ChemFOnt: Showing chemical card for 3-Methyl-5-pentyl-2-furanundecanoic acid (CFc000012208)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:00:12 UTC

Chemfont ID

CFc000012208

Molecule Identification

Common Name

3-Methyl-5-pentyl-2-furanundecanoic acid

Definition

3-methyl-5-pentyl-2-furanundecanoic acid is a furan fatty acid (F-acid). F-acids are heterocyclic fatty acids containing a central furan moiety with a carboxylalkyl chain (mostly 7, 9, 11, or 13 carbons) in the 2-position and an alkyl chain (mostly 3 or 5 carbons) in the 5-position. Despite being found in low concentrations in food lipids, they are excellent antixoxidants and radical scavengers. This allows them to play an important role in preventing lipid peroxidation and protecting polyunsaturated fatty acids. They are often incorporated into phospholipids and cholesterol esters of fish and other marine organisms. 3-methyl-5-pentyl-2-furanundecanoic acid, in particular, can be described by the shorthand notation 11M5. This refers to its 11-carbon carboxyalkyl moiety, the methyl substitution in the 3-position of its furan moiety, and its 5-carbon alkyl moiety. It is a constituent of fats of the liver and gonads of fishes, e.g. pike (Esox lucius).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Methyl-5-pentyl-2-furanundecanoate	Generator
F5 acid	HMDB
F5 Furan fatty acid	HMDB
MonoMe(11,5)	HMDB
11-(3-Methyl-5-pentylfuran-2-yl)-undecanoate	Generator

Chemical Formula

C₂₁H₃₆O₃

Average Molecular Weight

336.5087

Monoisotopic Molecular Weight

336.266445018

IUPAC Name

11-(3-methyl-5-pentylfuran-2-yl)undecanoic acid

Traditional Name

11-(3-methyl-5-pentylfuran-2-yl)undecanoic acid

CAS Registry Number

57818-37-8

SMILES

CCCCCC1=CC(C)=C(CCCCCCCCCCC(O)=O)O1

InChI Identifier

InChI=1S/C21H36O3/c1-3-4-11-14-19-17-18(2)20(24-19)15-12-9-7-5-6-8-10-13-16-21(22)23/h17H,3-16H2,1-2H3,(H,22,23)

InChI Key

QDTBMEGPXZUECM-UHFFFAOYSA-N

Chemical Taxonomy

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
Furanoid fatty acid
Heterocyclic fatty acid
Furan
Heteroaromatic compound
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0031005)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0031005)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031005)

Source

Endogenous

Endogenous (HMDB: HMDB0031005)

Animal

Animal (HMDB: HMDB0031005)

Exogenous

Food

Food (HMDB: HMDB0031005)

Aquatic origin

Fish

Fishes (FooDB: FOOD00865)

Exogenous (HMDB: HMDB0031005)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031005)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031005)

Lipid metabolism pathway (HMDB: HMDB0031005)

Cellular process

Cell signaling (HMDB: HMDB0031005)

Biochemical process

Lipid transport (HMDB: HMDB0031005)

Role

Biological role

Energy source (HMDB: HMDB0031005)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031005)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	6.89	ALOGPS
logP	7.09	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	99.84 m³·mol⁻¹	ChemAxon
Polarizability	43.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031005

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002994

KNApSAcK ID

Not Available

Chemspider ID

9231983

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11056824

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Methyl-5-pentyl-2-furanundecanoic acid (CFc000012208)

MOL for CFc000012208 (3-Methyl-5-pentyl-2-furanundecanoic acid)

3D MOL for CFc000012208 (3-Methyl-5-pentyl-2-furanundecanoic acid)

3D SDF for CFc000012208 (3-Methyl-5-pentyl-2-furanundecanoic acid)

3D-SDF for CFc000012208 (3-Methyl-5-pentyl-2-furanundecanoic acid)

PDB for CFc000012208 (3-Methyl-5-pentyl-2-furanundecanoic acid)

3D PDB for CFc000012208 (3-Methyl-5-pentyl-2-furanundecanoic acid)

SMILES for CFc000012208 (3-Methyl-5-pentyl-2-furanundecanoic acid)

INCHI for CFc000012208 (3-Methyl-5-pentyl-2-furanundecanoic acid)

Structure for CFc000012208 (3-Methyl-5-pentyl-2-furanundecanoic acid)

3D Structure for CFc000012208 (3-Methyl-5-pentyl-2-furanundecanoic acid)