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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:47:32 UTC

Update Date

2023-02-21 17:28:03 UTC

HMDB ID

HMDB0040256

Secondary Accession Numbers

HMDB40256

Metabolite Identification

Common Name

(S)-2-(4-Methoxyphenoxy)propanoic acid

Description

(S)-2-(4-Methoxyphenoxy)propanoic acid, also known as 2-PMP-pa or na-PMP, belongs to the class of organic compounds known as alkyloxyphenoxypropionic acids. These are aromatic compounds containing a phenoxypropionic acid that is para-substituted with an alkyl group. Based on a literature review very few articles have been published on (S)-2-(4-Methoxyphenoxy)propanoic acid.

Structure

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


  Mrv0541 05061311432D          

 14 14  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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    0.0000    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
    0.0000    0.8250    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
    0.7145   -0.4125    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
    0.0000    3.3000    0.0000 C   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
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  2  1  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 14  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040256

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-7(10(11)12)14-9-5-3-8(13-2)4-6-9/h3-7H,1-2H3,(H,11,12)

> <INCHI_KEY>
MIEKOFWWHVOKQX-UHFFFAOYSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.1999

> <EXACT_MASS>
196.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
19.611169110132856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-methoxyphenoxy)propanoic acid

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
1.7046508353333336

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.479797118838452

> <JCHEM_PKA_STRONGEST_BASIC>
-4.548287988023853

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
49.56290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-methoxyphenoxy)propanoic 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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   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       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   13                                                            
CONECT    3    5    8                                                       
CONECT    4    6    8                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7    1   10   14                                                  
CONECT    8    3    4   13                                                  
CONECT    9    5    6   14                                                  
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2    8                                                       
CONECT   14    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0040256
HETATM    1  C1  UNL     1      -4.699   0.363   0.034  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.865   0.591  -1.087  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.480   0.455  -0.951  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.943   0.102   0.268  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.577  -0.025   0.372  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.301   0.179  -0.663  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.655   0.054  -0.561  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.432  -0.283   0.526  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.241  -1.566   0.297  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.352   0.837   0.857  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.316   1.882   0.160  1.00  0.00           O  
HETATM   12  O4  UNL     1       4.252   0.742   1.931  1.00  0.00           O  
HETATM   13  C9  UNL     1      -0.262   0.535  -1.885  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.629   0.669  -2.018  1.00  0.00           C  
HETATM   15  H1  UNL     1      -5.735   0.710  -0.149  1.00  0.00           H  
HETATM   16  H2  UNL     1      -4.770  -0.736   0.222  1.00  0.00           H  
HETATM   17  H3  UNL     1      -4.340   0.918   0.926  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.576  -0.079   1.147  1.00  0.00           H  
HETATM   19  H5  UNL     1      -0.153  -0.302   1.328  1.00  0.00           H  
HETATM   20  H6  UNL     1       1.864  -0.486   1.472  1.00  0.00           H  
HETATM   21  H7  UNL     1       4.202  -1.488   0.836  1.00  0.00           H  
HETATM   22  H8  UNL     1       3.370  -1.706  -0.788  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.681  -2.453   0.671  1.00  0.00           H  
HETATM   24  H10 UNL     1       4.133   1.296   2.782  1.00  0.00           H  
HETATM   25  H11 UNL     1       0.334   0.720  -2.769  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.104   0.946  -2.957  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   18
CONECT    5    6    6   19
CONECT    6    7   13
CONECT    7    8
CONECT    8    9   10   20
CONECT    9   21   22   23
CONECT   10   11   11   12
CONECT   12   24
CONECT   13   14   14   25
CONECT   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-2-(4-Methoxyphenoxy)propanoate	Generator
2-PMP-PA	HMDB
2-(p-Methoxyphenoxy)propanoate	HMDB
Na-PMP	HMDB
2-(4-Methoxyphenoxy)propanoate	HMDB

Chemical Formula

C₁₀H₁₂O₄

Average Molecular Weight

196.1999

Monoisotopic Molecular Weight

196.073558872

IUPAC Name

2-(4-methoxyphenoxy)propanoic acid

Traditional Name

2-(4-methoxyphenoxy)propanoic acid

CAS Registry Number

4276-74-8

SMILES

COC1=CC=C(OC(C)C(O)=O)C=C1

InChI Identifier

InChI=1S/C10H12O4/c1-7(10(11)12)14-9-5-3-8(13-2)4-6-9/h3-7H,1-2H3,(H,11,12)

InChI Key

MIEKOFWWHVOKQX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyloxyphenoxypropionic acids. These are aromatic compounds containing a phenoxypropionic acid that is para-substituted with an alkyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

2-phenoxypropionic acids

Direct Parent

Alkyloxyphenoxypropionic acids

Alternative Parents

Substituents

Alkyloxyphenoxypropionic acid
Phenoxyacetate
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040256)
Cytoplasm (HMDB: HMDB0040256)

Source

Exogenous

Food

Food (HMDB: HMDB0040256)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040256)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	65 - 66 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3129 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	1.9 g/L	ALOGPS
logP	1.86	ALOGPS
logP	1.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	49.56 m³·mol⁻¹	ChemAxon
Polarizability	19.61 Å³	ChemAxon
Number of Rings	1	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]+	145.063	31661259
DarkChem	[M-H]-	143.843	31661259
DeepCCS	[M+H]+	141.395	30932474
DeepCCS	[M-H]-	139.023	30932474
DeepCCS	[M-2H]-	174.272	30932474
DeepCCS	[M+Na]+	149.493	30932474
AllCCS	[M+H]+	144.5	32859911
AllCCS	[M+H-H2O]+	140.4	32859911
AllCCS	[M+NH4]+	148.2	32859911
AllCCS	[M+Na]+	149.3	32859911
AllCCS	[M-H]-	144.2	32859911
AllCCS	[M+Na-2H]-	145.0	32859911
AllCCS	[M+HCOO]-	145.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-2-(4-Methoxyphenoxy)propanoic acid	COC1=CC=C(OC(C)C(O)=O)C=C1	2980.5	Standard polar	33892256
(S)-2-(4-Methoxyphenoxy)propanoic acid	COC1=CC=C(OC(C)C(O)=O)C=C1	1632.8	Standard non polar	33892256
(S)-2-(4-Methoxyphenoxy)propanoic acid	COC1=CC=C(OC(C)C(O)=O)C=C1	1621.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-2-(4-Methoxyphenoxy)propanoic acid,1TMS,isomer #1	COC1=CC=C(OC(C)C(=O)O[Si](C)(C)C)C=C1	1652.6	Semi standard non polar	33892256
(S)-2-(4-Methoxyphenoxy)propanoic acid,1TBDMS,isomer #1	COC1=CC=C(OC(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1	1888.9	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 - (S)-2-(4-Methoxyphenoxy)propanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-4900000000-1d85811ca90beb1dd560	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9510000000-1f899a28042ebabc03c6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic 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 - (S)-2-(4-Methoxyphenoxy)propanoic acid 10V, Positive-QTOF	splash10-002b-0900000000-48f2a83211eafeaa10a5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 20V, Positive-QTOF	splash10-004i-2900000000-b02557e0562a73ad6731	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 40V, Positive-QTOF	splash10-056r-8900000000-af409cd18cdf5f7777bb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 10V, Negative-QTOF	splash10-0002-0900000000-709c8bc703093b54f45e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 20V, Negative-QTOF	splash10-006t-0900000000-b80325c4e91e57b41eb6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 40V, Negative-QTOF	splash10-0a4i-2900000000-ab8685d860fc4500961a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 10V, Negative-QTOF	splash10-006t-3900000000-e1585c53cdae6532d6a2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 20V, Negative-QTOF	splash10-00di-9400000000-eb49e89a4e44e7535b9c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 40V, Negative-QTOF	splash10-0a6r-8900000000-ae013cf97a0c2c2c061c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 10V, Positive-QTOF	splash10-004j-0900000000-e20d615a1db8fda68595	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 20V, Positive-QTOF	splash10-0092-9800000000-a8d05ac872a4461117fa	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2-(4-Methoxyphenoxy)propanoic acid 40V, Positive-QTOF	splash10-05i1-9500000000-0f003f5262e51e5b7189	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB019973

KNApSAcK ID

Not Available

Chemspider ID

133262

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151199

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1620731

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 (S)-2-(4-Methoxyphenoxy)propanoic acid (HMDB0040256)

MOL for HMDB0040256 ((S)-2-(4-Methoxyphenoxy)propanoic acid)

3D MOL for HMDB0040256 ((S)-2-(4-Methoxyphenoxy)propanoic acid)

3D SDF for HMDB0040256 ((S)-2-(4-Methoxyphenoxy)propanoic acid)

3D-SDF for HMDB0040256 ((S)-2-(4-Methoxyphenoxy)propanoic acid)

PDB for HMDB0040256 ((S)-2-(4-Methoxyphenoxy)propanoic acid)

3D PDB for HMDB0040256 ((S)-2-(4-Methoxyphenoxy)propanoic acid)

SMILES for HMDB0040256 ((S)-2-(4-Methoxyphenoxy)propanoic acid)

INCHI for HMDB0040256 ((S)-2-(4-Methoxyphenoxy)propanoic acid)

Structure for HMDB0040256 ((S)-2-(4-Methoxyphenoxy)propanoic acid)

3D Structure for HMDB0040256 ((S)-2-(4-Methoxyphenoxy)propanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra