Showing Compound Calendic acid (FDB002944)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:35 UTC

Update date

2019-11-26 02:58:12 UTC

Primary ID

FDB002944

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Calendic acid

Description

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). An all-trans beta isomer has been described.

CAS Number

28872-28-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
trans-8, trans-10, cis-12-octadecatrienoic acid	biospider

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

Chemical Formula

C18H30O2

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

278.4296

Monoisotopic Molecular Weight

278.224580204

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

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

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 77.65%; H 10.86%; O 11.49%	DFC
Melting Point	Mp 40-40.5°	DFC
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
Predicted GC-MS	Calendic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9660000000-d828aaab6ed3d3077513	Spectrum
Predicted GC-MS	Calendic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01yc-9621000000-89f2294fe8e5a7fa99b1	Spectrum
Predicted GC-MS	Calendic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0190000000-31cd9fbd0511b99abd28	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-5890000000-72f37321b7fde75b1a82	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-8930000000-2ae64d84444e7d3105fe	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-f6df0fd86f077c397e84	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1090000000-74939ebc0a54bce2e7b6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9230000000-abe728a7db5610480673	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-12da14b99ffff5280158	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-1090000000-b00c3559d2e5d3b02239	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9510000000-62ae777e69970ad77555	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-3690000000-39d79ed7580ed5594c11	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05pn-9610000000-fb79ee2260a91fce9a2d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05po-9100000000-24bbf16380c1781b6791	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4445945

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5282818

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB30962

CRC / DFC (Dictionary of Food Compounds) ID

GZM12-R:CPM05-H

EAFUS ID

Not Available

Dr. Duke ID

Not Available

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

Calendic_acid

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

Showing Compound Calendic acid (FDB002944)

Structure for FDB002944 (Calendic acid)