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Record Information
Version2.0
Created at2022-04-28 01:09:45 UTC
Updated at2022-04-28 01:09:46 UTC
NP-MRD IDNP0054970
Secondary Accession NumbersNone
Natural Product Identification
Common Name18-Hydroxy-9-octadecenoic acid
Description18-Hydroxyoleic acid, also known as 19-home(9Z) or omega-hydroxyoleate, 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. 18-Hydroxyoleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 18-Hydroxy-9-octadecenoic acid is found in Arabidopsis thaliana. 18-Hydroxy-9-octadecenoic acid was first documented in 1973 (PMID: 4356240). An omega-hydroxy fatty acid that is 18-hydroxyoctadecanoic acid which has been dehydrogenated to introduce a trans double bond at the 9-10 position (PMID: 24673591) (PMID: 23205954).
Structure
Thumb
Synonyms
ValueSource
(9Z)-18-Hydroxyoctadecenoic acidChEBI
18-Hydroxy-9-octadecenoic acidChEBI
18-Hydroxy-9Z-octadecenoic acidChEBI
19-HOME(9Z)ChEBI
Omega-hydroxy-(9Z)-octadecenoic acidChEBI
Omega-hydroxyoleic acidChEBI
(9Z)-18-HydroxyoctadecenoateGenerator
18-Hydroxy-9-octadecenoateGenerator
18-Hydroxy-9Z-octadecenoateGenerator
Omega-hydroxy-(9Z)-octadecenoateGenerator
Omega-hydroxyoleateGenerator
18-HydroxyoleateGenerator
Chemical FormulaC18H34O3
Average Mass298.4670 Da
Monoisotopic Mass298.25079 Da
IUPAC Name(9Z)-18-hydroxyoctadec-9-enoic acid
Traditional Name(9Z)-18-hydroxyoctadec-9-enoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCCO)=C(/[H])CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O3/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h1-2,19H,3-17H2,(H,20,21)/b2-1-
InChI KeyLQUHZVLTTWMBTO-UPHRSURJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaPlant
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
  • Hydroxy 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
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP6.41ALOGPS
logP5.35ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity89.33 m³·mol⁻¹ChemAxon
Polarizability38.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0155793
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007439
Chemspider IDNot Available
KEGG Compound IDC19616
BioCyc ID18-HYDROXYOLEATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312773
PDB IDNot Available
ChEBI ID79312
Good Scents IDNot Available
References
General References
  1. Belge B, Llovera M, Comabella E, Graell J, Lara I: Fruit cuticle composition of a melting and a nonmelting peach cultivar. J Agric Food Chem. 2014 Apr 16;62(15):3488-95. doi: 10.1021/jf5003528. Epub 2014 Apr 4. [PubMed:24673591 ]
  2. Shi JX, Adato A, Alkan N, He Y, Lashbrooke J, Matas AJ, Meir S, Malitsky S, Isaacson T, Prusky D, Leshkowitz D, Schreiber L, Granell AR, Widemann E, Grausem B, Pinot F, Rose JKC, Rogachev I, Rothan C, Aharoni A: The tomato SlSHINE3 transcription factor regulates fruit cuticle formation and epidermal patterning. New Phytol. 2013 Jan;197(2):468-480. doi: 10.1111/nph.12032. Epub 2012 Dec 3. [PubMed:23205954 ]
  3. Kolattukudy PE, Walton TJ, Kushwaha RP: Biosynthesis of the C18 family of cutin acids: omega-hydroxyoleic acid, omega-hydroxy-9,10-epoxystearic acid, 9,10,18-trihydroxystearic acid, and their delta12-unsaturated analogs. Biochemistry. 1973 Oct 23;12(22):4488-98. doi: 10.1021/bi00746a029. [PubMed:4356240 ]