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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:49 UTC
NP-MRD IDNP0001131
Secondary Accession NumbersNone
Natural Product Identification
Common NameTricosanoic acid
DescriptionTricosanoic acid, also known as N-tricosanoate or 22FA, 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. Tricosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tricosanoic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
N-Tricosanoic acidChEBI
N-TricosanoateGenerator
TricosanoateGenerator
22FAHMDB
F23HMDB
Tricosanoic acid, aluminum saltHMDB
Tricosanoic acid, calcium saltHMDB
Tricosanoic acid, lead saltHMDB
TricosylateHMDB
23FAHMDB
Tricosylic acidHMDB
FA(23:0)HMDB
Tricosanoic acidMeSH
Chemical FormulaC23H46O2
Average Mass354.6101 Da
Monoisotopic Mass354.34978 Da
IUPAC Nametricosanoic acid
Traditional Nametricosanoic acid
CAS Registry Number2433-96-7
SMILES
CCCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C23H46O2/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/h2-22H2,1H3,(H,24,25)
InChI KeyXEZVDURJDFGERA-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Varshavi.d262021-07-25View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Aplysina lacunosa
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Callyspongia fallax
Capra aegagrus hircus
Carica papaya L.FooDB
Cecropia pachystachya
Cervidae
Cervus canadensis
Citrus bergamiaKNApSAcK Database
Columba
Columbidae
Curcuma ochrorhiza
Dromaius novaehollandiae
Equus caballus
Erylus formosus
Gallus gallus
Ganoderma applanatum
Hibiscus cannabinus
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Nelumbo nucifera
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Phoenix dactyliferaFooDB
Pinus radiata
Populus tremuloides
Psammosilene tunicoides
Punica granatum
Ruscus aculeatus
Saussurea medusa
Solanum tuberosumKNApSAcK Database
Struthio camelus
Suberites massa
Sus scrofa
Sus scrofa domestica
Traversia baccharoides
Tripneustes ventricosus
Tripterygium hypoglaucumKNApSAcK 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 Parents
Substituents
  • Very long-chain 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point77.0 - 79.0 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.9e-05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.6e-05 g/LALOGPS
logP9.39ALOGPS
logP9.37ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity109.29 m³·mol⁻¹ChemAxon
Polarizability49.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001160
DrugBank IDDB03500
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002894
KNApSAcK IDC00053866
Chemspider ID16170
KEGG Compound IDNot Available
BioCyc IDCPD-7834
BiGG IDNot Available
Wikipedia LinkTricosylic acid
METLIN ID4211
PubChem Compound17085
PDB IDNot Available
ChEBI ID42394
Good Scents IDrw1292281
References
General References
  1. GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
  2. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
  3. Vandenbrouck T, Jones OA, Dom N, Griffin JL, De Coen W: Mixtures of similarly acting compounds in Daphnia magna: from gene to metabolite and beyond. Environ Int. 2010 Apr;36(3):254-68. doi: 10.1016/j.envint.2009.12.006. Epub 2010 Feb 1. [PubMed:20117838 ]
  4. Kotlega D, Peda B, Palma J, Zembron-Lacny A, Golab-Janowska M, Masztalewicz M, Nowacki P, Szczuko M: Free Fatty Acids Are Associated with the Cognitive Functions in Stroke Survivors. Int J Environ Res Public Health. 2021 Jun 16;18(12). pii: ijerph18126500. doi: 10.3390/ijerph18126500. [PubMed:34208689 ]
  5. Li D, Misialek JR, Jing M, Tsai MY, Eckfeldt JH, Steffen LM, Knopman D, Wruck L, Gottesman R, Mosley TH, Sharrett AR, Alonso A: Plasma phospholipid very-long-chain SFAs in midlife and 20-year cognitive change in the Atherosclerosis Risk in Communities (ARIC): a cohort study. Am J Clin Nutr. 2020 Jun 1;111(6):1252-1258. doi: 10.1093/ajcn/nqaa048. [PubMed:32320012 ]
  6. Cain N, Alka O, Segelke T, von Wuthenau K, Kohlbacher O, Fischer M: Food fingerprinting: Mass spectrometric determination of the cocoa shell content (Theobroma cacao L.) in cocoa products by HPLC-QTOF-MS. Food Chem. 2019 Nov 15;298:125013. doi: 10.1016/j.foodchem.2019.125013. Epub 2019 Jun 24. [PubMed:31260999 ]
  7. Das N, Bhattacharya A, Kumar Mandal S, Debnath U, Dinda B, Mandal SC, Kumar Sinhamahapatra P, Kumar A, Dutta Choudhury M, Maiti S, Palit P: Ichnocarpus frutescens (L.) R. Br. root derived phyto-steroids defends inflammation and algesia by pulling down the pro-inflammatory and nociceptive pain mediators: An in-vitro and in-vivo appraisal. Steroids. 2018 Nov;139:18-27. doi: 10.1016/j.steroids.2018.09.005. Epub 2018 Sep 12. [PubMed:30217788 ]
  8. Moridi Farimani M, Nazarianpoor E, Rustaie A, Akhbari M: Phytochemical constituents and biological activities of Cleome iberica DC. Nat Prod Res. 2017 Jun;31(11):1329-1332. doi: 10.1080/14786419.2016.1239093. Epub 2016 Oct 12. [PubMed:27731648 ]
  9. Dogru-Koca A, Ozcan T, Yildirimli S: Chemotaxonomic perspectives of the Paracaryum (Cynoglosseae, Boraginaceae) taxa based on fruit fatty acid composition. Phytochemistry. 2016 Nov;131:100-106. doi: 10.1016/j.phytochem.2016.08.012. Epub 2016 Sep 3. [PubMed:27600716 ]
  10. http://www.patentstorm.us/patents/4874791-description.html [Link]
  11. http://www.rain-tree.com/peppertree.htm [Link]