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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:40:04 UTC
Update Date2018-03-12 22:07:53 UTC
HMDB IDHMDB0030962
Secondary Accession Numbers
  • HMDB30962
Metabolite Identification
Common NameCalendic acid
DescriptionCalendic 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
Thumb
Synonyms
ValueSource
8E,10E,12Z-Octadecatrienoic acidChEBI
alpha-Calendic acidChEBI
C18:3N-6,8,10ChEBI
Calendulic acidChEBI
trans-8, trans-10, cis-12-Octadecatrienoic acidChEBI
8E,10E,12Z-OctadecatrienoateGenerator
CalendateGenerator
a-CalendateGenerator
a-Calendic acidGenerator
alpha-CalendateGenerator
α-calendateGenerator
α-calendic acidGenerator
CalendulateGenerator
trans-8, trans-10, cis-12-OctadecatrienoateGenerator
Chemical FormulaC18H30O2
Average Molecular Weight278.4296
Monoisotopic Molecular Weight278.224580204
IUPAC Name(8E,10E,12Z)-octadeca-8,10,12-trienoic acid
Traditional Namecalendic acid
CAS Registry Number28872-28-8
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 KeyDQGMPXYVZZCNDQ-KBPWROHVSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point40 - 40.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00024 g/LALOGPS
logP6.66ALOGPS
logP6.06ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)4.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability36 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9660000000-d828aaab6ed3d3077513View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01yc-9621000000-89f2294fe8e5a7fa99b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0190000000-31cd9fbd0511b99abd28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-5890000000-72f37321b7fde75b1a82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-8930000000-2ae64d84444e7d3105feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f6df0fd86f077c397e84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1090000000-74939ebc0a54bce2e7b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-abe728a7db5610480673View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002944
KNApSAcK IDNot Available
Chemspider ID4445945
KEGG Compound IDNot Available
BioCyc IDCPD-8228
BiGG IDNot Available
Wikipedia LinkCalendic_acid
METLIN IDNot Available
PubChem Compound5282818
PDB IDNot Available
ChEBI ID86148
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.