NP-MRD: Showing NP-Card for bisphenol af (NP0164157)

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Record Information

Version

2.0

Created at

2022-09-02 22:59:00 UTC

Updated at

2022-09-02 22:59:00 UTC

NP-MRD ID

NP0164157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bisphenol af

Description

Bisphenol AF, also known as bpaf compound, belongs to the class of organic compounds known as bisphenols. These are methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). An organofluorine compound that is bisphenol A with its methyl hydrogens replaced by fluorines. bisphenol af is found in Apis cerana. Bisphenol AF is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
    4.4797    1.8793    1.5253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4110    1.1471    1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2496    1.0034    1.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1787    0.2767    1.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446   -0.3277    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0622   -1.0988   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1534   -0.2543   -0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3003   -0.5523    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4100    0.2748    0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4086    1.4545   -0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4949    2.3277   -0.3364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2800    1.7859   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1862    0.9672   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955   -2.2766    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429   -3.0878    0.4754 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3887   -1.9456    1.8153 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1214   -3.1141    0.0530 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2604   -1.6656   -1.7968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766   -0.7289   -2.7541 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -2.6239   -1.7115 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9120   -2.3368   -2.1165 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3967   -0.1785   -0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778    0.5436   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4161    2.3163    2.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1674    1.4661    2.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    0.2141    1.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654   -1.4774    0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2758   -0.0184    0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3469    2.0962    0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2290    2.7241   -1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924    1.2160   -1.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559   -0.6419   -1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3864    0.6357   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5 22  1  0
 22 23  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  6 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 23  2  1  0
 13  7  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
 22 32  1  0
 23 33  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
M  END


  Mrv0541 05031418392D          

 23 24  0  0  0  0            999 V2000
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    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
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    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
   -2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934    0.4125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684   -0.4125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684    1.2375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4934    0.4125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -0.4125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20 15  1  0  0  0  0
 21 15  1  0  0  0  0
 22 11  1  0  0  0  0
 23 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C(C1=CC=C(O)C=C1)(C(F)(F)F)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C15H10F6O2/c16-14(17,18)13(15(19,20)21,9-1-5-11(22)6-2-9)10-3-7-12(23)8-4-10/h1-8,22-23H

> <INCHI_KEY>
ZFVMWEVVKGLCIJ-UHFFFAOYSA-N

> <FORMULA>
C15H10F6O2

> <MOLECULAR_WEIGHT>
336.2291

> <EXACT_MASS>
336.058498794

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.030931686969485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxyphenyl)propan-2-yl]phenol

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
4.773829600666666

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.73790244813873

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.127074136083586

> <JCHEM_PKA_STRONGEST_BASIC>
-5.5529801322745636

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
81.14010000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bisphenol AF

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   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   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  F   UNK     0       0.000   0.000   0.000  0.00  0.00           F+0
HETATM   17  F   UNK     0       0.000   0.000   0.000  0.00  0.00           F+0
HETATM   18  F   UNK     0       0.000   0.000   0.000  0.00  0.00           F+0
HETATM   19  F   UNK     0       0.000   0.000   0.000  0.00  0.00           F+0
HETATM   20  F   UNK     0       0.000   0.000   0.000  0.00  0.00           F+0
HETATM   21  F   UNK     0       0.000   0.000   0.000  0.00  0.00           F+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    5    9                                                       
CONECT    2    6    9                                                       
CONECT    3    7   10                                                       
CONECT    4    8   10                                                       
CONECT    5    1   11                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   12                                                       
CONECT    9    1    2   13                                                  
CONECT   10    3    4   13                                                  
CONECT   11    5    6   22                                                  
CONECT   12    7    8   23                                                  
CONECT   13    9   10   14   15                                             
CONECT   14   13   16   17   18                                             
CONECT   15   13   19   20   21                                             
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   15                                                            
CONECT   21   15                                                            
CONECT   22   11                                                            
CONECT   23   12                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
2,2-Bis(4-hydroxyphenyl)perfluoropropane	ChEBI
2,2-Bis-(p-hydroxyphenyl)-hexafluoropropane	ChEBI
4,4'-(Hexafluoroisopropylidene)diphenol	ChEBI
Hexafluoroisopropylidenebis(4-hydroxybenzene)	ChEBI
2,2-Bis(4-hydroxyphenyl)hexafluoropropane	MeSH
4,4'-Hexafluorisopropylidene diphenol	MeSH
BPAF compound	MeSH

Chemical Formula

C₁₅H₁₀F₆O₂

Average Mass

336.2291 Da

Monoisotopic Mass

336.05850 Da

IUPAC Name

4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxyphenyl)propan-2-yl]phenol

Traditional Name

bisphenol AF

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C(C1=CC=C(O)C=C1)(C(F)(F)F)C(F)(F)F

InChI Identifier

InChI=1S/C15H10F6O2/c16-14(17,18)13(15(19,20)21,9-1-5-11(22)6-2-9)10-3-7-12(23)8-4-10/h1-8,22-23H

InChI Key

ZFVMWEVVKGLCIJ-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bisphenols. These are methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Bisphenols

Alternative Parents

Substituents

Bisphenol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organofluoride
Organohalogen compound
Alkyl halide
Alkyl fluoride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:72754 )
bisphenol (CHEBI:72754 )

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	4.23	ALOGPS
logP	4.77	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.14 m³·mol⁻¹	ChemAxon
Polarizability	26.03 Å³	ChemAxon
Number of Rings	2	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

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

C14350

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bisphenol_AF

METLIN ID

Not Available

PubChem Compound

73864

PDB ID

Not Available

ChEBI ID

72754

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for bisphenol af (NP0164157)

MOL for NP0164157 (bisphenol af)

3D MOL for NP0164157 (bisphenol af)

3D SDF for NP0164157 (bisphenol af)

3D-SDF for NP0164157 (bisphenol af)

PDB for NP0164157 (bisphenol af)

3D PDB for NP0164157 (bisphenol af)

SMILES for NP0164157 (bisphenol af)

INCHI for NP0164157 (bisphenol af)

Structure for NP0164157 (bisphenol af)

3D Structure for NP0164157 (bisphenol af)