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Showing metabocard for Ethoxyacetic acid (HMDB0031212)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:39 UTC
Update Date2023-02-21 17:20:04 UTC
HMDB IDHMDB0031212
Secondary Accession Numbers
  • HMDB31212
Metabolite Identification
Common NameEthoxyacetic acid
DescriptionEthoxyacetic acid, also known as ethoxyacetate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Ethoxyacetic acid has been detected, but not quantified in, herbs and spices and milk (cow). This could make ethoxyacetic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Ethoxyacetic acid.
Structure
Data?1677000004
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031212 (Ethoxyacetic acid)


  Mrv1652307171819242D          

  7  6  0  0  0  0            999 V2000
   -1.4289    0.0000    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    0.4125    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
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
M  END
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3D MOL for HMDB0031212 (Ethoxyacetic acid)

HMDB0031212
     RDKit          3D
Ethoxyacetic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.8211    0.7758   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.6796    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1398   -0.8537   -0.1355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -0.1046    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -0.4029    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4147   -1.2216   -0.5513 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008    0.2371    1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8489    1.3561    0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770    1.1760   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508    0.7813   -0.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -1.3295   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8258   -0.9792    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    0.9866    0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842   -0.4606    1.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8586    0.7187    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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3D SDF for HMDB0031212 (Ethoxyacetic acid)


  Mrv1652307171819242D          

  7  6  0  0  0  0            999 V2000
   -1.4289    0.0000    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    0.4125    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
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031212

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O3/c1-2-7-3-4(5)6/h2-3H2,1H3,(H,5,6)

> <INCHI_KEY>
YZGQDNOIGFBYKF-UHFFFAOYSA-N

> <FORMULA>
C4H8O3

> <MOLECULAR_WEIGHT>
104.1045

> <EXACT_MASS>
104.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.249967663017667

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethoxyacetic acid

> <ALOGPS_LOGP>
0.15

> <JCHEM_LOGP>
-0.04065930200000004

> <ALOGPS_LOGS>
0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.035443915397606

> <JCHEM_PKA_STRONGEST_BASIC>
-4.190902171907858

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
23.8457

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetic acid, ethoxy-

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0031212 (Ethoxyacetic acid)

HMDB0031212
     RDKit          3D
Ethoxyacetic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.8211    0.7758   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.6796    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1398   -0.8537   -0.1355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -0.1046    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770   -0.4029    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4147   -1.2216   -0.5513 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008    0.2371    1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8489    1.3561    0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770    1.1760   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8508    0.7813   -0.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -1.3295   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8258   -0.9792    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870    0.9866    0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4842   -0.4606    1.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8586    0.7187    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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PDB for HMDB0031212 (Ethoxyacetic acid)

HEADER    PROTEIN                                 17-JUL-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-18         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   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   0.770   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  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    7                                                       
CONECT    3    4    7                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    3                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0031212 (Ethoxyacetic acid)

COMPND    HMDB0031212
HETATM    1  C1  UNL     1      -1.821   0.776  -0.189  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.485  -0.680   0.062  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.140  -0.854  -0.135  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.663  -0.105   0.679  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.077  -0.403   0.345  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.415  -1.222  -0.551  1.00  0.00           O  
HETATM    7  O3  UNL     1       3.101   0.237   1.039  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.849   1.356   0.752  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.077   1.176  -0.907  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.851   0.781  -0.635  1.00  0.00           H  
HETATM   11  H4  UNL     1      -2.037  -1.329  -0.647  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.826  -0.979   1.079  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.487   0.987   0.619  1.00  0.00           H  
HETATM   14  H7  UNL     1       0.484  -0.461   1.735  1.00  0.00           H  
HETATM   15  H8  UNL     1       3.859   0.719   0.574  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4
CONECT    4    5   13   14
CONECT    5    6    6    7
CONECT    7   15
END
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SMILES for HMDB0031212 (Ethoxyacetic acid)

CCOCC(O)=O
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INCHI for HMDB0031212 (Ethoxyacetic acid)

InChI=1S/C4H8O3/c1-2-7-3-4(5)6/h2-3H2,1H3,(H,5,6)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
EthoxyacetateGenerator
Ethoxy-acetic acid anionChEMBL, HMDB
Ethoxy-acetate anionGenerator, HMDB
2-Ethoxy-acetic acidHMDB
2-Ethoxyacetic acidHMDB, MeSH
Ethoxy acetic acidHMDB
Ethoxy-acetic acidHMDB
ETHOXYACETIC ACID (egmee (110-80-5))HMDB
Glycolic acid ethyl etherHMDB
O-Ethylglycolic acidHMDB
2-EthoxyacetateGenerator
Ethoxyacetic acidMeSH
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name2-ethoxyacetic acid
Traditional Nameacetic acid, ethoxy-
CAS Registry Number627-03-2
SMILES
CCOCC(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-2-7-3-4(5)6/h2-3H2,1H3,(H,5,6)
InChI KeyYZGQDNOIGFBYKF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility408100 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility355 g/LALOGPS
logP0.15ALOGPS
logP-0.041ChemAxon
logS0.53ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity23.85 m³·mol⁻¹ChemAxon
Polarizability10.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+120.25631661259
DarkChem[M-H]-116.72531661259
DeepCCS[M+H]+134.73930932474
DeepCCS[M-H]-131.97930932474
DeepCCS[M-2H]-168.42130932474
DeepCCS[M+Na]+142.98130932474
AllCCS[M+H]+126.132859911
AllCCS[M+H-H2O]+121.832859911
AllCCS[M+NH4]+130.132859911
AllCCS[M+Na]+131.332859911
AllCCS[M-H]-125.932859911
AllCCS[M+Na-2H]-129.932859911
AllCCS[M+HCOO]-134.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.69 minutes32390414
Predicted by Siyang on May 30, 20229.9489 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.01 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid86.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1135.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid360.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid96.4 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid227.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid69.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid320.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid391.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)121.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid702.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid235.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid986.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid249.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid262.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate539.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA292.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water196.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethoxyacetic acidCCOCC(O)=O1674.1Standard polar33892256
Ethoxyacetic acidCCOCC(O)=O869.9Standard non polar33892256
Ethoxyacetic acidCCOCC(O)=O890.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethoxyacetic acid,1TMS,isomer #1CCOCC(=O)O[Si](C)(C)C991.8Semi standard non polar33892256
Ethoxyacetic acid,1TBDMS,isomer #1CCOCC(=O)O[Si](C)(C)C(C)(C)C1195.9Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003235
KNApSAcK IDNot Available
Chemspider ID11798
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12301
PDB IDNot Available
ChEBI ID741468
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1243041
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. de Jong E, Louisse J, Verwei M, Blaauboer BJ, van de Sandt JJ, Woutersen RA, Rietjens IM, Piersma AH: Relative developmental toxicity of glycol ether alkoxy acid metabolites in the embryonic stem cell test as compared with the in vivo potency of their parent compounds. Toxicol Sci. 2009 Jul;110(1):117-24. doi: 10.1093/toxsci/kfp083. Epub 2009 Apr 28. [PubMed:19401353 ]
  2. Montgomery-Brown J, Li Y, Ding WH, Mong GM, Campbell JA, Reinhard M: NP1EC degradation pathways under oxic and microxic conditions. Environ Sci Technol. 2008 Sep 1;42(17):6409-14. [PubMed:18800508 ]
  3. Johnson W Jr: Final report on the safety assessment of ethoxyethanol and ethoxyethanol acetate. Int J Toxicol. 2002;21 Suppl 1:9-62. [PubMed:12042060 ]
  4. Xu Y, Luo F, Pal A, Gin KY, Reinhard M: Occurrence of emerging organic contaminants in a tropical urban catchment in Singapore. Chemosphere. 2011 May;83(7):963-9. doi: 10.1016/j.chemosphere.2011.02.029. Epub 2011 Mar 9. [PubMed:21392814 ]
  5. Verwei M, van Burgsteden JA, Krul CA, van de Sandt JJ, Freidig AP: Prediction of in vivo embryotoxic effect levels with a combination of in vitro studies and PBPK modelling. Toxicol Lett. 2006 Aug 1;165(1):79-87. Epub 2006 Mar 3. [PubMed:16517103 ]
  6. Laitinen J, Pulkkinen J: Biomonitoring of 2-(2-alkoxyethoxy)ethanols by analysing urinary 2-(2-alkoxyethoxy)acetic acids. Toxicol Lett. 2005 Mar 28;156(1):117-26. [PubMed:15705492 ]
  7. Starek-Swiechowicz B, Miranowicz-Dzierzawska K, Szymczak W, Budziszewska B, Starek A: Hematological effects of exposure to mixtures of selected ethylene glycol alkyl ethers in rats. Pharmacol Rep. 2012;64(1):166-78. [PubMed:22580533 ]
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