NP-MRD: Showing NP-Card for Dyclocaine (NP0045138)

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Record Information

Version

2.0

Created at

2022-03-10 18:58:37 UTC

Updated at

2022-03-10 22:20:35 UTC

NP-MRD ID

NP0045138

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dyclocaine

Description

Dyclocaine or Dyclonine, also known as diclonina or dycloninum, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by an alkyl and a phenyl group. Dyclocaine is a potentially toxic compound. It is an oral anaesthetic found in Sucrets, an over the counter throat lozenge. It is also found in some varieties of the Cepacol sore throat spray. Dyclonine is only found in individuals that have used or taken this drug. Dyclonine blocks both the initiation and conduction of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade. It has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 49  0  0  0  0  0  0  0  0999 V2000
    7.3369   -0.6021   -0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2532   -0.4099    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6788    0.9879    0.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0827    1.3585   -1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0587    0.5510   -1.5334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210    0.2683   -1.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9903   -0.6423   -1.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7333   -0.9442   -1.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223   -0.3822   -0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086   -0.7242    0.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -1.5632   -0.3274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566   -0.1175    1.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9799   -0.7777    1.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8612   -0.5542    0.7412 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1361   -1.2324    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6975   -1.4144   -0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8860   -0.0201   -1.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4541    1.0464   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0856    0.8613    0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0046    0.5089    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2746    0.8157    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9766   -1.1603   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1272   -1.2411   -0.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8349    0.3503   -1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5757   -0.7234    1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4391   -1.1514   -0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5384    1.6889    0.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0256    1.0914    1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432    2.4001   -0.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8828    1.5064   -1.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4087   -1.0804   -2.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311   -1.6619   -1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0140   -0.2483    2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8703    0.9482    1.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077   -1.8662    1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4361   -0.3405    2.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9633   -2.2069    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8412   -0.6079    1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8819   -1.8778   -1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6155   -2.0225   -0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9994    0.1024   -1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4406    0.1312   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2032    1.2302    0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4363    2.0132   -0.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863    1.2637   -0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0619    1.4055    1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6236    0.9884    1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8350    1.5525    0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 20  1  0
 20 21  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 21  6  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
 20 47  1  0
 21 48  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
M  END

645
  Mrv1652303202018592D          

 21 22  0  0  0  0            999 V2000
    2.3645    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.0938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2 16  1  0  0  0  0
  2 19  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  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
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045138

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C18H27NO2/c1-2-3-15-21-17-9-7-16(8-10-17)18(20)11-14-19-12-5-4-6-13-19/h7-10H,2-6,11-15H2,1H3

> <INCHI_KEY>
BZEWSEKUUPWQDQ-UHFFFAOYSA-N

> <FORMULA>
C18H27NO2

> <MOLECULAR_WEIGHT>
289.4125

> <EXACT_MASS>
289.204179113

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.13910714431107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-butoxyphenyl)-3-(piperidin-1-yl)propan-1-one

> <ALOGPS_LOGP>
4.11

> <JCHEM_LOGP>
3.675998439999999

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.884370282015901

> <JCHEM_PKA_STRONGEST_BASIC>
8.36448774444315

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
87.06800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dyclonine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 645                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0       4.414   3.465   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748  -3.465   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       8.415   5.775   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.415   7.315   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.748   5.005   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.748   8.085   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.082   5.775   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082   7.315   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   5.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   3.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   1.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -5.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -1.155   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -4.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -6.545   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080  -8.085   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   16   19                                                       
CONECT    3    4    5    9                                                  
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    3   10                                                       
CONECT   10    9   11                                                       
CONECT   11    1   10   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   17                                                       
CONECT   14   12   18                                                       
CONECT   15   19   20                                                       
CONECT   16    2   17   18                                                  
CONECT   17   13   16                                                       
CONECT   18   14   16                                                       
CONECT   19    2   15                                                       
CONECT   20   15   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
1-(4-Butoxyphenyl)-3-(1-piperidinyl)-1-propanone	ChEBI
2-(1-Piperidyl)ethyl p-butoxyphenyl ketone	ChEBI
3-Piperidino-4'-butoxypropiophenone	ChEBI
4'-Butoxy-3-piperidinopropiophenone	ChEBI
4-Butoxy-beta-piperidinopropiophenone	ChEBI
4-N-Butoxy-beta-(1-piperidyl)propiophenone	ChEBI
Diclonina	ChEBI
Dycloninum	ChEBI
4-Butoxy-b-piperidinopropiophenone	Generator
4-Butoxy-β-piperidinopropiophenone	Generator
4-N-Butoxy-b-(1-piperidyl)propiophenone	Generator
4-N-Butoxy-β-(1-piperidyl)propiophenone	Generator
Sucrets	HMDB
Tanac	HMDB
Dyclone	HMDB
Dyclonine hydrochloride	HMDB
Dyclonine HCL	HMDB

Chemical Formula

C₁₈H₂₇NO₂

Average Mass

289.4125 Da

Monoisotopic Mass

289.20418 Da

IUPAC Name

1-(4-butoxyphenyl)-3-(piperidin-1-yl)propan-1-one

Traditional Name

dyclonine

CAS Registry Number

586-60-7

SMILES

CCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC1

InChI Identifier

InChI=1S/C18H27NO2/c1-2-3-15-21-17-9-7-16(8-10-17)18(20)11-14-19-12-5-4-6-13-19/h7-10H,2-6,11-15H2,1H3

InChI Key

BZEWSEKUUPWQDQ-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, 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
Cannabis sativa	NULL	Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Phenoxy compound
Benzoyl
Phenol ether
Aryl alkyl ketone
Alkyl aryl ether
Monocyclic benzene moiety
Beta-aminoketone
Piperidine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Ether
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:4724 )
aromatic ketone (CHEBI:4724 )

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	4.11	ALOGPS
logP	3.68	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	15.88	ChemAxon
pKa (Strongest Basic)	8.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	87.07 m³·mol⁻¹	ChemAxon
Polarizability	35.14 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