ChemFOnt: Showing chemical card for Calendic acid (CFc000012166)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:00:09 UTC

Chemfont ID

CFc000012166

Molecule Identification

Common Name

Calendic acid

Definition

Calendic acid is isolated from Calendula officinalis (pot marigold) seed oil Calendic acid (sometimes -Calendic acid) is an unsaturated fatty acid, named for the pot marigold (genus Calendula), from which it is obtained. It is chemically similar to the conjugated linoleic acids; laboratory work suggests it may have similar health benefits. Calendic acid is an omega-6 fatty acid. though not usually listed with this group. Calendic acid (8t,10t,12c-18:3) is synthesised in Calendula officinalis from linoleate (9c,12c-18:2) by an unusual 12-oleate desaturase (a FAD 2 variant) that converts the cis-double bond in position 9 to a trans,trans-conjugated double bond system (8t,10t). Calendic acid is an all-trans beta isomer has been described

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8E,10E,12Z-Octadecatrienoic acid	ChEBI
alpha-Calendic acid	ChEBI
C18:3N-6,8,10	ChEBI
Calendulic acid	ChEBI
trans-8, trans-10, cis-12-Octadecatrienoic acid	ChEBI
8E,10E,12Z-Octadecatrienoate	Generator
a-Calendate	Generator
a-Calendic acid	Generator
alpha-Calendate	Generator
Α-calendate	Generator
Α-calendic acid	Generator
Calendulate	Generator
trans-8, trans-10, cis-12-Octadecatrienoate	Generator
Calendate	Generator
Calendic acid	ChEBI

Chemical Formula

C₁₈H₃₀O₂

Average Molecular Weight

278.4296

Monoisotopic Molecular Weight

278.224580204

IUPAC Name

(8E,10E,12Z)-octadeca-8,10,12-trienoic acid

Traditional Name

calendic acid

CAS Registry Number

28872-28-8

SMILES

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

InChI Identifier

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10+

InChI Key

DQGMPXYVZZCNDQ-KBPWROHVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
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

omega-6 fatty acid (CHEBI:86148 )
conjugated linolenic acid (CHEBI:86148 )
Unsaturated fatty acids (LMFA01030144 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0030962)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030962)

Source

Endogenous

Endogenous (HMDB: HMDB0030962)

Animal

Animal (HMDB: HMDB0030962)

Exogenous

Food

Food (HMDB: HMDB0030962)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Exogenous (HMDB: HMDB0030962)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030962)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030962)

Lipid metabolism pathway (HMDB: HMDB0030962)

Cellular process

Cell signaling (HMDB: HMDB0030962)

Biochemical process

Lipid transport (HMDB: HMDB0030962)

Role

Biological role

Energy source (HMDB: HMDB0030962)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030962)

Laboratory chemical

Laboratory chemical (HMDB: HMDB0030962)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	6.66	ALOGPS
logP	6.06	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.96	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	89.64 m³·mol⁻¹	ChemAxon
Polarizability	36 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