alpha-Dimorphecolic acid (CHEM025062)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:06:50 UTC
Update Date2016-11-09 01:18:00 UTC
Accession NumberCHEM025062
Identification
Common Namealpha-Dimorphecolic acid
ClassSmall Molecule
DescriptionA 9-HODE in which the 9-hydroxy group has S-stereochemistry.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(10E,12Z)-(9S)-9-Hydroxyoctadeca-10,12-dienoic acidChEBI
(9S)-Hydroxyoctadecadienoic acidChEBI
(9S)-Hydroxyoctadecadinoiec acidChEBI
(10E,12Z)-(9S)-9-Hydroxyoctadeca-10,12-dienoateGenerator
(9S)-HydroxyoctadecadienoateGenerator
a-DimorphecolateGenerator
a-Dimorphecolic acidGenerator
alpha-DimorphecolateGenerator
Α-dimorphecolateGenerator
Α-dimorphecolic acidGenerator
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoateHMDB
(9S,10E,12Z)-9-Hydroxyoctadeca-10,12-dienoic acidHMDB
9(S)-HODEHMDB
9S-Hydroxy-10E,12Z-octadecadienoateHMDB
9S-Hydroxy-10E,12Z-octadecadienoic acidHMDB
alpha-DimorphecolicHMDB
[S-(e,Z)]-9-Hydroxy-10,12-octadecadienoateHMDB
[S-(e,Z)]-9-Hydroxy-10,12-octadecadienoic acidHMDB
9-Hydroxy-10,12-octadecadienoic acidHMDB
9-Hydroxy-10,12-octadecadienoic acid, (R-(e,Z))-isomerHMDB
9-HODEHMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-isomerHMDB
9-Hydroxy-10,12-octadecadienoic acid, (S-(e,Z))-isomerHMDB
9-Hydroxylinoleic acidHMDB
Dimorphecolic acidHMDB
9-OH-18:2DElta(10t,12t)HMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-(+-)-isomerHMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,e)-isomerHMDB
9-Hydroxy-10,12-octadecadienoic acid, (e,Z)-(+-)-isomerHMDB
9-Hydroxyoctadecadienoic acidHMDB
9S-HOD acidHMDB
(+)-alpha-Dimorphecolic acidHMDB
(+)-Α-dimorphecolic acidHMDB
(10E,12Z)-9-Hydroxy-10,12-octadecadienoic acidHMDB
(9S,10E,12Z)-9-Hydroxy-10,12-octadecadienoic acidHMDB
(±)-alpha-dimorphecolic acidHMDB
(±)-α-dimorphecolic acidHMDB
9-(e,Z)-HODEHMDB
9-Hydroxy-(10E,12Z)-octadeca-10,12-dienoic acidHMDB
9-Hydroxy-10(e),12(Z)-octadecadienoic acidHMDB
9-Hydroxy-10-trans,12-cis-octadecadienoic acidHMDB
9S-HODEHMDB
alpha-Dimorphecolic acidHMDB
Chemical FormulaC18H32O3
Average Molecular Mass296.445 g/mol
Monoisotopic Mass296.235 g/mol
CAS Registry Number73543-67-6
IUPAC Name(9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid
Traditional Nameα-dimorphecolic
SMILESCCCCC\C=C\C=C/C(O)CCCCCCCC(O)=O
InChI IdentifierInChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6+,14-11-
InChI KeyNPDSHTNEKLQQIJ-SQKGQWCESA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0032 g/LALOGPS
logP5.88ALOGPS
logP5.19ChemAxon
logS-5ALOGPS
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 Count14ChemAxon
Refractivity90.03 m³·mol⁻¹ChemAxon
Polarizability37.23 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4930000000-e1186c721ea6fb1169c7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-9133100000-615fce6d28e837fb087eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0090000000-9edfb0d1ce954a62c742Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-6590000000-bf044894de0d32745a88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9210000000-3859d2d1305a9293e4ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-cb87e5a91d0ade94a4daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-1290000000-b10feffea7912d994743Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9620000000-a030dd65d92c57156f49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-ac1c086be68f1b68836bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0190000000-8b6429d79d5d2e8d903dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ox-7970000000-39d40a54c2868e155bbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1390000000-84c6212593eb31771c8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08j0-6930000000-7d820298630f06567efdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-9100000000-0659e7446120fadecc13Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB07302
HMDB IDHMDB0004670
FooDB IDFDB003060
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB ID9HO
Wikipedia Link9-Hydroxyoctadecadienoic_acid
Chemspider ID4472255
ChEBI ID34496
PubChem Compound ID5312830
Kegg Compound IDC14767
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hattori T, Obinata H, Ogawa A, Kishi M, Tatei K, Ishikawa O, Izumi T: G2A plays proinflammatory roles in human keratinocytes under oxidative stress as a receptor for 9-hydroxyoctadecadienoic acid. J Invest Dermatol. 2008 May;128(5):1123-33. Epub 2007 Nov 22.
2. Marx N, Bourcier T, Sukhova GK, Libby P, Plutzky J: PPARgamma activation in human endothelial cells increases plasminogen activator inhibitor type-1 expression: PPARgamma as a potential mediator in vascular disease. Arterioscler Thromb Vasc Biol. 1999 Mar;19(3):546-51.
3. Hampel JK, Brownrigg LM, Vignarajah D, Croft KD, Dharmarajan AM, Bentel JM, Puddey IB, Yeap BB: Differential modulation of cell cycle, apoptosis and PPARgamma2 gene expression by PPARgamma agonists ciglitazone and 9-hydroxyoctadecadienoic acid in monocytic cells. Prostaglandins Leukot Essent Fatty Acids. 2006 May;74(5):283-93. Epub 2006 May 2.
4. Obinata H, Hattori T, Nakane S, Tatei K, Izumi T: Identification of 9-hydroxyoctadecadienoic acid and other oxidized free fatty acids as ligands of the G protein-coupled receptor G2A. J Biol Chem. 2005 Dec 9;280(49):40676-83. Epub 2005 Oct 19.
5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.