MiMeDB: Showing metabocard for 2-Ethylhexanoic acid (MMDBc0047640)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:35:26 UTC

Update Date

2024-04-30 20:28:23 UTC

Metabolite ID

MMDBc0047640

Metabolite Identification

Common Name

2-Ethylhexanoic acid

Description

2-Ethylhexanoic acid, also known as 2-ethylhexanoate or alpha-ethylcaproic acid, 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. 2-Ethylhexanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Ethylhexanoic acid is a potentially toxic compound.

Structure

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

Synonyms

Value	Source
2-Ethylhexanoate	Generator
Sinesto b	MeSH
(+/-)-2-ethylhexanoIC ACID	HMDB
2-Butylbutanoic acid	HMDB
2-Ethyl hexanoic acid	HMDB
2-Ethyl-1-hexanoic acid	HMDB
2-Ethyl-hexoic acid	HMDB
2-Ethyl-hexonic acid	HMDB
2-Ethylcaproic acid	HMDB
2-Ethylcapronic acid	HMDB
2-Ethylhexoic acid	HMDB
3-Heptanecarboxylic acid	HMDB
alpha-Ethylcaproic acid	HMDB
alpha-Ethylhexanoic acid	HMDB
Butylethylacetic acid	HMDB
a-Ethyl caproate	Generator, HMDB
a-Ethyl caproic acid	Generator, HMDB
alpha-Ethyl caproate	Generator, HMDB
Α-ethyl caproate	Generator, HMDB
Α-ethyl caproic acid	Generator, HMDB
2-Ethylhexanoic acid	MeSH
(±)-2-Ethylhexanoic acid	HMDB
Ethylhexanoic acid	HMDB
Octylic acid	HMDB
α-Ethylcaproic acid	HMDB
α-Ethylhexanoic acid	HMDB

Molecular Formula

C₈H₁₆O₂

Average Mass

144.2114

Monoisotopic Mass

144.115029756

IUPAC Name

2-ethylhexanoic acid

Traditional Name

2-ethylhexanoic acid

CAS Registry Number

Not Available

SMILES

CCCCC(CC)C(O)=O

InChI Identifier

InChI=1S/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)

InChI Key

OBETXYAYXDNJHR-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
Branched fatty acid
Monocarboxylic 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

Branched fatty acids (LMFA01020087 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.07 g/L	ALOGPS
logP	2.61	ALOGPS
logP	2.8	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	5.14	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	5	ChemAxon
Refractivity	40.25 m³·mol⁻¹	ChemAxon
Polarizability	16.99 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0fb9-3920000000-7e7fbb23d9bdc5a56044	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0079-9000000000-ad0258cbd5d18520beb9	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9300000000-2e3084f5a49e5800b8de	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05i9-9200000000-e7de4220461eedb062f6	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-3900000000-66559dd7e31088c2bff8	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052b-9400000000-2df69b4ff55243bf2d73	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-238efca128749a9ad743	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-4900000000-01f3d55a8d9b84636f29	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0005-9400000000-dec78c38085ece33408f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-9100000000-1e624a8a74aa0be27fb5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-91a6d7eda80533c9e0fe	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-9800000000-13ac5c9be6e1e9f1338a	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4947d130f0947648d859	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ap4-9300000000-dda58dd73483ccbb233c	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-9a67ce8419a78ee15eb1	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-e8e219fe66e140a203e4	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-059i-9000000000-8e486671e74560231b2a	2014-10-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		2014-10-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2014-10-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-30	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces
Sweat

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0038968	2-Ethylhexanoic acid	N-(2-Ethylhexanoyl)-4R-hydroxysphinganine	Alkaline ceramidase YPC1	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Autism		Association	Human Feces	HMDB	24130822

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected and Quantified	46.228	0	416.0559	nmol/g wet feces	Children (1 - 13 years old)	Both	Autism	HMDB	24130822
Human Feces	Detected and Quantified	115.571	0	808.998	nmol/g wet feces	Children (1 - 13 years old)	Both	Developmental Disorder Not Otherwise Specified	HMDB	24130822
Human Feces	Detected and Quantified	254.256	0	4345.472	nmol/g wet feces	Children (1 - 13 years old)	Both	Normal	HMDB	24130822
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Sweat	Detected but not Quantified					Adult	Both	Normal	HMDB	26755145
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050

External Links

HMDB ID

HMDB0031230

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003254

KNApSAcK ID

C00007414

Chemspider ID

8373

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Ethylhexanoic acid

METLIN ID

Not Available

PubChem Compound

8697

PDB ID

Not Available

ChEBI ID

89058

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2-Ethylhexanoic acid (MMDBc0047640)

MOL for #<Metabolite:0x00007fd0fc014288>

3D MOL for #<Metabolite:0x00007fd0fc014288>

3D SDF for #<Metabolite:0x00007fd0fc014288>

3D-SDF for #<Metabolite:0x00007fd0fc014288>

PDB for #<Metabolite:0x00007fd0fc014288>

3D PDB for #<Metabolite:0x00007fd0fc014288>

SMILES for #<Metabolite:0x00007fd0fc014288>

INCHI for #<Metabolite:0x00007fd0fc014288>

Structure for #<Metabolite:0x00007fd0fc014288>

3D Structure for #<Metabolite:0x00007fd0fc014288>