ChemFOnt: Showing chemical card for cis-4-Decenoic acid (CFc000002340)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:12 UTC

Chemfont ID

CFc000002340

Molecule Identification

Common Name

cis-4-Decenoic acid

Definition

cis-4-Decenoic acid, also known as obtusilic 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. cis-4-Decenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Decenoic acid (and other intermediates of unsaturated fatty acid oxidation) has been found in increased amounts in liver, skeletal muscle, and heart obtained post mortem from patients with medium-chain acyl-CoA dehydrogenase deficiency (MCADD), multiple acyl-CoA dehydrogenase deficiency (MADD), and very-long-chain acyl-CoA dehydrogenase deficiency (VLCADD) (PMID: 11486898 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Z)-4-Decenoic acid	ChEBI
10:1 (N-6)	ChEBI
4-Decenoic acid	ChEBI
C10:1 (N-6)	ChEBI
cis-Decen-4-saeure	ChEBI
cis-Delta(4)-Decenoic acid	ChEBI
cis-Obtusilic acid	ChEBI
Dec-4C-enoic acid	ChEBI
Dec-4C-ensaeure	ChEBI
Z-4-Decenoic acid	ChEBI
(Z)-4-Decenoate	Generator
4-Decenoate	Generator
cis-delta(4)-Decenoate	Generator
cis-Δ(4)-decenoate	Generator
cis-Δ(4)-decenoic acid	Generator
cis-Obtusilate	Generator
Dec-4C-enoate	Generator
Z-4-Decenoate	Generator
cis-4-Decenoate	Generator
(4Z)-4-Decenoic acid	HMDB
4-cis-Decenoic acid	HMDB
FA(10:1(4Z))	HMDB
FA(10:1n6)	HMDB
Obtusilic acid	HMDB
cis-4-Decenoic acid	HMDB
Dec-4-enoic acid	MeSH, HMDB
(Z)-Isomer OF 4-decenoic acid	MeSH, HMDB

Chemical Formula

C₁₀H₁₈O₂

Average Molecular Weight

170.2487

Monoisotopic Molecular Weight

170.13067982

IUPAC Name

(4Z)-dec-4-enoic acid

Traditional Name

4-decenoic acid

CAS Registry Number

505-90-8

SMILES

CCCCC\C=C/CCC(O)=O

InChI Identifier

InChI=1S/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h6-7H,2-5,8-9H2,1H3,(H,11,12)/b7-6-

InChI Key

XKZKQTCECFWKBN-SREVYHEPSA-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
Unsaturated 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

decenoic acid (CHEBI:32380 )
Unsaturated fatty acids (LMFA01030199 )

Functional Ontology

Liver (HMDB: HMDB0004980)
Heart (HMDB: HMDB0004980)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0004980)

Cellular substructure

Membrane (HMDB: HMDB0004980)
Extracellular (HMDB: HMDB0004980)

Source

Exogenous

Exogenous (HMDB: HMDB0004980)

Endogenous

Endogenous (HMDB: HMDB0004980)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	3.74	ALOGPS
logP	3.23	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.88	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	7	ChemAxon
Refractivity	50.59 m³·mol⁻¹	ChemAxon
Polarizability	20.34 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004980

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002991

KNApSAcK ID

Not Available

Chemspider ID

4471776

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7233

PubChem Compound

5312351

PDB ID

Not Available

ChEBI ID

32380

Food Biomarker Ontology

Not Available

References

Synthesis Reference

De Klein, W. J. Copper(II)-catalyzed formation of decenoic acids from manganese(III) acetate and 1-octene in acetic anhydride/acetic acid mixtures. Recueil des Travaux Chimiques des Pays-Bas (1975), 94(7), 151-3.

Showing chemical card for cis-4-Decenoic acid (CFc000002340)

MOL for CFc000002340 (cis-4-Decenoic acid)

3D MOL for CFc000002340 (cis-4-Decenoic acid)

3D SDF for CFc000002340 (cis-4-Decenoic acid)

3D-SDF for CFc000002340 (cis-4-Decenoic acid)

PDB for CFc000002340 (cis-4-Decenoic acid)

3D PDB for CFc000002340 (cis-4-Decenoic acid)

SMILES for CFc000002340 (cis-4-Decenoic acid)

INCHI for CFc000002340 (cis-4-Decenoic acid)

Structure for CFc000002340 (cis-4-Decenoic acid)

3D Structure for CFc000002340 (cis-4-Decenoic acid)