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Showing NP-Card for Choline chloride (NP0337830)

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Record Information
Version2.0
Created at2024-09-11 12:39:08 UTC
Updated at2024-09-11 12:39:08 UTC
NP-MRD IDNP0337830
Secondary Accession NumbersNone
Natural Product Identification
Common NameCholine chloride
DescriptionCholine chloride, also known as bilineurin chloride or biocolina, belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation. In foodstuffs the compound is often present as phosphatidylcholine. Choline chloride is an extremely weak basic (essentially neutral) compound (based on its pKa). Choline chloride is an organic compound and a quaternary ammonium salt. Other commercial choline salts are choline hydroxide and choline bitartrate. Choline chloride was first documented in 1994 (PMID: 8047569). Choline chloride is mass produced and is an important additive in feed especially for chickens where it accelerates growth (PMID: 12962717) (PMID: 17596274) (PMID: 20396712) (PMID: 24905385) (PMID: 25037344).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337830 (Choline chloride)


  Mrv0541 02241218472D          

  8  6  0  0  0  0            999 V2000
   -0.3095   -5.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050   -4.8615    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.1195   -5.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8340   -4.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5484   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050   -4.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095   -4.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -5.5882    0.0000 Cl  0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
M  CHG  2   2   1   8  -1
M  END
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3D MOL for NP0337830 (Choline chloride)

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3D SDF for NP0337830 (Choline chloride)

  Mrv0541 02241218472D          

  8  6  0  0  0  0            999 V2000
   -0.3095   -5.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050   -4.8615    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.1195   -5.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8340   -4.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5484   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050   -4.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3095   -4.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944   -5.5882    0.0000 Cl  0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
M  CHG  2   2   1   8  -1
M  END
> <DATABASE_ID>
NP0337830

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[Cl-].C[N+](C)(C)CCO

> <INCHI_IDENTIFIER>
InChI=1S/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1

> <INCHI_KEY>
SGMZJAMFUVOLNK-UHFFFAOYSA-M

> <FORMULA>
C5H14ClNO

> <MOLECULAR_WEIGHT>
139.624

> <EXACT_MASS>
139.076391782

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
12.565614618192706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-hydroxyethyl)trimethylazanium chloride

> <ALOGPS_LOGP>
-4.00

> <JCHEM_LOGP>
-4.662269162805079

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.968714076810006

> <JCHEM_PKA_STRONGEST_BASIC>
-3.249884462803304

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
42.193999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
choline chloride

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0337830 (Choline chloride)
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PDB for NP0337830 (Choline chloride)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.578  -9.845   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.756  -9.075   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       2.090  -9.845   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.423  -9.075   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.757  -9.845   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.756  -7.535   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.578  -8.305   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       0.736 -10.431   0.000  0.00  0.00          Cl-1
CONECT    1    2                                                            
CONECT    2    1    3    6    7                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2                                                            
CONECT    7    2                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   12    0
END

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3D PDB for NP0337830 (Choline chloride)
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SMILES for NP0337830 (Choline chloride)
[Cl-].C[N+](C)(C)CCO
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INCHI for NP0337830 (Choline chloride)
InChI=1S/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1
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Synonyms
ValueSource
(2-Hydroxyethyl)trimethylammonium chlorideChEBI
(beta-Hydroxyethyl)trimethylammonium chlorideChEBI
2-Hydroxy-N,N,N,-trimethylethanaminium chlorideChEBI
Bilineurin chlorideChEBI
BiocolinaChEBI
BiocolineChEBI
Chloride de cholineChEBI
Chlorure de cholineChEBI
Choline chlorhydrateChEBI
Choline hydrochlorideChEBI
Cholini chloridumChEBI
Cholinium chlorideChEBI
Cloruro de colinaChEBI
HepacholineChEBI
LipotrilChEBI
Luridin chlorideChEBI
ParesanChEBI
Trimethyl(2-hydroxyethyl)ammonium chlorideChEBI
(b-Hydroxyethyl)trimethylammonium chlorideGenerator
(Β-hydroxyethyl)trimethylammonium chlorideGenerator
Choline chlorhydric acidGenerator
Choline O-sulfateMeSH
Citrate, cholineMeSH
FagineMeSH
Hydroxide, cholineMeSH
VidineMeSH
Choline bitartrateMeSH
Choline hydroxideMeSH
Choline O sulfateMeSH
O-Sulfate, cholineMeSH
2-Hydroxy-N,N,N-trimethylethanaminiumMeSH
CholineMeSH
Bitartrate, cholineMeSH
BursineMeSH
Chloride, cholineMeSH
Choline citrateMeSH
Chemical FormulaC5H14ClNO
Average Mass139.6240 Da
Monoisotopic Mass139.07639 Da
IUPAC Name(2-hydroxyethyl)trimethylazanium chloride
Traditional Namecholine chloride
CAS Registry NumberNot Available
SMILES
[Cl-].C[N+](C)(C)CCO
InChI Identifier
InChI=1S/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1
InChI KeySGMZJAMFUVOLNK-UHFFFAOYSA-M
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 cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassQuaternary ammonium salts  
Direct ParentCholines  
Alternative Parents
Substituents
  • Choline
    • 

  • Tetraalkylammonium salt
    • 

  • 1,2-aminoalcohol
    • 

  • Alkanolamine
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic chloride salt
    • 

  • Organic salt
    • 

  • Organic zwitterion
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Amine
    • 

  • Alcohol
    • 

  • 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-4ALOGPS
logP-4.7ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)13.97ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.19 m³·mol⁻¹ChemAxon
Polarizability12.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029558  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000711  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCholine_chloride  
METLIN IDNot Available
PubChem Compound6209  
PDB IDNot Available
ChEBI ID133341  
Good Scents IDNot Available
References
General References
  1. Llerena JJ, Abad E, Caixach J, Rivera J: An episode of dioxin contamination in feedingstuff: the choline chloride case. Chemosphere. 2003 Nov;53(6):679-83. doi: 10.1016/S0045-6535(02)00825-1. [PubMed:12962717  ] 
  2. Mehta AK, Gaur SN, Arora N, Singh BP: Effect of choline chloride in allergen-induced mouse model of airway inflammation. Eur Respir J. 2007 Oct;30(4):662-71. doi: 10.1183/09031936.00019307. Epub 2007  Jun 27. [PubMed:17596274  ] 
  3. Svedentsov EP, Zaitseva OO, Tumanova TV, Solomina ON, Khudyakov AN: Use of choline chloride for leukocyte cryopreservation (-40 degrees C). Bull Exp Biol Med. 2009 Sep;148(3):461-3. doi: 10.1007/s10517-010-0736-3. [PubMed:20396712  ] 
  4. Bansal P, Saw S, Govindaraj D, Arora N: Intranasal administration of a combination of choline chloride, vitamin C, and selenium attenuates the allergic effect in a mouse model of airway disease. Free Radic Biol Med. 2014 Aug;73:358-65. doi:  10.1016/j.freeradbiomed.2014.05.018. Epub 2014 Jun 4. [PubMed:24905385  ] 
  5. Sousa AM, Souza HK, Latona N, Liu CK, Goncalves MP, Liu L: Choline chloride based ionic liquid analogues as tool for the fabrication of agar films with improved mechanical properties. Carbohydr Polym. 2014 Oct 13;111:206-14. doi: 10.1016/j.carbpol.2014.04.019. Epub  2014 Apr 19. [PubMed:25037344  ] 
  6. Locke KW, Fielding S: Enhancement of salt intake by choline chloride. Physiol Behav. 1994 Jun;55(6):1039-46. doi: 10.1016/0031-9384(94)90385-9. [PubMed:8047569  ]