NP-MRD: Showing NP-Card for 5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate (NP0251997)

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Record Information

Version

2.0

Created at

2022-09-07 15:22:31 UTC

Updated at

2022-09-07 15:22:31 UTC

NP-MRD ID

NP0251997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate

Description

5-Hydroxy-2-[2-(trimethylazaniumyl)ethyl]benzoate belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. 5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate is found in Naucleopsis ternstroemiiflora. 5-Hydroxy-2-[2-(trimethylazaniumyl)ethyl]benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.9899   -1.3806   -0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2356   -0.1814    0.1203 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5070    0.7875   -0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847    0.3775    1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462   -0.5781    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0247    0.6281    0.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624    0.3377    0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1207    0.2109    1.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4507   -0.0960    1.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1702   -0.2876    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5283   -0.6013    0.7545 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.5633   -0.1718   -0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937    0.1452   -0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    0.2906   -1.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    0.6976   -2.2740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267   -0.0425   -3.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8555   -1.1686   -0.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3384   -2.1002   -0.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510   -1.8861    0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2149    0.4558   -1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6323    0.8890   -0.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1532    1.8153   -0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919    0.4673    1.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2706    1.3816    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4075   -0.3311    2.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4886   -1.1635   -0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7636   -1.2887    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2638    1.0133    1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1903    1.4569   -0.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5033    0.3728    2.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9209   -0.1840    2.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1522   -0.3276   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292    0.4620   -4.0055 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 13  2  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
  8  7  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
 12 32  1  0
  9 31  1  0
  8 30  1  0
 16 33  1  0
M  CHG  2   2   1  11  -1
M  END


  Mrv1533004241523042D          

 16 16  0  0  0  0            999 V2000
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.8250    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.3000    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    2.0625    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
    1.4289    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  CHG  2   2   1  13  -1
M  END
> <DATABASE_ID>
NP0251997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+](C)(C)CCC1=C(C=C([O-])C=C1)C(O)=O

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

> <INCHI_KEY>
HTCQNXQVACMNDD-UHFFFAOYSA-N

> <FORMULA>
C12H17NO3

> <MOLECULAR_WEIGHT>
223.272

> <EXACT_MASS>
223.120843411

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.96400276936493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-carboxy-4-[2-(trimethylazaniumyl)ethyl]benzen-1-olate

> <ALOGPS_LOGP>
-1.98

> <JCHEM_LOGP>
-2.6050152421384114

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.643042725868344

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5396886726716192

> <JCHEM_PKA_STRONGEST_BASIC>
-5.985395197851994

> <JCHEM_POLAR_SURFACE_AREA>
60.36

> <JCHEM_REFRACTIVITY>
85.0567

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-carboxy-4-[2-(trimethylammonio)ethyl]benzenolate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0      -1.540   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O-1
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10                                                            
CONECT   14    8   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-2-[2-(trimethylazaniumyl)ethyl]benzoic acid	Generator

Chemical Formula

C₁₂H₁₇NO₃

Average Mass

223.2720 Da

Monoisotopic Mass

223.12084 Da

IUPAC Name

3-carboxy-4-[2-(trimethylazaniumyl)ethyl]benzen-1-olate

Traditional Name

3-carboxy-4-[2-(trimethylammonio)ethyl]benzenolate

CAS Registry Number

Not Available

SMILES

C[N+](C)(C)CCC1=C(C=C([O-])C=C1)C(O)=O

InChI Identifier

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

InChI Key

HTCQNXQVACMNDD-UHFFFAOYSA-N

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
Naucleopsis ternstroemiiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

Benzoic acid or derivatives
Benzoic acid
Phenethylamine
Benzoyl
Aralkylamine
Phenoxide
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organic salt
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	ALOGPS
logP	-2.6	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.54	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.06 m³·mol⁻¹	ChemAxon
Polarizability	23.96 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate (NP0251997)

MOL for NP0251997 (5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate)

3D MOL for NP0251997 (5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate)

3D SDF for NP0251997 (5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate)

3D-SDF for NP0251997 (5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate)

PDB for NP0251997 (5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate)

3D PDB for NP0251997 (5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate)

SMILES for NP0251997 (5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate)

INCHI for NP0251997 (5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate)

Structure for NP0251997 (5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate)

3D Structure for NP0251997 (5-hydroxy-2-[2-(trimethylammonio)ethyl]benzoate)