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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:26:08 UTC

Update Date

2021-09-26 22:53:47 UTC

HMDB ID

HMDB0245357

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,2'-Methylenediphenol

Description

2,2'-Methylenediphenol, also known as ortho, ortho-bisphenol F or 2,2'-bisphenol F, 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. Based on a literature review very few articles have been published on 2,2'-Methylenediphenol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,2'-methylenediphenol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,2'-Methylenediphenol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1572004221603132D          

 15 16  0  0  0  0            999 V2000
    0.0000    3.3000    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    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    2.4750    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    3.3000    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
   -0.7145    1.2375    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
    0.0000    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
    0.7145    1.2375    0.0000 C   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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12  7  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245357

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=CC=C1CC1=CC=CC=C1O

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

> <INCHI_KEY>
MQCPOLNSJCWPGT-UHFFFAOYSA-N

> <FORMULA>
C13H12O2

> <MOLECULAR_WEIGHT>
200.237

> <EXACT_MASS>
200.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.0967815195862

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2-hydroxyphenyl)methyl]phenol

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
3.457909199666666

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.899643935627207

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.256090159894404

> <JCHEM_PKA_STRONGEST_BASIC>
-5.495562843858228

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
59.757000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bisphenol F

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   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   4.620   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      -2.667   6.160   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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   13                                                       
CONECT    9   10   11                                                       
CONECT   10    5    9   12                                                  
CONECT   11    6    9   13                                                  
CONECT   12    7   10   14                                                  
CONECT   13    8   11   15                                                  
CONECT   14   12                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0245357
HETATM    1  O1  UNL     1       1.619  -2.265  -0.180  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.990  -0.952  -0.157  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.114  -0.634   0.606  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.565   0.657   0.675  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.877   1.630  -0.031  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.771   1.291  -0.775  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.275  -0.000  -0.873  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.038  -0.364  -1.600  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.184  -0.360  -0.768  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.744  -1.494  -0.227  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.897  -1.436   0.577  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.504  -0.242   0.850  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.968   0.903   0.324  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.833   0.842  -0.468  1.00  0.00           C  
HETATM   15  O2  UNL     1      -1.341   2.014  -0.973  1.00  0.00           O  
HETATM   16  H1  UNL     1       0.880  -2.602  -0.721  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.664  -1.392   1.163  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.451   0.927   1.270  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.238   2.642   0.028  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.253   2.065  -1.337  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.086   0.375  -2.447  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.129  -1.347  -2.132  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.339  -2.458  -0.406  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.330  -2.344   1.003  1.00  0.00           H  
HETATM   25  H10 UNL     1      -4.406  -0.189   1.481  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.473   1.831   0.561  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.760   2.904  -0.798  1.00  0.00           H  
CONECT    1    2   16
CONECT    2    3    3    7
CONECT    3    4   17
CONECT    4    5    5   18
CONECT    5    6   19
CONECT    6    7    7   20
CONECT    7    8
CONECT    8    9   21   22
CONECT    9   10   10   14
CONECT   10   11   23
CONECT   11   12   12   24
CONECT   12   13   25
CONECT   13   14   14   26
CONECT   14   15
CONECT   15   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bis(2-hydroxyphenyl)methane	Kegg
Ortho, ortho-bisphenol F	HMDB
(2,2'-Dihydroxydiphenyl)methane	HMDB
2,2'-Bisphenol F	HMDB

Chemical Formula

C₁₃H₁₂O₂

Average Molecular Weight

200.237

Monoisotopic Molecular Weight

200.083729626

IUPAC Name

2-[(2-hydroxyphenyl)methyl]phenol

Traditional Name

bisphenol F

CAS Registry Number

Not Available

SMILES

OC1=CC=CC=C1CC1=CC=CC=C1O

InChI Identifier

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

InChI Key

MQCPOLNSJCWPGT-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-4-unsubstituted benzenoid
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:34207 )

Ontology

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	2.55	ALOGPS
logP	3.46	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.26	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	21.1 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]+	141.3	30932474
DeepCCS	[M-H]-	138.905	30932474
DeepCCS	[M-2H]-	174.326	30932474
DeepCCS	[M+Na]+	149.102	30932474
AllCCS	[M+H]+	143.8	32859911
AllCCS	[M+H-H2O]+	139.3	32859911
AllCCS	[M+NH4]+	147.9	32859911
AllCCS	[M+Na]+	149.1	32859911
AllCCS	[M-H]-	144.2	32859911
AllCCS	[M+Na-2H]-	144.0	32859911
AllCCS	[M+HCOO]-	144.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,2'-Methylenediphenol	OC1=CC=CC=C1CC1=CC=CC=C1O	3390.8	Standard polar	33892256
2,2'-Methylenediphenol	OC1=CC=CC=C1CC1=CC=CC=C1O	1905.9	Standard non polar	33892256
2,2'-Methylenediphenol	OC1=CC=CC=C1CC1=CC=CC=C1O	2007.6	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 - 2,2'-Methylenediphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-6950000000-9c508c708e74d0d1633e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2'-Methylenediphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2'-Methylenediphenol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2'-Methylenediphenol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2'-Methylenediphenol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,2'-Methylenediphenol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2'-Methylenediphenol 45V, Negative-QTOF	splash10-0006-9000000000-c18c13080c5cda6b5298	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2'-Methylenediphenol 60V, Negative-QTOF	splash10-0006-9000000000-ad5313a9ac3db52aaac3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2'-Methylenediphenol 30V, Negative-QTOF	splash10-0006-9300000000-991149fbed2c49b19ff3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2'-Methylenediphenol 15V, Negative-QTOF	splash10-0007-9600000000-cbbe48b828bff9ae413e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2'-Methylenediphenol 75V, Negative-QTOF	splash10-0006-9000000000-e3890ff580dc3e9b9cc6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2'-Methylenediphenol 90V, Negative-QTOF	splash10-0006-9000000000-0318858d22f00ab4d5da	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2'-Methylenediphenol 30V, Positive-QTOF	splash10-0006-9200000000-c5d38cc7adb675661497	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2,2'-Methylenediphenol 45V, Positive-QTOF	splash10-0006-9000000000-b0cd33de259c9eacd13e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 10V, Positive-QTOF	splash10-0udi-0190000000-be5729bfc7d79c34d978	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 20V, Positive-QTOF	splash10-0udi-3980000000-73f4be4b38f1a4d1ab6e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 40V, Positive-QTOF	splash10-0a6r-9600000000-e4dcaba067f91f41b8a9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 10V, Negative-QTOF	splash10-0002-0900000000-ffa16c3c247df927d16c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 20V, Negative-QTOF	splash10-0002-1900000000-17fe1aa5df4c297e0393	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 40V, Negative-QTOF	splash10-0006-9500000000-b99e549d33c0c504304e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 10V, Positive-QTOF	splash10-0udi-0390000000-97aaded58d7634db944b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 20V, Positive-QTOF	splash10-0a6r-5910000000-168c280d3131386279a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 40V, Positive-QTOF	splash10-004i-9300000000-4811ac2fae696e2f4800	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 10V, Negative-QTOF	splash10-0002-0900000000-85db899e345a8672fcfe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 20V, Negative-QTOF	splash10-0007-9700000000-4d9172b0428b3416f795	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,2'-Methylenediphenol 40V, Negative-QTOF	splash10-0006-9500000000-0f1887ae9d69f0d60191	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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	Not Specified	Not Specified	Normal	31557052	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

68100

KEGG Compound ID

C14747

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75575

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1223721

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2,2'-Methylenediphenol (HMDB0245357)

MOL for HMDB0245357 (2,2'-Methylenediphenol)

3D MOL for HMDB0245357 (2,2'-Methylenediphenol)

3D SDF for HMDB0245357 (2,2'-Methylenediphenol)

3D-SDF for HMDB0245357 (2,2'-Methylenediphenol)

PDB for HMDB0245357 (2,2'-Methylenediphenol)

3D PDB for HMDB0245357 (2,2'-Methylenediphenol)

SMILES for HMDB0245357 (2,2'-Methylenediphenol)

INCHI for HMDB0245357 (2,2'-Methylenediphenol)

Structure for HMDB0245357 (2,2'-Methylenediphenol)

3D Structure for HMDB0245357 (2,2'-Methylenediphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra