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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:37 UTC

Update Date

2022-03-07 02:53:23 UTC

HMDB ID

HMDB0032583

Secondary Accession Numbers

HMDB32583

Metabolite Identification

Common Name

4'-Hydroxy-2-biphenylcarboxylic acid

Description

4'-Hydroxy-2-biphenylcarboxylic acid, also known as 4'-hydroxy-[1,1'-biphenyl]-2-carboxylate, belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. Based on a literature review very few articles have been published on 4'-Hydroxy-2-biphenylcarboxylic acid.

Structure

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

  Mrv0541 05061306342D          

 16 17  0  0  0  0            999 V2000
   -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
   -2.1434    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
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    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
   -4.2868    3.3000    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
   -1.4289    2.4750    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
   -5.0013    3.7125    0.0000 O   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
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  3  2  0  0  0  0
 11  9  1  0  0  0  0
 12  4  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032583

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC=CC=C1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H10O3/c14-10-7-5-9(6-8-10)11-3-1-2-4-12(11)13(15)16/h1-8,14H,(H,15,16)

> <INCHI_KEY>
WJRHSYCQNCDYMN-UHFFFAOYSA-N

> <FORMULA>
C13H10O3

> <MOLECULAR_WEIGHT>
214.2167

> <EXACT_MASS>
214.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.829064198066067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)benzoic acid

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
2.974488764333333

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.871790393726743

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6894410471551438

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4926689408466105

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
60.43130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-hydroxyphenyl)benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   3.850   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      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -9.336   6.930   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   11                                                       
CONECT    4    2   12                                                       
CONECT    5    7    9                                                       
CONECT    6    8    9                                                       
CONECT    7    5   10                                                       
CONECT    8    6   10                                                       
CONECT    9    5    6   11                                                  
CONECT   10    7    8   14                                                  
CONECT   11    3    9   12                                                  
CONECT   12    4   11   13                                                  
CONECT   13   12   15   16                                                  
CONECT   14   10                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0032583
HETATM    1  O1  UNL     1      -2.334   2.307   1.581  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.389   1.620   1.085  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.103   2.000   1.401  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.760   0.505   0.231  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.113   0.314  -0.058  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.563  -0.683  -0.893  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.656  -1.522  -1.466  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.299  -1.345  -1.186  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.850  -0.346  -0.348  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.562  -0.267  -0.075  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.451  -0.074  -1.139  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.807  -0.030  -0.922  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.276  -0.181   0.366  1.00  0.00           C  
HETATM   14  O3  UNL     1       4.664  -0.137   0.587  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.402  -0.373   1.416  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.040  -0.418   1.209  1.00  0.00           C  
HETATM   17  H1  UNL     1       0.221   2.948   1.322  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.855   0.981   0.395  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.616  -0.817  -1.107  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.989  -2.312  -2.126  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.639  -2.052  -1.680  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.058   0.043  -2.144  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.526   0.118  -1.722  1.00  0.00           H  
HETATM   24  H8  UNL     1       5.037   0.793   0.780  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.764  -0.492   2.432  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.358  -0.580   2.060  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    5    9
CONECT    5    6   18
CONECT    6    7    7   19
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12   22
CONECT   12   13   13   23
CONECT   13   14   15
CONECT   14   24
CONECT   15   16   16   25
CONECT   16   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-Hydroxy-2-biphenylcarboxylate	Generator
4'-Hydroxy-[1,1'-biphenyl]-2-carboxylate	HMDB

Chemical Formula

C₁₃H₁₀O₃

Average Molecular Weight

214.2167

Monoisotopic Molecular Weight

214.062994186

IUPAC Name

2-(4-hydroxyphenyl)benzoic acid

Traditional Name

2-(4-hydroxyphenyl)benzoic acid

CAS Registry Number

67526-82-3

SMILES

OC(=O)C1=CC=CC=C1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C13H10O3/c14-10-7-5-9(6-8-10)11-3-1-2-4-12(11)13(15)16/h1-8,14H,(H,15,16)

InChI Key

WJRHSYCQNCDYMN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
Benzoic acid
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032583)
Cell membrane (HMDB: HMDB0032583)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032583)

Source

Endogenous

Endogenous (HMDB: HMDB0032583)

Plant

Plant (HMDB: HMDB0032583)

Exogenous

Food

Food (HMDB: HMDB0032583)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0032583)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	206.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	553 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	3.37	ALOGPS
logP	2.97	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.69	ChemAxon
pKa (Strongest Basic)	-5.5	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	2	ChemAxon
Refractivity	60.43 m³·mol⁻¹	ChemAxon
Polarizability	21.83 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
DarkChem	[M+H]+	148.612	31661259
DarkChem	[M-H]-	146.327	31661259
DeepCCS	[M+H]+	146.624	30932474
DeepCCS	[M-H]-	144.228	30932474
DeepCCS	[M-2H]-	177.436	30932474
DeepCCS	[M+Na]+	152.537	30932474
AllCCS	[M+H]+	146.5	32859911
AllCCS	[M+H-H2O]+	142.3	32859911
AllCCS	[M+NH4]+	150.5	32859911
AllCCS	[M+Na]+	151.6	32859911
AllCCS	[M-H]-	146.5	32859911
AllCCS	[M+Na-2H]-	146.2	32859911
AllCCS	[M+HCOO]-	146.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4'-Hydroxy-2-biphenylcarboxylic acid	OC(=O)C1=CC=CC=C1C1=CC=C(O)C=C1	3434.3	Standard polar	33892256
4'-Hydroxy-2-biphenylcarboxylic acid	OC(=O)C1=CC=CC=C1C1=CC=C(O)C=C1	2011.0	Standard non polar	33892256
4'-Hydroxy-2-biphenylcarboxylic acid	OC(=O)C1=CC=CC=C1C1=CC=C(O)C=C1	2102.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4'-Hydroxy-2-biphenylcarboxylic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1C1=CC=C(O)C=C1	2141.9	Semi standard non polar	33892256
4'-Hydroxy-2-biphenylcarboxylic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2=CC=CC=C2C(=O)O)C=C1	2146.0	Semi standard non polar	33892256
4'-Hydroxy-2-biphenylcarboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1C1=CC=C(O[Si](C)(C)C)C=C1	2132.5	Semi standard non polar	33892256
4'-Hydroxy-2-biphenylcarboxylic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1C1=CC=C(O)C=C1	2431.8	Semi standard non polar	33892256
4'-Hydroxy-2-biphenylcarboxylic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC=CC=C2C(=O)O)C=C1	2450.2	Semi standard non polar	33892256
4'-Hydroxy-2-biphenylcarboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2635.4	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 - 4'-Hydroxy-2-biphenylcarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-0920000000-d94044e491d3cb7dfe76	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-5092000000-7bffd4a3398d384a8889	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 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 - 4'-Hydroxy-2-biphenylcarboxylic acid 10V, Positive-QTOF	splash10-014i-0390000000-d07c4152432432da326a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 20V, Positive-QTOF	splash10-00kb-0950000000-185e588723ec939002c4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 40V, Positive-QTOF	splash10-0006-2900000000-b7b1f031b853d12dd3f3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 10V, Negative-QTOF	splash10-03di-0390000000-5e94b5f03f35b2b07362	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 20V, Negative-QTOF	splash10-02t9-0950000000-4309a5031fedf5cc7ae9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 40V, Negative-QTOF	splash10-014i-0900000000-9ad5614472d4d131d4f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 10V, Positive-QTOF	splash10-0002-0930000000-fabd382fe3f6e258f8fb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 20V, Positive-QTOF	splash10-0002-0900000000-429c0de1074482bc06ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 40V, Positive-QTOF	splash10-014j-0900000000-557554b659428c47f2fb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 10V, Negative-QTOF	splash10-014i-0900000000-5f405abe20ed15fb1ad3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 20V, Negative-QTOF	splash10-014i-0900000000-53ec892a9fdf50d74651	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxy-2-biphenylcarboxylic acid 40V, Negative-QTOF	splash10-014i-0900000000-7aeee1c9adcdd44385a5	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB010520

KNApSAcK ID

Not Available

Chemspider ID

2040056

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2759303

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1830371

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4'-Hydroxy-2-biphenylcarboxylic acid (HMDB0032583)

MOL for HMDB0032583 (4'-Hydroxy-2-biphenylcarboxylic acid)

3D MOL for HMDB0032583 (4'-Hydroxy-2-biphenylcarboxylic acid)

3D SDF for HMDB0032583 (4'-Hydroxy-2-biphenylcarboxylic acid)

3D-SDF for HMDB0032583 (4'-Hydroxy-2-biphenylcarboxylic acid)

PDB for HMDB0032583 (4'-Hydroxy-2-biphenylcarboxylic acid)

3D PDB for HMDB0032583 (4'-Hydroxy-2-biphenylcarboxylic acid)

SMILES for HMDB0032583 (4'-Hydroxy-2-biphenylcarboxylic acid)

INCHI for HMDB0032583 (4'-Hydroxy-2-biphenylcarboxylic acid)

Structure for HMDB0032583 (4'-Hydroxy-2-biphenylcarboxylic acid)

3D Structure for HMDB0032583 (4'-Hydroxy-2-biphenylcarboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra