Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:32 UTC

Update Date

2023-02-21 17:16:03 UTC

HMDB ID

HMDB0002023

Secondary Accession Numbers

HMDB02023

Metabolite Identification

Common Name

Ethyladipic acid

Description

Adipic acid (IUPAC systematic name: hexanedioic acid) is a chemical compound of the class of carboxylic acids. Adipic acid is prepared from various fats using oxidation.By far the main use of adipic acid is as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming 6,6-nylon, the most common form of nylon. --Wikipedia.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      37.395  -7.751   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      28.059  -6.981   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      36.061  -5.441   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      29.393  -9.291   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      34.728  -7.751   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.394  -6.981   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.060  -7.751   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.728  -9.291   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.727  -6.981   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.394 -10.061   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.061  -6.981   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.393  -7.751   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    6    8   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8    5   10                                                       
CONECT    9    7   12                                                       
CONECT   10    8                                                            
CONECT   11    1    3    5                                                  
CONECT   12    2    4    9                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyladipate	Generator
2-Ethyladipate	HMDB
2-Ethyladipic acid	HMDB, MeSH

Chemical Formula

C₈H₁₄O₄

Average Molecular Weight

174.1944

Monoisotopic Molecular Weight

174.089208936

IUPAC Name

2-ethylhexanedioic acid

Traditional Name

ethyladipic acid

CAS Registry Number

22935-13-3

SMILES

CCC(CCCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H14O4/c1-2-6(8(11)12)4-3-5-7(9)10/h6H,2-5H2,1H3,(H,9,10)(H,11,12)

InChI Key

FANBESOFXBDQSH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Dicarboxylic acids (LMFA01170104 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0002023)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002023)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002023)

Source

Endogenous

Endogenous (HMDB: HMDB0002023)

Animal

Animal (HMDB: HMDB0002023)

Exogenous

Food

Food (HMDB: HMDB0002023)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0002023)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002023)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002023)

Lipid metabolism pathway (HMDB: HMDB0002023)

Cellular process

Cell signaling (HMDB: HMDB0002023)

Biochemical process

Lipid transport (HMDB: HMDB0002023)

Role

Biological role

Energy source (HMDB: HMDB0002023)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002023)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.34 g/L	ALOGPS
logP	0.89	ALOGPS
logP	1.48	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	41.91 m³·mol⁻¹	ChemAxon
Polarizability	17.92 Å³	ChemAxon
Number of Rings	0	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]+	142.061	31661259
DarkChem	[M-H]-	139.262	31661259
DeepCCS	[M+H]+	135.871	30932474
DeepCCS	[M-H]-	132.111	30932474
DeepCCS	[M-2H]-	169.613	30932474
DeepCCS	[M+Na]+	144.897	30932474
AllCCS	[M+H]+	141.3	32859911
AllCCS	[M+H-H2O]+	137.4	32859911
AllCCS	[M+NH4]+	144.9	32859911
AllCCS	[M+Na]+	145.9	32859911
AllCCS	[M-H]-	138.5	32859911
AllCCS	[M+Na-2H]-	140.1	32859911
AllCCS	[M+HCOO]-	141.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	3.41 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3338 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	111.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1426.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	293.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	111.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	128.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	359.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	381.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	777.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	326.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1045.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	291.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	424.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	216.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	263.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyladipic acid	CCC(CCCC(O)=O)C(O)=O	2403.2	Standard polar	33892256
Ethyladipic acid	CCC(CCCC(O)=O)C(O)=O	1271.4	Standard non polar	33892256
Ethyladipic acid	CCC(CCCC(O)=O)C(O)=O	1502.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyladipic acid,1TMS,isomer #1	CCC(CCCC(=O)O[Si](C)(C)C)C(=O)O	1539.6	Semi standard non polar	33892256
Ethyladipic acid,1TMS,isomer #2	CCC(CCCC(=O)O)C(=O)O[Si](C)(C)C	1531.0	Semi standard non polar	33892256
Ethyladipic acid,2TMS,isomer #1	CCC(CCCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1579.8	Semi standard non polar	33892256
Ethyladipic acid,1TBDMS,isomer #1	CCC(CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1780.4	Semi standard non polar	33892256
Ethyladipic acid,1TBDMS,isomer #2	CCC(CCCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1780.8	Semi standard non polar	33892256
Ethyladipic acid,2TBDMS,isomer #1	CCC(CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2042.1	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 - Ethyladipic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00c3-9600000000-22d30a671abe13eff9a1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyladipic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0fe0-9331000000-52482730ede4f40b5a88	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyladipic 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 - Ethyladipic acid 10V, Positive-QTOF	splash10-0a6r-0900000000-43313e3b565e0f143c66	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 20V, Positive-QTOF	splash10-06vr-5900000000-a28a099f2b81e61b58bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 40V, Positive-QTOF	splash10-015c-9100000000-8988b95998d44ed82f0a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 10V, Negative-QTOF	splash10-00di-0900000000-f1286a8f60417ada9bec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 20V, Negative-QTOF	splash10-0729-1900000000-0ca76a7cb253ce05de9a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 40V, Negative-QTOF	splash10-0a4l-9400000000-a796ab1da4f2c35d121f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 10V, Negative-QTOF	splash10-0c00-0900000000-5dd94a354b3ac614f31f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 20V, Negative-QTOF	splash10-0bvi-4900000000-c99dc8f999dcc9af7cca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 40V, Negative-QTOF	splash10-0006-9100000000-538896de4f07927502dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 10V, Positive-QTOF	splash10-014i-9800000000-652d86bdff3265e3b1e3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 20V, Positive-QTOF	splash10-0159-9200000000-eaeb151604eba968f04a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyladipic acid 40V, Positive-QTOF	splash10-0006-9000000000-0f9b89b2e5bddac59f38	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB022802

KNApSAcK ID

C00052149

Chemspider ID

134370

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6444

PubChem Compound

152459

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Franke, A.; Kroupa, A.; Schweitzer, F.; Winischhofer, M.; Klein-Lohr, H.; Just, M.; Hackl, M.; Reyher, I. v.; Bader, R. Cyclic ethers from glycols. Monatshefte fuer Chemie (1936), 69 167-203.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Ethyladipic acid (HMDB0002023)

MOL for HMDB0002023 (Ethyladipic acid)

3D MOL for HMDB0002023 (Ethyladipic acid)

3D SDF for HMDB0002023 (Ethyladipic acid)

3D-SDF for HMDB0002023 (Ethyladipic acid)

PDB for HMDB0002023 (Ethyladipic acid)

3D PDB for HMDB0002023 (Ethyladipic acid)

SMILES for HMDB0002023 (Ethyladipic acid)

INCHI for HMDB0002023 (Ethyladipic acid)

Structure for HMDB0002023 (Ethyladipic acid)

3D Structure for HMDB0002023 (Ethyladipic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra