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Showing NP-Card for Phenoxyacetic acid (NP0002890)

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Record Information
Version1.0
Created at2020-11-23 19:42:55 UTC
Updated at2021-08-19 23:59:29 UTC
NP-MRD IDNP0002890
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenoxyacetic acid
Provided ByBMRBBMRB logo
DescriptionPhenoxyacetic acid, also known as phenoxyacetate or POA, belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative. In humans, phenoxyacetic acid is involved in the rosiglitazone metabolism pathway. Phenoxyacetic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 1979 (PMID: 221276). Based on a literature review a small amount of articles have been published on Phenoxyacetic acid (PMID: 17984079) (PMID: 14687482) (PMID: 23838187) (PMID: 26188115).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002890 (Phenoxyacetic acid)


     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -4.6035   -1.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3439   -0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4195    1.2898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087   -0.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6735   -1.5754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5861   -0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104    0.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7700    1.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052    0.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1808   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213   -1.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7547    1.9733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6923   -2.2271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3251    0.4433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    1.4208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944    3.0498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3648    1.6827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5160   -1.3135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969   -2.9425    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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  4 13  1  1
  4 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D MOL for NP0002890 (Phenoxyacetic acid)

NP0002890
     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -4.1514    1.2095    0.4420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2480    0.4412   -0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6525   -0.6467   -0.7585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8298    0.7926    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108   -0.1810   -0.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3697   -0.1739   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0204   -1.2055   -0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786   -1.2812   -0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1198   -0.3359   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729    0.6908    0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0964    0.7736    0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3325   -1.3243   -0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6577    1.8072   -0.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858    0.8568    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -1.9824   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8652   -2.1089   -1.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1922   -0.3541   -0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0354    1.4501    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634    1.5723    0.8324 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0002890 (Phenoxyacetic acid)


     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -4.6035   -1.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3439   -0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4195    1.2898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087   -0.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6735   -1.5754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5861   -0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5104    0.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7700    1.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052    0.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1808   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213   -1.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7547    1.9733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6923   -2.2271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3251    0.4433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    1.4208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944    3.0498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3648    1.6827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5160   -1.3135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969   -2.9425    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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  4 13  1  1
  4 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
> <DATABASE_ID>
NP0002890

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)COC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

> <INCHI_KEY>
LCPDWSOZIOUXRV-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.934708183524695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-phenoxyacetic acid

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
1.2935578586666665

> <ALOGPS_LOGS>
-1.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6972195891353126

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889363118851274

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
38.6058

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenoxyacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002890 (Phenoxyacetic acid)

NP0002890
     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -4.1514    1.2095    0.4420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2480    0.4412   -0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6525   -0.6467   -0.7585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8298    0.7926    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108   -0.1810   -0.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3697   -0.1739   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0204   -1.2055   -0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786   -1.2812   -0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1198   -0.3359   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729    0.6908    0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0964    0.7736    0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3325   -1.3243   -0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6577    1.8072   -0.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858    0.8568    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -1.9824   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8652   -2.1089   -1.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1922   -0.3541   -0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0354    1.4501    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634    1.5723    0.8324 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
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PDB for NP0002890 (Phenoxyacetic acid)

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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    8   11                                                       
CONECT    7    4    5   11                                                  
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6    7                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002890 (Phenoxyacetic acid)

COMPND    NP0002890
HETATM    1  O1  UNL     1      -4.151   1.209   0.442  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.248   0.441  -0.032  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.653  -0.647  -0.758  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.830   0.793   0.244  1.00  0.00           C  
HETATM    5  O3  UNL     1      -1.011  -0.181  -0.368  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.370  -0.174  -0.318  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.020  -1.205  -0.973  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.379  -1.281  -0.979  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.120  -0.336  -0.335  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.473   0.691   0.317  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.096   0.774   0.326  1.00  0.00           C  
HETATM   12  H1  UNL     1      -4.333  -1.324  -0.459  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.658   1.807  -0.182  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.686   0.857   1.329  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.455  -1.982  -1.501  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.865  -2.109  -1.505  1.00  0.00           H  
HETATM   17  H6  UNL     1       4.192  -0.354  -0.312  1.00  0.00           H  
HETATM   18  H7  UNL     1       3.035   1.450   0.832  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.563   1.572   0.832  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6
CONECT    6    7    7   11
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   10   17
CONECT   10   11   11   18
CONECT   11   19
END
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SMILES for NP0002890 (Phenoxyacetic acid)

OC(=O)COC1=CC=CC=C1
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INCHI for NP0002890 (Phenoxyacetic acid)

InChI=1S/C8H8O3/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
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View in JSmol
Synonyms
ValueSource
Glycol acid phenyl etherChEBI
Phenoxacetic acidChEBI
PhenoxyacetateChEBI
PhenoxyessigsaeureChEBI
Phenoxyethanoic acidChEBI
POAChEBI
PhenoxacetateGenerator
PhenoxyethanoateGenerator
POA CPDHMDB
2-Phenoxy-acetic acidHMDB
FEMA 2872HMDB
Glycolic acid phenyl etherHMDB
Glycolic acid, phenyl etherHMDB
Glycollic acid phenyl etherHMDB
O-Phenylglycolic acidHMDB
Phenoxy acetic acidHMDB
Phenoxy-acetic acidHMDB
Phenxoyacetic acidHMDB
Phenyl ether glycolic acidHMDB
Phenoxyacetate derivativeHMDB
Phenoxyacetic acidKEGG
Chemical FormulaC8H8O3
Average Mass152.1473 Da
Monoisotopic Mass152.04734 Da
IUPAC Name2-phenoxyacetic acid
Traditional Namephenoxyacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)COC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
InChI KeyLCPDWSOZIOUXRV-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Theobroma cacaoFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentPhenoxyacetic acid derivatives
Alternative Parents
Substituents
  • Phenoxyacetate
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point99.00 to 103.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point285.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility12000 mg/L @ 10 °C (exp)The Good Scents Company Information System
LogP1.340The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP1.48ALOGPS
logP1.29ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.7ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.61 m³·mol⁻¹ChemAxon
Polarizability14.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031609
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008245
KNApSAcK IDNot Available
Chemspider ID18107
KEGG Compound IDC02181
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenoxyacetic acid
METLIN IDNot Available
PubChem Compound19188
PDB IDNot Available
ChEBI ID8075
Good Scents IDrw1033781
References
General References
  1. 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 ]
  2. Pritchard JB: Toxic substances and cell membrane function. Fed Proc. 1979 Jul;38(8):2220-5. [PubMed:221276 ]
  3. Zhao Y, Qiao H: Detection of specific IgE antibodies to major and minor antigenic determinants in sera of penicillin allergic patients. Chin Med J (Engl). 2003 Dec;116(12):1904-10. [PubMed:14687482 ]
  4. Garlantezec R, Warembourg C, Monfort C, Labat L, Pulkkinen J, Bonvallot N, Multigner L, Chevrier C, Cordier S: Urinary glycol ether metabolites in women and time to pregnancy: the PELAGIE cohort. Environ Health Perspect. 2013 Oct;121(10):1167-73. doi: 10.1289/ehp.1206103. Epub 2013 Jul 9. [PubMed:23838187 ]
  5. Troutman JA, Rick DL, Stuard SB, Fisher J, Bartels MJ: Development of a physiologically-based pharmacokinetic model of 2-phenoxyethanol and its metabolite phenoxyacetic acid in rats and humans to address toxicokinetic uncertainty in risk assessment. Regul Toxicol Pharmacol. 2015 Nov;73(2):530-43. doi: 10.1016/j.yrtph.2015.07.012. Epub 2015 Jul 16. [PubMed:26188115 ]