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Record Information
Version2.0
Created at2021-06-19 22:18:43 UTC
Updated at2021-06-29 23:59:33 UTC
NP-MRD IDNP0031148
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-hydroxy-octadeca-10,12,15-trienoic acid
Provided ByJEOL DatabaseJEOL Logo
Description9S-hotre 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. Thus, 9S-hotre is considered to be an octadecanoid. 9-hydroxy-octadeca-10,12,15-trienoic acid is found in Apis cerana and Artocarpus communis. 9-hydroxy-octadeca-10,12,15-trienoic acid was first documented in 2000 (PMID: 10830513). Based on a literature review a small amount of articles have been published on 9s-hotre (PMID: 21481031) (PMID: 23370715) (PMID: 23479199).
Structure
Thumb
Synonyms
ValueSource
(9S)-(10E,12Z,15Z)-9-Hydroxyoctadecatri-10,12,15-enoic acidChEBI
(9S,10E,12Z,15Z)-9-Hydroxyoctadecatrienoic acidChEBI
9(S)-HOTChEBI
9-Hydroxy-10,12,15-octadecatrienoic acidChEBI
9(S)-HOTrEKegg
(9S)-(10E,12Z,15Z)-9-Hydroxyoctadecatri-10,12,15-enoateGenerator
(9S,10E,12Z,15Z)-9-HydroxyoctadecatrienoateGenerator
9-Hydroxy-10,12,15-octadecatrienoateGenerator
(10E,12Z,15Z)-9-OH-10,12,15-ODTAMeSH
9-OH-10,12,15-ODTAMeSH
9S-HOTrEChEBI
Chemical FormulaC18H30O3
Average Mass294.4350 Da
Monoisotopic Mass294.21949 Da
IUPAC Name(9S,10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid
Traditional Name9(S)-HOTrE
CAS Registry NumberNot Available
SMILES
[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(O[H])C(\[H])=C(/[H])\C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])[H]
InChI Identifier
InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14,17,19H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3-,8-6-,14-11+/t17-/m1/s1
InChI KeyRIGGEAZDTKMXSI-MEBVTJQTSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Artocarpus altilisJEOL database
    • McLean, S., et al, Magn. Reson. Chem. 34, 719 (1996)
Isatis tinctoriaKNApSAcK Database
Chemical Taxonomy
Description 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
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • 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
logP5.31ALOGPS
logP4.83ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity91.15 m³·mol⁻¹ChemAxon
Polarizability34.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00048303
Chemspider ID4944252
KEGG Compound IDC16326
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID80447
Good Scents IDNot Available
References
General References
  1. Dong M, Oda Y, Hirota M: (10E,12Z,15Z)-9-hydroxy-10,12,15-octadecatrienoic acid methyl ester as an anti-inflammatory compound from Ehretia dicksonii. Biosci Biotechnol Biochem. 2000 Apr;64(4):882-6. doi: 10.1271/bbb.64.882. [PubMed:10830513 ]
  2. Lopez MA, Vicente J, Kulasekaran S, Vellosillo T, Martinez M, Irigoyen ML, Cascon T, Bannenberg G, Hamberg M, Castresana C: Antagonistic role of 9-lipoxygenase-derived oxylipins and ethylene in the control of oxidative stress, lipid peroxidation and plant defence. Plant J. 2011 Aug;67(3):447-58. doi: 10.1111/j.1365-313X.2011.04608.x. Epub 2011 Jun 6. [PubMed:21481031 ]
  3. Vellosillo T, Aguilera V, Marcos R, Bartsch M, Vicente J, Cascon T, Hamberg M, Castresana C: Defense activated by 9-lipoxygenase-derived oxylipins requires specific mitochondrial proteins. Plant Physiol. 2013 Feb;161(2):617-27. doi: 10.1104/pp.112.207514. Epub 2012 Dec 12. [PubMed:23370715 ]
  4. Saubeau G, Goulitquer S, Barloy D, Potin P, Andrivon D, Val F: Differential induction of oxylipin pathway in potato and tobacco cells by bacterial and oomycete elicitors. Plant Cell Rep. 2013 May;32(5):579-89. doi: 10.1007/s00299-012-1377-y. Epub 2013 Mar 12. [PubMed:23479199 ]
  5. McLean, S., et al. (1996). McLean, S., et al, Magn. Reson. Chem. 34, 719 (1996). Mag. Reson. Chem..