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Record Information
Version2.0
Created at2022-09-11 07:36:52 UTC
Updated at2022-09-11 07:36:52 UTC
NP-MRD IDNP0311549
Secondary Accession NumbersNone
Natural Product Identification
Common Namestearolic acid
DescriptionStearolic acid, also known as 9-stearolate or 9-ODA, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. stearolic acid is found in Jodina rhombifolia, Panax ginseng and Paramacrolobium coeruleum. stearolic acid was first documented in 2013 (PMID: 24062307). Based on a literature review a small amount of articles have been published on stearolic acid (PMID: 29625270) (PMID: 25264284) (PMID: 23870929) (PMID: 23797276).
Structure
Thumb
Synonyms
ValueSource
9-Octadecynoic acidChEBI
9-ODAChEBI
9-ODYAChEBI
9-Stearolic acidChEBI
9a-18:1ChEBI
Delta(9)-Octadecynoic acidChEBI
Octadec-9-insaeureChEBI
StearolsaeureChEBI
Octadec-9-ynoic acidKegg
9-OctadecynoateGenerator
9-StearolateGenerator
delta(9)-OctadecynoateGenerator
Δ(9)-octadecynoateGenerator
Δ(9)-octadecynoic acidGenerator
Octadec-9-ynoateGenerator
StearolateGenerator
Chemical FormulaC18H32O2
Average Mass280.4520 Da
Monoisotopic Mass280.24023 Da
IUPAC Nameoctadec-9-ynoic acid
Traditional Namestearolic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCC#CCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-8,11-17H2,1H3,(H,19,20)
InChI KeyRGTIBVZDHOMOKC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Jodina rhombifoliaLOTUS Database
Panax ginsengLOTUS Database
Paramacrolobium coeruleumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain 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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.73ChemAxon
pKa (Strongest Acidic)4.76ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity85.65 m³·mol⁻¹ChemAxon
Polarizability37.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001293
Chemspider ID61475
KEGG Compound IDC08459
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68167
PDB IDNot Available
ChEBI ID28801
Good Scents IDNot Available
References
General References
  1. Londero VS, da Costa-Silva TA, Gomes KS, Ferreira DD, Mesquita JT, Tempone AG, Young MCM, Jerz G, Lago JHG: Acetylenic fatty acids from Porcelia macrocarpa (Annonaceae) against trypomastigotes of Trypanosoma cruzi: Effect of octadec-9-ynoic acid in plasma membrane electric potential. Bioorg Chem. 2018 Aug;78:307-311. doi: 10.1016/j.bioorg.2018.03.025. Epub 2018 Mar 30. [PubMed:29625270 ]
  2. Baba T, Takai K, Takagi T, Kanamori T: Effect of the fluorination degree of hydrophobic chains on the monolayer behavior of unsaturated diacylphosphatidylcholines bearing partially fluorinated 9-octadecynoyl (stearoloyl) groups at the air-water interface. Colloids Surf B Biointerfaces. 2014 Nov 1;123:246-53. doi: 10.1016/j.colsurfb.2014.09.023. Epub 2014 Sep 22. [PubMed:25264284 ]
  3. Okada S, Zhou XR, Damcevski K, Gibb N, Wood C, Hamberg M, Haritos VS: Diversity of Delta12 fatty acid desaturases in santalaceae and their role in production of seed oil acetylenic fatty acids. J Biol Chem. 2013 Nov 8;288(45):32405-32413. doi: 10.1074/jbc.M113.511931. Epub 2013 Sep 23. [PubMed:24062307 ]
  4. Wang X, Zhang M, Zhao Y, Wang H, Liu T, Xin Z: Pentadecyl ferulate, a potent antioxidant and antiproliferative agent from the halophyte Salicornia herbacea. Food Chem. 2013 Dec 1;141(3):2066-74. doi: 10.1016/j.foodchem.2013.05.043. Epub 2013 May 21. [PubMed:23870929 ]
  5. Alloatti A, Tripodi KE, Uttaro AD: Synergistic effect of inhibitors of fatty acid desaturases on Trypanosoma parasites. Parasitol Res. 2013 Jun 25. doi: 10.1007/s00436-013-3508-y. [PubMed:23797276 ]
  6. LOTUS database [Link]