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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2020-11-01 17:55:11 UTC

Update Date

2022-03-07 03:18:20 UTC

HMDB ID

HMDB0240711

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bisphenol F

Description

Bisphenol F, also known as 4,4'-bisphenol F or BPF, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Bisphenol F exists in all living organisms, ranging from bacteria to humans. Bisphenol F is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Bisphenol F.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1533004241506182D          

 15 16  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 O   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
    2.8579   -1.6500    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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240711

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(CC2=CC=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8,14-15H,9H2

> <INCHI_KEY>
PXKLMJQFEQBVLD-UHFFFAOYSA-N

> <FORMULA>
C13H12O2

> <MOLECULAR_WEIGHT>
200.237

> <EXACT_MASS>
200.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.414528640867704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(4-hydroxyphenyl)methyl]phenol

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
3.457909199666666

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.44716590829258

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.83989655704596

> <JCHEM_PKA_STRONGEST_BASIC>
-5.45372392348471

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
59.757000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bis(4-hydroxyphenyl)methane

> <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  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7                                                       
CONECT   14    5   15                                                       
CONECT   15   14    2                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0240711
HETATM    1  O1  UNL     1      -4.576   1.121  -1.402  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.412   0.421  -1.069  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.139   0.023   0.221  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.976  -0.671   0.524  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.044  -0.995  -0.438  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.207  -1.737  -0.127  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.274  -0.758   0.208  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.076  -0.262  -0.781  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.064   0.651  -0.442  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.199   1.017   0.860  1.00  0.00           C  
HETATM   11  O2  UNL     1       4.200   1.942   1.205  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.392   0.520   1.863  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.418  -0.380   1.528  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.321  -0.593  -1.738  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.480   0.097  -2.032  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.541   2.152  -1.363  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.847   0.258   1.009  1.00  0.00           H  
HETATM   18  H3  UNL     1      -1.759  -0.988   1.554  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.054  -2.464   0.706  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.568  -2.312  -1.003  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.927  -0.587  -1.808  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.703   1.050  -1.214  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.977   2.911   1.195  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.525   0.834   2.904  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.758  -0.796   2.303  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.576  -0.856  -2.485  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.671   0.401  -3.064  1.00  0.00           H  
CONECT    1    2   16
CONECT    2    3    3   15
CONECT    3    4   17
CONECT    4    5    5   18
CONECT    5    6   14
CONECT    6    7   19   20
CONECT    7    8    8   13
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   11   12
CONECT   11   23
CONECT   12   13   13   24
CONECT   13   25
CONECT   14   15   15   26
CONECT   15   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,4'-Bisphenol F	ChEBI
4,4'-Dihydroxydiphenylmethane	ChEBI
4,4'-Methylenebis(phenol)	ChEBI
4,4'-Methylenediphenol	ChEBI
Bis(4-hydroxyphenyl)methane	ChEBI
Bis(p-hydroxyphenyl)methane	ChEBI
Bis(para-hydroxyphenyl)methane	ChEBI
BPF	ChEBI
p,P'-bis(hydroxyphenyl)methane	ChEBI
p-(p-Hydroxybenzyl)phenol	ChEBI
Para-(para-hydroxybenzyl)phenol	ChEBI
p-Hydroxydiphenylmethane	HMDB
4,4'-Methylenebis(phenol), disodium salt	HMDB
Bisphenol F	KEGG

Chemical Formula

C₁₃H₁₂O₂

Average Molecular Weight

200.237

Monoisotopic Molecular Weight

200.083729626

IUPAC Name

4-[(4-hydroxyphenyl)methyl]phenol

Traditional Name

bis(4-hydroxyphenyl)methane

CAS Registry Number

Not Available

SMILES

OC1=CC=C(CC2=CC=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C13H12O2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8,14-15H,9H2

InChI Key

PXKLMJQFEQBVLD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

diarylmethane (CHEBI:34575 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0240711)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.61	ALOGPS
logP	3.46	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	-5.5	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	2	ChemAxon
Refractivity	59.76 m³·mol⁻¹	ChemAxon
Polarizability	21.41 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	146.397	30932474
DeepCCS	[M-H]-	144.001	30932474
DeepCCS	[M-2H]-	178.073	30932474
DeepCCS	[M+Na]+	152.636	30932474
AllCCS	[M+H]+	144.4	32859911
AllCCS	[M+H-H2O]+	140.0	32859911
AllCCS	[M+NH4]+	148.5	32859911
AllCCS	[M+Na]+	149.6	32859911
AllCCS	[M-H]-	145.9	32859911
AllCCS	[M+Na-2H]-	145.8	32859911
AllCCS	[M+HCOO]-	145.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bisphenol F	OC1=CC=C(CC2=CC=C(O)C=C2)C=C1	4024.9	Standard polar	33892256
Bisphenol F	OC1=CC=C(CC2=CC=C(O)C=C2)C=C1	2199.0	Standard non polar	33892256
Bisphenol F	OC1=CC=C(CC2=CC=C(O)C=C2)C=C1	2065.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bisphenol F,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2=CC=C(O)C=C2)C=C1	2071.0	Semi standard non polar	33892256
Bisphenol F,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2=CC=C(O[Si](C)(C)C)C=C2)C=C1	2083.5	Semi standard non polar	33892256
Bisphenol F,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2=CC=C(O)C=C2)C=C1	2354.0	Semi standard non polar	33892256
Bisphenol F,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1	2658.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bisphenol F GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 10V, Positive-QTOF	splash10-0udi-0090000000-d5d25429146e5db52ae5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 20V, Positive-QTOF	splash10-0udi-0690000000-e9c9f9ab405e91a93786	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 40V, Positive-QTOF	splash10-0a7i-4900000000-2d488377fb7682ae2dd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 10V, Negative-QTOF	splash10-0002-0900000000-4e94a3f79c8823327fb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 20V, Negative-QTOF	splash10-0002-0900000000-7c09a1963726f69076a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 40V, Negative-QTOF	splash10-0005-3900000000-2438ce185772421e7603	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 10V, Positive-QTOF	splash10-0udi-0090000000-01d8d5f74b31bc5d92ef	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 20V, Positive-QTOF	splash10-0zfr-5890000000-ecf48cefe9bb2e62e373	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 40V, Positive-QTOF	splash10-004i-7900000000-c1a0e100b1b01e4d0a03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 10V, Negative-QTOF	splash10-0002-0900000000-85db899e345a8672fcfe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 20V, Negative-QTOF	splash10-0002-0900000000-fd0f19a2393be50a2fce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisphenol F 40V, Negative-QTOF	splash10-000x-4900000000-27a6f8c98ff0f8315528	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

11614

KEGG Compound ID

C14298

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bisphenol_F

METLIN ID

Not Available

PubChem Compound

12111

PDB ID

Not Available

ChEBI ID

34575

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1223831

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Bisphenol F (HMDB0240711)

MOL for HMDB0240711 (Bisphenol F)

3D MOL for HMDB0240711 (Bisphenol F)

3D SDF for HMDB0240711 (Bisphenol F)

3D-SDF for HMDB0240711 (Bisphenol F)

PDB for HMDB0240711 (Bisphenol F)

3D PDB for HMDB0240711 (Bisphenol F)

SMILES for HMDB0240711 (Bisphenol F)

INCHI for HMDB0240711 (Bisphenol F)

Structure for HMDB0240711 (Bisphenol F)

3D Structure for HMDB0240711 (Bisphenol F)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra