ChemFOnt: Showing chemical card for Palmitelaidic acid (CFc000007856)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:24 UTC

Chemfont ID

CFc000007856

Molecule Identification

Common Name

Palmitelaidic acid

Definition

Palmitelaidic acid is a trans fatty acid (the trans isomer of palmitoleic acid). Trans fatty acids are known to cause changes in plasma lipids and lipoprotein phenotypes, but the mechanisms involved are unknown. The major dietary sources of trans fatty acids are partly hydrogenated vegetable oils, mainly elaidic acid (t-18:1D9). Additional sources are animal and dairy fats [palmitelaidic acid (t-16:1D9) and t-vaccenic acid (t-18:1D11)] and partly hydrogenated fish oils. (very-long-chain trans fatty acids, ie, >C22) (PMID: 9734731 ). Palmitelaidic acid has been reported as the predominant trans-16:1 isomer in cheeses made with goat and ewe milks (PMID: 11026624 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(9E)-Hexadecenoic acid	ChEBI
(e)-9-Hexadecenoicacid	ChEBI
9-trans-Hexadecenoic acid	ChEBI
t-16:1D9	ChEBI
t-9-Hexadecenoic acid	ChEBI
trans-9-Hexadecenoic acid	ChEBI
trans-Delta(9)-Hexadecenoic acid	ChEBI
trans-Palmitoleic acid	ChEBI
(9E)-Hexadecenoate	Generator
9-trans-Hexadecenoate	Generator
t-9-Hexadecenoate	Generator
trans-9-Hexadecenoate	Generator
trans-delta(9)-Hexadecenoate	Generator
trans-Δ(9)-hexadecenoate	Generator
trans-Δ(9)-hexadecenoic acid	Generator
trans-Palmitoleate	Generator
Palmitelaidate	Generator
Palmitoleic acid	MeSH
Palmitoleic acid, (Z)-isomer	MeSH
Palmitoleic acid, sodium salt, (Z)-isomer	MeSH
C16:1 trans-9	MeSH
Palmitoleate	MeSH
Palmitoleic acid, (e)-isomer	MeSH
Palmitoleic acid, potassium salt, (Z)-isomer	MeSH
(9E)-9-Hexadecenoate	HMDB
(9E)-9-Hexadecenoic acid	HMDB
(e)-9-Hexadecenoate	HMDB
(e)-9-Hexadecenoic acid	HMDB
(e)-Hexadec-9-enoate	HMDB
(e)-Hexadec-9-enoic acid	HMDB
trans-9-Palmitoleate	Generator
Palmitelaidic acid	MeSH

Chemical Formula

C₁₆H₃₀O₂

Average Molecular Weight

254.4082

Monoisotopic Molecular Weight

254.224580204

IUPAC Name

(9E)-hexadec-9-enoic acid

Traditional Name

trans-palmitoleic acid

CAS Registry Number

10030-73-6

SMILES

CCCCCC\C=C\CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7+

InChI Key

SECPZKHBENQXJG-BQYQJAHWSA-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
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

long-chain fatty acid (CHEBI:59265 )
monounsaturated fatty acid (CHEBI:59265 )
Unsaturated fatty acids (LMFA01030057 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)
Saliva (HMDB: HMDB0012328)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0012328)

Excreta

Biofluid or Excreta

Feces (PMID: 24029555)
Urine (HMDB: HMDB0012328)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012328)

Source

Exogenous

Exogenous (HMDB: HMDB0012328)

Food

Food (HMDB: HMDB0012328)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0012328)

Animal

Animal (HMDB: HMDB0012328)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012328)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012328)

Lipid metabolism pathway (HMDB: HMDB0012328)

Cellular process

Cell signaling (HMDB: HMDB0012328)

Biochemical process

Lipid transport (HMDB: HMDB0012328)

Role

Biological role

Energy source (HMDB: HMDB0012328)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012328)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00045 g/L	ALOGPS
logP	6.71	ALOGPS
logP	5.89	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.99	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	13	ChemAxon
Refractivity	78.2 m³·mol⁻¹	ChemAxon
Polarizability	33.37 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

External Links

HMDB ID

HMDB0012328

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028947

KNApSAcK ID

C00052377

Chemspider ID

4445872

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282745

PDB ID

Not Available

ChEBI ID

59265

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Palmitelaidic acid (CFc000007856)

MOL for CFc000007856 (Palmitelaidic acid)

3D MOL for CFc000007856 (Palmitelaidic acid)

3D SDF for CFc000007856 (Palmitelaidic acid)

3D-SDF for CFc000007856 (Palmitelaidic acid)

PDB for CFc000007856 (Palmitelaidic acid)

3D PDB for CFc000007856 (Palmitelaidic acid)

SMILES for CFc000007856 (Palmitelaidic acid)

INCHI for CFc000007856 (Palmitelaidic acid)

Structure for CFc000007856 (Palmitelaidic acid)

3D Structure for CFc000007856 (Palmitelaidic acid)