NP-MRD: Showing NP-Card for 4-Hydroxybenzoyl choline (NP0138109)

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Record Information

Version

2.0

Created at

2022-05-31 16:58:48 UTC

Updated at

2022-05-31 16:58:48 UTC

NP-MRD ID

NP0138109

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Hydroxybenzoyl choline

Description

(4-Hydroxybenzoyl)choline, also known as parabens-choline, belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group (4-Hydroxybenzoyl)choline is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (4-Hydroxybenzoyl)choline has been detected, but not quantified in, herbs and spices. 4-Hydroxybenzoyl choline is found in Arabidopsis thaliana. This could make (4-hydroxybenzoyl)choline a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
   -3.2628    0.4096   -1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7720    0.0494    0.2402 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.4147   -1.1403    0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1383    1.1426    1.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3308   -0.0189    0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -1.2364   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087   -1.2092   -0.3936 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502   -0.1655   -0.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7748    0.7295   -1.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6162    0.0003   -0.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2408   -0.9281    0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5200   -0.7561    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3181    0.3371    0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5339    0.4781    0.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6815    1.2576   -0.8320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4047    1.0915   -1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3484    0.6229   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6831    1.2877   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1304   -0.4745   -1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4893   -0.8715    0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0086   -1.5101    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4687   -1.9421   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1859    1.4528    0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0088    0.8291    2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672    2.0191    1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9506    0.8997   -0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9248   -0.0180    1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0937   -1.2935   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1434   -2.1569    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477    0.4636   -2.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6925   -1.7649    0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0337   -1.4254    1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2723    2.0691   -1.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9254    1.7717   -1.8499 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  1  0
  8 10  2  3
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
M  CHG  1   2   1
M  END


  Mrv0541 05061304492D          

 16 16  0  0  0  0            999 V2000
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -3.7125    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
    0.0000    0.0000    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    0.7145    1.2375    0.0000 C   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
   -0.7145   -3.7125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  9  8  1  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  8  1  0  0  0  0
 14 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
M  CHG  1  13   1
M  END
> <DATABASE_ID>
NP0138109

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+](C)(C)CCOC(O)=C1C=CC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H17NO3/c1-13(2,3)8-9-16-12(15)10-4-6-11(14)7-5-10/h4-7H,8-9H2,1-3H3/p+1

> <INCHI_KEY>
BAPAICNRGIBFJT-UHFFFAOYSA-O

> <FORMULA>
C12H18NO3

> <MOLECULAR_WEIGHT>
224.2762

> <EXACT_MASS>
224.128668447

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.501697360662394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{2-[hydroxy(4-oxocyclohexa-2,5-dien-1-ylidene)methoxy]ethyl}trimethylazanium

> <ALOGPS_LOGP>
-2.16

> <JCHEM_LOGP>
-2.919981079138413

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.793370932654

> <JCHEM_PKA_STRONGEST_BASIC>
-5.019206328006078

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
86.70020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2-[hydroxy(4-oxocyclohexa-2,5-dien-1-ylidene)methoxy]ethyl}trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.874  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.334  -6.930   0.000  0.00  0.00           N+1
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4    6   10                                                       
CONECT    5    7   10                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8    9   13                                                       
CONECT    9    8   16                                                       
CONECT   10    4    5   12                                                  
CONECT   11    6    7   14                                                  
CONECT   12   10   15   16                                                  
CONECT   13    1    2    3    8                                             
CONECT   14   11                                                            
CONECT   15   12                                                            
CONECT   16    9   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
2-((4-Hydroxybenzoyl)oxy)-N,N,N-trimethyl-ethanaminium	HMDB
4-Hydroxybenzoylcholine	HMDB
Para-hydroxybenzoylcholine	HMDB
Parabens-choline	HMDB
p-Hydroxybenzoylcholine bisulfate	MeSH

Chemical Formula

C₁₂H₁₈NO₃

Average Mass

224.2762 Da

Monoisotopic Mass

224.12867 Da

IUPAC Name

{2-[hydroxy(4-oxocyclohexa-2,5-dien-1-ylidene)methoxy]ethyl}trimethylazanium

Traditional Name

{2-[hydroxy(4-oxocyclohexa-2,5-dien-1-ylidene)methoxy]ethyl}trimethylazanium

CAS Registry Number

5094-31-5

SMILES

C[N+](C)(C)CCOC(O)=C1C=CC(=O)C=C1

InChI Identifier

InChI=1S/C12H17NO3/c1-13(2,3)8-9-16-12(15)10-4-6-11(14)7-5-10/h4-7H,8-9H2,1-3H3/p+1

InChI Key

BAPAICNRGIBFJT-UHFFFAOYSA-O

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 p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Amine
Organic nitrogen compound
Organic salt
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen 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	ALOGPS
logP	-2.9	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.79	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.7 m³·mol⁻¹	ChemAxon
Polarizability	24.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029559

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000712

KNApSAcK ID

Not Available

Chemspider ID

133307

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151252

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Hydroxybenzoyl choline (NP0138109)

MOL for NP0138109 (4-Hydroxybenzoyl choline)

3D MOL for NP0138109 (4-Hydroxybenzoyl choline)

3D SDF for NP0138109 (4-Hydroxybenzoyl choline)

3D-SDF for NP0138109 (4-Hydroxybenzoyl choline)

PDB for NP0138109 (4-Hydroxybenzoyl choline)

3D PDB for NP0138109 (4-Hydroxybenzoyl choline)

SMILES for NP0138109 (4-Hydroxybenzoyl choline)

INCHI for NP0138109 (4-Hydroxybenzoyl choline)

Structure for NP0138109 (4-Hydroxybenzoyl choline)

3D Structure for NP0138109 (4-Hydroxybenzoyl choline)