structure for NP0321751 ((2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)

3D Structure for NP0321751 ((2r,4s)-2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane)