NP-MRD: Showing NP-Card for 2-Hexenoylcholine (NP0339202)

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Record Information

Version

2.0

Created at

2024-09-11 20:22:57 UTC

Updated at

2024-09-11 20:22:57 UTC

NP-MRD ID

NP0339202

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hexenoylcholine

Description

2-Hexenoylcholine belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH. Thus, 2-hexenoylcholine is considered to be a fatty ester lipid molecule. The pharmacological effects of a series of fatty acid-choline esters have been studied on the isolated rabbit heart, the isolated guinea-pig ileum and the rat stomach. 2-Hexenoylcholine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Medium-chain compounds had a stimulating effect on the isolated rabbit heart, a mixed spasmogenic and relaxant effect on the isolated guinea-pig ileum, and no effect on the rat stomach. The shortchain compounds produced depression of the isolated rabbit heart and spasm of the isolated guinea-pig ileum. Only one, butyrylcholine, had an erratic stimulating effect on hydrochloric acid secretion by the partially vagotomized rat stomach. Long-chain compounds blocked the effect of acetylcholine on the isolated rabbit heart and the isolated guinea-pig ileum; they also depressed spontaneous hydrochloric acid secretion by the rat stomach.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016502D          

 14 13  0  0  0  0            999 V2000
    8.3488   -9.7574    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.4922   -9.3449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0633   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6344  -10.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9363   -9.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7613  -10.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7778   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2067   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9212   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2067  -10.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6357   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3502   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0646   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7791   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  1  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  2  0  0  0  0
 11  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
M  CHG  1   1   1
M  END
> <DATABASE_ID>
NP0339202

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C\C(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C11H22NO2/c1-5-6-7-8-11(13)14-10-9-12(2,3)4/h7-8H,5-6,9-10H2,1-4H3/q+1/b8-7+

> <INCHI_KEY>
FEBXWAFFYJZFMS-BQYQJAHWSA-N

> <FORMULA>
C11H22NO2

> <MOLECULAR_WEIGHT>
200.2979

> <EXACT_MASS>
200.165053953

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
23.715452043376192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{2-[(2E)-hex-2-enoyloxy]ethyl}trimethylazanium

> <ALOGPS_LOGP>
-1.87

> <JCHEM_LOGP>
-1.9557450874717452

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-6.804237346701394

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
70.8687

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.34e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2-[(2E)-hex-2-enoyloxy]ethyl}trimethylazanium

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  N   UNK     0      15.584 -18.214   0.000  0.00  0.00           N+1
HETATM    2  O   UNK     0      19.585 -17.444   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      16.918 -17.444   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.251 -18.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.814 -16.880   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.354 -19.547   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.252 -18.214   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.919 -18.214   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.253 -17.444   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      20.919 -19.754   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      23.587 -18.214   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.920 -17.444   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.254 -18.214   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.588 -17.444   0.000  0.00  0.00           C+0
CONECT    1    3    4    5    6                                             
CONECT    2    7    8                                                       
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    2    3                                                       
CONECT    8    2    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₂₂NO₂

Average Mass

200.2979 Da

Monoisotopic Mass

200.16505 Da

IUPAC Name

{2-[(2E)-hex-2-enoyloxy]ethyl}trimethylazanium

Traditional Name

{2-[(2E)-hex-2-enoyloxy]ethyl}trimethylazanium

CAS Registry Number

Not Available

SMILES

CCC\C=C\C(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C11H22NO2/c1-5-6-7-8-11(13)14-10-9-12(2,3)4/h7-8H,5-6,9-10H2,1-4H3/q+1/b8-7+

InChI Key

FEBXWAFFYJZFMS-BQYQJAHWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Acyl cholines

Alternative Parents

Substituents

Acyl choline
Fatty acid ester
Fatty acyl
Tetraalkylammonium salt
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organic salt
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-1.9	ALOGPS
logP	-2	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-6.8	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	7	ChemAxon
Refractivity	70.87 m³·mol⁻¹	ChemAxon
Polarizability	23.72 Å³	ChemAxon
Number of Rings	0	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

HMDB0013162

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029317

KNApSAcK ID

Not Available

Chemspider ID

14582873

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22155829

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Hexenoylcholine (NP0339202)

MOL for NP0339202 (2-Hexenoylcholine)

3D MOL for NP0339202 (2-Hexenoylcholine)

3D SDF for NP0339202 (2-Hexenoylcholine)

3D-SDF for NP0339202 (2-Hexenoylcholine)

PDB for NP0339202 (2-Hexenoylcholine)

3D PDB for NP0339202 (2-Hexenoylcholine)

SMILES for NP0339202 (2-Hexenoylcholine)

INCHI for NP0339202 (2-Hexenoylcholine)

Structure for NP0339202 (2-Hexenoylcholine)

3D Structure for NP0339202 (2-Hexenoylcholine)