NP-MRD: Showing NP-Card for Diphenylacetic acid (NP0002872)

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Record Information

Version

1.0

Created at

2020-11-23 19:42:30 UTC

Updated at

2021-08-12 19:52:23 UTC

NP-MRD ID

NP0002872

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Diphenylacetic acid

Provided By

BMRB

Description

Diphenylacetic acid, also known as 2,2-diphenylacetate or a-phenylbenzeneacetate, 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. Diphenylacetic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 1977 (PMID: 414462). Based on a literature review a significant number of articles have been published on Diphenylacetic acid (PMID: 17984079) (PMID: 6128832) (PMID: 30286420) (PMID: 29408084) (PMID: 26146449) (PMID: 23461674).

Structure

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


     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -2.9174   -1.5949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5533   -2.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5947   -3.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341   -1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9480   -0.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1625    1.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765    2.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3759    2.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1614    1.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -0.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0851   -0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1264    0.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4456    1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7235    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3630   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9139   -4.4321    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -2.8240    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160    1.2638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909    3.6893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0898    3.7720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608    1.2162    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3829   -1.3169    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0766    1.7799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870    2.9219    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    1.3509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9601   -1.6480    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3216   -3.0759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10  5  1  0
 16 11  1  0
  3 17  1  0
  4 18  1  1
  6 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 12 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
M  END
> <DATABASE_ID>
NP0002872

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O2/c15-14(16)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H,(H,15,16)

> <INCHI_KEY>
PYHXGXCGESYPCW-UHFFFAOYSA-N

> <FORMULA>
C14H12O2

> <MOLECULAR_WEIGHT>
212.2439

> <EXACT_MASS>
212.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.610233233876944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-diphenylacetic acid

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.287784356333333

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4314729660892995

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
62.035100000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diphenylacetic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: DFA                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       1.930   1.312   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.930   2.852   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.071   3.622   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.737   2.852   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.737   1.312   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.071   0.542   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.405   1.312   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.405   2.852   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.596  -0.998   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.930  -1.768   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.930  -3.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.596  -4.078   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.737  -3.308   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.737  -1.768   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.596   0.542   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.264   0.542   0.000  0.00  0.00           O+0
CONECT    1    2   15   16                                                  
CONECT    2    1                                                            
CONECT    3    4    8                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7                                                       
CONECT    9   10   14   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    9   13                                                       
CONECT   15    1    5    9                                                  
CONECT   16    1                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    NP0002872
HETATM    1  O1  UNL     1      -0.055  -3.130  -1.369  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.051  -2.309  -0.417  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.122  -2.861   0.851  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.025  -0.882  -0.722  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.248  -0.255  -0.139  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.726  -0.513   1.112  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.863   0.087   1.618  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.577   0.992   0.858  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.127   1.272  -0.393  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.992   0.668  -0.886  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.196  -0.134  -0.337  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.572   0.924  -1.134  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.714   1.671  -0.826  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.483   1.377   0.265  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.105   0.319   1.060  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.971  -0.419   0.749  1.00  0.00           C  
HETATM   17  H1  UNL     1      -0.835  -3.579   0.998  1.00  0.00           H  
HETATM   18  H2  UNL     1       0.140  -0.757  -1.836  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.211  -1.206   1.747  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.222  -0.135   2.613  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.474   1.476   1.236  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.671   1.987  -1.023  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.645   0.898  -1.881  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.029   1.234  -2.018  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.019   2.512  -1.455  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.372   1.919   0.549  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.689   0.069   1.918  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.706  -1.229   1.383  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5   11   18
CONECT    5    6    6   10
CONECT    6    7   19
CONECT    7    8    8   20
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   23
CONECT   11   12   12   16
CONECT   12   13   24
CONECT   13   14   14   25
CONECT   14   15   26
CONECT   15   16   16   27
CONECT   16   28
END

View in JSmol

Synonyms

Value	Source
2,2-Diphenylacetic acid	ChEBI
alpha-Phenylbenzeneacetic acid	ChEBI
Diphenylethanoic acid	ChEBI
2,2-Diphenylacetate	Generator
a-Phenylbenzeneacetate	Generator
a-Phenylbenzeneacetic acid	Generator
alpha-Phenylbenzeneacetate	Generator
Α-phenylbenzeneacetate	Generator
Α-phenylbenzeneacetic acid	Generator
Diphenylethanoate	Generator
Diphenylacetate	Generator
Diphenylacetic acid, sodium salt	HMDB
Diphenylacetic acid, potassium salt	HMDB

Chemical Formula

C₁₄H₁₂O₂

Average Mass

212.2439 Da

Monoisotopic Mass

212.08373 Da

IUPAC Name

2,2-diphenylacetic acid

Traditional Name

diphenylacetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H12O2/c15-14(16)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H,(H,15,16)

InChI Key

PYHXGXCGESYPCW-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Not Available

Substituents

Not Available

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	2.79	ALOGPS
logP	3.29	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.43	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.04 m³·mol⁻¹	ChemAxon
Polarizability	22.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0251455

DrugBank ID

DB03588

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8030

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8333

PDB ID

Not Available

ChEBI ID

41967

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Dixon PA, Caldwell J, Smith RL: Metabolism of arylacetic acids. 3. The metabolic fate of diphenylacetic acid and its variation with species and dose. Xenobiotica. 1977 Dec;7(12):717-25. doi: 10.3109/00498257709038701. [PubMed:414462 ]
Michelot J, Madelmont JC, Rousset B, Labarre P, Mornex R, Meyniel G: Metabolism of adiphenine. II. Identification of major excretion metabolites in rats. Xenobiotica. 1982 Jul;12(7):457-62. doi: 10.3109/00498258209052487. [PubMed:6128832 ]
Niasar HS, Das S, Xu CC, Ray MB: Continuous column adsorption of naphthenic acids from synthetic and real oil sands process-affected water (OSPW) using carbon-based adsorbents. Chemosphere. 2019 Jan;214:511-518. doi: 10.1016/j.chemosphere.2018.09.078. Epub 2018 Sep 17. [PubMed:30286420 ]
Niasar HS, Li H, Das S, Kasanneni TVR, Ray MB, Xu CC: Preparation of activated petroleum coke for removal of naphthenic acids model compounds: Box-Behnken design optimization of KOH activation process. J Environ Manage. 2018 Apr 1;211:63-72. doi: 10.1016/j.jenvman.2018.01.051. Epub 2018 Feb 2. [PubMed:29408084 ]
Kabatc J, Kostrzewska K, Jurek K: Two-cationic 2-methylbenzothiazole derivatives as green light absorbed sensitizers in initiation of free radical polymerization. Colloid Polym Sci. 2015;293(7):1865-1876. doi: 10.1007/s00396-015-3572-1. Epub 2015 Apr 3. [PubMed:26146449 ]
Nakata K, Gotoh K, Ono K, Futami K, Shiina I: Kinetic resolution of racemic 2-hydroxy-gamma-butyrolactones by asymmetric esterification using diphenylacetic acid with pivalic anhydride and a chiral acyl-transfer catalyst. Org Lett. 2013 Mar 15;15(6):1170-3. doi: 10.1021/ol303453j. Epub 2013 Mar 5. [PubMed:23461674 ]

Showing NP-Card for Diphenylacetic acid (NP0002872)

MOL for NP0002872 (Diphenylacetic acid)

3D MOL for NP0002872 (Diphenylacetic acid)

3D SDF for NP0002872 (Diphenylacetic acid)

3D-SDF for NP0002872 (Diphenylacetic acid)

PDB for NP0002872 (Diphenylacetic acid)

3D PDB for NP0002872 (Diphenylacetic acid)

SMILES for NP0002872 (Diphenylacetic acid)

INCHI for NP0002872 (Diphenylacetic acid)

Structure for NP0002872 (Diphenylacetic acid)

3D Structure for NP0002872 (Diphenylacetic acid)