Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2006-05-22 14:17:31 UTC
Updated at2021-08-19 20:22:30 UTC
NP-MRD IDNP0000041
Secondary Accession NumbersNone
Natural Product Identification
Common NameTetracosanoic acid
DescriptionTetracosanoic acid is a C24 straight-chain saturated fatty acid. It has a role as a volatile oil component, a plant metabolite, a human metabolite and a Daphnia tenebrosa metabolite. It is a very long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetracosanoate. Tetracosanoic acid, also known as N-tetracosanoate or lignoceric acid, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Tetracosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tetracosanoic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
CH3-[CH2]22-COOHChEBI
Lignoceric acidChEBI
LignozerinsaeureChEBI
N-Tetracosanoic acidChEBI
Tetracosanic acidChEBI
TetracosansaeureChEBI
Tetracosoic acidChEBI
Tetraeicosanoic acidChEBI
Tetraicosanoic acidChEBI
LignocerateGenerator
N-TetracosanoateGenerator
TetracosanateGenerator
TetracosoateGenerator
TetraeicosanoateGenerator
TetraicosanoateGenerator
TetracosanoateGenerator
Lignoceric acid, silver (1+) saltHMDB
Lignoceric acid, sodium saltHMDB
Lignoceric acid, potassium saltHMDB
Tetracosanoic acid, potassium salt (1:1)HMDB
Potassium tetracosanoateHMDB
Tetracosanoic acidMeSH
FA(24:0)PhytoBank
Chemical FormulaC24H48O2
Average Mass368.6367 Da
Monoisotopic Mass368.36543 Da
IUPAC Nametetracosanoic acid
Traditional Namelignoceric acid
CAS Registry Number557-59-5
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)
InChI KeyQZZGJDVWLFXDLK-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)V.dorna832021-08-13View Spectrum
Species
Species of Origin
Species NameSourceReference
Adenanthera pavoninaKNApSAcK Database
Alpinia oxyphyllaKNApSAcK Database
Angelica sinensisKNApSAcK Database
Anisomeles indicaKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Bupleurum chinenseKNApSAcK Database
Calophyllum calabaKNApSAcK Database
Calophyllum inophyllumKNApSAcK Database
Clitoria ternataKNApSAcK Database
Mangifera indicaKNApSAcK Database
Notopterygium incisumKNApSAcK Database
Peucedanum govanianum var.bicoloKNApSAcK Database
Pinus koraiensisKNApSAcK Database
Pinus sibiricaKNApSAcK Database
Saposhnikovia divaricataKNApSAcK Database
Strychnos nitidaKNApSAcK Database
Trichosanthes kirilowiiKNApSAcK Database
Triticum aestivumKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point84.2 °CNot Available
Boiling Point405.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility5.9e-06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP11.400 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
logP9.56ALOGPS
logP9.81ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity113.89 m³·mol⁻¹ChemAxon
Polarizability51.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0002003
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004651
KNApSAcK IDC00001223
Chemspider ID10724
KEGG Compound IDC08320
BioCyc IDTETRACOSANOATE
BiGG ID2218057
Wikipedia LinkLignoceric_acid
METLIN ID6427
PubChem Compound11197
PDB IDNot Available
ChEBI ID28866
Good Scents IDrw1287001
References
General References
  1. Galloway JH, Cartwright IJ, Bennett MJ: Abnormal myocardial lipid composition in an infant with type II glutaric aciduria. J Lipid Res. 1987 Mar;28(3):279-84. [PubMed:3572253 ]
  2. Dhaunsi GS, Kaur J, Alsaeid K, Turner RB, Bitar MS: Very long chain fatty acids activate NADPH oxidase in human dermal fibroblasts. Cell Biochem Funct. 2005 Jan-Feb;23(1):65-8. [PubMed:15565636 ]
  3. Petroni A, Blasevich M, Uziel G: Effects of the testosterone metabolite dihydrotestosterone and 5 alpha-androstan-3 alpha,17 beta-diol on very long chain fatty acid metabolism in X-adrenoleukodystrophic fibroblasts. Life Sci. 2003 Aug 8;73(12):1567-75. [PubMed:12865096 ]
  4. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  5. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]