NP-MRD: Showing NP-Card for Undecanoylcholine (NP0339253)

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Record Information

Version

2.0

Created at

2024-09-11 20:42:41 UTC

Updated at

2024-09-11 20:42:42 UTC

NP-MRD ID

NP0339253

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Undecanoylcholine

Description

Undecanoylcholine 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, undecanoylcholine is considered to be a fatty ester lipid molecule. Undecanoylcholine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Only one, butyrylcholine, had an erratic stimulating effect on hydrochloric acid secretion by the partially vagotomized rat stomach. Undecanoylcholine is a fatty acid-choline as the ester product of undecanoic acid and cholinel. 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. The effect changed with increasing chain length, and three different types of response were observed. 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


  Mrv1652303102016522D          

 19 18  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
   15.4936   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2080   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9226   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6370   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3515   -9.7574    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  1  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
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
M  CHG  1   1   1
M  END
> <DATABASE_ID>
NP0339253

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H34NO2/c1-5-6-7-8-9-10-11-12-13-16(18)19-15-14-17(2,3)4/h5-15H2,1-4H3/q+1

> <INCHI_KEY>
WAKLSXXFSACOOZ-UHFFFAOYSA-N

> <FORMULA>
C16H34NO2

> <MOLECULAR_WEIGHT>
272.4467

> <EXACT_MASS>
272.258954337

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.412921798414985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
trimethyl[2-(undecanoyloxy)ethyl]azanium

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
0.035941414528254445

> <ALOGPS_LOGS>
-6.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-7.04717449773593

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
92.7804

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyl[2-(undecanoyloxy)ethyl]azanium

> <JCHEM_VEBER_RULE>
0

$$$$

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
HETATM   15  C   UNK     0      28.921 -18.214   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.255 -17.444   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.589 -18.214   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.922 -17.444   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.256 -18.214   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   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
Undecanoyl choline	HMDB

Chemical Formula

C₁₆H₃₄NO₂

Average Mass

272.4467 Da

Monoisotopic Mass

272.25895 Da

IUPAC Name

trimethyl[2-(undecanoyloxy)ethyl]azanium

Traditional Name

trimethyl[2-(undecanoyloxy)ethyl]azanium

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C16H34NO2/c1-5-6-7-8-9-10-11-12-13-16(18)19-15-14-17(2,3)4/h5-15H2,1-4H3/q+1

InChI Key

WAKLSXXFSACOOZ-UHFFFAOYSA-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
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Amine
Organooxygen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
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	0.43	ALOGPS
logP	0.036	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	-7	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	13	ChemAxon
Refractivity	92.78 m³·mol⁻¹	ChemAxon
Polarizability	35.41 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013322

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029383

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481666

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Undecanoylcholine (NP0339253)

MOL for NP0339253 (Undecanoylcholine)

3D MOL for NP0339253 (Undecanoylcholine)

3D SDF for NP0339253 (Undecanoylcholine)

3D-SDF for NP0339253 (Undecanoylcholine)

PDB for NP0339253 (Undecanoylcholine)

3D PDB for NP0339253 (Undecanoylcholine)

SMILES for NP0339253 (Undecanoylcholine)

INCHI for NP0339253 (Undecanoylcholine)

Structure for NP0339253 (Undecanoylcholine)

3D Structure for NP0339253 (Undecanoylcholine)