NP-MRD: Showing NP-Card for Fenoksan (NP0061514)

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Record Information

Version

2.0

Created at

2022-04-28 06:17:11 UTC

Updated at

2022-04-28 06:17:11 UTC

NP-MRD ID

NP0061514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fenoksan

Description

3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionic acid, also known as beta-(4-hydroxy-3,5-di-tert-butyl)phenylpropionic acid or fenozan, monolithium salt, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Fenoksan was first documented in 2021 (PMID: 34618444). Based on a literature review very few articles have been published on 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 46  0  0  0  0  0  0  0  0999 V2000
    0.8634    3.6302   -0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    2.7785   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9020    2.8048   -1.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4340    3.3835    0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1142    1.3668   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1148    0.9252    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3613   -0.3772    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6703   -0.8550    1.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450   -1.3530    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8338   -1.8046    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0585   -1.7393    1.8318 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8427   -2.3185   -0.2095 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2915   -1.2401    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9650   -0.8378    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0734   -1.8479    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176   -3.2026    0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147   -1.5088    1.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867   -1.9719   -1.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1584    0.4781   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4278    0.8876   -0.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5760    4.6638   -0.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815    3.3038   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1796    3.6575    0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643    3.3546   -2.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9063    3.2515   -1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9587    1.7865   -2.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047    3.4599   -0.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5182    2.7635    1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633    4.4201    0.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9380    1.6221    0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920   -1.6919    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228   -0.0491    1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0794   -2.2729   -0.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435   -0.5906   -0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6643   -1.7686   -0.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4204   -2.2781    0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4181   -3.8862    0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7727   -3.5946   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2244   -3.1664    1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2848   -2.2536    1.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1827   -1.5629    0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0632   -0.5356    1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515   -2.9779   -1.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5755   -1.9264   -1.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898   -1.2266   -1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2348    0.3001   -0.6394 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  7 13  2  0
 13 14  1  0
 14 19  2  0
 19 20  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 19  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 12 35  1  0
 13 36  1  0
 20 46  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
M  END


  Mrv1652304282208172D          

 20 20  0  0  0  0            999 V2000
    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   -0.4125    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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  2 16  1  0  0  0  0
  1 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C)C1=CC(CCC(O)=O)=CC(=C1O)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O3/c1-16(2,3)12-9-11(7-8-14(18)19)10-13(15(12)20)17(4,5)6/h9-10,20H,7-8H2,1-6H3,(H,18,19)

> <INCHI_KEY>
WPMYUUITDBHVQZ-UHFFFAOYSA-N

> <FORMULA>
C17H26O3

> <MOLECULAR_WEIGHT>
278.392

> <EXACT_MASS>
278.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
32.49976455454953

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
4.70

> <JCHEM_LOGP>
4.84210999

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.754646670608905

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.793907481370854

> <JCHEM_PKA_STRONGEST_BASIC>
-5.081788508247333

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
81.27929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.231  -2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.771   0.564   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.206   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   3.850   0.000  0.00  0.00           C+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16    2                                                            
CONECT   17    1   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionate	Generator
4-Hydroxy-3,5-di-tert-butylphenylpropionic acid	HMDB
beta-(4-Hydroxy-3,5-di-tert-butyl)phenylpropionic acid	HMDB
beta-(4-Hydroxy-3,5-di-tert-butyl)phenylpropionic acid, potassium salt	HMDB
beta-(4-Hydroxy-3,5-di-tert-butylphenyl)propionic acid	HMDB
beta-(4-Hydroxy-3,5-di-tertbutylphenyl) propionic acid	HMDB
Fenozan	HMDB
Fenozan, monolithium salt	HMDB
Fenozan, monopotassium salt	HMDB
Fenozan, monosodium salt	HMDB
Fenozan, nickel (2+) salt (2:1)	HMDB
Fenozan-K	HMDB
Phenozan	HMDB
Potassium fenozan	HMDB
Potassium phenosan	HMDB

Chemical Formula

C₁₇H₂₆O₃

Average Mass

278.3920 Da

Monoisotopic Mass

278.18819 Da

IUPAC Name

3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoic acid

Traditional Name

3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)(C)C1=CC(CCC(O)=O)=CC(=C1O)C(C)(C)C

InChI Identifier

InChI=1S/C17H26O3/c1-16(2,3)12-9-11(7-8-14(18)19)10-13(15(12)20)17(4,5)6/h9-10,20H,7-8H2,1-6H3,(H,18,19)

InChI Key

WPMYUUITDBHVQZ-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Phenylpropane
Phenol
Benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.7	ALOGPS
logP	4.84	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.79	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.28 m³·mol⁻¹	ChemAxon
Polarizability	32.5 Å³	ChemAxon
Number of Rings	1	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

HMDB0245577

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016759

Chemspider ID

79743

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

88389

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu R, Mabury SA: Rat Metabolism Study Suggests 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionic Acid as a Potential Urinary Biomarker of Human Exposure to Representative 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionate Antioxidants. Environ Sci Technol. 2021 Oct 19;55(20):14051-14058. doi: 10.1021/acs.est.1c03493. Epub 2021 Oct 7. [PubMed:34618444 ]

Showing NP-Card for Fenoksan (NP0061514)

MOL for NP0061514 (Fenoksan)

3D MOL for NP0061514 (Fenoksan)

3D SDF for NP0061514 (Fenoksan)

3D-SDF for NP0061514 (Fenoksan)

PDB for NP0061514 (Fenoksan)

3D PDB for NP0061514 (Fenoksan)

SMILES for NP0061514 (Fenoksan)

INCHI for NP0061514 (Fenoksan)

Structure for NP0061514 (Fenoksan)

3D Structure for NP0061514 (Fenoksan)