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Showing NP-Card for Butyrylcholine (NP0339223)

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Record Information
Version2.0
Created at2024-09-11 20:30:49 UTC
Updated at2024-09-11 20:30:49 UTC
NP-MRD IDNP0339223
Secondary Accession NumbersNone
Natural Product Identification
Common NameButyrylcholine
DescriptionButyrylcholine 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, butyrylcholine is considered to be a fatty ester lipid molecule. Butyrylcholine is a choline-based ester that can function as a neurotransmitter. Butyrylcholine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In humans, butyrylcholine is involved in irinotecan action pathway. Butyrylcholine is a synthetic compound and does not occur in the body naturally. It is similar to acetylcholine, with activation of some of the same receptors as acetylcholine. It is used as a clinical laboratory tool to distinguish between the cholinesterases; acetylcholinesterase and butyrylcholinesterase preferentially lyse acetylcholine and butyrylcholine, respectively.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339223 (Butyrylcholine)


  Mrv1652304302018042D          

 12 11  0  0  0  0            999 V2000
 9998.6249 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9100 9999.7745    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9999.3398 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1909 9999.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.910010000.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.055610000.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0554 9999.3628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7691 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4848 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.769110000.5992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.2006 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9143 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  CHG  1   2   1
M  END
Download

3D MOL for NP0339223 (Butyrylcholine)

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3D SDF for NP0339223 (Butyrylcholine)

  Mrv1652304302018042D          

 12 11  0  0  0  0            999 V2000
 9998.6249 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9100 9999.7745    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9999.3398 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1909 9999.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.910010000.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.055610000.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0554 9999.3628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.7691 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4848 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.769110000.5992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.2006 9999.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9143 9999.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
NP0339223

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H20NO2/c1-5-6-9(11)12-8-7-10(2,3)4/h5-8H2,1-4H3/q+1

> <INCHI_KEY>
YRIBGSCJIMXMPJ-UHFFFAOYSA-N

> <FORMULA>
C9H20NO2

> <MOLECULAR_WEIGHT>
174.2606

> <EXACT_MASS>
174.149403889

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
20.726997717196653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.52

> <JCHEM_LOGP>
-3.076039240471746

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-7.047066258269654

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
60.5734

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyrylcholine

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0339223 (Butyrylcholine)
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PDB for NP0339223 (Butyrylcholine)
HEADER    PROTEIN                                 30-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-20         0                                  
HETATM    1  C   UNK     0    8664.1008665.477   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8662.7658666.246   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0    8665.4348666.246   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8661.4238665.473   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8662.7658667.785   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8661.1708667.169   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8666.7708665.477   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8668.1028666.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8669.4388665.477   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8668.1028667.785   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8670.7748666.246   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8672.1078665.477   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5    6                                             
CONECT    3    1    7                                                       
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0339223 (Butyrylcholine)
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SMILES for NP0339223 (Butyrylcholine)
CCCC(=O)OCC[N+](C)(C)C
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INCHI for NP0339223 (Butyrylcholine)
InChI=1S/C9H20NO2/c1-5-6-9(11)12-8-7-10(2,3)4/h5-8H2,1-4H3/q+1
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View in JSmol
Synonyms
ValueSource
(2-Butyryloxy-ethyl)-trimethyl-ammoniumHMDB
N,N,N-Trimethyl-2-(1-oxobutoxy)ethanaminiumHMDB
ButyrylcholineHMDB
Chemical FormulaC9H20NO2
Average Mass174.2606 Da
Monoisotopic Mass174.14940 Da
IUPAC Name[2-(butanoyloxy)ethyl]trimethylazanium
Traditional Namebutyrylcholine
CAS Registry NumberNot Available
SMILES
CCCC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C9H20NO2/c1-5-6-9(11)12-8-7-10(2,3)4/h5-8H2,1-4H3/q+1
InChI KeyYRIBGSCJIMXMPJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot 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.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassQuaternary ammonium salts  
Direct ParentAcyl 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.5ALOGPS
logP-3.1ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.57 m³·mol⁻¹ChemAxon
Polarizability20.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013223  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029342  
KNApSAcK IDNot Available
Chemspider ID16312  
KEGG Compound IDNot Available
BioCyc IDCPD0-1675  
BiGG IDNot Available
Wikipedia LinkButyrylcholine  
METLIN IDNot Available
PubChem Compound17233  
PDB IDNot Available
ChEBI ID327449  
Good Scents IDNot Available
References
General ReferencesNot Available