Showing Compound Eicosanic acid (FDB004028)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:03 UTC

Update date

2019-11-26 02:59:45 UTC

Primary ID

FDB004028

Secondary Accession Numbers

FDB002927
FDB030681

Chemical Information

FooDB Name

Eicosanic acid

Description

Arachidic acid, also known as eicosanoic acid or eicosanoate, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, arachidic acid is considered to be a fatty acid lipid molecule. Arachidic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Arachidic acid can be found in a number of food items such as chinese cinnamon, strawberry, winged bean, and thistle, which makes arachidic acid a potential biomarker for the consumption of these food products. Arachidic acid can be found primarily in blood and feces. Moreover, arachidic acid is found to be associated with schizophrenia.

CAS Number

506-30-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Arachic acid	ChEBI
Arachidinic acid	ChEBI
Arachinsaeure	ChEBI
C20:0	ChEBI
CH3-[CH2]18-COOH	ChEBI
Eicosanoic acid	ChEBI
N-Eicosanoic acid	ChEBI
Arachate	Generator
Arachidinate	Generator
Eicosanoate	Generator
N-Eicosanoate	Generator
Arachidate	Generator
Eicosoic acid	ChEBI, HMDB
Icosanoic acid	ChEBI, HMDB
Eicosoate	Generator, HMDB
Icosanoate	Generator, HMDB
Arachidic acid	HMDB
C 20	HMDB
C20 fatty acid	HMDB
FA(20:0)	HMDB
Peanut acid	HMDB
n-Eicosanic acid	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	5.0e-05 g/L	ALOGPS
logP	8.53	ALOGPS
logP	8.03	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	4.95	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	18	ChemAxon
Refractivity	95.49 m³·mol⁻¹	ChemAxon
Polarizability	42.91 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H40O2

IUPAC name

icosanoic acid

InChI Identifier

InChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22)

InChI Key

VKOBVWXKNCXXDE-UHFFFAOYSA-N

Isomeric SMILES

CCCCCCCCCCCCCCCCCCCC(O)=O

Average Molecular Weight

312.5304

Monoisotopic Molecular Weight

312.302830524

Classification

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Straight chain 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

long-chain fatty acid (CHEBI:28822 )
straight-chain saturated fatty acid (CHEBI:28822 )
Straight chain fatty acids (C06425 )
Saturated fatty acids (C06425 )
Straight chain fatty acids (LMFA01010020 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0596-9100000000-091619221e36a7a177ff	Spectrum
GC-MS	Eicosanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0900000000-cc7f30812c4ef45583b1	Spectrum
GC-MS	Eicosanoic acid, 1 TMS, GC-MS Spectrum	splash10-0159-2901000000-7d146c5d993118307ce5	Spectrum
GC-MS	Eicosanoic acid, non-derivatized, GC-MS Spectrum	splash10-0596-9100000000-53a544b7fbf2ee3b176a	Spectrum
GC-MS	Eicosanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0900000000-cc7f30812c4ef45583b1	Spectrum
GC-MS	Eicosanoic acid, non-derivatized, GC-MS Spectrum	splash10-0159-2901000000-7d146c5d993118307ce5	Spectrum
GC-MS	Eicosanoic acid, non-derivatized, GC-MS Spectrum	splash10-014i-1900000000-33733dae76fd89dc7394	Spectrum
Predicted GC-MS	Eicosanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9450000000-ff95bd6be578f2c72ce9	Spectrum
Predicted GC-MS	Eicosanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0109-9560000000-d2d19ad6d5ef54fdf90a	Spectrum
Predicted GC-MS	Eicosanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0029000000-273e657da59fa67385c2	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9200000000-84b07a6d22109c441336	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9100000000-9d6e321e2bf8cd1f20e4	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0009000000-d7e3408b3b2e854229b0	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0109000000-c0ed9d28e54855b40069	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a6r-0013493000-832a78a9cf97d74660ea	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-06vi-0012391000-e4dcf31aba99059fcf39	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-0193000000-031626259c4a17016165	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a4i-0091000000-9389b44ea9cfe1afe40b	Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-03di-0009000000-6bf31eaaa3592667dc53	Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-03di-0009000000-32767cc1909515840261	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03e9-3409000000-c86c0c5c2a80a4d1a6d6	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-545adcea3fffd230d8c7	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0092000000-c40a8544a31d253f26c6	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0i01-2491000000-60bf2b9a6912f287f6f0	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfu-8970000000-fd0569abd03da6142ee2	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0092000000-c40a8544a31d253f26c6	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0i01-2491000000-60bf2b9a6912f287f6f0	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfu-8970000000-fd0569abd03da6142ee2	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0049000000-54fd1cf54bdd386d406e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xu-1095000000-2584a862e47ea0cb88f2	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9140000000-2caaff4da05fbcb0fdf7	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0049000000-54fd1cf54bdd386d406e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xu-1095000000-2584a862e47ea0cb88f2	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9140000000-2caaff4da05fbcb0fdf7	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

EICOSANIC-ACID

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound Eicosanic acid (FDB004028)

Structure for FDB004028 (Eicosanic acid)