NP-MRD: Showing NP-Card for [2-(benzoyloxy)ethyl]trimethylazanium (NP0310146)

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Record Information

Version

2.0

Created at

2022-09-11 05:15:01 UTC

Updated at

2022-09-11 05:15:01 UTC

NP-MRD ID

NP0310146

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[2-(benzoyloxy)ethyl]trimethylazanium

Description

BENZOYLCHOLINE belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. [2-(benzoyloxy)ethyl]trimethylazanium is found in Arabidopsis thaliana. [2-(benzoyloxy)ethyl]trimethylazanium was first documented in 2010 (PMID: 20004171). Based on a literature review a small amount of articles have been published on BENZOYLCHOLINE (PMID: 28723110) (PMID: 27062891) (PMID: 25264279) (PMID: 25054547).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -3.4619    1.0518   -1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0364    0.3062   -0.0811 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8031    0.8146    1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -1.1044   -0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6414    0.5237    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7204   -0.3808   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6051   -0.0837   -0.1554 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7112   -0.7223   -0.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4900   -1.6147   -1.5461 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0754   -0.4223   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259   -1.1056   -0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4315   -0.8449   -0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6874    0.1232    0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6125    0.7887    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3056    0.5570    0.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229    1.5252   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1724    1.8733   -0.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0137    0.3714   -1.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4743    1.8278    1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8725    0.8541    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7484    0.1011    1.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4682   -1.1729   -0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0122   -1.5780    0.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9151   -1.5717   -1.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218    1.5972    0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5403    0.3501    1.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0009   -1.4329   -0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8907   -0.3230   -1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9390   -1.8825   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2213   -1.3920   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7183    0.3608    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8091    1.5491    1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4483    1.0566    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
M  CHG  1   2   1
M  END


  Mrv1652309112207152D          

 15 15  0  0  0  0            999 V2000
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -1.5395    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
NP0310146

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+](C)(C)CCOC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H18NO2/c1-13(2,3)9-10-15-12(14)11-7-5-4-6-8-11/h4-8H,9-10H2,1-3H3/q+1

> <INCHI_KEY>
HOPVGFKDVOOCHD-UHFFFAOYSA-N

> <FORMULA>
C12H18NO2

> <MOLECULAR_WEIGHT>
208.28

> <EXACT_MASS>
208.133205244

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.376439629687624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-(benzoyloxy)ethyl]trimethylazanium

> <JCHEM_LOGP>
-2.166969314138413

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-6.903314171200306

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
72.01600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[2-(benzoyloxy)ethyl]trimethylazanium

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.334   8.470   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0      -2.874   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.206   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₈NO₂

Average Mass

208.2800 Da

Monoisotopic Mass

208.13321 Da

IUPAC Name

[2-(benzoyloxy)ethyl]trimethylazanium

Traditional Name

[2-(benzoyloxy)ethyl]trimethylazanium

CAS Registry Number

Not Available

SMILES

C[N+](C)(C)CCOC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H18NO2/c1-13(2,3)9-10-15-12(14)11-7-5-4-6-8-11/h4-8H,9-10H2,1-3H3/q+1

InChI Key

HOPVGFKDVOOCHD-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

Species Name	Source	Reference
Arabidopsis thaliana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic salt
Amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	-2.2	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.02 m³·mol⁻¹	ChemAxon
Polarizability	23.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

15769

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16632

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xie L, Huang X, Su B: Portable Sensor for the Detection of Choline and Its Derivatives Based on Silica Isoporous Membrane and Gellified Nanointerfaces. ACS Sens. 2017 Jun 23;2(6):803-809. doi: 10.1021/acssensors.7b00166. Epub 2017 Apr 24. [PubMed:28723110 ]
Lozano-Paniagua D, Gomez-Martin A, Gil F, Parron T, Alarcon R, Requena M, Lacasana M, Hernandez AF: Activity and determinants of cholinesterases and paraoxonase-1 in blood of workers exposed to non-cholinesterase inhibiting pesticides. Chem Biol Interact. 2016 Nov 25;259(Pt B):160-167. doi: 10.1016/j.cbi.2016.04.008. Epub 2016 Apr 7. [PubMed:27062891 ]
Delacour H, Lushchekina S, Mabboux I, Ceppa F, Masson P, Schopfer LM, Lockridge O: Characterization of a novel butyrylcholinesterase point mutation (p.Ala34Val), "silent" with mivacurium. Biochem Pharmacol. 2014 Dec 1;92(3):476-83. doi: 10.1016/j.bcp.2014.09.014. Epub 2014 Sep 28. [PubMed:25264279 ]
Delacour H, Lushchekina S, Mabboux I, Bousquet A, Ceppa F, Schopfer LM, Lockridge O, Masson P: Characterization of a novel BCHE "silent" allele: point mutation (p.Val204Asp) causes loss of activity and prolonged apnea with suxamethonium. PLoS One. 2014 Jul 23;9(7):e101552. doi: 10.1371/journal.pone.0101552. eCollection 2014. [PubMed:25054547 ]
Masson P, Lockridge O: Butyrylcholinesterase for protection from organophosphorus poisons: catalytic complexities and hysteretic behavior. Arch Biochem Biophys. 2010 Feb 15;494(2):107-20. doi: 10.1016/j.abb.2009.12.005. Epub 2009 Dec 11. [PubMed:20004171 ]
LOTUS database [Link]

Showing NP-Card for [2-(benzoyloxy)ethyl]trimethylazanium (NP0310146)

MOL for NP0310146 ([2-(benzoyloxy)ethyl]trimethylazanium)

3D MOL for NP0310146 ([2-(benzoyloxy)ethyl]trimethylazanium)

3D SDF for NP0310146 ([2-(benzoyloxy)ethyl]trimethylazanium)

3D-SDF for NP0310146 ([2-(benzoyloxy)ethyl]trimethylazanium)

PDB for NP0310146 ([2-(benzoyloxy)ethyl]trimethylazanium)

3D PDB for NP0310146 ([2-(benzoyloxy)ethyl]trimethylazanium)

SMILES for NP0310146 ([2-(benzoyloxy)ethyl]trimethylazanium)

INCHI for NP0310146 ([2-(benzoyloxy)ethyl]trimethylazanium)

Structure for NP0310146 ([2-(benzoyloxy)ethyl]trimethylazanium)

3D Structure for NP0310146 ([2-(benzoyloxy)ethyl]trimethylazanium)